PhytoHub: Showing entry for 3-O-Caffeoylquinic acid

3-O-Caffeoylquinic acid

Identification

PhytoHub ID

PHUB000530

Name

3-O-Caffeoylquinic acid

Systematic Name

3-Caffeoylquinic acid

Synonyms

3-(3,4-Dihydroxycinnamoyl)quinic acid
3-Caffeoylquinic acid
chlorogenic acid
Neochlorogenic acid

CAS Number

327-97-9

Average Mass

354.311

Monoisotopic Mass

354.09508216

Chemical Formula

C₁₆H₁₈O₉

IUPAC Name

3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

InChI Key

CWVRJTMFETXNAD-DUXPYHPUSA-N

InChI Identifier

InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+

SMILES

[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OC1CC(O)(CC(O)C1O)C(O)=O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 3.44e+00 g/l
LogS (ALOGPS): -2.01
LogP (ALOGPS): 0.17
Hydrogen Acceptors: 8
Hydrogen Donors: 6
Rotatable Bond Count: 5
Polar Surface Area: 164.74999999999997
Refractivity: 83.23469999999999
Polarizability: 33.92029446068079
Formal Charge: 0
Physiological Charge: -1
pKa (strongest basic): -3.2318239809154075
pKa (strongest acidic): 3.3338531471838464
Number of Rings: 2
Rule of Five: No
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

ChEBI: 16112
PubChem: 5315832
Phenol-Explorer: 467

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Phenolic acids
Sub-class: Hydroxycinnamic acids

Taxonomy as Metabolite

Metabolite Family: (Poly)phenol metabolites
Metabolite Class: Phenolic acid metabolites
Metabolite Sub-class: Cinnamic acids

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
3-O-Caffeoylquinic acid	Polyphenols	Phenolic acids	Hydroxycinnamic acids	Show Food Phytochemical

Spectra from Phytohub

	Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Food Sources

Name	Group
Apricot	Fruit, Drupes	Publications	Show
Broccoli	Vegetables, Cabbages	Publications	Show
Brussel sprouts	Vegetables, Cabbages	Publications	Show
Carrot	Vegetables, Root vegetables	Publications	Show
Coffee	Coffee and coffee products	Publications	Show
Common cabbage	Vegetables, Cabbages	Publications	Show
European plum	Fruit, Drupes	Publications	Show
Kale	Vegetables, Cabbages	Publications	Show
Mate	Teas and herbal teas	Publications	Show
Peach	Fruit, Drupes	Publications	Show
Sweet cherry	Fruit, Drupes	Publications	Show

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
3-O-Caffeoylquinic acid	Apricot	Fruit, Drupes	Publications	Show
3-O-Caffeoylquinic acid	Broccoli	Vegetables, Cabbages	Publications	Show
3-O-Caffeoylquinic acid	Brussel sprouts	Vegetables, Cabbages	Publications	Show
3-O-Caffeoylquinic acid	Carrot	Vegetables, Root vegetables	Publications	Show
3-O-Caffeoylquinic acid	Coffee	Coffee and coffee products	Publications	Show
3-O-Caffeoylquinic acid	Common cabbage	Vegetables, Cabbages	Publications	Show
3-O-Caffeoylquinic acid	European plum	Fruit, Drupes	Publications	Show
3-O-Caffeoylquinic acid	Kale	Vegetables, Cabbages	Publications	Show
3-O-Caffeoylquinic acid	Mate	Teas and herbal teas	Publications	Show
3-O-Caffeoylquinic acid	Peach	Fruit, Drupes	Publications	Show
3-O-Caffeoylquinic acid	Sweet cherry	Fruit, Drupes	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	3-O-Caffeoylquinic acid		3-O-Caffeoylquinic acid	human	plasma, serum, urine	unchanged	1h-3h	<20 nmol/L	<1%	C₁₆H₁₈O₉	354.09508216	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value
	3-O-Caffeoylquinic acid		3-O-Caffeoylquinic acid	Microbiota	Effect, clusters	Publications

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Showing entry for 3-O-Caffeoylquinic acid