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Record Information
Version3.6
Creation Date2006-05-22 15:12:08 UTC
Update Date2016-02-11 01:05:48 UTC
HMDB IDHMDB02757
Secondary Accession NumbersNone
Metabolite Identification
Common NameCysteic acid
DescriptionCysteic acid is a crystalline amino acid formed in the oxidation of cysteine; it is a precursor of taurine.
Structure
Thumb
Synonyms
ValueSource
3-SulfoalanineChEBI
beta-SulfoalanineChEBI
Cysteine sulfonic acidChEBI
3-SulphoalanineGenerator
CysteateGenerator
b-SulfoalanineGenerator
b-SulphoalanineGenerator
beta-SulphoalanineGenerator
β-sulfoalanineGenerator
β-sulphoalanineGenerator
Cysteine sulfonateGenerator
Cysteine sulphonateGenerator
Cysteine sulphonic acidGenerator
2-amino-3-SulfopropanoateHMDB
2-amino-3-Sulfopropanoic acidHMDB
2-amino-3-SulfopropionateHMDB
2-amino-3-Sulfopropionic acidHMDB
CepteateHMDB
Cepteic acidHMDB
CipteateHMDB
Cipteic acidHMDB
CysteinateHMDB
CysteinesulfonateHMDB
Cysteinesulfonic acidHMDB
Cysteinic acidHMDB
CysterateHMDB
Cysteric acidHMDB
L-CysteateHMDB
L-Cysteic acidHMDB
Chemical FormulaC3H7NO5S
Average Molecular Weight169.156
Monoisotopic Molecular Weight169.004493029
IUPAC Name2-amino-3-sulfopropanoic acid
Traditional Namecysteic acid
CAS Registry Number498-40-8
SMILES
NC(CS(O)(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)
InChI KeyInChIKey=XVOYSCVBGLVSOL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Mitochondria
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 Solubility73.6 mg/mLALOGPS
logP-2.4ALOGPS
logP-3ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)-1.7ChemAxon
pKa (Strongest Basic)8.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.43 m3·mol-1ChemAxon
Polarizability13.56 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1900000000-00b8a4b9bbedfa9bf252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9800000000-18c40d4b99159222b563View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-7a313e5ca76d5a55eb56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-5900000000-967c249c15d798909745View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9200000000-c02c1daafa3bc2cec519View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-80973e7856292311a36dView in MoNA
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Taurine and Hypotaurine MetabolismSMP00021map00430
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023061
KNApSAcK IDNot Available
Chemspider ID23942
KEGG Compound IDC00506
BioCyc IDL-CYSTEATE
BiGG ID35186
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02757
Metagene LinkHMDB02757
METLIN ID332
PubChem Compound25701
PDB IDNot Available
ChEBI ID21260
References
Synthesis ReferenceZhao, Chong-tao; Wang, Qing-ping; Lin, Wan-zhen; Chen, Ping. Synthesis of L-cysteic acid by indirect electrooxidation. Jingxi Huagong (2003), 20(4), 237-238, 253.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jasin HE: Oxidative modification of inflammatory synovial fluid immunoglobulin G. Inflammation. 1993 Apr;17(2):167-81. [8387962 ]
  2. Sarwar G, Botting HG, Peace RW: Complete amino acid analysis in hydrolysates of foods and feces by liquid chromatography of precolumn phenylisothiocyanate derivatives. J Assoc Off Anal Chem. 1988 Nov-Dec;71(6):1172-5. [3240976 ]
  3. Paroni R, De Vecchi E, Fermo I, Arcelloni C, Diomede L, Magni F, Bonini PA: Total urinary hydroxyproline determined with rapid and simple high-performance liquid chromatography. Clin Chem. 1992 Mar;38(3):407-11. [1547560 ]

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic acid + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic acid + L-Glutamic aciddetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD2
Uniprot ID:
Q05329
Molecular weight:
65410.77
Reactions
Cysteic acid → Taurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the production of GABA.
Gene Name:
GAD1
Uniprot ID:
Q99259
Molecular weight:
66896.065
Reactions
Cysteic acid → Taurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Not Available
Gene Name:
CSAD
Uniprot ID:
Q9Y600
Molecular weight:
55022.79
Reactions
Cysteic acid → Taurine + Carbon dioxidedetails