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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:38 UTC
Update Date2019-08-22 16:37:19 UTC
HMDB IDHMDB0002135
Secondary Accession Numbers
  • HMDB02135
Metabolite Identification
Common NameS-(3-Oxo-3-carboxy-n-propyl)cysteine
DescriptionS-(3-oxo-3-carboxy-n-propyl)cysteine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. S-(3-oxo-3-carboxy-n-propyl)cysteine is a very strong basic compound (based on its pKa).
Structure
Data?1566491839
Synonyms
ValueSource
4-[(2-Amino-2-carboxyethyl)sulfanyl]-2-oxobutanoateHMDB
4-[(2-Amino-2-carboxyethyl)sulphanyl]-2-oxobutanoateHMDB
4-[(2-Amino-2-carboxyethyl)sulphanyl]-2-oxobutanoic acidHMDB
4-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-oxobutanoic acidHMDB
OCPCHMDB
S-(3-Oxo-3-carboxy-n-propyl) cysteineHMDB
S-(3-Oxo-3-carboxy-n-propyl)cysteineHMDB
Chemical FormulaC7H11NO5S
Average Molecular Weight221.23
Monoisotopic Molecular Weight221.035793632
IUPAC Name4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-oxobutanoic acid
Traditional Name4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-oxobutanoic acid
CAS Registry Number87458-26-2
SMILES
N[C@@H](CSCCC(=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H11NO5S/c8-4(6(10)11)3-14-2-1-5(9)7(12)13/h4H,1-3,8H2,(H,10,11)(H,12,13)/t4-/m0/s1
InChI KeyMXVUEJUCBIAFCN-BYPYZUCNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-cysteine-s-conjugates. These are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • L-alpha-amino acid
  • Alpha-amino acid
  • Thia fatty acid
  • Short-chain keto acid
  • Fatty acyl
  • Keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Amino acid
  • Ketone
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.24 g/LALOGPS
logP-2.6ALOGPS
logP-2.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.76ChemAxon
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.05 m³·mol⁻¹ChemAxon
Polarizability20.67 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Not SpecifiedNot SpecifiedCystathioninuria details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022861
KNApSAcK IDNot Available
Chemspider ID13628297
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54097042
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Okada T, Takechi T, Wakiguchi H, Kurashige T, Sugahara K, Kodama H: Identification of new cystathionine mono-oxo acids, S-(3-oxo-3-carboxy-n-propyl) cysteine and S-(2-oxo-2-carboxyethyl) homocysteine, in the urine of a patient with cystathioninuria. Arch Biochem Biophys. 1993 Sep;305(2):385-91. [PubMed:8373176 ]