4-Glutathionyl cyclophosphamide (PAMDB000936)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000936
Identification
Name: 4-Glutathionyl cyclophosphamide
Description:4-glutathionyl cyclophosphamide belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-amino-5-3-2-Bis(2-chloroethyl)amino-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-ylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • 2-amino-5-3-2-bis(2-chloroethyl)amino-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-ylsulfanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • 2-amino-5-3-2-Bis(2-chloroethyl)amino-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-ylsulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoate
  • 2-amino-5-3-2-Bis(2-chloroethyl)amino-2-oxo-1,3,2$l^{5}-oxazaphosphinan-4-ylsulphanyl-1-(carboxymethylamino)-1-oxopropan-2-ylamino-5-oxopentanoic acid
  • g-Glutamyl-S-{2-bis(2-chloroethyl)amino-2-oxido-1,3,2-oxazaphosphinan-4-yl}cysteinylglycine
  • Gamma-Glutamyl-S-{2-bis(2-chloroethyl)amino-2-oxido-1,3,2-oxazaphosphinan-4-yl}cysteinylglycine
  • γ-Glutamyl-S-{2-bis(2-chloroethyl)amino-2-oxido-1,3,2-oxazaphosphinan-4-yl}cysteinylglycine
Chemical Formula: C17H30Cl2N5O8PS
Average Molecular Weight: 566.394
Monoisotopic Molecular Weight: 565.092975577
InChI Key: CXEDBYAXQXFDHD-UHFFFAOYSA-N
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)
CAS number: Not Available
IUPAC Name:2-amino-4-{[2-({2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2???oxazaphosphinan-4-yl}sulfanyl)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name: C17H30cl2N5O8PS
SMILES:NC(CCC(O)=NC(CSC1CCOP(=O)(N1)N(CCCl)CCCl)C(O)=NCC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Peptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Nitrogen mustard
  • Phosphoric monoester diamide
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Oxazaphosphinane
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.185 mg/mLALOGPS
logP-1.7ALOGPS
logP-2.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area207.37 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity125.88 m3·mol-1ChemAxon
Polarizability52.99 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-3139020000-046b94793b5ffdc91fefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9724100000-8aaf34c2e69014649e08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9130000000-3b7c56c19d5091ab9e50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zgj-0212590000-d3604655628d2a5897dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9016000000-bf78140826d14fe805c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9841000000-f940fa82fb8f8898fd89View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB60387
Pubchem Compound ID443288
Kegg IDC11583
ChemSpider ID391534
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
• GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Locus Tag:
PA1033
Molecular weight:
24.5 kDa