6,11-Dimethyl-3-(3-methyl-but-2-enyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol (pentazocine)

ID: ALA60542

Chembl Id: CHEMBL60542

Max Phase: Preclinical

Molecular Formula: C19H27NO

Molecular Weight: 285.43

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: (+)-Pentazocine

Synonyms from Alternative Forms(2): (+)-[3H]-Pentazocine | [3H]-(+)-Pentazocine

Canonical SMILES:  CC(C)=CCN1CC[C@]2(C)c3cc(O)ccc3C[C@H]1[C@H]2C

Standard InChI:  InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m1/s1

Standard InChI Key:  VOKSWYLNZZRQPF-CCKFTAQKSA-N

Alternative Forms

  1. Parent:

  2. Alternative Forms:

Associated Targets(Human)

SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
5637 (630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RT-4 (268 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-427 (643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Skin (286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DAN-G (242 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRIN2B Tclin Glutamate [NMDA] receptor subunit epsilon 2 (467 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprm1 Mu opioid receptor (6060 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Kappa opioid receptor (4577 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sigmar1 Sigma opioid receptor (1607 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Opioid receptor (994 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Drd1 Dopamine D1 receptor (1900 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Drd2 Dopamine D2 receptor (7893 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm1 Muscarinic acetylcholine receptor M1 (3437 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrm2 Muscarinic acetylcholine receptor M2 (1011 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grin1 Glutamate NMDA receptor (6467 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cavia porcellus (23802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EBP 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase (132 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Sigma-1 receptor (3326 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NET Transporter (332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a4 Serotonin transporter (6087 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc6a3 Dopamine transporter (6071 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Mu opioid receptor (3620 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Delta opioid receptor (3911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Slc18a3 Vesicular acetylcholine transporter (102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ZNF664 Zinc finger protein 664 (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tmem97 Sigma intracellular receptor 2 (922 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
661W (31 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 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: 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: 285.43Molecular Weight (Monoisotopic): 285.2093AlogP: 3.88#Rotatable Bonds: 2
Polar Surface Area: 23.47Molecular Species: BASEHBA: 2HBD: 1
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 10.42CX Basic pKa: 9.57CX LogP: 3.89CX LogD: 1.99
Aromatic Rings: 1Heavy Atoms: 21QED Weighted: 0.83Np Likeness Score: 1.75

References

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72. Utech T, Köhler J, Wünsch B..  (2011)  Synthesis of 4-(aminoalkyl) substituted 1,3-dioxanes as potent NMDA and σ receptor antagonists.,  46  (6): [PMID:21444132] [10.1016/j.ejmech.2011.02.070]
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76. Schläger T, Schepmann D, Lehmkuhl K, Holenz J, Vela JM, Buschmann H, Wünsch B..  (2011)  Combination of two pharmacophoric systems: synthesis and pharmacological evaluation of spirocyclic pyranopyrazoles with high σ₁ receptor affinity.,  54  (19): [PMID:21859078] [10.1021/jm200585k]
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124. Weber F, Brune S, Börgel F, Lange C, Korpis K, Bednarski PJ, Laurini E, Fermeglia M, Pricl S, Schepmann D, Wünsch B..  (2016)  Rigidity versus Flexibility: Is This an Issue in σ1 Receptor Ligand Affinity and Activity?,  59  (11): [PMID:27156565] [10.1021/acs.jmedchem.6b00585]
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