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]-4-(4-nitrophenyl)-(Z)-2-butenamide

ID: ALA108406

PubChem CID: 44337275

Max Phase: Preclinical

Molecular Formula: C30H31N3O6

Molecular Weight: 529.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12Oc3c(O)ccc4c3C13CCN(CC1CC1)C(C4)[C@]3(NC(=O)/C=C/c1ccc([N+](=O)[O-])cc1)CCC2=O

Standard InChI:  InChI=1S/C30H31N3O6/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/h4-11,19,23,34H,2-3,12-17H2,1H3,(H,31,36)/b11-6+/t23?,28-,29?,30+/m0/s1

Standard InChI Key:  RIXFPTSTMBDFAF-JHMKZUJTSA-N

Molfile:  

     RDKit          2D

 39 45  0  0  1  0  0  0  0  0999 V2000
    3.0792   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -4.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -1.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -2.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8542   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -2.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0792   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -4.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -1.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -3.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4417   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4292   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6042   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -4.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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 17  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
 16 12  1  0
 17 34  1  0
 18  8  1  0
 19  6  2  0
 20 14  1  0
 21 18  1  0
 22 16  1  0
 23  9  1  0
 24  9  2  0
 25 22  2  0
 26 21  1  0
 27 21  1  0
 28 10  1  0
 29 13  1  0
 30 13  2  0
 31 16  2  0
 32 28  2  0
 33 37  1  0
 34 38  2  0
  3 35  1  1
 36 25  1  0
 37 36  2  0
 38 36  1  0
 39 19  1  0
  6  5  1  0
  8  7  1  0
  7 11  1  0
 29 15  1  0
 19 32  1  0
 27 26  1  0
 33 17  2  0
M  CHG  2   9   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA108406

   (E)-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)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: 529.59

Molecular Weight (Monoisotopic): 529.2213

AlogP: 3.66

#Rotatable Bonds: 6

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: 8.47

CX LogP: 3.93

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.33

Np Likeness Score: 0.50

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