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

Molecular Formula	C14H20N6O5S
Molecular Weight	384.411
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Rapid conversion of tea catechins to monomethylated products by rat liver cytosolic catechol-O-methyltransferase.	2001 Dec	11780762
Mechanisms of aldosterone's action on epithelial Na + transport.	2001 Dec 1	11891557
Computational characterization of substrate binding and catalysis in S-adenosylhomocysteine hydrolase.	2001 Dec 18	11735397
S-Adenosyl-L-homocysteine hydrolase is sequestered into actin rods in Dictyostelium discoideum spores.	2001 Nov 23	11728467
Targeting "hydrolytic" activity of the S-adenosyl-L-homocysteine hydrolase.	2001 Sep	12369977
High dietary folate supplementation: effects on diet utilization and methionine metabolism in aged rats.	2002	11813082
S-adenosylhomocysteine, but not homocysteine, is toxic to yeast lacking cystathionine beta-synthase.	2002 Apr	12051965
LuxS: its role in central metabolism and the in vitro synthesis of 4-hydroxy-5-methyl-3(2H)-furanone.	2002 Apr	11932438
The receptor docking segment and S-adenosyl-L-homocysteine bind independently to the methyltransferase of bacterial chemotaxis.	2002 Apr 1	11983418
RNA:(guanine-N2) methyltransferases RsmC/RsmD and their homologs revisited--bioinformatic analysis and prediction of the active site based on the uncharacterized Mj0882 protein structure.	2002 Apr 3	11929612
The curly-tail (ct) mouse, an animal model of neural tube defects, displays altered homocysteine metabolism without folate responsiveness or a defect in Mthfr.	2002 Aug	12208134
Elevated plasma total homocysteine in severe methionine adenosyltransferase I/III deficiency.	2002 Aug	12145770
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
3-OMD and homocysteine plasma levels in parkinsonian patients.	2002 Feb	12075857
Crystallization of PNMT, the adrenaline-synthesizing enzyme, is critically dependent on a high protein concentration.	2002 Feb	11807261
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
Mutations in human glycine N-methyltransferase give insights into its role in methionine metabolism.	2002 Jan	11810299
Studies of methionine cycle intermediates (SAM, SAH), DNA methylation and the impact of folate deficiency on tumor numbers in Min mice.	2002 Jan	11756224
New neplanocin analogues. 12. Alternative synthesis and antimalarial effect of (6'R)-6'-C-methylneplanocin A, a potent AdoHcy hydrolase inhibitor.	2002 Jan 31	11806727
Folate deficiency, methionine metabolism, and alcoholic liver disease.	2002 Jul	12163145
Alcohol abuse: an important cause of severe hyperhomocysteinemia.	2002 Jul	12144201
3-deazaneplanocin A induces massively increased interferon-alpha production in Ebola virus-infected mice.	2002 Jul	12076759
Quantification of plasma S-adenosylmethionine and S-adenosylhomocysteine as their fluorescent 1,N(6)-etheno derivatives: an adaptation of previously described methodology.	2002 Jul 31	12093531
Crystal structure of guanidinoacetate methyltransferase from rat liver: a model structure of protein arginine methyltransferase.	2002 Jul 5	12079381
Structural basis for the modulation of lignin monomer methylation by caffeic acid/5-hydroxyferulic acid 3/5-O-methyltransferase.	2002 Jun	12084826
Catechol-O-Methyltransferase (COMT)-mediated methylation metabolism of endogenous bioactive catechols and modulation by endobiotics and xenobiotics: importance in pathophysiology and pathogenesis.	2002 Jun	12083324
The effect of troglitazone on plasma homocysteine, hepatic and red blood cell S-adenosyl methionine, and S-adenosyl homocysteine and enzymes in homocysteine metabolism in Zucker rats.	2002 Jun	12037736
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
S-adenosylmethionine conformations in solution and in protein complexes: conformational influences of the sulfonium group.	2002 Jun 18	12056895
Catalytic mechanism of S-adenosylhomocysteine hydrolase. Site-directed mutagenesis of Asp-130, Lys-185, Asp-189, and Asn-190.	2002 Jun 21	11927587
Contributions of active site residues to the partial and overall catalytic activities of human S-adenosylhomocysteine hydrolase.	2002 Jun 25	12069606
An RNA cap (nucleoside-2'-O-)-methyltransferase in the flavivirus RNA polymerase NS5: crystal structure and functional characterization.	2002 Jun 3	12032088
Sugar-modified conjugated diene analogues of adenosine and uridine: synthesis, interaction with S-adenosyl-L-homocysteine hydrolase, and antiviral and cytostatic effects.	2002 Jun 6	12036374
Identification and characterization of tRNA (Gm18) methyltransferase from Thermus thermophilus HB8: domain structure and conserved amino acid sequence motifs.	2002 Mar	11918670
Identification of an S-adenosylhomocysteine hydrolase-like transcript induced during dendritic cell differentiation.	2002 Mar	11904675
Adenosine kinase deficiency is associated with developmental abnormalities and reduced transmethylation.	2002 Mar	11891238
Crystal structure of human L-isoaspartyl-O-methyl-transferase with S-adenosyl homocysteine at 1.6-A resolution and modeling of an isoaspartyl-containing peptide at the active site.	2002 Mar	11847284
Inhibition of S-adenosylhomocysteine hydrolase by acyclic sugar adenosine analogue D-eritadenine. Crystal structure of S-adenosylhomocysteine hydrolase complexed with D-eritadenine.	2002 Mar 1	11741948
Crystal structure of human L-isoaspartyl methyltransferase.	2002 Mar 22	11792715
Mechanisms of apoptosis induced by purine nucleosides in astrocytes.	2002 May	11968056
Diethanolamine induces hepatic choline deficiency in mice.	2002 May	11961214
Prenylcysteine carboxymethyltransferase type III activity is decreased in retinoic acid-treated SH-SY5Y neuroblastoma cells.	2002 May	11906819
Characterization of human soluble high and low activity catechol-O-methyltransferase catalyzed catechol estrogen methylation.	2002 Oct	12360102
Characterization of the cAMP binding site of purified S-adenosyl-homocysteine hydrolase from bovine kidney.	2002 Oct 15	12234600
Stereoselective synthesis of a novel apio analogue of neplanocin A as potential S-adenosylhomocysteine hydrolase inhibitor.	2002 Oct 3	12323054
Methods for measuring sulfur amino acid metabolism.	2002 Sep	12172474
Effect of hyperhomocysteinemia on plasma or tissue adenosine levels and renal function.	2002 Sep 3	12208805

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:51:20 UTC 2023` Edited by `admin` on `Sat Dec 16 10:51:20 UTC 2023`
Record UNII	8K31Q2S66S
Record Status	`Validated (UNII)`
Record Version

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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