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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:43 UTC
HMDB IDHMDB00996
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Sulfinoalanine
Description3-Sulfinoalanine or cysteinesulfinic acid is a N-methyl-D-aspartate agonist. It is a product of cysteine dioxygenase or CDO [EC 1.13.11.20]. In humans cysteine catabolism is tightly regulated via regulation of cysteine dioxygenase (CDO) levels in the liver, with the turnover of CDO protein being dramatically decreased when intracellular cysteine levels increase. This occurs in response to changes in the intracellular cysteine concentration via changes in the rate of CDO ubiquitination and degradation. Expressed at high levels in the liver with lower levels in the kidney, brain, and lung, cysteine dioxygenase catalyzes the addition of molecular oxygen to the sulfhydryl group of cysteine, yielding cysteinesulfinic acid. The oxidative catabolism of cysteine to cysteinesulfinate by CDO represents an irreversible loss of cysteine from the free amino acid pool. Once generated, cysteinesulfinate is shuttled into several pathways including hypotaurine/taurine synthesis, sulfite/sulfate production, and the generation of pyruvate.
Structure
Thumb
Synonyms
  1. 3-Sulfino- Alanine
  2. 3-Sulfino-L-alanine
  3. 3-Sulphino-L-alanine
  4. Alanine 3-sulfinic acid
  5. Cysteine hydrogen sulfite ester
  6. Cysteine sulfinate
  7. Cysteine sulfinic acid
  8. L-Cysteine sulfinic acid
  9. L-Cysteinesulfinic acid
Chemical FormulaC3H7NO4S
Average Molecular Weight153.157
Monoisotopic Molecular Weight153.009578407
IUPAC Name(2R)-2-amino-3-sulfonylpropanoic acid
Traditional IUPAC Name(2R)-2-amino-3-sulfonylpropanoic acid
CAS Registry Number1115-65-7
SMILES
N[C@@H](CS(=O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2,9H,1,4H2,(H,5,6)/t2-/m0/s1
InChI KeyWVMUCBHSEHBMKA-REOHCLBHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Cysteine metabolism
  • Component of Taurine and hypotaurine metabolism
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 solubility54.6 g/LALOGPS
logP-2.7ALOGPS
logP-4.6ChemAxon
logS-0.45ALOGPS
pKa (strongest acidic)1.2ChemAxon
pKa (strongest basic)8.2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area97.46ChemAxon
rotatable bond count3ChemAxon
refractivity28.67ChemAxon
polarizability12.75ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Cysteine MetabolismSMP00013map00270
Taurine and Hypotaurine MetabolismSMP00021map00430
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.38 +/- 0.28 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified28.4 +/- 7.7 uMChildren (1-13 years old)Not SpecifiedMethotrexate treatment details
Associated Disorders and Diseases
Disease References
Methotrexate treatment
  1. Quinn CT, Griener JC, Bottiglieri T, Hyland K, Farrow A, Kamen BA: Elevation of homocysteine and excitatory amino acid neurotransmitters in the CSF of children who receive methotrexate for the treatment of cancer. J Clin Oncol. 1997 Aug;15(8):2800-6. Pubmed: 9256122
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022358
KNApSAcK IDNot Available
Chemspider ID16743745
KEGG Compound IDC00606
BioCyc ID3-SULFINOALANINE
BiGG ID35482
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00996
Metagene LinkHMDB00996
METLIN ID5927
PubChem Compound439270
PDB IDCSW
ChEBI ID41721
References
Synthesis ReferenceKissman, Henry M.; Baker, B. R. Preparation of various amides of p-methoxy-L-phenylalanine. Journal of Medicinal & Pharmaceutical Chemistry (1960), 2 415-23.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lin SY, Nui DM, Tu CP, Cheng YD, Lin HL: Evidence of L-cysteinesulfinic acid in PKU neonatal hair roots, with disappearance after dietary control. Ultrastruct Pathol. 2000 Sep-Oct;24(5):351-2. Pubmed: 11071575
  2. Hoeltzli SD, Kelley LK, Moe AJ, Smith CH: Anionic amino acid transport systems in isolated basal plasma membrane of human placenta. Am J Physiol. 1990 Jul;259(1 Pt 1):C47-55. Pubmed: 1973601

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
3-Sulfinoalanine + Oxoglutaric acid → B-Sulfinyl pyruvate + 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
3-Sulfinoalanine + Oxoglutaric acid → B-Sulfinyl pyruvate + 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
3-Sulfinoalanine → Hypotaurine + 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
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in carboxy-lyase activity
Specific function:
Not Available
Gene Name:
CSAD
Uniprot ID:
Q9Y600
Molecular weight:
55022.79
Reactions
3-Sulfinoalanine → Hypotaurine + CO(2)details
3-Sulfinoalanine → Hypotaurine + Carbon dioxidedetails
General function:
Involved in iron ion binding
Specific function:
Initiates several important metabolic pathways related to pyruvate and several sulfurate compounds including sulfate, hypotaurine and taurine. Critical regulator of cellular cysteine concentrations. Has an important role in maintaining the hepatic concentation of intracellular free cysteine within a proper narrow range.
Gene Name:
CDO1
Uniprot ID:
Q16878
Molecular weight:
22971.745
Reactions
L-Cysteine + Oxygen → 3-Sulfinoalaninedetails
General function:
Involved in iron ion binding
Specific function:
L-CYSTEINE + O(2) = 3-SULFINOALANINE
Gene Name:
CDO-1
Uniprot ID:
Q16857
Molecular weight:
6589.4