1N-[4-cyclopropylmethyl-10-hydroxy-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: ALA317035

PubChem CID: 44337276

Max Phase: Preclinical

Molecular Formula: C29H27N3O6

Molecular Weight: 513.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)N[C@@]12C=CC(=O)[C@@H]3Oc4c(O)ccc5c4C31CCN(CC1CC1)C2C5

Standard InChI:  InChI=1S/C29H27N3O6/c33-21-9-6-19-15-23-29(30-24(35)10-5-17-3-7-20(8-4-17)32(36)37)12-11-22(34)27-28(29,25(19)26(21)38-27)13-14-31(23)16-18-1-2-18/h3-12,18,23,27,33H,1-2,13-16H2,(H,30,35)/b10-5+/t23?,27-,28?,29+/m0/s1

Standard InChI Key:  ZJKCEVULTASPKD-XKOFYKQRSA-N

Molfile:  

     RDKit          2D

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    0.6292   -4.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -5.0375    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 21  1  0
  9 18  1  0
 10  3  2  0
 11  2  1  0
 12 10  1  0
  2 13  1  1
 14  4  1  0
 15  1  1  0
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 18 33  2  0
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 25  9  2  0
 26 23  2  0
 27 22  1  0
 28 22  1  0
 29 10  1  0
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 31 17  2  0
 32 29  2  0
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 34 36  2  0
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 37 35  2  0
 38 20  1  0
  4 39  1  1
  5  6  1  0
  8  7  1  0
 16 11  2  0
  7 12  1  0
 20 32  1  0
 28 27  1  0
 34 18  1  0
M  CHG  2   9   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA317035

   (E)-N-[(4aS,7aR)-3-(cyclopropylmethyl)-9-hydroxy-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: 513.55

Molecular Weight (Monoisotopic): 513.1900

AlogP: 3.05

#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: 8.26

CX LogP: 3.69

CX LogD: 2.91

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.35

Np Likeness Score: 0.60

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