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discounted EARLY registration ends Dec 31, 2014
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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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


Report Errors or Provide Feedback
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 Sat Dec 20, 2014, BIOCYC13A.