N-[(2S,4aS,7aR,12aR,14S)-5-(cyclopropylmethyl)-9-hydroxy-2,4a,5,6,7,12-hexahydro-1H-2,7a-ethanoindeno[1,2-d]-quinolin-14-yl]-N-methylbenzamide hydrochloride

ID: ALA3613170

PubChem CID: 122188799

Max Phase: Preclinical

Molecular Formula: C30H35ClN2O2

Molecular Weight: 454.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C(=O)c1ccccc1)[C@H]1C[C@@]23CCN(CC4CC4)[C@H]4C=C[C@@H]1C[C@]42Cc1ccc(O)cc13.Cl

Standard InChI:  InChI=1S/C30H34N2O2.ClH/c1-31(28(34)21-5-3-2-4-6-21)26-18-29-13-14-32(19-20-7-8-20)27-12-10-23(26)17-30(27,29)16-22-9-11-24(33)15-25(22)29;/h2-6,9-12,15,20,23,26-27,33H,7-8,13-14,16-19H2,1H3;1H/t23-,26+,27+,29-,30-;/m1./s1

Standard InChI Key:  BZHSMEWFZDVZAT-VFTKGZTKSA-N

Molfile:  

     RDKit          2D

 37 42  0  0  0  0  0  0  0  0999 V2000
    5.7754   -5.5744    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9804   -8.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0078   -7.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -8.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4133   -1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0997   -5.8333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753   -4.8404    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106  -10.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270  -12.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555  -12.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324  -11.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1488  -10.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
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  7  2  1  0
  8 13  1  0
  8  9  2  0
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 10 11  1  0
 12 11  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 19  1  0
 10 17  1  0
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 18 17  1  0
 19  7  1  6
 12 19  1  0
  5 20  1  0
 17 21  1  1
 21 22  1  0
 21 23  1  0
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 10 31  1  6
 13 32  1  1
 25 33  2  0
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 37 25  1  0
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: 454.61

Molecular Weight (Monoisotopic): 454.2620

AlogP: 4.78

#Rotatable Bonds: 4

Polar Surface Area: 43.78

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.41

CX Basic pKa: 10.03

CX LogP: 3.97

CX LogD: 2.32

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.68

Np Likeness Score: 0.63

References

1. Nakajima R, Yamamoto N, Hirayama S, Iwai T, Saitoh A, Nagumo Y, Fujii H, Nagase H..  (2015)  Synthesis of new opioid derivatives with a propellane skeleton and their pharmacologies: Part 5, novel pentacyclic propellane derivatives with a 6-amide side chain.,  23  (19): [PMID:26346669] [10.1016/j.bmc.2015.08.036]

Source

Source(1):

• Scientific Literature