3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-8-carboxylic acid amide

ID: ALA297428

Chembl Id: CHEMBL297428

PubChem CID: 9839245

Max Phase: Preclinical

Molecular Formula: C19H26N2O

Molecular Weight: 298.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rac-8-Carboxamidocyclazocine | CHEMBL297428|Rac-8-Carboxamidocyclazocine|BDBM50101160|PD090880|3-Cyclopropylmethyl-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-8-carboxylic acid amide

Canonical SMILES:  CC1C2Cc3ccc(C(N)=O)cc3C1(C)CCN2CC1CC1

Standard InChI:  InChI=1S/C19H26N2O/c1-12-17-10-14-5-6-15(18(20)22)9-16(14)19(12,2)7-8-21(17)11-13-3-4-13/h5-6,9,12-13,17H,3-4,7-8,10-11H2,1-2H3,(H2,20,22)

Standard InChI Key:  FAVQVALXVLMHLE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA297428

   Rac-8-Carboxamidocyclazocine

Molecule Features

Natural Product: No

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: 298.43

Molecular Weight (Monoisotopic): 298.2045

AlogP: 2.72

#Rotatable Bonds: 3

Polar Surface Area: 46.33

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.33

CX LogP: 2.86

CX LogD: 0.03

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.93

Np Likeness Score: 0.72

References

1. Wentland MP, Lou R, Dehnhardt CM, Duan W, Cohen DJ, Bidlack JM..  (2001)  3-Carboxamido analogues of morphine and naltrexone. synthesis and opioid receptor binding properties.,  11  (13): [PMID:11425545] [10.1016/s0960-894x(01)00278-5]

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. Wentland MP, Jo S, Gargano JM, VanAlstine MA, Cohen DJ, Bidlack JM..  (2012)  Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 8. High affinity ligands for opioid receptors in the picomolar Ki range: oxygenated N-(2-[1,1'-biphenyl]-4-ylethyl) analogues of 8-CAC.,  22  (24): [PMID:23142613] [10.1016/j.bmcl.2012.10.081]

4. 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