MetaCyc Compound: S-adenosyl-L-homocysteine

Abbrev Name: SAH

Synonyms: S-adenosylhomocysteine, 2-S-adenosyl-L-homocysteine, AdoHcy, 2-S-adenosyl-L-homocysteine, S-adenosyl-homocysteine, S-adenosylhomocysteine, adenosyl-homo-cys, adenosylhomocysteine, adenosylhomo-cys, SAH

Superclasses: an acid all carboxy acids a carboxylate an amino acid an alpha amino acid a non-standard alpha amino acid
an amino acid or its derivative an amino acid an alpha amino acid a non-standard alpha amino acid

Chemical Formula: C14H20N6O5S

Molecular Weight: 384.41 Daltons

Monoisotopic Molecular Weight: 384.1215884737 Daltons

<i>S</i>-adenosyl-L-homocysteine compound structure

SMILES: C(SCC3(C(O)C(O)C(N2(C1(N=CN=C(N)C=1N=C2)))O3))CC(C([O-])=O)[N+]

InChI: 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


Unification Links: CAS:979-92-0 , ChEBI:57856 , HMDB:HMDB00939 , IAF1260:33543 , KEGG:C00021 , MetaboLights:MTBLC57856 , PubChem:25246222

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 84.0534 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

autoinducer AI-2 biosynthesis I , autoinducer AI-2 biosynthesis II (Vibrio) , S-adenosyl-L-methionine cycle I :
S-adenosyl-L-homocysteine + H2O → S-ribosyl-L-homocysteine + adenine

Not in pathways:
2 a [methionine synthase]-methylcob(I)alamin + 2 S-adenosyl-L-homocysteine + NADP+ → 2 a [methionine synthase]-cob(II)alamin + 2 S-adenosyl-L-methionine + NADPH + H+

3-hydroxy-L-homotyrosine biosynthesis :
4-(4-hydroxyphenyl)-2-oxobutanoate + an amino acidL-homotyrosine + a 2-oxo acid

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

(S)-reticuline biosynthesis I :
(S)-norcoclaurine + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + (S)-coclaurine + H+
3'-hydroxy-N-methyl-(S)-coclaurine + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + (S)-reticuline + H+
(S)-coclaurine + S-adenosyl-L-methionine → (S)-N-methylcoclaurine + S-adenosyl-L-homocysteine + H+

(S)-reticuline biosynthesis II :
S-norlaudanosoline + 3 S-adenosyl-L-methionine → (S)-reticuline + 3 S-adenosyl-L-homocysteine + 3 H+

1,3,5-trimethoxybenzene biosynthesis :
phloroglucinol + S-adenosyl-L-methionine → 3,5-dihydroxyanisole + S-adenosyl-L-homocysteine + H+
3,5-dihydroxyanisole + S-adenosyl-L-methionine → 3,5-dimethoxyphenol + S-adenosyl-L-homocysteine + H+
3,5-dimethoxyphenol + S-adenosyl-L-methionine → 1,3,5-trimethoxybenzene + S-adenosyl-L-homocysteine + H+

2-methylisoborneol biosynthesis :
S-adenosyl-L-methionine + geranyl diphosphate → S-adenosyl-L-homocysteine + (E)-2-methylgeranyl diphosphate + H+

3,5-dimethoxytoluene biosynthesis :
3-methoxy-5-hydroxytoluene + S-adenosyl-L-methionine → 3,5-dimethoxytoluene + S-adenosyl-L-homocysteine + H+
orcinol + S-adenosyl-L-methionine → 3-methoxy-5-hydroxytoluene + S-adenosyl-L-homocysteine + H+

3-methylarginine biosynthesis :
5-guanidino-2-oxo-pentanoate + S-adenosyl-L-methionine → 5-guanidino-3-methyl-2-oxo-pentanoate + S-adenosyl-L-homocysteine + H+

5-(carboxymethoxy)uridine biosynthesis :
a 5-hydroxyuridine34 in tRNA + carboxy-S-adenosyl-L-methionine → a 5-(carboxymethoxy)uridine34 in tRNA + S-adenosyl-L-homocysteine + H+

6-gingerol biosynthesis :
1-(3,4-dihydroxyphenyl)-5-hydroxy-3-decanone + S-adenosyl-L-methionine → 6-gingerol + S-adenosyl-L-homocysteine + H+

6-methoxymellein biosynthesis :
6-hydroxymellein + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + 6-methoxymellein + H+

7-(3-amino-3-carboxypropyl)-wyosine biosynthesis :
guanine37 in tRNAPhe + S-adenosyl-L-methionine → N1-methylguanine37 in tRNAPhe + S-adenosyl-L-homocysteine + H+
S-adenosyl-L-methionine + 7-[(3S)-3-amino-3-carboxypropyl]-4-demethylwyosine37 in tRNAPheS-adenosyl-L-homocysteine + 7-[(3S)-(3-amino-3-carboxypropyl)]-wyosine37 in tRNAPhe + H+

7-dehydroporiferasterol biosynthesis :
S-adenosyl-L-methionine + cycloartenol → S-adenosyl-L-homocysteine + 24-methylenecycloartanol + H+

8-amino-7-oxononanoate biosynthesis I :
a malonyl-[acp] + S-adenosyl-L-methionine → a malonyl-[acp] methyl ester + S-adenosyl-L-homocysteine

acacetin biosynthesis :
apigenin + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + acacetin + H+

aclacinomycin biosynthesis :
S-adenosyl-L-methionine + aklanonate → S-adenosyl-L-homocysteine + methyl aklanonate

acridone alkaloid biosynthesis , N-methylanthraniloyl-β-D-glucopyranose biosynthesis , superpathway avenacin A biosynthesis :
anthranilate + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + N-methylanthranilate + H+

aflatoxins B1 and G1 biosynthesis :
sterigmatocystin + S-adenosyl-L-methionine → 8-O-methylsterigmatocystin + S-adenosyl-L-homocysteine + H+

aflatoxins B2 and G2 biosynthesis :
dihydrodemethylsterigmatocystin + S-adenosyl-L-methionine → dihydrosterigmatocystin + S-adenosyl-L-homocysteine + H+
dihydrosterigmatocystin + S-adenosyl-L-methionine → 8-O-methyldihydrosterigmatocystin + S-adenosyl-L-homocysteine + H+

ajmaline and sarpagine biosynthesis :
norajmaline + S-adenosyl-L-methionine → ajmaline + S-adenosyl-L-homocysteine + H+

Reactions known to both consume and produce the compound:

L-methionine degradation I (to L-homocysteine) , S-adenosyl-L-methionine cycle II :
S-adenosyl-L-homocysteine + H2O ↔ L-homocysteine + adenosine

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
S-adenosyl-L-homocysteine + H2O = ammonium + S-Inosyl-L-homocysteine

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

Enzymes inhibited by S-adenosyl-L-homocysteine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: cyclopropane fatty acyl phospholipid synthase [Grogan97, Taylor79, Guerard04] , S-adenosylmethionine:tRNA ribosyltransferase-isomerase [Van03] , tRNA m1G37 methyltransferase [Hjalmarsson83, Lahoud11] , DNA-cytosine methyltransferase [Crooks84] , chemotaxis protein methyltransferase [Neidhardt96] , o-dihydric phenol O-methyltransferase (para-methylation) [Tsang79] , esculetin 6-O-methyltransferase (meta-methylation) [Tsang79] , 23S rRNA (adenine1067-2'-O)-methyltransferase [Bechthold94] , 5'-fluoro-5'-deoxyadenosine synthase [Schaffrath03] , sterigmatocystin O-methyltransferase [Liu99a] , SAM: anol-O-methyltransferase [Kemmerer96] , isoliquiritigenin-2'-O-methyltransferase [Maxwell92] , isoflavone-7-O-methyltransferase [Edwards91] , DNA (cytosine-5) methyltransferase [Simon78] , nicotinate N-methyltransferase [Upmeier88] , lysine 2,3-aminomutase [Chirpich70] , catechol O-methyltransferase [Rivett82] , putrescine N-methyltransferase [Hibi92]

Inhibitor (Uncompetitive) of: 3,7,3'-methylquercetagetin 6-O-methyltransferase [De85] , 3,7-dimethylquercetin 4'-O-methyltransferase [De85] , quercetin 3-O-methyltransferase [De85]

Inhibitor (Noncompetitive) of: 8-hydroxykaempferol 8-O-methyltransferase [Jay85] , 3-O-methylquercetin 7-O-methyltransferase [Khouri88] , desmethyl dehydrophos O-methyltransferase [Lee10] , isoflavone-4'-O-methyltransferase [Wengenmayer74] , putrescine N-methyltransferase [Hibi92]

Inhibitor (Allosteric) of: uroporphyrin-III (C7)-methyltransferase [Warren02]

Inhibitor (Mechanism unknown) of: biotin synthase [Farrar10] , trans-aconitate 2-methyltransferase [Cai99] , 5'-methylthioadenosine nucleosidase [Cornell98] , ribonucleoside-triphosphate reductase [Eliasson92] , phosphatidylethanolamine N-methyltransferase [Gaynor90] , phosphatidyl-N-methylethanolamine N-methyltransferase [Gaynor90] , phosphatidylethanolamine N-methyltransferase [Ridgway88] , phosphatidyl-N-methylethanolamine N-methyltransferase [Ridgway88] , phosphatidyl-N-dimethylethanolamine N-methyltransferase [Ridgway88] , 16-hydroxytabersonine-O-methyltransferase [Levac08] , histamine N-methyltransferase [Girard94] , loganic acid O-methyltransferase [Murata08] , S-adenosyl-L-methionine:N-methyl-β-alanine N-methyltransferase [Rathinasabapath01] , glycine-sarcosine methyltransferase [Nyyssola01] , sarcosine-dimethylglycine methyltransferase [Nyyssola01] , DIMBOA-glucoside 4-O-methyltransferase [Oikawa02] , MTR kinase [Guranowski83] , pectin methyltransferase [Ishikawa00] , homoserine O-acetyltransferase [Yamagata87] , glycine-sarcosine methyltransferase [Waditee03] , sarcosine-dimethylglycine methyltransferase [Waditee03] , dimethylglycine-betaine methyltransferase [Waditee03] , S-adenosyl-L-methionine: (S)-scoulerine 9-O-methyltransferase [Muemmler85] , S-adenosyl-L-methionine:β-alanine N-methyltransferase [Rathinasabapath01] , S-adenosyl-L-methionine:N,N-dimethyl-β-alanine N-methyltransferase [Rathinasabapath01] , apigenin 4'-O-methyltransferase [Kuroki81] , tetrahydroprotoberberine-cis-N-methyltransferase [Reuffer90] , columbamine O-methyltransferase [Rueffer86]

Inhibitor (Other types) of: S-adenosyl-L-methionine:norcoclaurine 6-O-methyltransferase [Sato94]

This compound has been characterized as an alternative substrate of the following enzymes: 6-aminodeoxyfutalosine deaminase


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Reuffer90: Reuffer, Martina, Zumstein, Gitta, Zenk, Meinhart (1990). "Partial purification and properties of S-adenosyl-L-methionine: (S)-tetrahydroprotoberberine-cis-N-methyltransferase from suspension-cultured cells of Eschscholtzia and Corydalis." Phytochemistry, 29(12):3727-3733.

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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