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),8,10,15-tetraen-17-yl]-4-(4-nitrophenyl)-(Z)-2-butenamide

ID: ALA110666

PubChem CID: 44337316

Max Phase: Preclinical

Molecular Formula: C28H27N3O6

Molecular Weight: 501.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H27N3O6/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/h4-13,21H,14-16H2,1-3H3,(H,29,33)/b11-6+/t21?,26-,27?,28+/m0/s1

Standard InChI Key:  OIFWWNKFALFTTK-WJLVKOQPSA-N

Molfile:  

     RDKit          2D

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    2.2667   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8625   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6292   -4.2042    0.0000 O   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 18  1  0
  9  4  2  0
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 12 23  1  0
  2 13  1  1
 14  3  1  0
 15  1  1  0
 16 14  1  0
 17 13  1  0
 18 30  1  0
 19  6  2  0
 20 17  1  0
 21  8  1  0
 22  8  2  0
 23 15  1  0
 24 20  2  0
 25  9  1  0
 26 14  2  0
 27 17  2  0
 28 25  2  0
 29 33  1  0
 30 34  2  0
  3 31  1  1
 32 24  1  0
 33 32  2  0
 34 32  1  0
 35 19  1  0
 36 12  1  0
 37 35  1  0
  6  5  1  0
 12  7  1  0
  7 11  1  0
 16 10  2  0
 19 28  1  0
 29 18  2  0
M  CHG  2   8   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA110666

   (E)-N-[(4aS,7aR)-9-methoxy-3,7a-dimethyl-7-oxo-1,2,4,13-tetrahydro-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: 501.54

Molecular Weight (Monoisotopic): 501.1900

AlogP: 2.96

#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: 13.31

CX Basic pKa: 7.65

CX LogP: 3.63

CX LogD: 3.19

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.38

Np Likeness Score: 0.62

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