1N-[4-cyclopropylmethyl-10-hydroxy-13-methyl-14-oxo-(13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-17-yl]-3-(4-nitrophenyl)propanamide

ID: ALA105827

PubChem CID: 44337274

Max Phase: Preclinical

Molecular Formula: C30H33N3O6

Molecular Weight: 531.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12Oc3c(O)ccc4c3C13CCN(CC1CC1)C(C4)[C@]3(NC(=O)CCc1ccc([N+](=O)[O-])cc1)CCC2=O

Standard InChI:  InChI=1S/C30H33N3O6/c1-28-24(35)12-13-30(31-25(36)11-6-18-4-8-21(9-5-18)33(37)38)23-16-20-7-10-22(34)27(39-28)26(20)29(28,30)14-15-32(23)17-19-2-3-19/h4-5,7-10,19,23,34H,2-3,6,11-17H2,1H3,(H,31,36)/t23?,28-,29?,30+/m0/s1

Standard InChI Key:  PDLDCRKROORTJW-QSUQFICRSA-N

Molfile:  

     RDKit          2D

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  2  1  1  0
  3  1  1  0
  4  1  1  0
  3  5  1  0
  6  4  1  0
  7  2  1  0
  8 20  1  0
  9 16  1  0
 10  4  2  0
 11 10  1  0
  2 12  1  1
 13  3  1  0
 14  1  1  0
 15  2  1  0
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 17  8  1  0
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 25 21  1  0
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 27 13  1  0
 28 13  2  0
 29 18  2  0
 30 26  2  0
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  3 33  1  1
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 36 35  2  0
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 38 19  1  0
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  6  5  1  0
  8  7  1  0
  7 11  1  0
 27 15  1  0
 19 30  1  0
 25 24  1  0
 31 16  2  0
M  CHG  2   9   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA105827

   N-[(4aS,7aR)-3-(cyclopropylmethyl)-9-hydroxy-7a-methyl-7-oxo-1,2,4,5,6,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(4-nitrophenyl)propanamide

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: 531.61

Molecular Weight (Monoisotopic): 531.2369

AlogP: 3.58

#Rotatable Bonds: 7

Polar Surface Area: 122.01

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.79

CX Basic pKa: 8.42

CX LogP: 3.86

CX LogD: 2.95

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.41

Np Likeness Score: 0.39

References

1. Sebastian A, Bidlack JM, Jiang Q, Deecher D, Teitler M, Glick SD, Archer S..  (1993)  14 beta-[(p-nitrocinnamoyl)amino]morphinones, 14 beta-[(p-nitrocinnamoyl)amino]-7,8-dihydromorphinones, and their codeinone analogues: synthesis and receptor activity.,  36  (21): [PMID:7693944] [10.1021/jm00073a015]

Source

Source(1):

• Scientific Literature