2-Amino-4-[2-benzyloxycarbonylsulfanyl-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

ID: ALA169316

PubChem CID: 44380789

Max Phase: Preclinical

Molecular Formula: C18H23N3O8S

Molecular Weight: 441.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CCC(=O)NC(CSC(=O)OCc1ccccc1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C18H23N3O8S/c19-12(17(26)27)6-7-14(22)21-13(16(25)20-8-15(23)24)10-30-18(28)29-9-11-4-2-1-3-5-11/h1-5,12-13H,6-10,19H2,(H,20,25)(H,21,22)(H,23,24)(H,26,27)

Standard InChI Key:  ASKLIFLGJJZFTM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.5542   -1.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5875   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    0.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -1.1917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4125    0.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  8  1  0
  4  1  1  0
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  9 18  1  0
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 25 24  1  0
 26 25  2  0
 27 25  1  0
 28 27  2  0
 29 26  1  0
 30 28  1  0
 29 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA169316

   2-Amino-4-[2-benzyloxycarbonylsulfanyl-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

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: 441.46

Molecular Weight (Monoisotopic): 441.1206

AlogP: -0.07

#Rotatable Bonds: 12

Polar Surface Area: 185.12

Molecular Species: ZWITTERION

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.71

CX Basic pKa: 9.31

CX LogP: -2.79

CX LogD: -6.04

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: 0.37

References

1. Bush PE, Norton SJ..  (1985)  S-(nitrocarbobenzoxy)glutathiones: potent competitive inhibitors of mammalian glyoxalase II.,  28  (6): [PMID:4009606] [10.1021/jm00383a025]

Source

Source(1):

• Scientific Literature