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Human Metabolome Database Version 3.5

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Showing metabocard for Homocysteine thiolactone (HMDB02287)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:46 -0600
Update Date 2013-05-29 13:35:25 -0600
HMDB ID HMDB02287
Secondary Accession Numbers None
Metabolite Identification
Common Name Homocysteine thiolactone
Description Elevated level of the nonprotein amino acid homocysteine (Hcy) is a risk factor for cardiovascular diseases, neurodegenerative diseases, and neural tube defects. Metabolic conversion of Hcy to a chemically reactive metabolite, Hcy-thiolactone, catalyzed by methionyl-tRNA synthetase is the first step in a pathway that contributes to Hcy toxicity in humans. (PMID 16702349 Link_out). The only known source of Hcy in the human body is dietary protein methionine; subsequent examinations of individual dietary amino acids have led to the conclusion that methionine, ingested in excess, is the most toxic amino acid. (Harper AE, Benevenga NJ, Wohlheuter RM. Effects of ingestion of disproportionate amounts of amino acids. Physiol Rev. 1970;50: 428 - 58; Benevenga NJ, Steele RD. Adverse effects of excessive consumption of amino acids. Annu Rev Nutr. 1984; 4:157-81). Animals fed high-protein or high-methionine diets for 2 years developed hyperhomocysteinemia and evidence of vascular disease (Fau D, Preret J, Hadjiisky P. Effects of ingestion of high protein or excess methionine diets by rats for two years. J Nutr. 1988; 118:128-33).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. ( -)-3-Amino-2-thiolanon
  2. ( -)-3-Aminotetrahydro-2-thiophenon
  3. (+-)-3-Aminodihydro-2(3H)-thiophenone
  4. 3-Aminodihydro-2(3H)-thiophenone
  5. DL-3-Aminotetrahydro-2-thiophenone
  6. DL-Homocysteine thiolactone
  7. L-Homocysteine thiolactone
Chemical Formula C4H7NOS
Average Molecular Weight 117.169
Monoisotopic Molecular Weight 117.024834541
IUPAC Name 3-aminothiolan-2-one
Traditional IUPAC Name 3-aminothiolan-2-one
CAS Registry Number 3622-59-1
SMILES NC1CCSC1=O
InChI Identifier InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2
InChI Key KIWQWJKWBHZMDT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Thiolanes
Sub Class N/A
Other Descriptors
  • Thioesters
Substituents
  • Primary Aliphatic Amine (Alkylamine)
  • Thiocarboxylic Acid Ester
  • Thiolactone
Direct Parent Thiolanes
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
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
LogP -0.51 ALOGPS
LogP -0.25 ChemAxon
LogS -0.30 ALOGPS
pKa (strongest basic) 7.83 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 43.09 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 29.76 ChemAxon
Polarizability 11.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00282 +/- 0.00613 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
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 FDB022949
KNApSAcK ID Not Available
Chemspider ID 96881 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02287 Link_out
Metagene Link HMDB02287 Link_out
METLIN ID 6594 Link_out
PubChem Compound 107712 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Takehara, Jun; Ichikawa, Shuji; Iwane, Hiroshi. Preparation of DL-homocysteine thiolactone inorganic acid salts. Jpn. Kokai Tokkyo Koho (1998), 4 pp.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Ricci G, Santoro L, Achilli M, Matarese RM, Nardini M, Cavallini D: Similarity of the oxidation products of L-cystathionine by L-amino acid oxidase to those excreted by cystathioninuric patients. J Biol Chem. 1983 Sep 10;258(17):10511-7. Pubmed: 6885789 Link_out
  2. Jakubowski H: Homocysteine thiolactone: metabolic origin and protein homocysteinylation in humans. J Nutr. 2000 Feb;130(2S Suppl):377S-381S. Pubmed: 10721911 Link_out
  3. Jakubowski H: Protein homocysteinylation: possible mechanism underlying pathological consequences of elevated homocysteine levels. FASEB J. 1999 Dec;13(15):2277-83. Pubmed: 10593875 Link_out
  4. Kerkeni M, Addad F, Chauffert M, Chuniaud L, Miled A, Trivin F, Maaroufi K: Hyperhomocysteinemia, paraoxonase activity and risk of coronary artery disease. Clin Biochem. 2006 Aug;39(8):821-5. Epub 2006 Jun 7. Pubmed: 16875684 Link_out
  5. Chwatko G, Jakubowski H: The determination of homocysteine-thiolactone in human plasma. Anal Biochem. 2005 Feb 15;337(2):271-7. Pubmed: 15691507 Link_out
  6. Jakubowski H: Pathophysiological consequences of homocysteine excess. J Nutr. 2006 Jun;136(6 Suppl):1741S-1749S. Pubmed: 16702349 Link_out