1N-[10-hydroxy-4,13-dimethyl-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]-4-(4-nitrophenyl)-(Z)-2-butenamide

ID: ALA107164

PubChem CID: 44337271

Max Phase: Preclinical

Molecular Formula: C27H27N3O6

Molecular Weight: 489.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC23c4c5ccc(O)c4O[C@@]2(C)C(=O)CC[C@@]3(NC(=O)/C=C/c2ccc([N+](=O)[O-])cc2)C1C5

Standard InChI:  InChI=1S/C27H27N3O6/c1-25-21(32)11-12-27(28-22(33)10-5-16-3-7-18(8-4-16)30(34)35)20-15-17-6-9-19(31)24(36-25)23(17)26(25,27)13-14-29(20)2/h3-10,20,31H,11-15H2,1-2H3,(H,28,33)/b10-5+/t20?,25-,26?,27+/m0/s1

Standard InChI Key:  CEBCASROENGJPG-HVCZEULHSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  1  0  0  0  0  0999 V2000
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    3.4917   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8667   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6917   -4.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6167   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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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 17  1  0
  9  4  2  0
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 11 22  1  0
  2 12  1  1
 13  3  1  0
 14  1  1  0
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 17 30  1  0
 18  6  2  0
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 20  8  1  0
 21  8  2  0
 22 14  1  0
 23 19  2  0
 24  9  1  0
 25 13  1  0
 26 13  2  0
 27 16  2  0
 28 24  2  0
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 30 34  2  0
  3 31  1  1
 32 23  1  0
 33 32  2  0
 34 32  1  0
 35 18  1  0
 36 11  1  0
  6  5  1  0
 11  7  1  0
  7 10  1  0
 25 15  1  0
 18 28  1  0
 29 17  2  0
M  CHG  2   8   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA107164

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

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: 489.53

Molecular Weight (Monoisotopic): 489.1900

AlogP: 2.88

#Rotatable Bonds: 4

Polar Surface Area: 122.01

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.77

CX Basic pKa: 7.80

CX LogP: 3.24

CX LogD: 2.78

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.38

Np Likeness Score: 0.71

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