1N-[10-methoxy-4-methyl-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: ALA108794

PubChem CID: 44336988

Max Phase: Preclinical

Molecular Formula: C27H25N3O6

Molecular Weight: 487.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H25N3O6/c1-29-14-13-26-23-17-6-9-20(35-2)24(23)36-25(26)19(31)11-12-27(26,21(29)15-17)28-22(32)10-5-16-3-7-18(8-4-16)30(33)34/h3-12,21,25H,13-15H2,1-2H3,(H,28,32)/b10-5+/t21?,25-,26?,27+/m0/s1

Standard InChI Key:  HNILKBVMVGBUJQ-WXYYCSAXSA-N

Molfile:  

     RDKit          2D

 37 42  0  0  1  0  0  0  0  0999 V2000
    0.5292   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -1.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2542    1.1708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    2.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    1.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1625    1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667    0.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542    1.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -1.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    1.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0167    1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042    1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -1.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042    2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -1.7250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  4  6  1  0
  7  2  1  0
  8 18  1  0
  9  3  2  0
 10  2  1  0
 11  9  1  0
 12 23  1  0
  2 13  1  1
 14  4  1  0
 15  1  1  0
 16 14  1  0
 17 13  1  0
 18 29  1  0
 19  5  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  2  0
 30 32  1  0
 31 24  1  0
 32 31  2  0
 33 31  1  0
 34 19  1  0
 35 12  1  0
 36 34  1  0
  4 37  1  1
  5  6  1  0
 12  7  1  0
 16 10  2  0
  7 11  1  0
 19 28  1  0
 18 30  2  0
M  CHG  2   8   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA108794

   (E)-N-[(4aS,7aR)-9-methoxy-3-methyl-7-oxo-2,4,7a,13-tetrahydro-1H-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: 487.51

Molecular Weight (Monoisotopic): 487.1743

AlogP: 2.57

#Rotatable Bonds: 5

Polar Surface Area: 111.01

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.28

CX Basic pKa: 7.57

CX LogP: 3.20

CX LogD: 2.80

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.39

Np Likeness Score: 0.66

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