L-Homocysteic acid (CHEM035369)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:42:25 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035369
Identification
Common NameL-Homocysteic acid
ClassSmall Molecule
DescriptionA homocysteic acid with L-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass183.183 g/mol
Monoisotopic Mass183.020 g/mol
CAS Registry Number14857-77-3
IUPAC Name(2S)-2-amino-4-sulfobutanoic acid
Traditional NameL-homocysteic acid
SMILESN[C@@H](CCS(O)(=O)=O)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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, 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
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, Positivesplash10-052r-2900000000-582366e5c041b3a0c9e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-ab6b416d6b40d5adca0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-a84ce26c9131a9e0222aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-0900000000-88837f57ed9e6288ce19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9300000000-9ef50dfa13539152f167Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-a6fb8cd4d3dc149be309Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002205
FooDB IDFDB022905
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6545
PDB IDNot Available
Wikipedia LinkHomocysteic_acid
Chemspider ID154529
ChEBI ID132223
PubChem Compound ID177491
Kegg Compound IDC16511
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25592718
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=27046337
3. Jolles-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.
4. Jolles-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.
5. 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.
6. 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.