trans-caffeic acid (CHEBI:16433)

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CHEBI:16433 - trans-caffeic acid

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ChEBI Name	trans-caffeic acid

ChEBI ID	CHEBI:16433

ChEBI ASCII Name	trans-caffeic acid

Definition	The trans-isomer of caffeic acid.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:12870, CHEBI:41964, CHEBI:1379, CHEBI:11691, CHEBI:11692, CHEBI:19877

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

Molfile

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Mrv0541 02211414593D

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21 21 0 0 0 0 999 V2000

5.5750 -2.6310 -1.9670 C 0 0 0 0 0 0 0 0 0 0 0 0

6.2930 -3.4540 -1.4250 O 0 0 0 0 0 0 0 0 0 0 0 0

4.4030 -1.9600 -1.3690 C 0 0 0 0 0 0 0 0 0 0 0 0

4.0440 -2.2310 -0.0950 C 0 0 0 0 0 0 0 0 0 0 0 0

2.9210 -1.6310 0.6080 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8780 -1.6520 2.0020 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8000 -1.0790 2.6760 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7640 -0.4840 1.9550 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8070 -0.4630 0.5610 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8850 -1.0360 -0.1120 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2950 0.0790 2.6010 O 0 0 0 0 0 0 0 0 0 0 0 0

1.7690 -1.1040 4.0370 O 0 0 0 0 0 0 0 0 0 0 0 0

5.7310 -2.1840 -3.2350 O 0 0 0 0 0 0 0 0 0 0 0 0

3.8610 -1.2470 -1.9800 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6470 -2.9440 0.4790 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6820 -2.1140 2.5720 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0030 -0.0010 -0.0060 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9040 -1.0130 -1.1990 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0740 -0.5130 4.3680 H 0 0 0 0 0 0 0 0 0 0 0 0

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6.4990 -2.6010 -3.6800 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 13 1 0 0 0 0

3 4 2 0 0 0 0

3 14 1 0 0 0 0

4 5 1 0 0 0 0

4 15 1 0 0 0 0

5 6 4 0 0 0 0

5 10 4 0 0 0 0

6 7 4 0 0 0 0

6 16 1 0 0 0 0

7 8 4 0 0 0 0

7 12 1 0 0 0 0

8 9 4 0 0 0 0

8 11 1 0 0 0 0

9 10 4 0 0 0 0

9 17 1 0 0 0 0

10 18 1 0 0 0 0

11 20 1 0 0 0 0

12 19 1 0 0 0 0

13 21 1 0 0 0 0

M END): 16 ms

reading 21 atoms

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Wikipedia	License
Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is chemically unrelated to caffeine; the related name is due to its presence in coffee.
Read full article at Wikipedia

Formula

C9H8O4

Net Charge

Average Mass

180.15740

Monoisotopic Mass

180.04226

InChI

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

InChIKey

QAIPRVGONGVQAS-DUXPYHPUSA-N

SMILES

OC(=O)\C=C\c1ccc(O)c(O)c1

Metabolite of Species	Details
Solanum campaniforme (IPNI:818569-1)	Found in leaf (BTO:0000713). Dried leaves were extracted with ethyl alcohol. See: PubMed
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. (via caffeic acid ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via caffeic acid ) EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33). (via caffeic acid ) EC 2.5.1.18 (glutathione transferase) inhibitor An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of a glutathione transferase (EC 2.5.1.18). (via caffeic acid ) EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34). (via caffeic acid ) EC 3.5.1.98 (histone deacetylase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). (via caffeic acid )

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	trans-caffeic acid (CHEBI:16433) has role geroprotector (CHEBI:176497) trans-caffeic acid (CHEBI:16433) has role mouse metabolite (CHEBI:75771) trans-caffeic acid (CHEBI:16433) is a caffeic acid (CHEBI:36281) trans-caffeic acid (CHEBI:16433) is conjugate acid of trans-caffeate (CHEBI:57770)

Incoming	(2S,3R)-trans-caftaric acid (CHEBI:76075) has functional parent trans-caffeic acid (CHEBI:16433) 1,3,4,5-tetracaffeoylquinic acid (CHEBI:512) has functional parent trans-caffeic acid (CHEBI:16433) 1,3-dicaffeoylquinic acid (CHEBI:520) has functional parent trans-caffeic acid (CHEBI:16433) 1-O-caffeoylquinic acid (CHEBI:136555) has functional parent trans-caffeic acid (CHEBI:16433) 1-caffeoyl-β-D-glucose (CHEBI:614) has functional parent trans-caffeic acid (CHEBI:16433) 1-caffeoyl-5-feruloylquinic acid (CHEBI:88343) has functional parent trans-caffeic acid (CHEBI:16433) 2-O-caffeoyl maslinic acid (CHEBI:65547) has functional parent trans-caffeic acid (CHEBI:16433) 3,4-dihydroxy-5-prenylcinnamic acid (CHEBI:65784) has functional parent trans-caffeic acid (CHEBI:16433) 3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has functional parent trans-caffeic acid (CHEBI:16433) 3-O-β-D-glucosyl-trans-caffeic acid (CHEBI:3293) has functional parent trans-caffeic acid (CHEBI:16433) 4-O-β-D-glucosyl-trans-caffeic acid (CHEBI:142393) has functional parent trans-caffeic acid (CHEBI:16433) 4-O-trans-caffeoylquinic acid (CHEBI:75491) has functional parent trans-caffeic acid (CHEBI:16433) 5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) has functional parent trans-caffeic acid (CHEBI:16433) 7-O-[6-(6-methoxycaffeoyl)glucosyl]isovitexin (CHEBI:75420) has functional parent trans-caffeic acid (CHEBI:16433) Cuscuta propenamide 1 (CHEBI:65700) has functional parent trans-caffeic acid (CHEBI:16433) N-caffeoylspermidine (CHEBI:138030) has functional parent trans-caffeic acid (CHEBI:16433) N¹,N⁵,N¹⁰-tris-(E)-caffeoyl spermidine (CHEBI:232324) has functional parent trans-caffeic acid (CHEBI:16433) N¹,N⁸-bis(caffeoyl)spermidine (CHEBI:138028) has functional parent trans-caffeic acid (CHEBI:16433) trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) has functional parent trans-caffeic acid (CHEBI:16433) trans-caffeoyl-CoA (CHEBI:87449) has functional parent trans-caffeic acid (CHEBI:16433) acteoside (CHEBI:132853) has functional parent trans-caffeic acid (CHEBI:16433) caffeic acid 3-sulfate (CHEBI:90242) has functional parent trans-caffeic acid (CHEBI:16433) caffeic acid 3-sulfate(2−) (CHEBI:133740) has functional parent trans-caffeic acid (CHEBI:16433) caffeoylglycolic acid methyl ester (CHEBI:65548) has functional parent trans-caffeic acid (CHEBI:16433) calabricoside B (CHEBI:65551) has functional parent trans-caffeic acid (CHEBI:16433) chlorogenic acid (CHEBI:16112) has functional parent trans-caffeic acid (CHEBI:16433) ethyl trans-caffeate (CHEBI:132714) has functional parent trans-caffeic acid (CHEBI:16433) evolvoid A (CHEBI:65890) has functional parent trans-caffeic acid (CHEBI:16433) gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) has functional parent trans-caffeic acid (CHEBI:16433) litseaefoloside C (CHEBI:66582) has functional parent trans-caffeic acid (CHEBI:16433) malvidin 3-O-{6-O-[(E)-caffeoyl]-β-D-glucoside} (CHEBI:131453) has functional parent trans-caffeic acid (CHEBI:16433) methyl 3,4-dicaffeoylquinate (CHEBI:85153) has functional parent trans-caffeic acid (CHEBI:16433) quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) has functional parent trans-caffeic acid (CHEBI:16433) quercetin 3-O-[(6-O-caffeoyl-β-D-glucosyl)-(1→2)-β-D-glucoside] (CHEBI:145787) has functional parent trans-caffeic acid (CHEBI:16433) rosmarinic acid (CHEBI:17226) has functional parent trans-caffeic acid (CHEBI:16433) subulatin (CHEBI:66533) has functional parent trans-caffeic acid (CHEBI:16433) trans-caffeate (CHEBI:57770) is conjugate base of trans-caffeic acid (CHEBI:16433)

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Synonyms	Sources
3,4-dihydroxy-trans-cinnamate	ChEBI
3,4-Dihydroxy-trans-cinnamate	KEGG COMPOUND
3,4-Dihydroxy-trans-cinnamate	KEGG COMPOUND
3,4-Dihydroxycinnamic acid	KEGG COMPOUND
CAFFEIC ACID	PDBeChem
Caffeic acid	KEGG COMPOUND
trans-caffeate	ChEBI
trans-Caffeate	KEGG COMPOUND

Manual Xrefs	Databases
C00000615	KNApSAcK
C01197	KEGG COMPOUND
C01481	KEGG COMPOUND
Caffeic_acid	Wikipedia
DHC	PDBeChem
HMDB0001964	HMDB
View more database links

Registry Numbers	Types	Sources
1954563	Reaxys Registry Number	Reaxys
331-39-5	CAS Registry Number	KEGG COMPOUND
501-16-6	CAS Registry Number	ChemIDplus

Citation

Pietsch K, Saul N, Chakrabarti S, Stürzenbaum SR, Menzel R, Steinberg CE (2011)
Hormetins, antioxidants and prooxidants: defining quercetin-, caffeic acid- and rosmarinic acid-mediated life extension in C. elegans.
Biogerontology 12, 329-347 [PubMed:21503726]
[show Abstract]

Last Modified

21 October 2024

CHEBI:16433 - trans-caffeic acid

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