SID14720521

ID: ALA1540577

PubChem CID: 697726

Max Phase: Preclinical

Molecular Formula: C17H16N2O3

Molecular Weight: 296.33

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc(-c3cc(OC)ccc3O)[nH]n2)cc1

Standard InChI:  InChI=1S/C17H16N2O3/c1-21-12-5-3-11(4-6-12)15-10-16(19-18-15)14-9-13(22-2)7-8-17(14)20/h3-10,20H,1-2H3,(H,18,19)

Standard InChI Key:  RZODUFKQXLUCTQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -2.5917    2.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2661    4.5214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -1.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.5615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7503    0.7769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1628    2.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1628    2.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5753    0.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8302    1.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8773    3.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602    0.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483    3.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483    4.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8773    4.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7247   -0.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8807    0.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1628    4.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0301   -1.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2096   -1.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3656   -0.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2661    5.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1794   -2.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0
  2 13  1  0
  2 21  1  0
  3 18  1  0
  3 22  1  0
  4  5  1  0
  4  6  1  0
  5  8  2  0
  6  7  1  0
  6  9  2  0
  7 10  1  0
  7 12  2  0
  8  9  1  0
  8 11  1  0
 10 14  2  0
 11 15  2  0
 11 16  1  0
 12 13  1  0
 13 17  2  0
 14 17  1  0
 15 19  1  0
 16 20  2  0
 18 19  2  0
 18 20  1  0
M  END

Associated Targets(Human)

LMNA Tbio Prelamin-A/C (36751 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
microRNA 21 (64692 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMN1 Tchem Survival motor neuron protein (34246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPT Tclin Microtubule-associated protein tau (95507 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPC1 Tchem Niemann-Pick C1 protein (18985 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NPSR1 Tchem Neuropeptide S receptor (15785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLI Tchem DNA polymerase iota (116820 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rorc Nuclear receptor ROR-gamma (89407 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Impa1 Inositol monophosphatase 1 (16203 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NS1 Nonstructural protein 1 (33327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ampC Beta-lactamase AmpC (62480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Luciferin 4-monooxygenase (66902 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
vpr Aberrant vpr protein (14595 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tb08.30K1.730 Putative uncharacterized protein (6616 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Alox15 Arachidonate 15-lipoxygenase (53 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: 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: 296.33Molecular Weight (Monoisotopic): 296.1161AlogP: 3.47#Rotatable Bonds: 4
Polar Surface Area: 67.37Molecular Species: NEUTRALHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 9.46CX Basic pKa: 2.39CX LogP: 3.26CX LogD: 3.26
Aromatic Rings: 3Heavy Atoms: 22QED Weighted: 0.77Np Likeness Score: -0.66

References

1. PubChem BioAssay data set, 
2. Fullam E, Talbot J, Abuhammed A, Westwood I, Davies SG, Russell AJ, Sim E..  (2013)  Design, synthesis and structure-activity relationships of 3,5-diaryl-1H-pyrazoles as inhibitors of arylamine N-acetyltransferase.,  23  (9): [PMID:23518278] [10.1016/j.bmcl.2013.02.052]
3. Armstrong MM, Freedman CJ, Jung JE, Zheng Y, Kalyanaraman C, Jacobson MP, Simeonov A, Maloney DJ, van Leyen K, Jadhav A, Holman TR..  (2016)  A potent and selective inhibitor targeting human and murine 12/15-LOX.,  24  (6): [PMID:26899595] [10.1016/j.bmc.2016.01.042]
4. Garner AL, Lorenz DA, Sandoval J, Gallagher EE, Kerk SA, Kaur T, Menon A..  (2019)  Tetracyclines as Inhibitors of Pre-microRNA Maturation: A Disconnection between RNA Binding and Inhibition.,  10  (5): [PMID:31098005] [10.1021/acsmedchemlett.9b00091]