4-Glutathionyl cyclophosphamide

ID: ALA3706539

Cas Number: 77273-67-7

PubChem CID: 71317120

Max Phase: Preclinical

Molecular Formula: C17H30Cl2N5O8PS

Molecular Weight: 566.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](CSC1CCOP(=O)(N(CCCl)CCCl)N1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C17H30Cl2N5O8PS/c18-4-6-24(7-5-19)33(31)23-14(3-8-32-33)34-10-12(16(28)21-9-15(26)27)22-13(25)2-1-11(20)17(29)30/h11-12,14H,1-10,20H2,(H,21,28)(H,22,25)(H,23,31)(H,26,27)(H,29,30)/t11-,12-,14?,33?/m0/s1

Standard InChI Key:  CXEDBYAXQXFDHD-XNZWOTSQSA-N

Molfile:  

     RDKit          2D

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    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2999    2.2084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536    2.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029    3.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036    4.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060    5.6579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8999    2.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9394    1.6091    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4431  -10.3638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815  -10.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7798  -11.7187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8218   -9.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297   -5.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -3.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2321   -3.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -1.5053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4928   -0.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4933    0.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5324    1.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4541    1.3463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  6  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  3  8  2  0
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  7 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
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 16 15  1  1
 17 16  1  0
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 17 18  2  0
 17 19  1  0
 20 21  1  0
 22 21  1  0
 22 23  2  0
 22 24  1  0
 25 24  1  1
 26 25  1  0
 25 28  1  0
 26 27  2  0
 26 30  1  0
 28 29  1  0
 31 30  1  0
 32 31  1  0
 32 33  2  0
 32 34  1  0
  1 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706539

   L-gamma-Glutamyl-S-{2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2lambda~5~-oxazaphosphinan-4-yl}-L-cysteinylglycine

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: 566.40

Molecular Weight (Monoisotopic): 565.0930

AlogP: -0.18

#Rotatable Bonds: 16

Polar Surface Area: 200.39

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.80

CX Basic pKa: 9.31

CX LogP: -4.40

CX LogD: -7.56

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.11

Np Likeness Score: 0.32

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