(1S,5S,9R)-(+)-5-(3-hydroxyphenyl)-2-(4-nitrophenethyl)-2-azabicyclo[3.3.1]nonan-9-ol oxalate

ID: ALA4093929

PubChem CID: 137654005

Max Phase: Preclinical

Molecular Formula: C24H28N2O8

Molecular Weight: 382.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C(=O)O.O=[N+]([O-])c1ccc(CCN2CC[C@]3(c4cccc(O)c4)CCC[C@H]2[C@@H]3O)cc1

Standard InChI:  InChI=1S/C22H26N2O4.C2H2O4/c25-19-4-1-3-17(15-19)22-11-2-5-20(21(22)26)23(14-12-22)13-10-16-6-8-18(9-7-16)24(27)28;3-1(4)2(5)6/h1,3-4,6-9,15,20-21,25-26H,2,5,10-14H2;(H,3,4)(H,5,6)/t20-,21-,22-;/m0./s1

Standard InChI Key:  HHZWUDAEAJEIIA-SGIIKHNDSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
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   24.8584  -23.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5666  -23.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8584  -22.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4419  -23.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1501  -24.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   20.4405  -22.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7308  -22.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3030  -22.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3002  -21.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5834  -20.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.7355  -22.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0179  -23.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5776  -22.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2363  -21.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9998  -22.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6586  -21.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4481  -21.7223    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.4162  -21.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0746  -21.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9732  -20.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2077  -20.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5526  -20.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6665  -20.0047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5584  -19.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4659  -20.3415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  2  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  7 13  1  1
 15 19  1  0
 12 20  1  1
  7 21  1  0
 21 22  1  0
 11 23  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 11 27  1  6
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 26  1  0
 33 34  2  0
 33 35  1  0
 30 33  1  0
M  CHG  2  33   1  35  -1
M  END

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: 382.46

Molecular Weight (Monoisotopic): 382.1893

AlogP: 3.40

#Rotatable Bonds: 5

Polar Surface Area: 86.84

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.06

CX Basic pKa: 9.16

CX LogP: 3.59

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: 0.27

References

1. Truong PM, Hassan SA, Lee YS, Kopajtic TA, Katz JL, Chadderdon AM, Traynor JR, Deschamps JR, Jacobson AE, Rice KC..  (2017)  Modulation of opioid receptor affinity and efficacy via N-substitution of 9β-hydroxy-5-(3-hydroxyphenyl)morphan: Synthesis and computer simulation study.,  25  (8): [PMID:28314512] [10.1016/j.bmc.2017.02.064]

Source

Source(1):

• Scientific Literature