17-Cyclopropylmethyl-3,14beta-dihydroxy-4,5alpha-epoxy-6alpha-(benzothiophene-2-carboxamido)morphinan hydrochloride

ID: ALA4552786

PubChem CID: 155555908

Max Phase: Preclinical

Molecular Formula: C29H31ClN2O4S

Molecular Weight: 502.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.O=C(N[C@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5)c1cc2ccccc2s1

Standard InChI:  InChI=1S/C29H30N2O4S.ClH/c32-20-8-7-18-14-23-29(34)10-9-19(30-27(33)22-13-17-3-1-2-4-21(17)36-22)26-28(29,24(18)25(20)35-26)11-12-31(23)15-16-5-6-16;/h1-4,7-8,13,16,19,23,26,32,34H,5-6,9-12,14-15H2,(H,30,33);1H/t19-,23+,26-,28-,29+;/m0./s1

Standard InChI Key:  CPBDGQAKAQLVTP-XQLHXREKSA-N

Molfile:  

     RDKit          2D

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   15.8167  -11.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2273  -10.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7929  -10.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8167   -9.2254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2273   -8.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0525   -8.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7782   -8.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.3923   -9.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.3430  -14.3845    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   18.6891  -12.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2175  -13.0940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7698  -12.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3532  -11.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7698  -10.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3453  -12.9046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6420  -10.0324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 17 33  1  1
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  4 38  1  6
  3 39  1  1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 502.64

Molecular Weight (Monoisotopic): 502.1926

AlogP: 3.97

#Rotatable Bonds: 4

Polar Surface Area: 82.03

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.29

CX Basic pKa: 9.51

CX LogP: 3.38

CX LogD: 1.56

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.50

Np Likeness Score: 0.39

References

1. Ma H, Obeng S, Wang H, Zheng Y, Li M, Jali AM, Stevens DL, Dewey WL, Selley DE, Zhang Y..  (2019)  Application of Bivalent Bioisostere Concept on Design and Discovery of Potent Opioid Receptor Modulators.,  62  (24): [PMID:31782922] [10.1021/acs.jmedchem.9b01767]

Source

Source(1):

• Scientific Literature