2-Amino-5-[[1-(carboxymethylamino)-1-oxo-3-(3-oxopropylsulfanyl)propan-2-yl]amino]-5-oxopentanoic acid

ID: ALA3706542

PubChem CID: 54261059

Max Phase: Preclinical

Molecular Formula: C13H21N3O7S

Molecular Weight: 363.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CCC(=O)NC(CSCCC=O)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C13H21N3O7S/c14-8(13(22)23)2-3-10(18)16-9(7-24-5-1-4-17)12(21)15-6-11(19)20/h4,8-9H,1-3,5-7,14H2,(H,15,21)(H,16,18)(H,19,20)(H,22,23)

Standard InChI Key:  RDNSBKKJIQKSJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 23  0  0  0  0  0  0  0  0999 V2000
    1.3000    1.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7999    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1030    2.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4038    2.9994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4069    4.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7077    5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7102    6.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    0.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -1.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000    1.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6999    0.7500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0648    2.8526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7459    4.6470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6393    0.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  2 14  2  0
  3 15  1  0
  6 16  2  0
  8 17  1  0
 17 18  1  0
  9 19  2  0
 12 20  1  0
 22 23  1  0
 23 24  2  0
 18 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706542

   2-Amino-5-[[1-(carboxymethylamino)-1-oxo-3-(3-oxopropylsulfanyl)propan-2-yl]amino]-5-oxopentanoic acid

Molecule Features

Natural Product: Yes

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: 363.39

Molecular Weight (Monoisotopic): 363.1100

AlogP: -1.81

#Rotatable Bonds: 13

Polar Surface Area: 175.89

Molecular Species: ZWITTERION

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.81

CX Basic pKa: 9.31

CX LogP: -5.03

CX LogD: -8.22

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.19

Np Likeness Score: 0.66

References

1. Zhong S, Huang M, Yang X, Liang L, Wang Y, Romkes M, Duan W, Chan E, Zhou SF..  (2006)  Relationship of glutathione S-transferase genotypes with side-effects of pulsed cyclophosphamide therapy in patients with systemic lupus erythematosus.,  62  (4): [PMID:16995867] [10.1111/j.1365-2125.2006.02690.x]

Source

Source(1):

• Curated Drug Metabolism Pathways