1N-[10-methoxy-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: ALA320060

PubChem CID: 44337264

Max Phase: Preclinical

Molecular Formula: C28H29N3O6

Molecular Weight: 503.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c1O[C@@]1(C)C(=O)CC[C@@]4(NC(=O)/C=C/c5ccc([N+](=O)[O-])cc5)C(C2)N(C)CCC314

Standard InChI:  InChI=1S/C28H29N3O6/c1-26-22(32)12-13-28(29-23(33)11-6-17-4-8-19(9-5-17)31(34)35)21-16-18-7-10-20(36-3)25(37-26)24(18)27(26,28)14-15-30(21)2/h4-11,21H,12-16H2,1-3H3,(H,29,33)/b11-6+/t21?,26-,27?,28+/m0/s1

Standard InChI Key:  NCKYLAKJHDNXGI-WJLVKOQPSA-N

Molfile:  

     RDKit          2D

 37 42  0  0  1  0  0  0  0  0999 V2000
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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
 15  2  1  0
 16 12  1  0
 17 30  1  0
 18  6  2  0
 19 16  1  0
 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
 29 33  1  0
 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
 37 35  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:

   

   ALA320060

   (E)-N-[(4aS,7aR)-9-methoxy-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: 503.56

Molecular Weight (Monoisotopic): 503.2056

AlogP: 3.18

#Rotatable Bonds: 5

Polar Surface Area: 111.01

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.80

CX LogP: 3.48

CX LogD: 2.93

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.38

Np Likeness Score: 0.54

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