Record Information
Version1.0
Creation date2011-09-21 01:53:01 UTC
Update date2015-07-21 06:59:40 UTC
Primary IDFDB029277
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameS-(PGA2)-glutathione
DescriptionS-(PGA2)-glutathione is the glutathione conjugate of prostaglanding A2 PGA2 is converted to its glutathione conjugate by human mu-class GST M1a-a. Vertebrate alpha-, mu-, and pi-class GSTs were found to enhance PGA2 conjugation with glutathione, suggesting that the overexpression of GST forms could modulate the cytotoxic effects of cyclopentenone prostaglandins. Mammalian GSTs also have the ability to non-catalytically bind lipophilic, amphipathic ligands, including PGJ2, via noncovalent interactions, which effectively sequester these ligands in the cytosol away from their nuclear targets (i.e., peroxisomal proliferator-activated receptor, PPAR) [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
11-(S-Glutathionyl)-prostaglandin a(,2)HMDB
GSPGA2HMDB
(5Z)-7-[(1R,2S)-3-{[(2S)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoateGenerator
(5Z)-7-[(1R,2S)-3-{[(2S)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoateGenerator
(5Z)-7-[(1R,2S)-3-{[(2S)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acidGenerator
11-(S-glutathionyl)-prostaglandin A(,2)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP-1.2ALOGPS
logP-0.98ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area233.42 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity165.04 m³·mol⁻¹ChemAxon
Polarizability68.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H47N3O10S
IUPAC name(5Z)-7-[(1R,2S)-3-{[(2S)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-2-[(1E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
InChI IdentifierInChI=1S/C30H47N3O10S/c1-2-3-6-9-19(34)12-13-21-20(10-7-4-5-8-11-27(37)38)24(35)16-25(21)44-18-23(29(41)32-17-28(39)40)33-26(36)15-14-22(31)30(42)43/h4,7,12-13,19-23,25,34H,2-3,5-6,8-11,14-18,31H2,1H3,(H,32,41)(H,33,36)(H,37,38)(H,39,40)(H,42,43)/b7-4-,13-12+/t19?,20-,21+,22-,23-,25?/m1/s1
InChI KeyXUKIKVBUXFVHNV-MFAQWRDPSA-N
Isomeric SMILESCCCCCC(O)\C=C\[C@@H]1C(CC(=O)[C@@H]1C\C=C/CCCC(O)=O)SC[C@@H](NC(=O)CC[C@@H](N)C(O)=O)C(=O)NCC(O)=O
Average Molecular Weight641.773
Monoisotopic Molecular Weight641.298215429
Classification
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Prostaglandin skeleton
  • Eicosanoid
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • D-alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Cyclic ketone
  • Ketone
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Dialkylthioether
  • Carboxylic acid
  • Sulfenyl compound
  • Thioether
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSS-(PGA2)-glutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dj-2100091000-9f0c291ab99e3d8cbc13Spectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSS-(PGA2)-glutathione, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05i1-0011179000-3a9d05d089ebd11bca96Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-4900361000-5933d21da7c11037d695Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r01-9301320000-0c3a5ed25ecf94c34077Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xv-0016059000-846862813ec4ca3bccb0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0009010000-c6932bc4c2554632d9cdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-4903000000-0054a59a657d70c34856Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0004129000-f31832b1dc9bfd524351Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avj-4006978000-ccd2f8160bb26a19ce57Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9601230000-2ca5ceaf9cfb16a35240Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-0020019000-53a7d0310e1b862240c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0096-2930123000-7543c83cf255d7074216Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-9c70a5f0faccbbc906acSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481602
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13062
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference