| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 3-Sulfino- Alanine
- 3-Sulfino-L-alanine
- 3-Sulphino-L-alanine
- Alanine 3-sulfinic acid
- Cysteine hydrogen sulfite ester
- Cysteine sulfinate
- Cysteine sulfinic acid
- L-Cysteine sulfinic acid
- 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 |
|
| Biofunction |
- Component of Cysteine metabolism
- Component of Taurine and hypotaurine metabolism
|
| Application |
Not Available |
| Cellular locations |
|
| 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 |
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| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
|
| Tissue Location |
Not Available
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| Pathways |
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
1.38 +/- 0.28 uM |
Adult (>18 years old) |
Both |
Normal |
Measurement of excitatory sulfur amino acids,...
|
| Cerebrospinal Fluid (CSF) |
Detected and not Quantified |
|
Not Applicable |
Children (1-13 year old) |
Not Specified |
Normal |
Not detected
|
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| Abnormal Concentrations |
|---|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
28.4 +/- 7.7 uM |
Children (1-13 year old) |
Not Specified |
Methotrexate treatment |
Not Available |
|
| 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
|
|
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank 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 |
| KEGG Compound ID |
C00606 |
| BioCyc ID |
3-SULFINOALANINE |
| BiGG ID |
35482 |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB00996 |
| Metagene Link |
HMDB00996 |
| METLIN ID |
5927 |
| PubChem Compound |
439270 |
| PDB ID |
CSW |
| ChEBI ID |
41721 |
| 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 |
- 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
- 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
|
