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
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
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 |
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Target ID: P23526 Gene ID: 191.0 Gene Symbol: AHCY Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28933241 |
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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 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Simultaneous determination of adenosine, S-adenosylhomocysteine and S-adenosylmethionine in biological samples using solid-phase extraction and high-performance liquid chromatography. | 1999 Mar 19 |
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Determination of S-adenosylmethionine and S-adenosylhomocysteine in plasma and cerebrospinal fluid by stable-isotope dilution tandem mass spectrometry. | 2000 Oct |
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Sequence determination and analysis of S-adenosyl-L-homocysteine hydrolase from yellow lupine (Lupinus luteus). | 2001 |
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E1 mice epilepsy shows genetic polymorphism for S-Adenosyl-L-homocysteine hydrolase. | 2001 Apr |
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Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase. | 2001 Dec |
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Computational characterization of substrate binding and catalysis in S-adenosylhomocysteine hydrolase. | 2001 Dec 18 |
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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 |
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Disturbed ratio of erythrocyte and plasma S-adenosylmethionine/S-adenosylhomocysteine in peripheral arterial occlusive disease. | 2001 Jan |
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Purification and properties of recombinant Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase. | 2001 Jan |
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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 |
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Wy-14,643-induced hypomethylation of the c-myc gene in mouse liver. | 2001 Jul |
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Effects of methylmercury and organic acid mercurials on the disposition of exogenous selenium in rats. | 2001 Jul 15 |
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Decrease of methionine and S-adenosylmethionine and increase of homocysteine in treated patients with Parkinson's disease. | 2001 Jul 27 |
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Effect of vitamin B6 deficiency on the synthesis and accumulation of S-adenosylhomocysteine and S-adenosylmethionine in rat tissues. | 2001 Jun |
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Blood determinations of S-adenosylmethionine, S-adenosylhomocysteine, and homocysteine: correlations with diet. | 2001 Jun |
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A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from the S-adenosyl-L-methionine cycle. | 2001 Jun 15 |
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S-Adenosyl-L-homocysteine hydrolase is sequestered into actin rods in Dictyostelium discoideum spores. | 2001 Nov 23 |
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Crystal structure of a protein repair methyltransferase from Pyrococcus furiosus with its L-isoaspartyl peptide substrate. | 2001 Nov 9 |
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COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk. | 2001 Oct |
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Metabolic consequences of hyperhomocysteinemia in uremia. | 2001 Oct |
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Nongenomic regulation of ENaC by aldosterone. | 2001 Oct |
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Abnormal folate metabolism and genetic polymorphism of the folate pathway in a child with Down syndrome and neural tube defect. | 2001 Oct 1 |
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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 |
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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 |
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S-adenosyl-methionine-induced apoptosis in PC12 cells. | 2002 Aug 15 |
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Altered levels of S-adenosylmethionine and S-adenosylhomocysteine in the brains of L-isoaspartyl (D-Aspartyl) O-methyltransferase-deficient mice. | 2002 Aug 2 |
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Synthesis of an alpha-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase. | 2002 Feb 11 |
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Tissue levels of S-adenosylhomocysteine in the rat kidney: effects of ischemia and homocysteine. | 2002 Feb 15 |
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Water-assisted dual mode cofactor recognition by HhaI DNA methyltransferase. | 2002 Feb 8 |
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Crystal structure of guanidinoacetate methyltransferase from rat liver: a model structure of protein arginine methyltransferase. | 2002 Jul 5 |
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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 |
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Contributions of active site residues to the partial and overall catalytic activities of human S-adenosylhomocysteine hydrolase. | 2002 Jun 25 |
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Mechanisms of apoptosis induced by purine nucleosides in astrocytes. | 2002 May |
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Methods for measuring sulfur amino acid metabolism. | 2002 Sep |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7278517
Curator's Comment: Inhibition by S-adenosylhomocysteine (AdoHcy) of the three reactions of phosphatidylethanolamine methyltransferase which catalyzes the production of phosphatidylcholine from phosphatidylethanolamine in guinea pig and rat liver microsomes has been evaluated. The Ki values for the rate-limiting reactions were 3.8 microM and 68 microM in rat and guinea pig livers, respectively. An AdoMet : AdoHcy ratio of 12 : 1 in developing liver was found to decline to a constant value in the adult of 5 : 1.
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80174-6
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80176-1
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C73539
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80175-3
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C103149
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8K31Q2S66S
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213-560-8
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DB01752
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DTXSID30895860
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439155
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57856
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S-Adenosyl-L-homocysteine
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979-92-0
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1012112
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16680
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PARENT (METABOLITE)
SUBSTANCE RECORD