S-アデノシルホモシステイン
WordNet
- the 19th letter of the Roman alphabet (同)s
PrepTutorEJDIC
- sulfurの化学記号 / {略}South[ern]
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/10/22 14:54:03」(JST)
[Wiki en表示]
S-Adenosyl-L-homocysteine
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Names |
IUPAC name
S-(5'-Deoxyadenos-5'-yl)-L-homocysteine
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Other names
AdoHcy, 2-S-adenosyl-L-homocysteine,
5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine S-adenosylhomocysteine, SAH
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Identifiers |
CAS Registry Number
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979-92-0 Y |
ChEBI |
CHEBI:16680 Y |
ChEMBL |
ChEMBL418052 Y |
ChemSpider |
388301 Y |
InChI
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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 Y
Key: ZJUKTBDSGOFHSH-WFMPWKQPSA-N Y
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InChI=1/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
Key: ZJUKTBDSGOFHSH-WFMPWKQPBX
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IUPHAR/BPS
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5265 |
Jmol-3D images |
Image |
KEGG |
C00021 Y |
MeSH |
S-Adenosylhomocysteine |
PubChem |
439155 |
SMILES
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O=C(O)[C@@H](N)CCSC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O
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Properties |
Chemical formula
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C14H20N6O5S |
Molar mass |
384.412 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Y verify (what is: Y/N?) |
Infobox references |
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S-Adenosyl-L-homocysteine (SAH) is an amino acid derivative used in several metabolic pathways in most organisms. It is an intermediate in the synthesis of cysteine and adenosine.
SAH is formed by the demethylation of S-adenosyl-L-methionine (SAM), which can be inhibited by 3-Deazaneplanocin_A.
External links
- BioCYC E.Coli K-12 Compound: S-adenosyl-L-homocysteine
Amino acid metabolism metabolic intermediates
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K→acetyl-CoA |
lysine→
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- Saccharopine
- Allysine
- α-Aminoadipic acid
- α-Ketoadipate
- Glutaryl-CoA
- Glutaconyl-CoA
- Crotonyl-CoA
- β-Hydroxybutyryl-CoA
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leucine→
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- α-Ketoisocaproic acid
- Isovaleryl-CoA
- 3-Methylcrotonyl-CoA
- 3-Methylglutaconyl-CoA
- HMG-CoA
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tryptophan→alanine→
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- N'-Formylkynurenine
- Kynurenine
- Anthranilic acid
- 3-Hydroxykynurenine
- 3-Hydroxyanthranilic acid
- 2-Amino-3-carboxymuconic semialdehyde
- 2-Aminomuconic semialdehyde
- 2-Aminomuconic acid
- Glutaryl-CoA
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G |
G→pyruvate→citrate
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glycine→serine→
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- glycine→creatine: Glycocyamine
- Phosphocreatine
- Creatinine
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G→glutamate→
α-ketoglutarate
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histidine→
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- Urocanic acid
- Imidazol-4-one-5-propionic acid
- Formiminoglutamic acid
- Glutamate-1-semialdehyde
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proline→
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- 1-Pyrroline-5-carboxylic acid
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arginine→
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- Agmatine
- Ornithine
- Cadaverine
- Putrescine
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other
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- cysteine+glutamate→glutathione: γ-Glutamylcysteine
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G→propionyl-CoA→
succinyl-CoA
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valine→
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- α-Ketoisovaleric acid
- Isobutyryl-CoA
- Methacrylyl-CoA
- 3-Hydroxyisobutyryl-CoA
- 3-Hydroxyisobutyric acid
- 2-Methyl-3-oxopropanoic acid
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isoleucine→
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- 2,3-Dihydroxy-3-methylpentanoic acid
- 2-Methylbutyryl-CoA
- Tiglyl-CoA
- 2-Methylacetoacetyl-CoA
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methionine→
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- generation of homocysteine: S-Adenosyl methionine
- S-Adenosyl-L-homocysteine
- Homocysteine
- conversion to cysteine: Cystathionine
- alpha-Ketobutyric acid+Cysteine
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threonine→
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propionyl-CoA→
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G→fumarate
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phenylalanine→tyrosine→
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- 4-Hydroxyphenylpyruvic acid
- Homogentisic acid
- 4-Maleylacetoacetic acid
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G→oxaloacetate
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Other |
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Index of inborn errors of metabolism
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Description |
- Metabolism
- Enzymes and pathways: citric acid cycle
- pentose phosphate
- glycoproteins
- glycosaminoglycans
- phospholipid
- cholesterol and steroid
- sphingolipids
- eicosanoids
- amino acid
- urea cycle
- nucleotide
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Disorders |
- Citric acid cycle and electron transport chain
- Glycoprotein
- Proteoglycan
- Fatty-acid
- Phospholipid
- Cholesterol and steroid
- Eicosanoid
- Amino acid
- Purine-pyrimidine
- Heme metabolism
- Symptoms and signs
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Treatment |
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Index of biochemical families
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
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UpToDate Contents
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English Journal
- Reduced adenosine release from the aged mammalian heart.
- Fenton RA, Dobson JG Jr.SourceDepartment of Microbiology and Physiological Systems, University of Massachusetts Medical School, Worcester, MA 01655, USA. richard.fenton@umassmed.edu
- Journal of cellular physiology.J Cell Physiol.2012 Nov;227(11):3709-14. doi: 10.1002/jcp.24079.
- Adenosine (ADO) released in the heart results in enhanced coronary blood flow and reduced catecholamine release and myocardial responsiveness to adrenergic stimulation (anti-adrenergic action). ADO release from the adrenergic-stimulated aged heart is less than that from the young adult heart. Becaus
- PMID 22378276
- Genetic polymorphisms modulate the folate metabolism of Brazilian individuals with Down syndrome.
- Biselli JM, Zampieri BL, Goloni-Bertollo EM, Haddad R, Fonseca MF, Eberlin MN, Vannucchi H, Carvalho VM, Pavarino EC.SourceDepartamento de Biologia Molecular, Faculdade de Medicina de São José do Rio Preto (FAMERP), Unidade de Pesquisa em Genética e Biologia Molecular (UPGEM), Av. Brigadeiro Faria Lima, n.o 5416-Bloco U-6, São José do Rio Preto, SP, CEP: 15.090-000, Brazil.
- Molecular biology reports.Mol Biol Rep.2012 Oct;39(10):9277-84. Epub 2012 Aug 19.
- Individuals with Down syndrome (DS) carry three copies of the Cystathionine β-synthase (CβS) gene. The increase in the dosage of this gene results in an altered profile of metabolites involved in the folate pathway, including reduced homocysteine (Hcy), methionine, S-adenosylhomocysteine (SAH) and
- PMID 22903356
Japanese Journal
- Factors Contributing to the Resistivity of a Higher Casein Diet against Choline Deficiency-Induced Hyperhomocysteinemia in Rats
- LIU Yi-qun,LIU Ying,MORITA Tatsuya [他],MORI Makoto,SUGIYAMA Kimio
- Journal of Nutritional Science and Vitaminology 58(2), 78-87, 2012
- … Choline deprivation-induced increases in hepatic S-adenosylhomocysteine and homocysteine concentrations were significantly suppressed by supplementation with glycine+serine and further suppressed by BCAA+AAA. …
- NAID 130002103035
- Determination of S-Adenosylmethionine and S-Adenosylhomocysteine by LC-MS/MS and evaluation of their stability in mice tissues
- KRIJT Jakub,DUTA Alena,KOZICH Viktor
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877(22), 2061-2066, 2009-07-15
- NAID 10028020293
- Hepatic Cystathionine β-Synthase Activity Does Not Increase in Response to Methionine Supplementation in Rats Fed a Low Casein Diet : Association with Plasma Homocysteine Concentrations
- Ohuchi Seiya,Morita Tatsuya,Mori Makoto [他],SUGIYAMA Kimio
- Journal of nutritional science and vitaminology 55(2), 178-185, 2009-04-01
- … Increased concentrations of hepatic S-adenosylhomocysteine and homocysteine due to methionine supplementation were also significantly suppressed by glycine+serine. … In contrast, the activity of hepatic betaine-homocysteine S-methyltransferase (BHMT) significantly increased with increase in both dietary casein level and dietary methionine level. …
- NAID 10025970986
Related Links
- Amino Acid Derivative . 5 mg · 10 mg · 25 mg · 50 mg ... S-Adenosyl-L-homocysteine (SAH) is an amino acid derivative and an intermediate, by-product, or modulator of several metabolic pathways, including the activated methyl ...
- Research Topics, Scientific Experts, Genomes and Genes, Species, Publications, Research Grants about s adenosylhomocysteine ... ..The method is linear over ranges of 1-100 microM SAM and 1-250 microM SAH. This method ...
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