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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: salicylate

Synonyms: salicylic acid, o-hydroxybenzoic acid, 2-hydroxybenzoic acid, SA, 2-HBA, 2-hydroxybenzoate, o-hydroxybenzoate

Superclasses: an acid all carboxy acids a carboxylate an aromatic carboxylate
an aromatic compound an aromatic carboxylate

Summary:
Salicylate is widely used in organic synthesis and functions as a plant hormone. The source of the name salicylate (salicylic acid) comes from the name of the willow tree, Salix, from whose bark it can be obtained.

Chemical Formula: C7H5O3

Molecular Weight: 137.12 Daltons

Monoisotopic Molecular Weight: 138.0316940589 Daltons

SMILES: C(C1(=CC=CC=C1O))([O-])=O

InChI: InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)/p-1

InChIKey: InChIKey=YGSDEFSMJLZEOE-UHFFFAOYSA-M

Unification Links: CAS:69-72-7 , ChEBI:30762 , ChemSpider:4964 , HMDB:HMDB01895 , KEGG:C00805 , KNApSAcK:C00000206 , PubChem:54675850 , Wikipedia:Salicylate

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -41.486458 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

pyochelin biosynthesis , salicylate degradation IV , yersiniabactin biosynthesis :
salicylate + ATP + H+ → salicylate-adenylate + diphosphate

salicylate degradation I :
salicylate + NADH + 2 H+ + oxygen → catechol + CO2 + NAD+ + H2O

salicylate degradation II , salicylate glucosides biosynthesis II :
salicylate + NADH + oxygen + H+ → gentisate + NAD+ + H2O

salicylate glucosides biosynthesis III :
salicylate + UDP-α-D-glucose → salicylate β-D-glucose ester + UDP

salicylate glucosides biosynthesis IV :
salicylate + UDP-α-D-glucose → salicylate 2-O-β-D-glucoside + UDP + H+

volatile benzenoid biosynthesis I (ester formation) :
salicylate + S-adenosyl-L-methionine → 1-O-methylsalicylate + S-adenosyl-L-homocysteine

Not in pathways:
salicylate + oxygen → 2-oxohepta--3,5-dienedioate + H+
salicylate + 2 L-cysteine + S-adenosyl-L-methionine + NADPH → pyochelin + S-adenosyl-L-homocysteine + NADP+ + 4 H2O

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


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:

2,2'-dihydroxybiphenyl degradation , dibenzofuran degradation :
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O → 2-oxopent-4-enoate + salicylate + H+

naphthalene degradation (aerobic) :
salicylaldehyde + NAD+ + H2O → salicylate + NADH + 2 H+

salicylate biosynthesis I :
isochorismate → salicylate + pyruvate

salicylate biosynthesis II :
salicyloyl-CoA + H2O → salicylate + coenzyme A + H+

Not in pathways:
aspirin + H2O → acetate + salicylate + H+
1-O-methylsalicylate + H2O → salicylate + methanol + H+


an aryl aldehyde + oxygen + H2O → an aromatic carboxylate + hydrogen peroxide

3,3'-thiodipropionate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropionate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+


an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

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

In Reactions of unknown directionality:

salicylate degradation III :
salicylate + H+ = phenol + CO2

Not in pathways:
benzoate + NADPH + H+ + oxygen = salicylate + NADP+ + H2O


AMP + an aryl aldehyde + NADP+ + diphosphate = ATP + an aromatic carboxylate + NADPH
an aryl aldehyde + NAD+ + H2O = an aromatic carboxylate + NADH + H+


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
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 electron acceptor + H2O = a carboxylate + a reduced 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 activated by salicylate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: kaempferol synthase [Xu12a] , naringenin 3-dioxygenase [Xu12a] , dihydrokaempferol 4-reductase [Hua13] , UDP-glucose:curcumin glucosyltransferase [Kaminaga04] , UDP-glucose:curcumin monoglucoside glucosyltransferase [Kaminaga04]

Enzymes inhibited by salicylate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: arylamine N-acetyltransferase [Yamamura00, Comment 1] , N-benzoyl-L-glutamate synthetase [Okrent09]

Inhibitor (Noncompetitive) of: p-hydroxybenzoate hydroxylase [Hosokawa66]

Inhibitor (Mechanism unknown) of: pectate lyase [Tardy97] , pectate lyase [Tardy97] , pectate lyase [Tardy97]


References

Hosokawa66: Hosokawa K, Stanier RY (1966). "Crystallization and properties of p-hydroxybenzoate hydroxylase from Pseudomonas putida." J Biol Chem 241(10);2453-60. PMID: 4380381

Hua13: Hua C, Linling L, Shuiyuan C, Fuliang C, Feng X, Honghui Y, Conghua W (2013). "Molecular Cloning and Characterization of Three Genes Encoding Dihydroflavonol-4-Reductase from Ginkgo biloba in Anthocyanin Biosynthetic Pathway." PLoS One 8(8);e72017. PMID: 23991027

Kaminaga04: Kaminaga Y, Sahin FP, Mizukami H (2004). "Molecular cloning and characterization of a glucosyltransferase catalyzing glucosylation of curcumin in cultured Catharanthus roseus cells." FEBS Lett 567(2-3);197-202. PMID: 15178322

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Okrent09: Okrent RA, Brooks MD, Wildermuth MC (2009). "Arabidopsis GH3.12 (PBS3) conjugates amino acids to 4-substituted benzoates and is inhibited by salicylate." J Biol Chem 284(15);9742-54. PMID: 19189963

Tardy97: Tardy F, Nasser W, Robert-Baudouy J, Hugouvieux-Cotte-Pattat N (1997). "Comparative analysis of the five major Erwinia chrysanthemi pectate lyases: enzyme characteristics and potential inhibitors." J Bacteriol 179(8);2503-11. PMID: 9098045

Xu12a: Xu F, Li L, Zhang W, Cheng H, Sun N, Cheng S, Wang Y (2012). "Isolation, characterization, and function analysis of a flavonol synthase gene from Ginkgo biloba." Mol Biol Rep 39(3);2285-96. PMID: 21643949

Yamamura00: Yamamura E, Sayama M, Kakikawa M, Mori M, Taketo A, Kodaira K (2000). "Purification and biochemical properties of an N-hydroxyarylamine O-acetyltransferase from Escherichia coli." Biochim Biophys Acta 2000;1475(1);10-6. PMID: 10806332


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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
Page generated by SRI International Pathway Tools version 18.5 on Tue Nov 25, 2014, BIOCYC13A.