3-(2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-2-oxo-4-phenyl-butyric acid methyl ester

ID: ALA116623

PubChem CID: 44344050

Max Phase: Preclinical

Molecular Formula: C25H30N2O6

Molecular Weight: 454.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C(=O)C(Cc1ccccc1)NC(=O)C(CC(C)C)NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C25H30N2O6/c1-17(2)14-21(27-25(31)33-16-19-12-8-5-9-13-19)23(29)26-20(22(28)24(30)32-3)15-18-10-6-4-7-11-18/h4-13,17,20-21H,14-16H2,1-3H3,(H,26,29)(H,27,31)

Standard InChI Key:  KRHPPVCFVFNRMO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.5167   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -3.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0917   -4.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -3.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -5.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3042   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -5.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4625   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -5.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -7.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -6.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7042   -6.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  2  1  0
  5  8  1  0
  6  1  1  0
  7  3  1  0
  8  7  1  0
  9  1  2  0
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 24 19  2  0
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 26 20  1  0
 27 20  1  0
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 29 22  1  0
 30 23  2  0
 31 25  2  0
 32 31  1  0
 33 30  1  0
 29 33  2  0
 28 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA116623

   3-(2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-2-oxo-4-phenyl-butyric acid methyl ester

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: 454.52

Molecular Weight (Monoisotopic): 454.2104

AlogP: 2.80

#Rotatable Bonds: 11

Polar Surface Area: 110.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.39

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -0.06

References

1. Li Z, Patil GS, Golubski ZE, Hori H, Tehrani K, Foreman JE, Eveleth DD, Bartus RT, Powers JC..  (1993)  Peptide alpha-keto ester, alpha-keto amide, and alpha-keto acid inhibitors of calpains and other cysteine proteases.,  36  (22): [PMID:8230139] [10.1021/jm00074a031]

Source

Source(1):

• Scientific Literature