Biphenyl-4-carboxylic acid methyl-[(3-nitro-4-piperidin-1-yl-phenylcarbamoyl)-methyl]-amide

ID: ALA481480

PubChem CID: 44567922

Max Phase: Preclinical

Molecular Formula: C27H28N4O4

Molecular Weight: 472.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CC(=O)Nc1ccc(N2CCCCC2)c([N+](=O)[O-])c1)C(=O)c1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C27H28N4O4/c1-29(27(33)22-12-10-21(11-13-22)20-8-4-2-5-9-20)19-26(32)28-23-14-15-24(25(18-23)31(34)35)30-16-6-3-7-17-30/h2,4-5,8-15,18H,3,6-7,16-17,19H2,1H3,(H,28,32)

Standard InChI Key:  XQUKOEMEWVXVDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.9004   -7.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5345   -4.1764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2436   -6.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6706   -6.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6693   -5.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547   -5.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3827   -6.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3812   -7.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0957   -7.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8123   -7.4809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8099   -6.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0948   -6.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  1  6  1  0
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 18 20  1  0
  9 10  2  0
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  5  6  1  0
 26 27  2  0
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  5  7  1  0
 28 29  2  0
 29 23  1  0
 13 14  2  0
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 30 31  2  0
 12 13  1  0
 31 32  1  0
  1  2  1  0
 32 33  2  0
 10 16  1  0
 33 34  1  0
  7  8  2  0
 34 35  2  0
 35 30  1  0
 27 30  1  0
M  CHG  2  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA481480

   Biphenyl-4-carboxylic acid methyl-[(3-nitro-4-piperidin-1-yl-phenylcarbamoyl)-methyl]-amide

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: 472.55

Molecular Weight (Monoisotopic): 472.2111

AlogP: 4.96

#Rotatable Bonds: 7

Polar Surface Area: 95.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.50

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.73

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.39

Np Likeness Score: -1.80

References

1. Dömling A, Antuch W, Beck B, Schauer-Vukasinović V..  (2008)  Isosteric exchange of the acylsulfonamide moiety in Abbott's Bcl-XL protein interaction antagonist.,  18  (14): [PMID:18583128] [10.1016/j.bmcl.2008.05.096]

Source

Source(1):

• Scientific Literature