6,11-Dimethyl-3-(tetrahydro-furan-2-ylmethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol

ID: ALA2367604

Chembl Id: CHEMBL2367604

Max Phase: Preclinical

Molecular Formula: C19H27NO2

Molecular Weight: 301.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@H]2Cc3ccc(O)cc3[C@@]1(C)CCN2C[C@@H]1CCCO1

Standard InChI:  InChI=1S/C19H27NO2/c1-13-18-10-14-5-6-15(21)11-17(14)19(13,2)7-8-20(18)12-16-4-3-9-22-16/h5-6,11,13,16,18,21H,3-4,7-10,12H2,1-2H3/t13-,16-,18+,19-/m0/s1

Standard InChI Key:  NLKLXMMOJZHSCB-IVJVFBROSA-N

Alternative Forms

1. Parent:

   

   ALA2367604

   ---

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: 301.43

Molecular Weight (Monoisotopic): 301.2042

AlogP: 3.10

#Rotatable Bonds: 2

Polar Surface Area: 32.70

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.43

CX Basic pKa: 9.59

CX LogP: 2.94

CX LogD: 1.02

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.91

Np Likeness Score: 1.36

References

1. Klein P, Nelson WL..  (1991)  Electrophilic gamma-lactone kappa-opioid receptor probes. Analogues of 2'-hydroxy-2-tetrahydrofurfuryl-5,9-dimethyl-6,7-benzomorphan diastereomers.,  34  (8): [PMID:1652019] [10.1021/jm00112a019]

2. Wentland MP, Ye Y, Cioffi CL, Lou R, Zhou Q, Xu G, Duan W, Dehnhardt CM, Sun X, Cohen DJ, Bidlack JM..  (2003)  Syntheses and opioid receptor binding affinities of 8-amino-2,6-methano-3-benzazocines.,  46  (5): [PMID:12593663] [10.1021/jm020429w]

3. 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]

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