HOMOCYSTINE, L-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H16N2O4S2
Molecular Weight	268.354
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CCSSCC[C@H](N)C(O)=O)C(O)=O

InChI

InChIKey=ZTVZLYBCZNMWCF-WDSKDSINSA-N

InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6-/m0/s1

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Importance of the trans-sulfuration pathway in cancer prevention and promotion.	2007-07	17180248
Metabolic derangement of methionine and folate metabolism in mice deficient in methionine synthase reductase.	2007-05	17369066
Influence of combined methionine synthase (MTR 2756A > G) and methylenetetrahydrofolate reductase (MTHFR 677C > T) polymorphisms to plasma homocysteine levels in Korean patients with ischemic stroke.	2007-04-30	17461517
A rationale for cystine supplementation in severe homocystinuria.	2007-02	17186416
Targeting of metallothionein by L-homocysteine: a novel mechanism for disruption of zinc and redox homeostasis.	2007-01	17082481
Thermolabile methylenetetrahydrofolate reductase C677T polymorphism and homocysteine are risk factors for coronary artery disease in Moroccan population.	2007	17497026
Differential effects of endogenous cysteine analogs on peripheral thermal nociception in intact rats.	2006-11	16782275
Homocysteine, vitamin B12 and folate levels in premature coronary artery disease.	2006-09-26	17002799
The screening power of methylenetetrahydrofolate reductase C677T polymorphism versus plasma homocysteine concentration in patients with stenosis of the internal carotid artery.	2006-09-25	16999862
A new method for determination of plasma homocystine by isotope dilution and electrospray tandem mass spectrometry.	2006-09-14	16787765
Folate and vitamin B6 rapidly normalize endothelial dysfunction in children with type 1 diabetes mellitus.	2006-07	16818571
California Men's Health Study (CMHS): a multiethnic cohort in a managed care setting.	2006-06-30	16813653
Rationale and design for the CARDIOVIT Study (Cardiovit, Atherosclerotic vascular disease and hypeRhomocysteinemia: an epiDemiological study in Indians, additionally evaluating the effect of Oral VITamin supplementation).	2006-04	16684424
Homocysteine transport by human aortic endothelial cells: identification and properties of import systems.	2006-02-15	16455044
Homocyst(e)ine and stroke.	2006-02	16479441
Mining literature for a comprehensive pathway analysis: a case study for retrieval of homocysteine related genes for genetic and epigenetic studies.	2006-01-23	16430779
Comparison of isocaloric very low carbohydrate/high saturated fat and high carbohydrate/low saturated fat diets on body composition and cardiovascular risk.	2006-01-11	16403234
Methylenetetrahydrofolate reductase polymorphism 677C>T is associated with peripheral arterial disease in type 2 diabetes.	2005-11-07	16274479
Workgroup report: Biomonitoring study design, interpretation, and communication--lessons learned and path forward.	2005-11	16263520
Fibrinogen, homocyst(e)ine, and C-reactive protein concentrations relative to sex and socioeconomic status in British young people.	2005-10-29	16254908
Homocyst(e)ine-lowering therapy does not affect plasma asymmetrical dimethylarginine concentrations in patients with peripheral artery disease.	2005-04	15634723
Aleurone flour increases red-cell folate and lowers plasma homocyst(e)ine substantially in man.	2005-03	15877875
Hyperhomocyst(e)inemia impairs angiogenesis in a murine model of limb ischemia.	2005-02	15920995
Asymmetric dimethyl-L-arginine (ADMA): a possible link between homocyst(e)ine and endothelial dysfunction.	2005-02	15720202
Endothelial dysfunction: cardiovascular risk factors, therapy, and outcome.	2005	17319104
Pyridoxine supplementation corrects vitamin B6 deficiency but does not improve inflammation in patients with rheumatoid arthritis.	2005	16277693
Inflammation causes tissue-specific depletion of vitamin B6.	2005	16277678
Is Hyperhomocyst(e)inemia a humoral predictor of coronary heart disease?	2005	16026288
High levels of homocysteine inhibit lysyl oxidase (LOX) and downregulate LOX expression in vascular endothelial cells.	2004-11	15488859
Hyperhomocyst(e)inemia is an important risk factor for vascular disease in subjects with high-molecular weight apo(a) isoforms.	2004-10-16	15483732
The C677T methylenetetrahydrofolate reductase variant and third trimester obstetrical complications in women with unexplained elevations of maternal serum alpha-fetoprotein.	2004-09-07	15352998
[A case of young adult presenting with cerebral infarction caused by homocystinuria].	2004-09	15552867
Homocysteine and reactive oxygen species in metabolic syndrome, type 2 diabetes mellitus, and atheroscleropathy: the pleiotropic effects of folate supplementation.	2004-05-10	15134582
Methylenetetrahydrofolate reductase 677 C-->T polymorphism and plasma folate in relation to pre-eclampsia risk among Peruvian women.	2004-05	15280126
Long-term treatment with probucol improves endothelial function in patients with coronary artery disease.	2004-05	15198477
[Prevention of dementia (including Alzheimer's disease)].	2004-05	15141356
The C677 mutation in methylene tetrahydrofolate reductase gene: correlation with uric acid and cardiovascular risk factors in elderly Korean men.	2004-04	15082892
Folic acid improves endothelial function in children and adolescents with type 1 diabetes.	2004-04	15069400
L-Homocysteine and L-homocystine stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells.	2004-03-01	14980706
Methylenetetrahydrofolate reductase and transcobalamin genetic polymorphisms in human spontaneous abortion: biological and clinical implications.	2004-02-17	14969589
Comparing the ESA HPLC total homocysteine assay with electrochemical detection to the CDC in-house HPLC assay with fluorescence detection.	2004-02	14734212
Endothelial dysfunction induced by hyperhomocyst(e)inemia: role of asymmetric dimethylarginine.	2003-08-26	12912818
Distribution of serum total homocysteine and its association with diabetes and cardiovascular risk factors of the insulin resistance syndrome in Mexican American men: the Third National Health and Nutrition Examination Survey.	2003-08-05	12952548
Effects of vitamin supplementation and hyperhomocysteinemia on atherosclerosis in apoE-deficient mice.	2003-06	12801608
Low vitamin B6 but not homocyst(e)ine is associated with increased risk of stroke and transient ischemic attack in the era of folic acid grain fortification.	2003-06	12738890
Association between homocyst(e)ine levels and risk of vascular events.	2003-03	12730702
Study of total homocyst(e)ine levels in type 2 diabetic patients with silent brain infarction.	2003	15526524
2 minute non-invasive screening for cardio-vascular diseases: relative limitation of C-Reactive Protein compared with more sensitive L-Homocystine as cardio-vascular risk factors; safe and effective treatment using the selective drug uptake enhancement method.	2003	12934959
Established and recently identified coronary heart disease risk factors in young people: the influence of physical activity and physical fitness.	2003	12846588
Patients with atherosclerotic vascular disease: how low should plasma homocyst(e)ine levels go?	2001	14728038

Patents

Name

Type

Language

BUTANOIC ACID, 4,4'-DITHIOBIS(2-AMINO-, (2S,2'S)-

Preferred Name

English

HOMOCYSTINE, L-

Systematic Name

English

HOMOCYSTINE

Systematic Name

English

HOMOCYSTINE, (+)-

Systematic Name

English

BUTYRIC ACID, 4,4'-DITHIOBIS(2-AMINO-, L-

Common Name

English

L-HOMOCYSTINE [MI]

Common Name

English

BUTANOIC ACID, 4,4'-DITHIOBIS(2-AMINO-, (S-(R*,R*))-

Common Name

English

Classification Tree Code System Code

LOINC

55879-1