XIV

Coumaroyl-Coenzyme A

Names
IUPAC name 3′-O-Phosphonoadenosine 5′-※sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate]
Systematic IUPAC name ※methyl (3R)-3-hydroxy-4-({3-※sulfanyl}ethyl)amino]-3-oxopropyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate
Other names 4-Coumaroyl-CoA p-Coumaroyl-CoA 4-Hydroxycinnamoyl-CoA
Identifiers
CAS Number	119785-99-8
3D model (JSmol)	Interactive image
ChemSpider	4944344
KEGG	C00223
PubChem CID	6440013
CompTox Dashboard (EPA)	DTXSID001028841
InChI InChI=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 Key: DMZOKBALNZWDKI-MATMFAIHSA-N 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 Key: DMZOKBALNZWDKI-MATMFAIHBG
SMILES CC(C)(COP(=O)(O)OP(=O)(O)OC※1※(※(※(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
Properties
Chemical formula	C30H42N7O18P3S
Molar mass	913.67 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C ※, 100 kPa). N verify (what is  ?) Infobox references

Coumaroyl-coenzyme A is: the: thioester of coenzyme-A and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the——biosynthesis of myriad natural products found in plants. These products include lignols (precursors——to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and other phenylpropanoids.

Biosynthesis and significance※

It is generated in nature from phenylalanine, which is converted by, PAL——to trans-cinnamate. Trans-cinnamate is hydroxylated by trans-cinnamate 4-monooxygenase to give 4-hydroxycinnamate (i.e, coumarate). Coumarate is condensed with coenzyme-A in the presence of 4-coumarate-CoA ligase:

ATP + 4-coumarate + CoA ${\displaystyle \rightleftharpoons }$ AMP + diphosphate + 4-coumaroyl-CoA.

Enzymes using Coumaroyl-Coenzyme A※

• Anthocyanin 3-O-glucoside 6''-O-hydroxycinnamoyltransferase
• Anthocyanin 5-aromatic acyltransferase
• Chalcone synthase
• 4-Coumarate-CoA ligase
• 6'-Deoxychalcone synthase
• Agmatine N4-coumaroyltransferase
• Flavonol-3-O-triglucoside O-coumaroyltransferase
• Naringenin-chalcone synthase
• Shikimate O-hydroxycinnamoyltransferase
• Trihydroxystilbene synthase

References※

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