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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 406237041 |
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| Watchedfields = changed |
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| Name = Coumaroyl-Coenzyme A |
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| verifiedrevid = 426717604 |
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| ImageFile = 4-Coumaroyl-CoA.svg |
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| Name = Coumaroyl-Coenzyme A |
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| ImageSize = 250px |
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| ImageFile = 4-Coumaroyl-CoA.svg |
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| IUPACName = <nowiki>S-methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3, |
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| ImageSize = 250px |
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3-dimethylbutanoyl]amino]propanoylamino]ethyl](E)-3-(4-hydroxyphenyl)prop-2-enethioate</nowiki> |
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| IUPACName = 3′-''O''-Phosphonoadenosine 5′-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate] |
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| OtherNames = 4-]-]<br>p-Coumaroyl-CoA<br>4-Hydroxycinnamoyl-CoA |
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| SystematicName = methyl (3''R'')-3-hydroxy-4-({3-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = ]-]<br>p-Coumaroyl-CoA<br>4-Hydroxycinnamoyl-CoA |
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| CASNo = 119785-99-8 |
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|Section1={{Chembox Identifiers |
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| PubChem = 5280329 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| SMILES = CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSC(=O)C=CC4=CC=C(C=C4)O)O |
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| CASNo = 119785-99-8 |
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| MeSHName = |
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| PubChem = 6440013 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4944344 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C00223 |
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| SMILES = CC(C)(COP(=O)(O)OP(=O)(O)OC1(((O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)(C(=O)NCCC(=O)NCCSC(=O)/C=C/C4=CC=C(C=C4)O)O |
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| InChI = 1/C30H42N7O18P3S/c1-30(2,25(42)28(43)33-10-9-20(39)32-11-12-59-21(40)8-5-17-3-6-18(38)7-4-17)14-52-58(49,50)55-57(47,48)51-13-19-24(54-56(44,45)46)23(41)29(53-19)37-16-36-22-26(31)34-15-35-27(22)37/h3-8,15-16,19,23-25,29,38,41-42H,9-14H2,1-2H3,(H,32,39)(H,33,43)(H,47,48)(H,49,50)(H2,31,34,35)(H2,44,45,46)/b8-5+/t19-,23-,24-,25+,29-/m1/s1 |
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| InChIKey = DMZOKBALNZWDKI-MATMFAIHBG |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C30H42N7O18P3S/c1-30(2,25(42)28(43)33-10-9-20(39)32-11-12-59-21(40)8-5-17-3-6-18(38)7-4-17)14-52-58(49,50)55-57(47,48)51-13-19-24(54-56(44,45)46)23(41)29(53-19)37-16-36-22-26(31)34-15-35-27(22)37/h3-8,15-16,19,23-25,29,38,41-42H,9-14H2,1-2H3,(H,32,39)(H,33,43)(H,47,48)(H,49,50)(H2,31,34,35)(H2,44,45,46)/b8-5+/t19-,23-,24-,25+,29-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DMZOKBALNZWDKI-MATMFAIHSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>30</sub>H<sub>42</sub>N<sub>7</sub>O<sub>18</sub>P<sub>3</sub>S |
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| Formula = C<sub>30</sub>H<sub>42</sub>N<sub>7</sub>O<sub>18</sub>P<sub>3</sub>S |
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| MolarMass = 913.67 g/mol |
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| MolarMass = 913.67 g/mol |
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| Appearance = |
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| ExactMass = 913.151988 |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| Solubility = |
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'''Coumaroyl-coenzyme A''' is the ] of ] and ]. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include ] (precursors to ] and ]), ], ], ]s, ], ], ], and other ]s.<ref>{{cite journal|journal=Molecular Plant|year=2010|pages=2–20|doi=10.1093/mp/ssp106|title=Phenylpropanoid Biosynthesis|author=Vogt, T.|pmid=20035037|volume=3|doi-access=free}}</ref> |
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'''Coumaroyl-Coenzyme A''' is a chemical compound used in ] production, a key compound in the ]s and ]s biosynthesis pathways in plants. |
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==Biosynthesis and significance== |
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] is also synthetized via coumaroyl-coA<ref></ref>. |
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It is generated in nature from ], which is converted by ] to trans-]. Trans-cinnamate is hydroxylated by ] to give 4-hydroxycinnamate (i.e, coumarate). Coumarate is condensed with coenzyme-A in the presence of ]: |
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:ATP + 4-coumarate + CoA <math>\rightleftharpoons</math> AMP + diphosphate + 4-coumaroyl-CoA. |
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==Enzymes using Coumaroyl-Coenzyme A== |
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== Enzymes using Coumaroyl-Coenzyme A == |
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==References== |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{Hydroxycinnamic acid}} |
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{{DEFAULTSORT:Coumaroyl-Coa}} |
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{{DEFAULTSORT:Coumaroyl-Coa}} |
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] |
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{{Aromatic-stub}} |
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{{organic-compound-stub}} |
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] |
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] |
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