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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:08 UTC
Update Date2021-09-14 15:00:09 UTC
HMDB IDHMDB0002757
Secondary Accession Numbers
  • HMDB02757
Metabolite Identification
Common NameCysteic acid
DescriptionCysteic acid, also known as cysteate or 3-sulfoalanine, 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). An amino sulfonic acid that is the sulfonic acid analogue of cysteine. Cysteic acid is a very strong basic compound (based on its pKa). Cysteic acid exists in all living species, ranging from bacteria to humans. Within humans, cysteic acid participates in a number of enzymatic reactions. In particular, cysteic acid can be converted into taurine through its interaction with the enzyme cysteine sulfinic acid decarboxylase. In addition, cysteic acid can be converted into taurine through its interaction with the enzyme glutamate decarboxylase 1. In humans, cysteic acid is involved in taurine and hypotaurine metabolism.
Structure
Data?1582752255
Synonyms
ValueSource
3-SulfoalanineChEBI
beta-SulfoalanineChEBI
Cysteine sulfonic acidChEBI
3-SulphoalanineGenerator
b-SulfoalanineGenerator
b-SulphoalanineGenerator
beta-SulphoalanineGenerator
Β-sulfoalanineGenerator
Β-sulphoalanineGenerator
Cysteine sulfonateGenerator
Cysteine sulphonateGenerator
Cysteine sulphonic acidGenerator
CysteateGenerator
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
3 SulfoalanineHMDB
Acid, cysteicHMDB
beta SulfoalanineHMDB
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 KeyXVOYSCVBGLVSOL-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility73.6 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.44 m³·mol⁻¹ChemAxon
Polarizability13.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available120.55http://allccs.zhulab.cn/database/detail?ID=AllCCS00000053
DarkChem[M+H]+PredictedNot Available135.12231661259
DarkChem[M-H]-PredictedNot Available127.231661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Cysteic acid,1TMS,#11672.8573https://arxiv.org/abs/1905.12712
Cysteic acid,1TMS,#21717.6848https://arxiv.org/abs/1905.12712
Cysteic acid,1TMS,#31665.3595https://arxiv.org/abs/1905.12712
Cysteic acid,1TBDMS,#11937.8813https://arxiv.org/abs/1905.12712
Cysteic acid,1TBDMS,#21952.2891https://arxiv.org/abs/1905.12712
Cysteic acid,1TBDMS,#31936.1392https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-4987d9a40ecc2c214dc32016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9200000000-63aac0a32cfc85b50ddd2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-e495810d64e3e38da2bd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uxr-0900000000-02df293f7975b82ac3b72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-47bca80f8407522228fc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100000000-45eccf44b0be54ef57032021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00lr-9800000000-32b77b0eb11d32fe32bd2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-47bca80f8407522228fc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-6103b341ba1eeaf705ef2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-b3cbcae68d66f83d26cc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0159-9800000000-c9f345d26f9e3b45c6072021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-e31af2162892af2242832021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-d763c2e7d917148c530c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-0158ea55e5c9dfde9dc72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0089-9000000000-510d6054b2f3b09e29202021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-cfa2835cc0b2b29ec1102021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-aa53bbb90f5cdd3a6d832021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0abc-3900000000-0626b1961d05178614512021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-29ef424c41f3119ec6332021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-cc1dd155bb25f8c9a20f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-05fr-2900000000-8fc583c963f43919bf502021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-1900000000-00b8a4b9bbedfa9bf2522015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9800000000-18c40d4b99159222b5632015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-7a313e5ca76d5a55eb562015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-5900000000-967c249c15d7989097452015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9200000000-c02c1daafa3bc2cec5192015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-80973e7856292311a36d2015-09-15View Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
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 IDFDB023061
KNApSAcK IDNot Available
Chemspider ID23942
KEGG Compound IDC00506
BioCyc IDNot Available
BiGG ID35186
Wikipedia LinkCysteic_acid
METLIN ID332
PubChem Compound25701
PDB IDNot Available
ChEBI ID21260
Food Biomarker OntologyNot Available
VMH IDLCYST
MarkerDB IDNot Available
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. 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. [PubMed:3240976 ]
  2. 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. [PubMed:1547560 ]
  3. Jasin HE: Oxidative modification of inflammatory synovial fluid immunoglobulin G. Inflammation. 1993 Apr;17(2):167-81. [PubMed:8387962 ]

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