(2S,6R,11S)-6,11-Dimethyl-3-(2-phenylamino-ethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-ol

ID: ALA287794

Chembl Id: CHEMBL287794

PubChem CID: 10664642

Max Phase: Preclinical

Molecular Formula: C22H28N2O

Molecular Weight: 336.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1[C@@H]2Cc3ccc(O)cc3[C@]1(C)CCN2CCNc1ccccc1

Standard InChI:  InChI=1S/C22H28N2O/c1-16-21-14-17-8-9-19(25)15-20(17)22(16,2)10-12-24(21)13-11-23-18-6-4-3-5-7-18/h3-9,15-16,21,23,25H,10-14H2,1-2H3/t16-,21+,22-/m1/s1

Standard InChI Key:  WWOVBVYUUUDWEQ-URZJWIJPSA-N

Alternative Forms

1. Parent:

   

   ALA287794

   (1R,9S,13S)-10-(2-anilinoethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-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: 336.48

Molecular Weight (Monoisotopic): 336.2202

AlogP: 4.03

#Rotatable Bonds: 4

Polar Surface Area: 35.50

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.45

CX Basic pKa: 9.63

CX LogP: 3.77

CX LogD: 1.82

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: 0.63

References

1. Ronsisvalle G, Marrazzo A, Prezzavento O, Pasquinucci L, Vittorio F, Pittalà V, Pappalardo MS, Cacciaguerra S, Spampinato S..  (1998)  (+)-cis-N-ethyleneamino-N-normetazocine derivatives. Novel and selective sigma ligands with antagonist properties.,  41  (10): [PMID:9572883] [10.1021/jm970333f]

2. Zhuang T, Xiong J, Hao S, Du W, Liu Z, Liu B, Zhang G, Chen Y..  (2021)  Bifunctional μ opioid and σ₁ receptor ligands as novel analgesics with reduced side effects.,  223  [PMID:34175542] [10.1016/j.ejmech.2021.113658]

3. Turnaturi R, Montenegro L, Marrazzo A, Parenti R, Pasquinucci L, Parenti C..  (2018)  Benzomorphan skeleton, a versatile scaffold for different targets: A comprehensive review.,  155  [PMID:29908442] [10.1016/j.ejmech.2018.06.017]

Source

Source(1):

• Scientific Literature