Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2015-10-09 22:30:38 UTC
Primary IDFDB001491
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Homocysteine
DescriptionA high level of blood serum homocysteine is a powerful risk factor for cardiovascular disease. Unfortunately, one study which attempted to decrease the risk by lowering homocysteine was not fruitful. This study was conducted on nearly 5000 Norwegian heart attack survivors who already had severe, late-stage heart disease. No study has yet been conducted in a preventive capacity on subjects who are in a relatively good state of health.; Elevated levels of homocysteine have been linked to increased fractures in elderly persons. The high level of homocysteine will auto-oxidize and react with reactive oxygen intermediates and damage endothelial cells and has a higher risk to form a thrombus. Homocysteine does not affect bone density. Instead, it appears that homocysteine affects collagen by interfering with the cross-linking between the collagen fibers and the tissues they reinforce. Whereas the HOPE-2 trial showed a reduction in stroke incidence, in those with stroke there is a high rate of hip fractures in the affected side. A trial with 2 homocysteine-lowering vitamins (folate and B12) in people with prior stroke, there was an 80% reduction in fractures, mainly hip, after 2 years. Interestingly, also here, bone density (and the number of falls) were identical in the vitamin and the placebo groups.; Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Although its concentration in plasma is only about 10 micromolar (uM), even moderate hyperhomocysteinemia is associated with increased incidence of cardiovascular disease and Alzheimer's disease. Elevations in plasma homocysteine are commonly found as a result of vitamin deficiencies, polymorphisms of enzymes of methionine metabolism, and renal disease. Pyridoxal, folic acid, riboflavin, and Vitamin B(12) are all required for methionine metabolism, and deficiency of each of these vitamins result in elevated plasma homocysteine. A polymorphism of methylenetetrahydrofolate reductase (C677T), which is quite common in most populations with a homozygosity rate of 10-15 %, is associated with moderate hyperhomocysteinemia, especially in the context of marginal folate intake. Plasma homocysteine is inversely related to plasma creatinine in patients with renal disease. This is due to an impairment in homocysteine removal in renal disease. The role of these factors, and of modifiable lifestyle factors, in affecting methionine metabolism and in determining plasma homocysteine levels is discussed. Homocysteine is an independent cardiovascular disease (CVD) risk factor modifiable by nutrition and possibly exercise. Homocysteine was first identified as an important biological compound in 1932 and linked with human disease in 1962 when elevated urinary homocysteine levels were found in children with mental retardation. This condition, called homocysteinuria, was later associated with premature occlusive CVD, even in children. These observations led to research investigating the relationship of elevated homocysteine levels and CVD in a wide variety of populations including middle age and elderly men and women with and without traditional risk factors for CVD. (PMID 17136938, 15630149); Homocysteine is an amino acid with the formula HSCH2CH2CH(NH2)CO2H. It is a homologue of the amino acid cysteine, differing by an additional methylene (-CH2-) group. It is biosynthesized from methionine by the removal of its terminal C? methyl group. Homocysteine can be recycled into methionine or converted into cysteine with the aid of B-vitamins.; Studies reported in 2006 have shown that giving vitamins [folic acid, B6 and B12] to reduce homocysteine levels may not quickly offer benefit, however a significant 25% reduction in stroke was found in the HOPE-2 study even in patients mostly with existing serious arterial decline although the overall death rate was not significantly changed by the intervention in the trial. Clearly, reducing homocysteine does not quickly repair existing structural damage of the artery architecture. However, the science is strongly supporting the biochemistry that homocysteine degrades and inhibits the formation of the three main structural components of the artery, collagen, elastin and the proteoglycans. Homocysteine permanently degrades cysteine disulfide bridges and lysine amino acid residues in proteins, gradually affecting function and structure. Simply put, homocysteine is a 'corrosive' of long-living proteins, i.e. collagen or elastin, or life-long proteins, i.e. fibrillin. These long-term effects are difficult to establish in clinical trials focusing on groups with existing artery decline. The main role of reducing homocysteine is possibly in 'prevention' but studies thus far have not found benefits from it, and some have actually seen increased risks from consuming B vitamins, leading them to conclude that supplementation is not recommended.
CAS Number454-29-5
Structure
Thumb
Synonyms
SynonymSource
2-Amino-4-mercaptobutyric acidChEBI
HcyChEBI
2-Amino-4-mercaptobutyrateGenerator
(+-)-HomocysteineHMDB
(S)-2-Amino-4-mercapto-butanoateHMDB
(S)-2-Amino-4-mercapto-butanoic acidHMDB
2-Amino-4-mercapto-butanoateHMDB
2-Amino-4-mercapto-butanoic acidHMDB
2-Amino-4-mercapto-butyric acidHMDB
2-Amino-4-mercapto-DL-butyrateHMDB
2-Amino-4-mercapto-DL-butyric acidHMDB
2-Amino-4-sulfanylbutanoateHMDB
2-Amino-4-sulfanylbutanoic acidHMDB
D,L-HomocysteineHMDB
DL-2-Amino-4-mercapto-butyric acidHMDB
DL-2-Amino-4-mercaptobutyric acidHMDB
DL-HomocysteineHMDB
DL-Homocysteine (free base)HMDB
Homo-cysHMDB
L-2-Amino-4-mercapto-butyric acidHMDB
L-HomocysteineHMDB
Usaf b-12HMDB
Homocysteine, L isomerHMDB
Homocysteine, L-isomerHMDB
2 Amino 4 mercaptobutyric acidHMDB
L-Isomer homocysteineHMDB
(+-)-homocysteinebiospider
(2S)-2-amino-4-sulfanylbutanoic acidbiospider
(S)-2-amino-4-mercapto-Butanoatebiospider
(S)-2-amino-4-mercapto-Butanoic acidbiospider
2 amino 4 mercaptobutyric acidbiospider
2-amino-4-mercapto-Butanoatebiospider
2-amino-4-mercapto-Butanoic acidbiospider
2-amino-4-mercapto-Butyric acidbiospider
2-amino-4-mercapto-DL-Butyratebiospider
2-amino-4-mercapto-DL-Butyric acidbiospider
2-amino-4-MercaptobutyrateGenerator
2-Amino-4-mercaptobutyric acid (VAN)biospider
2-amino-4-sulfanylbutanoatebiospider
2-amino-4-sulfanylbutanoic acidbiospider
Butanoic acid, 2-amino-4-mercapto-biospider
Butanoic acid, 2-amino-4-mercapto- (VAN)biospider
Butanoic acid, 2-amino-4-mercapto-, (S)-biospider
Butyric acid, 2-amino-4-mercapto-biospider
Butyric acid, 2-amino-4-mercapto-, DL-biospider
Butyric acid, 2-amino-4-mercapto-, DL- (9CI)biospider
Butyric acid, 2-amino-4-mercapto-, L-biospider
D,l-homocysteinebiospider
DL-2-amino-4-mercapto-Butyric acidbiospider
DL-homocysteinebiospider
DL-homocysteine (free base)biospider
Homo-CYSbiospider
Homocysteinebiospider
Homocysteine (van)biospider
Homocysteine, l isomerbiospider
Homocysteine, l-biospider
Homocysteine, l-isomerbiospider
L-2-amino-4-mercapto-Butyric acidbiospider
l-2-amino-4-mercaptobutyric acidbiospider
L-isomer homocysteinebiospider
Predicted Properties
PropertyValueSource
Water Solubility14.8 g/LALOGPS
logP-2.3ALOGPS
logP-2.6ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)2.46ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.94 m³·mol⁻¹ChemAxon
Polarizability13.44 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H9NO2S
IUPAC name2-amino-4-sulfanylbutanoic acid
InChI IdentifierInChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)
InChI KeyFFFHZYDWPBMWHY-UHFFFAOYSA-N
Isomeric SMILESNC(CCS)C(O)=O
Average Molecular Weight135.185
Monoisotopic Molecular Weight135.035399227
Classification
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
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point232-233 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKa2.22
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0059-0930000000-b4e6d47b81f1810f1f31JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0910000000-7b3c5664e3b6b1930674JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0910000000-0dbe4ce28b468fb874f0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9730000000-952f5d413ee77e474820JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03yi-3900000000-b5bcb65d1cfa2f5b4a83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0059-1950000000-09d1f6d02198624082eaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0059-0981000000-c6d399e1bddf1f7bc057JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0059-0930000000-b4e6d47b81f1810f1f31JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9730000000-952f5d413ee77e474820JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03yi-3900000000-b5bcb65d1cfa2f5b4a83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0059-1950000000-09d1f6d02198624082eaJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-1f800d28bca4b2b7a49fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-9700000000-368cb861e20b107da57aJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9300000000-a8fd35730e901755194eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-0e79cc37f5cb8f05cd37JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9000000000-694b412a6bed9a77958eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9700000000-2e1b7e55ed5da543b557JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-7e82906cac0f17bd5123JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9000000000-7c49d870f77950b940a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3900000000-4e1b7a42d769b9c2574cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-7900000000-35b3c5fd78dec88148fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-533b0cacf1e578850e94JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID757
ChEMBL IDCHEMBL310604
KEGG Compound IDC05330
Pubchem Compound ID778
Pubchem Substance IDNot Available
ChEBI ID17230
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00742
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDL-HOMOCYSTEINE
BIGG ID45588
KNApSAcK IDC00001365
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHomocysteine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
seasoningDUKE
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Betaine MetabolismSMP00123 map00260
Catecholamine BiosynthesisSMP00012 map00350
Glycine and Serine MetabolismSMP00004 map00260
Homocysteine DegradationSMP00455 Not Available
Methionine MetabolismSMP00033 map00270
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.