2-Amino-4-[1-(carboxymethyl-carbamoyl)-2-(3-nitro-benzyloxycarbonylsulfanyl)-ethylcarbamoyl]-butyric acid

ID: ALA355031

PubChem CID: 44380793

Max Phase: Preclinical

Molecular Formula: C18H22N4O10S

Molecular Weight: 486.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CCC(=O)NC(CSC(=O)OCc1cccc([N+](=O)[O-])c1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C18H22N4O10S/c19-12(17(27)28)4-5-14(23)21-13(16(26)20-7-15(24)25)9-33-18(29)32-8-10-2-1-3-11(6-10)22(30)31/h1-3,6,12-13H,4-5,7-9,19H2,(H,20,26)(H,21,23)(H,24,25)(H,27,28)

Standard InChI Key:  OLLNYAGAESAEGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.1417   -5.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -1.6042    0.0000 N   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
   -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
    4.1417   -6.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -4.9125    0.0000 O   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
    2.6917    1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4250   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4167   -2.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2750   -2.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    2.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3000   -4.0917    0.0000 O   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
   -2.3083   -2.4375    0.0000 N   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
    3.4125    0.8750    0.0000 O   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
    1.9917   -4.9167    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
  2 14  1  0
  3  2  1  0
  4 19  1  0
  5  2  1  0
  6  1  1  0
  7 20  1  0
  8  5  1  0
  9  3  1  0
 10  1  1  0
 11  1  2  0
 12  4  1  0
 13 23  1  0
 14 12  1  0
 15  4  2  0
 16  6  1  0
 17  3  2  0
 18  7  2  0
 19 29  1  0
 20 24  1  0
 21  8  2  0
 22 13  2  0
 23  9  1  0
 24 25  1  0
 25  8  1  0
 26  7  1  0
 27 16  2  0
 28 20  1  0
 29 27  1  0
 30 13  1  0
 31  6  2  0
 32 31  1  0
 33 32  2  0
 33 27  1  0
M  CHG  2   1   1  10  -1
M  END

Alternative Forms

1. Parent:

   

   ALA355031

   2-Amino-4-[1-(carboxymethyl-carbamoyl)-2-(3-nitro-benzyloxycarbonylsulfanyl)-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: 486.46

Molecular Weight (Monoisotopic): 486.1057

AlogP: -0.16

#Rotatable Bonds: 13

Polar Surface Area: 228.26

Molecular Species: ZWITTERION

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.71

CX Basic pKa: 9.31

CX LogP: -2.85

CX LogD: -6.10

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.14

Np Likeness Score: -0.09

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