You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:41 UTC
Update Date2020-02-26 21:23:56 UTC
HMDB IDHMDB0002205
Secondary Accession Numbers
  • HMDB02205
Metabolite Identification
Common NameL-Homocysteic acid
DescriptionShort-term incubation of lymphocytes with homocysteine or its oxidation product homocysteinic acid increased the formation of reactive oxygen species and cell necrosis.
Structure
Data?1582752236
Synonyms
ValueSource
(2S)-2-Amino-4-sulfobutyric acidChEBI
(S)-2-Amino-4-sulfobutanoic acidChEBI
(S)-2-Amino-4-sulfobutyric acidChEBI
Homocysteic acidChEBI
L-2-Amino-4-sulfobutyric acidChEBI
(2S)-2-Amino-4-sulfobutanoic acidKegg
(2S)-2-Amino-4-sulfobutyrateGenerator
(2S)-2-Amino-4-sulphobutyrateGenerator
(2S)-2-Amino-4-sulphobutyric acidGenerator
(S)-2-Amino-4-sulfobutanoateGenerator
(S)-2-Amino-4-sulphobutanoateGenerator
(S)-2-Amino-4-sulphobutanoic acidGenerator
(S)-2-Amino-4-sulfobutyrateGenerator
(S)-2-Amino-4-sulphobutyrateGenerator
(S)-2-Amino-4-sulphobutyric acidGenerator
HomocysteateGenerator
L-2-Amino-4-sulfobutyrateGenerator
L-2-Amino-4-sulphobutyrateGenerator
L-2-Amino-4-sulphobutyric acidGenerator
(2S)-2-Amino-4-sulfobutanoateGenerator
(2S)-2-Amino-4-sulphobutanoateGenerator
(2S)-2-Amino-4-sulphobutanoic acidGenerator
L-HomocysteateGenerator
Chemical FormulaC4H9NO5S
Average Molecular Weight183.183
Monoisotopic Molecular Weight183.020143093
IUPAC Name(2S)-2-amino-4-sulfobutanoic acid
Traditional NameL-homocysteic acid
CAS Registry Number14857-77-3
SMILES
N[C@@H](CCS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1
InChI KeyVBOQYPQEPHKASR-VKHMYHEASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point261 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility64.3 g/LALOGPS
logP-2.4ALOGPS
logP-2.9ChemAxon
logS-0.45ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability15.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5c-9200000000-227327e2ea07b407a345Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-6900000000-31638e5ec109cfafd44eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-1900000000-9e519a1dc69bad6b052aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-0969185dbffad2caca30Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-6000560b5af6914a56f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3900000000-850821a58ef9d7da6dd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9500000000-56e02bca51cc72bc4c65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-c4b654f035544d07c77eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00li-0900000000-14ffff3301fb95818ba1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-4900000000-937b06eba260edf97366Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-adb2ff0a0fa33a9254c0Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022905
KNApSAcK IDNot Available
Chemspider ID154529
KEGG Compound IDC16511
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHomocysteic_acid
METLIN ID6545
PubChem Compound177491
PDB IDNot Available
ChEBI ID132223
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceJolles-Bergeret, Bernadette. Synthesis and properties of L- and DL-homocysteine sulfinic and L-homocysteic acids. Bulletin de la Societe de Chimie Biologique (1966), 48(11), 1265-78.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Boldyrev AA: Homocysteinic acid causes oxidative stress in lymphocytes by potentiating toxic effect of NMDA. Bull Exp Biol Med. 2005 Jul;140(1):33-7. [PubMed:16254614 ]
  2. Piraud M, Vianey-Saban C, Bourdin C, Acquaviva-Bourdain C, Boyer S, Elfakir C, Bouchu D: A new reversed-phase liquid chromatographic/tandem mass spectrometric method for analysis of underivatised amino acids: evaluation for the diagnosis and the management of inherited disorders of amino acid metabolism. Rapid Commun Mass Spectrom. 2005;19(22):3287-97. [PubMed:16235234 ]