HOMOCYSTEINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C4H9NO2S
Molecular Weight	135.185
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FFFHZYDWPBMWHY-VKHMYHEASA-N

InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C4H9NO2S
Molecular Weight	135.185
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27198616 | https://www.ncbi.nlm.nih.gov/pubmed/22270909 | https://www.ncbi.nlm.nih.gov/pubmed/10063987

Homocysteine, an amino acid synthesized intracellularly by removal of the N-methyl group from the essential amino acid methionine. High plasma level of homocysteine is called hyperhomocysteinemia is a clinical biomarker for increased risk of cardiovascular disease, thromboembolic diseases, and myocardial infarction. It was shown, that hyperhomocysteinemia could be an independent risk factor for dementia and Alzheimer's disease. The falling of homocysteine concentrations in response to increasing B-group-vitamin status, have the hope that mental decline, or Alzheimer's disease, could be prevented by dietary modification or food fortification. Besides, homocysteine can behave as an anti-oxidant agent by increasing the antioxidant capacity of the tumor and endothelial cells.

Approval Year

PubMed

Title	Date	PubMed
Mutations in the regulatory domain of cystathionine beta synthase can functionally suppress patient-derived mutations in cis.	2001-03-15	11230183
Plasma folate, vitamin B(12), and homocyst(e)ine concentrations in preeclamptic and normotensive Peruvian women.	2001-03-01	11226979
Mice deficient in methylenetetrahydrofolate reductase exhibit hyperhomocysteinemia and decreased methylation capacity, with neuropathology and aortic lipid deposition.	2001-03-01	11181567
Interaction of estrogen replacement therapy with the thrombophilic 20210 G/A prothrombin gene mutation for atherothrombotic vascular disease: a cross-sectional study of 275 hyperlipidemic women.	2001-03	11230792
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.	2001-03	11223523
Hyperhomocysteinemia and hypercholesterolemia associated with hypothyroidism in the third US National Health and Nutrition Examination Survey.	2001-03	11223442
The effects of oral methionine and homocysteine on endothelial function.	2001-03	11179277
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.	2001-03	11179081
Effect of nicotinic acid administration on hepatic very low density lipoprotein-triglyceride production.	2001-03	11171611
Hyperhomocysteinemia is associated with venous thrombosis in patients with short bowel syndrome.	2001-02-24	11190983
Genetic determinants of homocysteine thiolactonase activity in humans: implications for atherosclerosis.	2001-02-23	11226414
Supplementation of atherogenic diet with B vitamins does not prevent atherosclerosis or vascular dysfunction in monkeys.	2001-02-20	11181477
Differences between cysteine and homocysteine in the induction of deoxyribose degradation and DNA damage.	2001-02-15	11182290
Does renal failure cause an atherosclerotic milieu in patients with end-stage renal disease?	2001-02-15	11182106
[Folates, vitamin B12, homocysteine and neural tube defects].	2001-02-15	11174111
[Plasma homocysteine measurement: a study of pre-analytical variation factors for conditions for total plasma homocysteine concentration].	2001-02-15	11174098
Serum homocysteine and stroke in atrial fibrillation.	2001-02-06	11177349
Homocysteine, fibrinogen, and lipoprotein(a) levels are simultaneously reduced in patients with chronic renal failure treated with folic acid, pyridoxine, and cyanocobalamin.	2001-02	11229418
Mutations in the gene for methylenetetrahydrofolate reductase, homocysteine levels, and vitamin status in women with a history of preeclampsia.	2001-02	11228493
Randomized control study of the effects of raloxifene on serum lipids and homocysteine in older women.	2001-02	11228485
Hypercoagulable thrombophilic defects and hyperhomocysteinemia in patients with recurrent pregnancy loss.	2001-02	11216876
Beneficial effects of a soy-based dietary supplement on lipid levels and cardiovascular risk markers in type 2 diabetic subjects.	2001-02	11213870
Determinants of changes in plasma homocysteine in hyperthyroidism and hypothyroidism.	2001-02	11207634
Homocysteine and stroke.	2001-02	11176224
Established and emerging cardiovascular risk factors.	2001-02	11174359
C-reactive protein is not associated with the presence or extent of calcified subclinical atherosclerosis.	2001-02	11174333
Vitamin Intervention for Stroke Prevention (VISP) trial: rationale and design.	2001-02	11174041
Crystallization and preliminary X-ray diffraction analysis of the active core of human recombinant cystathionine beta-synthase: an enzyme involved in vascular disease.	2001-02	11173483
Low seminal plasma folate concentrations are associated with low sperm density and count in male smokers and nonsmokers.	2001-02	11172823
Elevation of asymmetrical dimethylarginine may mediate endothelial dysfunction during experimental hyperhomocyst(e)inaemia in humans.	2001-02	11171285
Protein-bound uremic solutes: the forgotten toxins.	2001-02	11169024
Homocysteine, its metabolites, and B-group vitamins in renal transplant patients.	2001-02	11169023
Is there a role of cyclosporine A on total homocysteine export from human renal proximal tubular epithelial cells?	2001-02	11169022
Characterization of the zinc sites in cobalamin-independent and cobalamin-dependent methionine synthase using zinc and selenium X-ray absorption spectroscopy.	2001-01-30	11170420
[Homocysteine--CRP--lipoprotein (a). When do you evaluate the "new" risk factors].	2001-01-25	11219276
Unsuspected hyperhomocysteinemia in chronically anticoagulated patients.	2001-01	11229831
Longitudinal vitamin and homocysteine levels in normal pregnancy.	2001-01	11227033
[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options].	2001-01	11220081
Homocysteine stimulates the expression of monocyte chemoattractant protein-1 in endothelial cells leading to enhanced monocyte chemotaxis.	2001-01	11216856
[Plasma homocysteine predicts mortality independently of traditional risk factors and C-reactive protein in patients with angiographically defined coronary artery disease].	2001-01	11216087
Effects of methionine loading on plasma and erythrocyte sulphur amino acids and sulph-hydryls before and after co-factor supplementation in haemodialysis patients.	2001-01	11209001
Plasma total homocysteine concentration in nephrotic patients with idiopathic membranous nephropathy.	2001-01	11208992
The direct electrochemistry of myoglobin at a DL-homocysteine self-assembled gold electrode.	2001-01	11206930
Gene-environment and gene-gene interaction in the determination of plasma homocysteine levels in healthy middle-aged men.	2001-01	11204591
Relationships between homocysteine, folate and vitamin B12 levels with the methylenetetrahydrofolate reductase polymorphism, in Indians from Western Venezuela.	2001-01	11204578
Homocysteine: a new cardiac risk factor?	2001-01	11195611
Cause and management of heart failure in patients with chronic renal disease.	2001-01	11172554
Risk factors for atherosclerosis in survivors of myocardial infarction and their spouses: comparison to controls without personal and family history of atherosclerosis.	2001-01	11172470
Activation of the ventrolateral periaqueductal gray reduces locomotion but not mean arterial pressure in awake, freely moving rats.	2001	11182252
Homocysteine and human reproduction.	2000	11214939

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:20:34 GMT 2025` Edited by `admin` on `Mon Mar 31 18:20:34 GMT 2025`
Record UNII	0LVT1QZ0BA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HOMOCYSTEINE

Systematic Name

English

NSC-43117

Preferred Name

English

HOMOCYSTEINE, L-

Systematic Name

English

L-HOMOCYSTEINE

Systematic Name

English

(S)-2-AMINO-4-MERCAPTOBUTANOIC ACID

Systematic Name

English

HOMOCYSTEINE [MI]

Common Name

English

(S)-HOMOCYSTEINE

Systematic Name

English

NSC-118376

Code

English

Classification Tree Code System Code

LOINC

54301-7