Cinnamoyl-CoA - Misplaced Pages

Cinnamoyl-Coenzyme A
Names

IUPAC name 3′-O-Phosphonoadenosine 5′-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl dihydroxen diphosphate]
Systematic IUPAC name methyl (3R)-3-hydroxy-2,2-dimethyl-4-({3-sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl dihydrogen diphosphate
Other names Cinnamoyl-coa (E)-cinnamoyl-CoA Coenzyme A, S-(3-phenyl-2-propenoate) (E)-benzylideneacetyl-CoA 3-phenylacryloyl-CoA
Identifiers
CAS Number	76109-04-1 30801-99-1 (non-specific)
3D model (JSmol)	Interactive image
ChemSpider	4947984
PubChem CID	6444037
UNII	6YVQ9P5RAT
CompTox Dashboard (EPA)	DTXSID501030398
InChI InChI=1S/C30H42N7O17P3S/c1-30(2,25(41)28(42)33-11-10-20(38)32-12-13-58-21(39)9-8-18-6-4-3-5-7-18)15-51-57(48,49)54-56(46,47)50-14-19-24(53-55(43,44)45)23(40)29(52-19)37-17-36-22-26(31)34-16-35-27(22)37/h3-9,16-17,19,23-25,29,40-41H,10-15H2,1-2H3,(H,32,38)(H,33,42)(H,46,47)(H,48,49)(H2,31,34,35)(H2,43,44,45)/b9-8+/t19-,23-,24-,25+,29-/m1/s1Key: JVNVHNHITFVWIX-KZKUDURGSA-N InChI=1/C30H42N7O17P3S/c1-30(2,25(41)28(42)33-11-10-20(38)32-12-13-58-21(39)9-8-18-6-4-3-5-7-18)15-51-57(48,49)54-56(46,47)50-14-19-24(53-55(43,44)45)23(40)29(52-19)37-17-36-22-26(31)34-16-35-27(22)37/h3-9,16-17,19,23-25,29,40-41H,10-15H2,1-2H3,(H,32,38)(H,33,42)(H,46,47)(H,48,49)(H2,31,34,35)(H2,43,44,45)/b9-8+/t19-,23-,24-,25+,29-/m1/s1Key: JVNVHNHITFVWIX-KZKUDURGBU
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=CC=C4)O
Properties
Chemical formula	C₃₀H₄₂N₇O₁₇P₃S
Molar mass	897.68 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Cinnamoyl-coenzyme A is an intermediate in the phenylpropanoid metabolic pathway.

Enzymes using cinnamoyl-coenzyme A

Cinnamoyl-CoA reductase, an enzyme that catalyzes the chemical reaction cinnamaldehyde + CoA + NADP+ → cinnamoyl-CoA + NADPH + H+
Pinosylvin synthase, an enzyme that catalyzes the chemical reaction 3 malonyl-CoA + cinnamoyl-CoA → 4 CoA + pinosylvin + 4 CO₂
Cinnamoyl-CoA:phenyllactate CoA-transferase, an enzyme that catalyzes the chemical reaction (E)-cinnamoyl-CoA + (R)-phenyllactate → (E)-cinnamate + (R)-phenyllactyl-CoA

References

Types of hydroxycinnamic acids

Aglycones

Precursor	Cinnamic acid
Monohydroxycinnamic acids (Coumaric acids)	p-Coumaric acid o-Coumaric acid m-Coumaric acid
Dihydroxycinnamic acids	Caffeic acid (3,4-dihydroxycinnamic acid) Umbellic acid (2,4-dihydroxycinnamic acid) 2,3-Dihydroxycinnamic acid 2,5-Dihydroxycinnamic acid 3,5-Dihydroxycinnamic acid
Trihydroxycinnamic acids	2,4,5-Trihydroxycinnamic acid 3,4,5-Trihydroxycinnamic acid
O-methylated forms	Ferulic acid 5-Hydroxyferulic acid Isoferulic acid Sinapinic acid
others	Plicatin A Plicatin B

Esters

glycoside-likes

Esters of
caffeic acid
with cyclitols

esters of quinic acid	Chlorogenic acid (3-caffeoylquinic acid) Cryptochlorogenic acid (4-O-caffeoylquinic acid) Neochlorogenic acid (5-O-Caffeoylquinic acid) Cynarine (1,5-dicaffeoylquinic acid) 3,4-dicaffeoylquinic acid 3,5-dicaffeoylquinic acid
esters of shikimic acid	Dactylifric acid (3-O-caffeoylshikimic acid)

Glycosides

Tartaric acid esters

Caftaric acid
Chicoric acid (dicaffeoyltartaric acid)
Coutaric acid
Fertaric acid
Grape reaction product (caftaric acid conjugated with glutathione)

Other esters
with caffeic acid

Caffeoylmalic acid
Ethyl caffeate
Methyl caffeate
Caffeic acid phenethyl ester (CAPE)
Rosmarinic acid (ester with 3,4-dihydroxyphenyllactic acid)

Caffeoyl phenylethanoid
glycoside (CPG)

Echinacoside
Calceolarioside A, B, C, F
Chiritoside A, B, C
Cistanoside A, B, C, D, E, F, G, H
Conandroside
Myconoside
Pauoifloside
Plantainoside A
Plantamajoside
Tubuloside B
Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)

Oligomeric forms

Dimers	Diferulic acids (DiFA) : 5,5′-Diferulic acid, 8-O-4′-Diferulic acid, 8,5′-Diferulic acid, 8,5′-DiFA (DC), 8,5′-DiFA (BF), 8,8′-Diferulic acid
Trimers	Triferulic acids : 5-5′,8′-O-4″-Triferulic acid
Tetramers	Tetraferulic acids

Conjugates with
coenzyme A (CoA)

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