Human Metabolome Database Version 3.5

Showing metabocard for 3-Sulfinoalanine (HMDB00996)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:43 -0700
HMDB ID HMDB00996
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Sulfinoalanine
Description 3-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C3H7NO4S
Average Molecular Weight 153.157
Monoisotopic Molecular Weight 153.009578407
IUPAC Name (2R)-2-amino-3-sulfonylpropanoic acid
Traditional IUPAC Name (2R)-2-amino-3-sulfonylpropanoic acid
CAS Registry Number 1115-65-7
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 Key WVMUCBHSEHBMKA-REOHCLBHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Cysteine metabolism
  • Component of Taurine and hypotaurine metabolism
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 54.6 g/L ALOGPS
LogP -2.66 ALOGPS
LogP -4.6 ChemAxon
LogS -0.45 ALOGPS
pKa (strongest acidic) 1.2 ChemAxon
pKa (strongest basic) 8.2 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 97.46 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 28.67 ChemAxon
Polarizability 12.75 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Taurine and Hypotaurine Metabolism SMP00021 map00430 Link_out
Cysteine Metabolism SMP00013 map00270 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.38 +/- 0.28 uM Adult (>18 years old) Both Comment Normal
Cerebrospinal Fluid (CSF) Detected but not Quantified
Not Applicable Children (1-13 year old) Not Specified Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 28.4 +/- 7.7 uM Children (1-13 year old) Not Specified Methotrexate treatment
Associated Disorders and Diseases
Disease References
Methotrexate treatment
  • 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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022358
      KNApSAcK ID Not Available
      Chemspider ID 16743745 Link_out
      KEGG Compound ID C00606 Link_out
      BioCyc ID 3-SULFINOALANINE Link_out
      BiGG ID 35482 Link_out
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00996 Link_out
      Metagene Link HMDB00996 Link_out
      METLIN ID 5927 Link_out
      PubChem Compound 439270 Link_out
      PDB ID CSW Link_out
      ChEBI ID 41721 Link_out
      References
      Synthesis Reference Kissman, 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 Link_out
      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 Link_out

      Enzymes
      Name: Aspartate aminotransferase, cytoplasmic
      Reactions:
      3-Sulfinoalanine + Oxoglutaric acid unknown B-Sulfinyl pyruvate + L-Glutamic acid details
      Gene Name: GOT1
      Uniprot ID: P17174 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aspartate aminotransferase, mitochondrial
      Reactions:
      3-Sulfinoalanine + Oxoglutaric acid unknown B-Sulfinyl pyruvate + L-Glutamic acid details
      Gene Name: GOT2
      Uniprot ID: P00505 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glutamate decarboxylase 2
      Reactions:
      3-Sulfinoalanine unknown Hypotaurine + Carbon dioxide details
      Gene Name: GAD2
      Uniprot ID: Q05329 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Glutamate decarboxylase 1
      Reactions:
      3-Sulfinoalanine unknown Hypotaurine + Carbon dioxide details
      Gene Name: GAD1
      Uniprot ID: Q99259 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cysteine sulfinic acid decarboxylase
      Reactions:
      3-Sulfinoalanine unknown Hypotaurine + CO(2) details
      3-Sulfinoalanine unknown Hypotaurine + Carbon dioxide details
      Gene Name: CSAD
      Uniprot ID: Q9Y600 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cysteine dioxygenase type 1
      Reactions:
      L-Cysteine + Oxygen unknown 3-Sulfinoalanine details
      Gene Name: CDO1
      Uniprot ID: Q16878 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cysteine dioxygenase
      Reactions: Not Available
      Gene Name: CDO-1
      Uniprot ID: Q16857 Link_out
      Protein Sequence: FASTA