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Details

Stereochemistry ABSOLUTE
Molecular Formula C4H9NO2S.ClH
Molecular Weight 171.646
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HOMOCYSTEINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=PDUMWBLAPMSFGD-DFWYDOINSA-N
InChI=1S/C4H9NO2S.ClH/c5-3(1-2-8)4(6)7;/h3,8H,1-2,5H2,(H,6,7);1H/t3-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

PubMed

TitleDatePubMed
Mutations in the regulatory domain of cystathionine beta synthase can functionally suppress patient-derived mutations in cis.
2001-03-15
Plasma folate, vitamin B(12), and homocyst(e)ine concentrations in preeclamptic and normotensive Peruvian women.
2001-03-01
Mice deficient in methylenetetrahydrofolate reductase exhibit hyperhomocysteinemia and decreased methylation capacity, with neuropathology and aortic lipid deposition.
2001-03-01
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
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.
2001-03
Hyperhomocysteinemia and hypercholesterolemia associated with hypothyroidism in the third US National Health and Nutrition Examination Survey.
2001-03
The effects of oral methionine and homocysteine on endothelial function.
2001-03
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.
2001-03
Effect of nicotinic acid administration on hepatic very low density lipoprotein-triglyceride production.
2001-03
Hyperhomocysteinemia is associated with venous thrombosis in patients with short bowel syndrome.
2001-02-24
Genetic determinants of homocysteine thiolactonase activity in humans: implications for atherosclerosis.
2001-02-23
Supplementation of atherogenic diet with B vitamins does not prevent atherosclerosis or vascular dysfunction in monkeys.
2001-02-20
Differences between cysteine and homocysteine in the induction of deoxyribose degradation and DNA damage.
2001-02-15
Does renal failure cause an atherosclerotic milieu in patients with end-stage renal disease?
2001-02-15
[Folates, vitamin B12, homocysteine and neural tube defects].
2001-02-15
[Plasma homocysteine measurement: a study of pre-analytical variation factors for conditions for total plasma homocysteine concentration].
2001-02-15
Serum homocysteine and stroke in atrial fibrillation.
2001-02-06
Homocysteine, fibrinogen, and lipoprotein(a) levels are simultaneously reduced in patients with chronic renal failure treated with folic acid, pyridoxine, and cyanocobalamin.
2001-02
Mutations in the gene for methylenetetrahydrofolate reductase, homocysteine levels, and vitamin status in women with a history of preeclampsia.
2001-02
Randomized control study of the effects of raloxifene on serum lipids and homocysteine in older women.
2001-02
Hypercoagulable thrombophilic defects and hyperhomocysteinemia in patients with recurrent pregnancy loss.
2001-02
Beneficial effects of a soy-based dietary supplement on lipid levels and cardiovascular risk markers in type 2 diabetic subjects.
2001-02
Determinants of changes in plasma homocysteine in hyperthyroidism and hypothyroidism.
2001-02
Homocysteine and stroke.
2001-02
Established and emerging cardiovascular risk factors.
2001-02
C-reactive protein is not associated with the presence or extent of calcified subclinical atherosclerosis.
2001-02
Vitamin Intervention for Stroke Prevention (VISP) trial: rationale and design.
2001-02
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
Low seminal plasma folate concentrations are associated with low sperm density and count in male smokers and nonsmokers.
2001-02
Elevation of asymmetrical dimethylarginine may mediate endothelial dysfunction during experimental hyperhomocyst(e)inaemia in humans.
2001-02
Protein-bound uremic solutes: the forgotten toxins.
2001-02
Homocysteine, its metabolites, and B-group vitamins in renal transplant patients.
2001-02
Is there a role of cyclosporine A on total homocysteine export from human renal proximal tubular epithelial cells?
2001-02
Characterization of the zinc sites in cobalamin-independent and cobalamin-dependent methionine synthase using zinc and selenium X-ray absorption spectroscopy.
2001-01-30
[Homocysteine--CRP--lipoprotein (a). When do you evaluate the "new" risk factors].
2001-01-25
Unsuspected hyperhomocysteinemia in chronically anticoagulated patients.
2001-01
Longitudinal vitamin and homocysteine levels in normal pregnancy.
2001-01
[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options].
2001-01
Homocysteine stimulates the expression of monocyte chemoattractant protein-1 in endothelial cells leading to enhanced monocyte chemotaxis.
2001-01
[Plasma homocysteine predicts mortality independently of traditional risk factors and C-reactive protein in patients with angiographically defined coronary artery disease].
2001-01
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
Plasma total homocysteine concentration in nephrotic patients with idiopathic membranous nephropathy.
2001-01
The direct electrochemistry of myoglobin at a DL-homocysteine self-assembled gold electrode.
2001-01
Gene-environment and gene-gene interaction in the determination of plasma homocysteine levels in healthy middle-aged men.
2001-01
Relationships between homocysteine, folate and vitamin B12 levels with the methylenetetrahydrofolate reductase polymorphism, in Indians from Western Venezuela.
2001-01
Homocysteine: a new cardiac risk factor?
2001-01
Cause and management of heart failure in patients with chronic renal disease.
2001-01
Risk factors for atherosclerosis in survivors of myocardial infarction and their spouses: comparison to controls without personal and family history of atherosclerosis.
2001-01
Activation of the ventrolateral periaqueductal gray reduces locomotion but not mean arterial pressure in awake, freely moving rats.
2001
Homocysteine and human reproduction.
2000
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:09:39 GMT 2025
Edited
by admin
on Mon Mar 31 18:09:39 GMT 2025
Record UNII
N5USW93BVS
Record Status Validated (UNII)
Record Version
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Name Type Language
HOMOCYSTEINE HYDROCHLORIDE
Systematic Name English
(S)-2-AMINO-4-MERCAPTOBUTANOIC ACID HYDROCHLORIDE
Preferred Name English
L-HOMOCYSTEINE, HYDROCHLORIDE
Systematic Name English
HOMOCYSTEINE HYDROCHLORIDE, L-
Systematic Name English
Code System Code Type Description
PUBCHEM
71587034
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
PRIMARY
FDA UNII
N5USW93BVS
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
PRIMARY
EPA CompTox
DTXSID50174088
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
PRIMARY
CAS
20244-20-6
Created by admin on Mon Mar 31 18:09:39 GMT 2025 , Edited by admin on Mon Mar 31 18:09:39 GMT 2025
PRIMARY
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