(1R,2S,4aR,13bS,14aS)-2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

ID: ALA15245

Chembl Id: CHEMBL15245

Max Phase: Approved

Molecular Formula: C21H26N2O3

Molecular Weight: 354.45

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Yohimbine | Yohimbinum

Synonyms from Alternative Forms(5): Yohimbine hydrochloride | Yohimbine hcl | NSC-19509 | Prowess plain | Yocon

Canonical SMILES:  COC(=O)[C@@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O

Standard InChI:  InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1

Standard InChI Key:  BLGXFZZNTVWLAY-SCYLSFHTSA-N

Alternative Forms

  1. Parent:

    ALA15245

    YOHIMBINE
  2. Alternative Forms:

Associated Targets(Human)

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Adrenergic receptor alpha-2 (812 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Adrenergic receptor alpha-1 (948 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SCN1A Tclin Sodium channel alpha subunits; brain (Types I, II, III) (374 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin receptor (2b and 2c) (118 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT2A Tchem Histone acetyltransferase GCN5 (14285 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATXN2 Tbio Ataxin-2 (54410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KPNB1 Tbio Importin subunit beta-1/Snurportin-1 (25097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB3 Tclin Beta-3 adrenergic receptor (5850 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR2 Tchem Angiotensin II type 2 (AT-2) receptor (2549 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CALCR Tclin Calcitonin receptor (2215 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR2 Tchem C-C chemokine receptor type 2 (5628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR4 Tclin C-C chemokine receptor type 4 (2819 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR5 Tclin C-C chemokine receptor type 5 (5640 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCR1 Tchem Interleukin-8 receptor A (2256 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCR2 Tchem Interleukin-8 receptor B (3491 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCKAR Tclin Cholecystokinin A receptor (4460 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2E1 Tchem Cytochrome P450 2E1 (2174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD4 Tchem Dopamine D4 receptor (7907 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EDNRA Tclin Endothelin receptor ET-A (5008 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR2 Tclin Estrogen receptor beta (9272 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH1 Tclin Histamine H1 receptor (7573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH2 Tclin Histamine H2 receptor (5428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HMGCR Tclin HMG-CoA reductase (2475 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYSLTR1 Tclin Cysteinyl leukotriene receptor 1 (2118 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC3R Tchem Melanocortin receptor 3 (5659 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC4R Tclin Melanocortin receptor 4 (10016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC5R Tchem Melanocortin receptor 5 (4283 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM4 Tclin Muscarinic acetylcholine receptor M4 (6041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM5 Tclin Muscarinic acetylcholine receptor M5 (4677 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPY1R Tchem Neuropeptide Y receptor type 1 (5019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPY2R Tchem Neuropeptide Y receptor type 2 (3731 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRD1 Tclin Delta opioid receptor (15096 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Tclin Kappa opioid receptor (16155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE5A Tclin Phosphodiesterase 5A (5113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTAFR Tchem Platelet activating factor receptor (2575 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP1 Tchem Caspase-1 (6235 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CTSG Tchem Cathepsin G (2304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ELANE Tclin Leukocyte elastase (8173 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MMP9 Tchem Matrix metalloproteinase 9 (6779 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCA Tchem Protein kinase C alpha (5923 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK3 Tchem MAP kinase ERK1 (4725 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPP3CA Tchem Serine/threonine protein phosphatase 2B catalytic subunit, alpha isoform (1831 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FYN Tclin Tyrosine-protein kinase FYN (5308 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPRC Tchem Leukocyte common antigen (2317 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR6 Tchem Serotonin 6 (5-HT6) receptor (9749 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TACR1 Tclin Neurokinin 1 receptor (6273 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TACR2 Tchem Neurokinin 2 receptor (3341 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXAS1 Tchem Thromboxane-A synthase (3355 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT1 Tclin Vascular endothelial growth factor receptor 1 (6262 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VIPR1 Tchem Vasoactive intestinal polypeptide receptor 1 (1904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (16955 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDC25A Tchem Dual specificity phosphatase Cdc25A (619 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ARSA Tbio Cerebroside-sulfatase (655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB11 Tchem Bile salt export pump (2311 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR8 Tchem C-C chemokine receptor type 8 (339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CNR2 Tchem Cannabinoid CB2 receptor (16942 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCR4 Tclin C-X-C chemokine receptor type 4 (3338 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FPR1 Tchem Formyl peptide receptor 1 (1372 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GPR119 Tclin Glucose-dependent insulinotropic receptor (4762 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCRTR2 Tclin Orexin receptor 2 (5902 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPSR1 Tchem Neuropeptide S receptor (15785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRLHR Tchem Prolactin-releasing peptide receptor (450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGIR Tclin Prostanoid IP receptor (1280 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCR3 Tchem C-C chemokine receptor type 3 (1666 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CX3CR1 Tchem C-X3-C chemokine receptor 1 (1686 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FSHR Tclin Follicle stimulating hormone receptor (234 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OXTR Tclin Oxytocin receptor (1962 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GIPR Tchem Gastric inhibitory polypeptide receptor (542 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCKBR Tclin Cholecystokinin B receptor (3550 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GCGR Tclin Glucagon receptor (2563 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GHSR Tclin Ghrelin receptor (6229 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EDNRB Tclin Endothelin receptor ET-B (1928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BDKRB1 Tchem Bradykinin B1 receptor (1859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRHR1 Tclin Corticotropin releasing factor receptor 1 (2996 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CRHR2 Tchem Corticotropin releasing factor receptor 2 (399 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4D Tclin Phosphodiesterase 4D (3546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MLNR Tchem Motilin receptor (1724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NTSR1 Tchem Neurotensin receptor 1 (1525 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
F2 Tclin Thrombin (11687 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GABRA1 Tclin Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2 (1034 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDE4A Tclin Phosphodiesterase 4A (1943 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Adra1b Adrenergic receptor alpha-1 (5652 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2c Adrenergic receptor alpha-2 (3313 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Drd2 Dopamine D2 receptor (7893 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1b Adrenergic receptor alpha (950 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cavia porcellus (23802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1d Alpha-1d adrenergic receptor (1475 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Alpha-2a adrenergic receptor (3 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2b Alpha-2 adrenergic receptor (120 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Alpha-1a adrenergic receptor (303 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cacna1c Voltage-gated L-type calcium channel alpha-1C subunit (1321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ache Acetylcholinesterase (2577 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor (3770 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Drd5 Dopamine receptor (1304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2b Serotonin 2b (5-HT2b) receptor (321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2a Serotonin 2a (5-HT2a) receptor (3540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr2c Serotonin 2c (5-HT2c) receptor (18 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adora2b Adenosine A2b receptor (205 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Drd3 Dopamine D3 receptor (1050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Alpha-2a adrenergic receptor (162 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2A Cerebral cortex alpha adrenergic receptor (44 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oryctolagus cuniculus (11301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra2b Alpha-2b adrenergic receptor (94 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ache Acetylcholinesterase (12221 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
mex-5 Zinc finger protein mex-5 (1676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pos-1 Cytoplasmic zinc-finger protein (1690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1a Alpha-1a adrenergic receptor (3346 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Adra1b Alpha-1b adrenergic receptor (2470 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Akr1b1 Aldose reductase (4007 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Glra2 Glycine receptor (1745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Insr Insulin receptor (1750 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LTC4S Leukotriene C4 synthase (1746 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15 Arachidonate 15-lipoxygenase (2064 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos1 Nitric-oxide synthase, brain (2987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nos2 Nitric oxide synthase, inducible (3573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Progesterone receptor (1742 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACE Angiotensin-converting enzyme (2863 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr1a Serotonin 1a (5-HT1a) receptor (8655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Htr1b Serotonin 1b (5-HT1b) receptor (2343 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR4 Serotonin 4 (5-HT4) receptor (2870 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ar Androgen Receptor (5522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
clpP ATP-dependent Clp protease proteolytic subunit (20705 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grin1 Glutamate (NMDA) receptor subunit zeta 1 (2166 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gabra1 GABA receptor alpha-1 subunit (2848 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cacna1b Voltage-gated N-type calcium channel alpha-1B subunit (471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ptgs1 Cyclooxygenase-1 (1373 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 354.45Molecular Weight (Monoisotopic): 354.1943AlogP: 2.65#Rotatable Bonds: 1
Polar Surface Area: 65.56Molecular Species: NEUTRALHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 7.22CX LogP: 2.10CX LogD: 1.88
Aromatic Rings: 2Heavy Atoms: 26QED Weighted: 0.77Np Likeness Score: 1.17

References

1. Miller DD, Hamada A, Clark MT, Adejare A, Patil PN, Shams G, Romstedt KJ, Kim SU, Intrasuksri U, McKenzie JL..  (1990)  Synthesis and alpha 2-adrenoceptor effects of substituted catecholimidazoline and catecholimidazole analogues in human platelets.,  33  (4): [PMID:2157007] [10.1021/jm00166a009]
2. Strobl GR, von Kruedener S, Stöckigt J, Guengerich FP, Wolff T..  (1993)  Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies.,  36  (9): [PMID:8487254] [10.1021/jm00061a004]
3. Saari WS, Halczenko W, Huff JR, Guare JP, Hunt CA, Randall WC, Lotti VJ, Yarbrough GG..  (1984)  Adrenoceptor and tetrabenazine antagonism activities of some pyridinyltetrahydropyridines.,  27  (9): [PMID:6088770] [10.1021/jm00375a017]
4. DeMarinis RM, Hieble JP..  (1983)  l-1,2,3,4-Tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine: a potent and selective agonist at alpha 1-adrenoceptors.,  26  (9): [PMID:6136611] [10.1021/jm00363a002]
5. Van Dort M, Neubig R, Counsell RE..  (1987)  Radioiodinated p-iodoclonidine: a high-affinity probe for the alpha 2-adrenergic receptor.,  30  (7): [PMID:3037080] [10.1021/jm00390a021]
6. Caroon JM, Clark RD, Kluge AF, Nelson JT, Strosberg AM, Unger SH, Michel AD, Whiting RL..  (1981)  Synthesis and antihypertensive activity of a series of 8-substituted 1-oxa-3,8-diazaspiro[4.5]decan-2-ones.,  24  (11): [PMID:7310808] [10.1021/jm00143a012]
7. Vizi ES, Toth I, Somogyi GT, Szabo L, Harsing LG, Szantay C..  (1987)  Berbanes: a new class of selective alpha 2-adrenoceptor antagonists.,  30  (8): [PMID:2886664] [10.1021/jm00391a015]
8. Guérémy C, Audiau F, Renault C, Benavides J, Uzan A, Le Fur G..  (1986)  4-Amino-6-chloro-2-piperazinopyrimidines with selective affinity for alpha 2-adrenoceptors.,  29  (8): [PMID:3016265] [10.1021/jm00158a013]
9. Timmermans PB, van Zwieten PA..  (1982)  alpha 2 adrenoceptors: classification, localization, mechanisms, and targets for drugs.,  25  (12): [PMID:6296387] [10.1021/jm00354a001]
10. Marciniak G, Delgado A, Leclerc G, Velly J, Decker N, Schwartz J..  (1989)  New 1,4-dihydropyridine derivatives combining calcium antagonism and alpha-adrenolytic properties.,  32  (6): [PMID:2542561] [10.1021/jm00126a042]
11. Ward TJ, White JF, Lattimer N, Rhodes KF, Sharma S, Waterfall JF..  (1988)  Synthesis and structure-activity relationships of 2-sulfonamido-1,3,4,6,7,11b alpha-hexahydro-2H-benzo[a]quinolizines as alpha 2-adrenoceptor antagonists.,  31  (7): [PMID:2838634] [10.1021/jm00402a029]
12. Wentland MP, Bailey DM, Alexander EJ, Castaldi MJ, Ferrari RA, Haubrich DR, Luttinger DA, Perrone MH..  (1987)  Synthesis and antidepressant properties of novel 2-substituted 4,5-dihydro-1H-imidazole derivatives.,  30  (8): [PMID:3039138] [10.1021/jm00391a034]
13. Foulon C, Kung MP, Kung HF..  (1993)  Synthesis of (R,S)-2'-trans-7-hydroxy-2-[N-n-propyl-N-(3'-iodo-2'- propenyl)-amino]tetralin (trans-7-OH-PIPAT): a new D3 dopamine receptor ligand.,  36  (10): [PMID:8098771] [10.1021/jm00062a025]
14. Hlasta DJ, Luttinger D, Perrone MH, Silbernagel MJ, Ward SJ, Haubrich DR..  (1987)  Alpha 2-adrenergic agonists/antagonists: the synthesis and structure-activity relationships of a series of indolin-2-yl and tetrahydroquinolin-2-yl imidazolines.,  30  (9): [PMID:2887657] [10.1021/jm00392a005]
15. Andrews PR, Craik DJ, Martin JL..  (1984)  Functional group contributions to drug-receptor interactions.,  27  (12): [PMID:6094812] [10.1021/jm00378a021]
16. Saari WS, Halczenko W, King SW, Huff JR, Guare JP, Hunt CA, Randall WC, Anderson PS, Lotti VJ, Taylor DA..  (1983)  Pyridinylpiperazines, a new class of selective alpha 2-adrenoceptor antagonists.,  26  (12): [PMID:6139479] [10.1021/jm00366a007]
17. Huff JR, Anderson PS, Baldwin JJ, Clineschmidt BV, Guare JP, Lotti VJ, Pettibone DJ, Randall WC, Vacca JP..  (1985)  N-(1,3,4,6,7,12b-hexahydro-2H-benzo[b]furo[2,3-a]quinolizin -2-yl)-N- methyl-2-hydroxyethane-sulfonamide: a potent and selective alpha 2-adrenoceptor antagonist.,  28  (12): [PMID:2999400] [10.1021/jm00150a002]
18. Suomalainen P, Johans C, Söderlund T, Kinnunen PK..  (2004)  Surface activity profiling of drugs applied to the prediction of blood-brain barrier permeability.,  47  (7): [PMID:15027870] [10.1021/jm0309001]
19. Clark RD, Repke DB, Kilpatrick AT, Brown CM, MacKinnon AC, Clague RU, Spedding M..  (1989)  (8a alpha,12a alpha,13a alpha)-5,8,8a,9,10,11,12,12a,13,13a-decahydro- 3-methoxy-12-(methylsulfonyl)-6H-isoquino[2,1-g][1,6]naphthyridi ne, a potent and highly selective alpha 2-adrenoceptor antagonist.,  32  (9): [PMID:2570150] [10.1021/jm00129a002]
20. Berglund J, Nicholls IA, Lindbladh C, Mosbach K.  (1996)  Recognition in molecularly imprinted polymer 2-adrenoreceptor mimics,  (18): [10.1016/0960-894X(96)00406-4]
21. Chumpradit S, Kung MP, Billings J, Mach R, Kung HF..  (1993)  Fluorinated and iodinated dopamine agents: D2 imaging agents for PET and SPECT.,  36  (2): [PMID:8093734] [10.1021/jm00054a005]
22. Audia JE, Evrard DA, Murdoch GR, Droste JJ, Nissen JS, Schenck KW, Fludzinski P, Lucaites VL, Nelson DL, Cohen ML..  (1996)  Potent, selective tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT2B) contractile receptor in the rat stomach fundus.,  39  (14): [PMID:8709108] [10.1021/jm960062t]
23. Perrone R, Berardi F, Leopoldo M, Tortorella V, Fornaretto MG, Caccia C, McArthur RA..  (1996)  1-aryl-4-[(1-tetralinyl)alkyl]piperazines: alkylamido and alkylamino derivatives. Synthesis, 5-HT1A receptor affinity, and selectivity. 3.,  39  (16): [PMID:8759642] [10.1021/jm960087s]
24. Hieble JP, Bondinell WE, Ruffolo RR..  (1995)  Alpha- and beta-adrenoceptors: from the gene to the clinic. 1. Molecular biology and adrenoceptor subclassification.,  38  (18): [PMID:7658428] [10.1021/jm00018a001]
25. Mayer P, Brunel P, Chaplain C, Piedecoq C, Calmel F, Schambel P, Chopin P, Wurch T, Pauwels PJ, Marien M, Vidaluc JL, Imbert T..  (2000)  New substituted 1-(2,3-dihydrobenzo[1, 4]dioxin-2-ylmethyl)piperidin-4-yl derivatives with alpha(2)-adrenoceptor antagonist activity.,  43  (20): [PMID:11020279] [10.1021/jm991121g]
26. Ruffolo RR, Bondinell W, Hieble JP..  (1995)  Alpha- and beta-adrenoceptors: from the gene to the clinic. 2. Structure-activity relationships and therapeutic applications.,  38  (19): [PMID:7562902] [10.1021/jm00019a001]
27. McNeal ET, Lewandowski GA, Daly JW, Creveling CR..  (1985)  [3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.,  28  (3): [PMID:2579237] [10.1021/jm00381a019]
28. Perrone R, Berardi F, Colabufo NA, Leopoldo M, Tortorella V, Fornaretto MG, Caccia C, McArthur RA..  (1996)  Structure-activity relationship studies on the 5-HT(1A) receptor affinity of 1-phenyl-4-[omega-(alpha- or beta-tetralinyl)alkyl]piperazines. 4.,  39  (25): [PMID:8960552] [10.1021/jm9604538]
29. Timmermans PB, de Jonge A, Thoolen MJ, Wilffert B, Batink H, van Zwieten PA..  (1984)  Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists.,  27  (4): [PMID:6142954] [10.1021/jm00370a011]
30. Belliotti TR, Wustrow DJ, Brink WA, Zoski KT, Shih YH, Whetzel SZ, Georgic LM, Corbin AE, Akunne HC, Heffner TG, Pugsley TA, Wise LD..  (1999)  A series of 6- and 7-piperazinyl- and -piperidinylmethylbenzoxazinones with dopamine D4 antagonist activity: discovery of a potential atypical antipsychotic agent.,  42  (25): [PMID:10602703] [10.1021/jm990277d]
31. Chapleo CB, Myers PL, Butler RC, Davis JA, Doxey JC, Higgins SD, Myers M, Roach AG, Smith CF, Stillings MR..  (1984)  Alpha-adrenoreceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on alpha-adrenoreceptor activity.,  27  (5): [PMID:6143826] [10.1021/jm00371a003]
32. Klein JT, Davis L, Olsen GE, Wong GS, Huger FP, Smith CP, Petko WW, Cornfeldt M, Wilker JC, Blitzer RD, Landau E, Haroutunian V, Martin LL, Effland RC..  (1996)  Synthesis and structure-activity relationships of N-propyl-N-(4-pyridinyl)-1H-indol-1-amine (besipirdine) and related analogs as potential therapeutic agents for Alzheimer's disease.,  39  (2): [PMID:8558529] [10.1021/jm9506433]
33. Clark RD, Berger J, Garg P, Weinhardt KK, Spedding M, Kilpatrick AT, Brown CM, MacKinnon AC..  (1990)  Affinity of 2-(tetrahydroisoquinolin-2-ylmethyl)- and 2-(isoindolin-2-ylmethyl)imidazolines for alpha-adrenoceptors. Differential affinity of imidazolines for the [3H]idazoxan-labeled alpha 2-adrenoceptor vs the [3H]yohimbine-labeled site.,  33  (2): [PMID:2153820] [10.1021/jm00164a021]
34. Zheng W, Lei L, Lalchandani S, Sun G, Feller DR, Miller DD..  (2000)  Yohimbine dimers exhibiting binding selectivities for human alpha2a- versus alpha2b-adrenergic receptors.,  10  (7): [PMID:10762040] [10.1016/s0960-894x(00)00068-8]
35. Caroon JM, Clark RD, Kluge AF, Olah R, Repke DB, Unger SH, Michel AD, Whiting RL..  (1982)  Structure-activity relationships for 2-substituted imidazoles as alpha 2-adrenoceptor antagonists.,  25  (6): [PMID:6124635] [10.1021/jm00348a012]
36. Clark RD, Repke DB, Berger J, Nelson JT, Kilpatrick AT, Brown CM, MacKinnon AC, Clague RU, Spedding M..  (1991)  Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.,  34  (2): [PMID:1671705] [10.1021/jm00106a036]
37. Chapleo CB, Myers PL, Butler RC, Doxey JC, Roach AG, Smith CF..  (1983)  alpha-adrenoreceptor reagents. 1. Synthesis of some 1,4-benzodioxans as selective presynaptic alpha 2-adrenoreceptor antagonists and potential antidepressants.,  26  (6): [PMID:6133953] [10.1021/jm00360a008]
38. Kemp CA, Flanagan JU, van Eldik AJ, Maréchal JD, Wolf CR, Roberts GC, Paine MJ, Sutcliffe MJ..  (2004)  Validation of model of cytochrome P450 2D6: an in silico tool for predicting metabolism and inhibition.,  47  (22): [PMID:15481972] [10.1021/jm049934e]
39. Mustafa SM, Bavadekar SA, Ma G, Moore BM, Feller DR, Miller DD..  (2005)  Synthesis and biological studies of yohimbine derivatives on human alpha2C-adrenergic receptors.,  15  (11): [PMID:15911252] [10.1016/j.bmcl.2005.03.116]
40. Minetti P, Tinti MO, Carminati P, Castorina M, Di Cesare MA, Di Serio S, Gallo G, Ghirardi O, Giorgi F, Giorgi L, Piersanti G, Bartoccini F, Tarzia G..  (2005)  2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacological characterization.,  48  (22): [PMID:16250647] [10.1021/jm058018d]
41. Cesari N, Biancalani C, Vergelli C, Dal Piaz V, Graziano A, Biagini P, Ghelardini C, Galeotti N, Giovannoni MP..  (2006)  Arylpiperazinylalkylpyridazinones and analogues as potent and orally active antinociceptive agents: synthesis and studies on mechanism of action.,  49  (26): [PMID:17181165] [10.1021/jm060743g]
42. Giovannoni MP, Cesari N, Vergelli C, Graziano A, Biancalani C, Biagini P, Ghelardini C, Vivoli E, Dal Piaz V..  (2007)  4-amino-5-substituted-3(2H)-pyridazinones as orally active antinociceptive agents: synthesis and studies on the mechanism of action.,  50  (16): [PMID:17629262] [10.1021/jm070161e]
43. Grice CA, Tays KL, Savall BM, Wei J, Butler CR, Axe FU, Bembenek SD, Fourie AM, Dunford PJ, Lundeen K, Coles F, Xue X, Riley JP, Williams KN, Karlsson L, Edwards JP..  (2008)  Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity.,  51  (14): [PMID:18588282] [10.1021/jm701575k]
44. Gafner S, Dietz BM, McPhail KL, Scott IM, Glinski JA, Russell FE, McCollom MM, Budzinski JW, Foster BC, Bergeron C, Rhyu MR, Bolton JL..  (2006)  Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro.,  69  (3): [PMID:16562853] [10.1021/np058114h]
45. Itoh A, Kumashiro T, Yamaguchi M, Nagakura N, Mizushina Y, Nishi T, Tanahashi T..  (2005)  Indole alkaloids and other constituents of Rauwolfia serpentina.,  68  (6): [PMID:15974606] [10.1021/np058007n]
46. Itoh A, Kumashiro T, Yamaguchi M, Nagakura N, Mizushina Y, Nishi T, Tanahashi T..  (2005)  Indole alkaloids and other constituents of Rauwolfia serpentina.,  68  (6): [PMID:15974606] [10.1021/np058007n]
47. Mroue MA, Euler KL, Ghuman MA, Alam M.  (1996)  Indole Alkaloids of Haplophyton crooksii 1 ,  59  (9): [10.1021/np960070c]
48. Jain KS, Bariwal JB, Kathiravan MK, Phoujdar MS, Sahne RS, Chauhan BS, Shah AK, Yadav MR..  (2008)  Recent advances in selective alpha1-adrenoreceptor antagonists as antihypertensive agents.,  16  (9): [PMID:18378462] [10.1016/j.bmc.2008.02.091]
49. Vilardaga JP, Steinmeyer R, Harms GS, Lohse MJ..  (2005)  Molecular basis of inverse agonism in a G protein-coupled receptor.,  (1): [PMID:16407989] [10.1038/nchembio705]
50. PubChem BioAssay data set, 
51. PubChem BioAssay data set, 
52. Liu H, Altenbach RJ, Carr TL, Chandran P, Hsieh GC, Lewis LG, Manelli AM, Milicic I, Marsh KC, Miller TR, Strakhova MI, Vortherms TA, Wakefield BD, Wetter JM, Witte DG, Honore P, Esbenshade TA, Brioni JD, Cowart MD..  (2008)  cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain responses against carrageenan-induced hyperalgesia.,  51  (22): [PMID:18983139] [10.1021/jm8007618]
53. Hayashi S, Nakata E, Morita A, Mizuno K, Yamamura K, Kato A, Ohashi K..  (2010)  Discovery of {1-[4-(2-{hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl}-1H-benzimidazol-1-yl)piperidin-1-yl]cyclooctyl}methanol, systemically potent novel non-peptide agonist of nociceptin/orphanin FQ receptor as analgesic for the treatment of neuropathic pain: design, synthesis, and structure-activity relationships.,  18  (21): [PMID:20875743] [10.1016/j.bmc.2010.07.034]
54. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]
55. Dolusić E, Larrieu P, Moineaux L, Stroobant V, Pilotte L, Colau D, Pochet L, Van den Eynde B, Masereel B, Wouters J, Frédérick R..  (2011)  Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators.,  54  (15): [PMID:21726069] [10.1021/jm2006782]
56. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS..  (2001)  Rational use of in vitro P-glycoprotein assays in drug discovery.,  299  (2): [PMID:11602674]
57. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 
58. Sun H..  (2012)  Capture hydrolysis signals in the microsomal stability assay: molecular mechanisms of the alkyl ester drug and prodrug metabolism.,  22  (2): [PMID:22197392] [10.1016/j.bmcl.2011.12.005]
59. Mammoli V, Bonifazi A, Del Bello F, Diamanti E, Giannella M, Hudson AL, Mattioli L, Perfumi M, Piergentili A, Quaglia W, Titomanlio F, Pigini M..  (2012)  Favourable involvement of α2A-adrenoreceptor antagonism in the I₂-imidazoline binding sites-mediated morphine analgesia enhancement.,  20  (7): [PMID:22370341] [10.1016/j.bmc.2012.02.016]
60. Del Bello F, Diamanti E, Giannella M, Mammoli V, Marchioro C, Mattioli L, Titomanlio F, Piergentili A, Quaglia W, Benedetti G, Varrone M, Pigini M..  (2012)  Low Doses of Allyphenyline and Cyclomethyline, Effective against Morphine Dependence, Elicit an Antidepressant-like Effect.,  (7): [PMID:24900506] [10.1021/ml300064v]
61. Lachance H, Wetzel S, Kumar K, Waldmann H..  (2012)  Charting, navigating, and populating natural product chemical space for drug discovery.,  55  (13): [PMID:22537178] [10.1021/jm300288g]
62. Giorgioni G, Accorroni B, Di Stefano A, Marucci G, Siniscalchi A, Claudi F.  (2005)  Benzimidazole, Benzoxazole and Benzothiazole Derivatives as 5HT2B Receptor Ligands. Synthesis and Preliminary Pharmacological Evaluation,  14  (2): [10.1007/s00044-005-0125-z]
63. PubChem BioAssay data set, 
64. Veinberg G, Vorona M, Zvejniece L, Vilskersts R, Vavers E, Liepinsh E, Kazoka H, Belyakov S, Mishnev A, Kuznecovs J, Vikainis S, Orlova N, Lebedev A, Ponomaryov Y, Dambrova M..  (2013)  Synthesis and biological evaluation of 2-(5-methyl-4-phenyl-2-oxopyrrolidin-1-yl)-acetamide stereoisomers as novel positive allosteric modulators of sigma-1 receptor.,  21  (10): [PMID:23582449] [10.1016/j.bmc.2013.03.016]
65. Germain AR, Carmody LC, Nag PP, Morgan B, Verplank L, Fernandez C, Donckele E, Feng Y, Perez JR, Dandapani S, Palmer M, Lander ES, Gupta PB, Schreiber SL, Munoz B..  (2013)  Cinnamides as selective small-molecule inhibitors of a cellular model of breast cancer stem cells.,  23  (6): [PMID:23403082] [10.1016/j.bmcl.2013.01.025]
66. Cappelli A, Manini M, Valenti S, Castriconi F, Giuliani G, Anzini M, Brogi S, Butini S, Gemma S, Campiani G, Giorgi G, Mennuni L, Lanza M, Giordani A, Caselli G, Letari O, Makovec F..  (2013)  Synthesis and structure-activity relationship studies in serotonin 5-HT(1A) receptor agonists based on fused pyrrolidone scaffolds.,  63  [PMID:23466604] [10.1016/j.ejmech.2013.01.044]
67. Unpublished dataset, 
68. Rajagopalan R, Bandyopadhyaya A, Rajagopalan DR, Rajagopalan P..  (2014)  The synthesis and comparative receptor binding affinities of novel, isomeric pyridoindolobenzazepine scaffolds.,  24  (2): [PMID:24365159] [10.1016/j.bmcl.2013.12.024]
69. Kołaczkowski M, Marcinkowska M, Bucki A, Pawłowski M, Mitka K, Jaśkowska J, Kowalski P, Kazek G, Siwek A, Wasik A, Wesołowska A, Mierzejewski P, Bienkowski P..  (2014)  Novel arylsulfonamide derivatives with 5-HT₆/5-HT₇ receptor antagonism targeting behavioral and psychological symptoms of dementia.,  57  (11): [PMID:24805037] [10.1021/jm401895u]
70. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]
71. Kołaczkowski M, Marcinkowska M, Bucki A, Śniecikowska J, Pawłowski M, Kazek G, Siwek A, Jastrzębska-Więsek M, Partyka A, Wasik A, Wesołowska A, Mierzejewski P, Bienkowski P..  (2015)  Novel 5-HT6 receptor antagonists/D2 receptor partial agonists targeting behavioral and psychological symptoms of dementia.,  92  [PMID:25557493] [10.1016/j.ejmech.2014.12.045]
72. PubChem BioAssay data set, 
73. Waszkielewicz AM, Gunia-Krzyżak A, Powroźnik B, Słoczyńska K, Pękala E, Walczak M, Bednarski M, Żesławska E, Nitek W, Marona H..  (2016)  Design, physico-chemical properties and biological evaluation of some new N-[(phenoxy)alkyl]- and N-{2-[2-(phenoxy)ethoxy]ethyl}aminoalkanols as anticonvulsant agents.,  24  (8): [PMID:26988801] [10.1016/j.bmc.2016.03.006]
74. WHO Anatomical Therapeutic Chemical Classification, 
75. Gunia-Krzyżak A, Żelaszczyk D, Rapacz A, Żesławska E, Waszkielewicz AM, Pańczyk K, Słoczyńska K, Pękala E, Nitek W, Filipek B, Marona H..  (2017)  Structure-anticonvulsant activity studies in the group of (E)-N-cinnamoyl aminoalkanols derivatives monosubstituted in phenyl ring with 4-Cl, 4-CH3 or 2-CH3.,  25  (2): [PMID:27876250] [10.1016/j.bmc.2016.11.014]
76. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]
77. Unpublished dataset, 
78. Norwood VM, Brice-Tutt AC, Eans SO, Stacy HM, Shi G, Ratnayake R, Rocca JR, Abboud KA, Li C, Luesch H, McLaughlin JP, Huigens RW..  (2020)  Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity.,  63  (10): [PMID:31913038] [10.1021/acs.jmedchem.9b01924]
79. Obeng S, Kamble SH, Reeves ME, Restrepo LF, Patel A, Behnke M, Chear NJ, Ramanathan S, Sharma A, León F, Hiranita T, Avery BA, McMahon LR, McCurdy CR..  (2020)  Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.,  63  (1): [PMID:31834797] [10.1021/acs.jmedchem.9b01465]
80. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
81. Paciaroni NG,Norwood VM,Ratnayake R,Luesch H,Huigens RW.  (2020)  Yohimbine as a Starting Point to Access Diverse Natural Product-Like Agents with Re-programmed Activities against Cancer-Relevant GPCR Targets.,  28  (14): [PMID:32616180] [10.1016/j.bmc.2020.115546]
82. Kamboj A, Sihag B, Brar DS, Kaur A, Salunke DB..  (2021)  Structure activity relationship in β-carboline derived anti-malarial agents.,  221  [PMID:34058709] [10.1016/j.ejmech.2021.113536]
83. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]