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Record Information

Version

2.0

Creation Date

2012-05-31 14:26:48 -0600

Update Date

2015-06-03 17:19:17 -0600

Secondary Accession Numbers

ECMDB20088

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

MOL SDF PDB SMILES InChI

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

Weight:

Average: 566.394
Monoisotopic: 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-1,3,2λ⁵-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

Description

belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Nitrogen mustard
Phosphoric monoester diamide
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Organic phosphoric acid derivative
Oxazaphosphinane
Fatty acyl
Organic phosphoric acid amide
Fatty acid
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Dialkylthioether
Sulfenyl compound
Thioether
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Azacycle
Organonitrogen compound
Alkyl halide
Primary aliphatic amine
Organopnictogen compound
Alkyl chloride
Primary amine
Organic oxide
Carbonyl group
Organooxygen compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Organosulfur compound
Organohalogen compound
Organic nitrogen compound
Organochloride
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

peptide (CHEBI:1831 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.8	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	1.9	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	207.37 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	125.88 m³·mol⁻¹	ChemAxon
Polarizability	52.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Aldophosphamide + Glutathione <> 4-Glutathionyl cyclophosphamide + Water

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9440780000-72a130ffdc0663407ea5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-06y6-5051192000-85c6673bb5eb4869b5f4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("4-Glutathionyl cyclophosphamide,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-3139020000-046b94793b5ffdc91fef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9724100000-8aaf34c2e69014649e08	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9130000000-3b7c56c19d5091ab9e50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zgj-0212590000-d3604655628d2a5897dc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9016000000-bf78140826d14fe805c3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9841000000-f940fa82fb8f8898fd89	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0001960000-dca074efa713b2affcfa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ki-1036920000-4965fe95e9631cf5a4dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-9005200000-ddb699d034625c7b8bf2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-1000190000-8abecb432b7850e834a8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-024i-4922220000-411f179e15245039ed8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9820100000-30f2da94e763624e1fab	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

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

Links

External Links:

Resource	Link
CHEBI ID	1831
HMDB ID	HMDB0060387
Pubchem Compound ID	443288
Kegg ID	C11583
ChemSpider ID	391534
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Glutathione S-transferase

General function:: Involved in protein binding
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles
Gene Name:: gst
Uniprot ID:: P0A9D2
Molecular weight:: 22868

Reactions

RX + glutathione = HX + R-S-glutathione.

Protein Details

2. GSH-dependent disulfide bond oxidoreductase

General function:: Not Available
Specific function:: Not Available
Gene Name:: yfcG
Uniprot ID:: P77526
Molecular weight:: Not Available

Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

4-Glutathionyl cyclophosphamide (M2MDB000936)

Structure for #<Compound:0xa8b50740>

Enzymes

Reactions