(E)-N-[(2S,4aS,7aR,12aR,14R)-5-(cyclopropylmethyl)-9-hydroxy-2,3,4,4a,5,6,7,12-octahydro-1H-2,7a-ethanoindeno-[1,2-d]quinolin-14-yl]-3-(furan-2-yl)-N-methylacrylamide hydrochloride

ID: ALA3613171

PubChem CID: 122188801

Max Phase: Preclinical

Molecular Formula: C30H37ClN2O3

Molecular Weight: 472.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C(=O)/C=C/c1ccoc1)[C@@H]1C[C@@]23CCN(CC4CC4)[C@H]4CC[C@@H]1C[C@]42Cc1ccc(O)cc13.Cl

Standard InChI:  InChI=1S/C30H36N2O3.ClH/c1-31(28(34)9-4-21-10-13-35-19-21)26-17-29-11-12-32(18-20-2-3-20)27-8-6-23(26)16-30(27,29)15-22-5-7-24(33)14-25(22)29;/h4-5,7,9-10,13-14,19-20,23,26-27,33H,2-3,6,8,11-12,15-18H2,1H3;1H/b9-4+;/t23-,26-,27+,29-,30-;/m1./s1

Standard InChI Key:  JXWCMWQRMRFPLA-PYRSVMMESA-N

Molfile:  

     RDKit          2D

 38 43  0  0  0  0  0  0  0  0999 V2000
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    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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    2.3127  -10.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318  -12.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7033  -13.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8046  -14.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847  -14.2814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058  -12.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6734   -6.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -3.4246   -7.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8 13  1  0
  8  9  1  0
 10  9  1  0
 10 11  1  0
 12 11  1  6
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 13 14  1  0
 14 15  1  0
 15 16  1  0
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 10 17  1  0
 19 18  1  0
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 12 19  1  0
  5 20  1  0
 17 21  1  6
 21 22  1  0
 21 23  1  0
 22 24  2  0
 22 25  1  0
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 14 32  1  0
 32 33  1  0
 34 33  1  0
 35 34  1  0
 33 35  1  0
 12 36  1  0
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 10 37  1  6
 13 38  1  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: 472.63

Molecular Weight (Monoisotopic): 472.2726

AlogP: 4.99

#Rotatable Bonds: 5

Polar Surface Area: 56.92

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.64

CX Basic pKa: 10.71

CX LogP: 3.37

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.62

Np Likeness Score: 1.07

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