(4aS,9aR)-4a-Ethyl-2-phenethyl-1,2,3,4,4a,9a-hexahydro-benzo[4,5]furo[2,3-c]pyridin-6-ol

ID: ALA72180

Chembl Id: CHEMBL72180

PubChem CID: 44311351

Max Phase: Preclinical

Molecular Formula: C21H25NO2

Molecular Weight: 323.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@]12CCN(CCc3ccccc3)C[C@@H]1Oc1ccc(O)cc12

Standard InChI:  InChI=1S/C21H25NO2/c1-2-21-11-13-22(12-10-16-6-4-3-5-7-16)15-20(21)24-19-9-8-17(23)14-18(19)21/h3-9,14,20,23H,2,10-13,15H2,1H3/t20-,21-/m0/s1

Standard InChI Key:  GZBURIYLLVULIF-SFTDATJTSA-N

Alternative Forms

1. Parent:

   

   ALA72180

   (4aS,9aR)-4a-ethyl-2-(2-phenylethyl)-1,3,4,9a-tetrahydro-[1]benzofuro[2,3-c]pyridin-6-ol

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: 323.44

Molecular Weight (Monoisotopic): 323.1885

AlogP: 3.75

#Rotatable Bonds: 4

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: 9.98

CX Basic pKa: 9.01

CX LogP: 3.97

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.93

Np Likeness Score: 0.70

References

1. Hutchison AJ, de Jesus R, Williams M, Simke JP, Neale RF, Jackson RH, Ambrose F, Barbaz BJ, Sills MA..  (1989)  Benzofuro[2,3-c]pyridin-6-ols: synthesis, affinity for opioid-receptor subtypes, and antinociceptive activity.,  32  (9): [PMID:2549247] [10.1021/jm00129a031]

2. Zhang Y, Lee YS, Rothman RB, Dersch CM, Deschamps JR, Jacobson AE, Rice KC..  (2009)  Probes for narcotic receptor mediated phenomena. 39. Enantiomeric N-substituted benzofuro[2,3-c]pyridin-6-ols: synthesis and topological relationship to oxide-bridged phenylmorphans.,  52  (23): [PMID:19627147] [10.1021/jm9004225]

3. Iyer MR, Lee YS, Deschamps JR, Rothman RB, Dersch CM, Jacobson AE, Rice KC..  (2010)  Probes for narcotic receptor mediated phenomena. 40. N-substituted cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-8-ols.,  18  (1): [PMID:20005115] [10.1016/j.bmc.2009.11.022]

4. Iyer MR, Rothman RB, Dersch CM, Jacobson AE, Rice KC..  (2013)  Probes for narcotic receptor mediated phenomena. 47. Novel C4a- and N-substituted-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ols.,  21  (11): [PMID:23618710] [10.1016/j.bmc.2013.02.060]

Source

Source(1):

• Scientific Literature