3-Cyclopropylmethyl-6-ethyl-8-hydroxy-11-methyl-3,4,5,6-tetrahydro-2H-2,6-methano-benzo[d]azocin-1-one

ID: ALA55033

Chembl Id: CHEMBL55033

PubChem CID: 4491166

Max Phase: Preclinical

Molecular Formula: C19H25NO2

Molecular Weight: 299.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC12CCN(CC3CC3)C(C(=O)c3ccc(O)cc31)C2C

Standard InChI:  InChI=1S/C19H25NO2/c1-3-19-8-9-20(11-13-4-5-13)17(12(19)2)18(22)15-7-6-14(21)10-16(15)19/h6-7,10,12-13,17,21H,3-5,8-9,11H2,1-2H3

Standard InChI Key:  SEJUQQOPVAUETF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA55033

   (+/-)-Ethylketocyclazocine

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 299.41

Molecular Weight (Monoisotopic): 299.1885

AlogP: 3.36

#Rotatable Bonds: 3

Polar Surface Area: 40.54

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: 7.04

CX LogP: 3.00

CX LogD: 3.09

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.93

Np Likeness Score: 0.91

References

1. Ronsisvalle G, Pasquinucci L, Pappalardo MS, Vittorio F, Fronza G, Romagnoli C, Pistacchio E, Spampinato S, Ferri S..  (1993)  Non-peptide ligands for opioid receptors. Design of kappa-specific agonists.,  36  (13): [PMID:8390575] [10.1021/jm00065a009]

2. Wentland MP, Lou R, Lu Q, Bu Y, VanAlstine MA, Cohen DJ, Bidlack JM..  (2009)  Syntheses and opioid receptor binding properties of carboxamido-substituted opioids.,  19  (1): [PMID:19027293] [10.1016/j.bmcl.2008.10.134]

3. Turnaturi R, Marrazzo A, Parenti C, Pasquinucci L..  (2018)  Benzomorphan scaffold for opioid analgesics and pharmacological tools development: A comprehensive review.,  148  [PMID:29477074] [10.1016/j.ejmech.2018.02.046]

Source

Source(1):

• Scientific Literature