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

ID: ALA50249

PubChem CID: 44295373

Max Phase: Preclinical

Molecular Formula: C18H23N3O8S

Molecular Weight: 441.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](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)/t12-,13-/m0/s1

Standard InChI Key:  ASKLIFLGJJZFTM-STQMWFEESA-N

Molfile:  

     RDKit          2D

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    6.4917   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -0.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -2.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -1.4792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9250   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125    1.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    1.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -3.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7667    0.4083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000    1.8333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -4.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  8  1  0
  1  4  1  6
  5 15  1  0
  6  4  1  0
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  8 10  1  0
  9 18  1  0
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 15 19  1  0
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 19 20  1  0
 20  6  1  0
 21  5  1  0
 15 22  1  1
 23  9  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
 30 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA50249

   (S)-2-Amino-4-[(R)-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. Hsu YR, Norton SJ..  (1983)  S-carbobenzoxyglutathione: a competitive inhibitor of mammalian glyoxalase II.,  26  (12): [PMID:6644749] [10.1021/jm00366a027]

Source

Source(1):

• Scientific Literature