S-ADENOSYL-L-HOMOCYSTEINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H20N6O5S
Molecular Weight	384.411
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C(N)N=CN=C23)C(O)=O

InChI

InChIKey=ZJUKTBDSGOFHSH-WFMPWKQPSA-N

InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15057524 | https://www.ncbi.nlm.nih.gov/pubmed/28684218 | https://www.ncbi.nlm.nih.gov/pubmed/10400831

S-Adenosyl-L-homocysteine (SAH), a potent methyltransferase inhibitor and a substrate of the s-adenosylhomocysteine hydrolase, is an amino acid derivative and an intermediator or modulator of several metabolic pathways, including the activated methyl cycle and cysteine biosynthesis. It was shown, that the plasma SAH might be a novel biomarker for the early clinical identification of cardiovascular disease. In addition, the elevated SAH in Alzheimer's brain was related to markers of disease progression and cognitive impairment.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosylhomocysteinase 5 Target ID: P23526 Gene ID: 191.0 Gene Symbol: AHCY Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28933241	Substrate 661
Phosphatidylethanolamine N-methyltransferase 1 Target ID: Q9UBM1\|\|\|Q9Y6V9 Gene ID: 10400.0 Gene Symbol: PEMT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7278517	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cardiovascular diseases 71 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28684218	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15057524	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Simultaneous determination of adenosine, S-adenosylhomocysteine and S-adenosylmethionine in biological samples using solid-phase extraction and high-performance liquid chromatography.	1999 Mar 19	10219663
Determination of S-adenosylmethionine and S-adenosylhomocysteine in plasma and cerebrospinal fluid by stable-isotope dilution tandem mass spectrometry.	2000 Oct	11017945
Sequence determination and analysis of S-adenosyl-L-homocysteine hydrolase from yellow lupine (Lupinus luteus).	2001	11732617
E1 mice epilepsy shows genetic polymorphism for S-Adenosyl-L-homocysteine hydrolase.	2001 Apr	11137630
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.	2001 Dec	11780762
Computational characterization of substrate binding and catalysis in S-adenosylhomocysteine hydrolase.	2001 Dec 18	11735397
In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense.	2001 Feb 15	11226379
Disturbed ratio of erythrocyte and plasma S-adenosylmethionine/S-adenosylhomocysteine in peripheral arterial occlusive disease.	2001 Jan	11137094
Purification and properties of recombinant Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase.	2001 Jan	11134963
S-Adenosyl-L-homocysteine hydrolase inhibitor mediates immunosuppressive effects in vivo: suppression of delayed type hypersensitivity ear swelling and peptidoglycan polysaccharide-induced arthritis.	2001 Jan	11123369
Wy-14,643-induced hypomethylation of the c-myc gene in mouse liver.	2001 Jul	11399790
Effects of methylmercury and organic acid mercurials on the disposition of exogenous selenium in rats.	2001 Jul 15	11446833
Decrease of methionine and S-adenosylmethionine and increase of homocysteine in treated patients with Parkinson's disease.	2001 Jul 27	11445284
Effect of vitamin B6 deficiency on the synthesis and accumulation of S-adenosylhomocysteine and S-adenosylmethionine in rat tissues.	2001 Jun	11575573
Blood determinations of S-adenosylmethionine, S-adenosylhomocysteine, and homocysteine: correlations with diet.	2001 Jun	11401915
A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from the S-adenosyl-L-methionine cycle.	2001 Jun 15	11418110
S-Adenosyl-L-homocysteine hydrolase is sequestered into actin rods in Dictyostelium discoideum spores.	2001 Nov 23	11728467
Crystal structure of a protein repair methyltransferase from Pyrococcus furiosus with its L-isoaspartyl peptide substrate.	2001 Nov 9	11700066
COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk.	2001 Oct	11577006
Metabolic consequences of hyperhomocysteinemia in uremia.	2001 Oct	11576929
Nongenomic regulation of ENaC by aldosterone.	2001 Oct	11546647
Abnormal folate metabolism and genetic polymorphism of the folate pathway in a child with Down syndrome and neural tube defect.	2001 Oct 1	11568918
Reversed-phase high-performance liquid chromatography procedure for the simultaneous determination of S-adenosyl-L-methionine and S-adenosyl-L-homocysteine in mouse liver and the effect of methionine on their concentrations.	2001 Oct 5	11589459
DNA cleavage by type III restriction-modification enzyme EcoP15I is independent of spacer distance between two head to head oriented recognition sites.	2001 Sep 28	11575924
S-adenosyl-methionine-induced apoptosis in PC12 cells.	2002 Aug 15	12210845
Altered levels of S-adenosylmethionine and S-adenosylhomocysteine in the brains of L-isoaspartyl (D-Aspartyl) O-methyltransferase-deficient mice.	2002 Aug 2	12023972
Synthesis of an alpha-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase.	2002 Feb 11	11814819
Tissue levels of S-adenosylhomocysteine in the rat kidney: effects of ischemia and homocysteine.	2002 Feb 15	11992651
Water-assisted dual mode cofactor recognition by HhaI DNA methyltransferase.	2002 Feb 8	11729191
Crystal structure of guanidinoacetate methyltransferase from rat liver: a model structure of protein arginine methyltransferase.	2002 Jul 5	12079381
Interaction of S-adenosylhomocysteine hydrolase of Xenopus laevis with mRNA(guanine-7-)methyltransferase: implication on its nuclear compartmentalisation and on cap methylation of hnRNA.	2002 Jun 12	12063172
Contributions of active site residues to the partial and overall catalytic activities of human S-adenosylhomocysteine hydrolase.	2002 Jun 25	12069606
Mechanisms of apoptosis induced by purine nucleosides in astrocytes.	2002 May	11968056
Methods for measuring sulfur amino acid metabolism.	2002 Sep	12172474

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

S-ADENOSYL-L-HOMOCYSTEINE

Common Name

English

S-ADENOSYL-L-HOMOCYSTEINE [USP-RS]

Common Name

English

L-HOMOCYSTEINE, S-(5'-DEOXYADENOSIN-5'-YL)-

Systematic Name

English

S-(5'-ADENOSYL)-L-HOMOCYSTEINE

Systematic Name

English

ADENOSYLHOMOCYSTEINE

Common Name

English

Classification Tree Code System Code

LOINC

80174-6