Identification

PhytoHub ID
PHUB000513
Name
1,5-Dicaffeoylquinic acid
Systematic Name
1,5-Dicaffeoylquinic acid
Synonyms
  • 1,3-dicaffeoylquinic acid
  • 1,5-Di-O-caffeoylquinic acid
  • Cynarin
CAS Number
30964-13-7
Average Mass
516.455
Monoisotopic Mass
516.126776213
Chemical Formula
C25H24O12
IUPAC Name
(5S)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
InChI Key
YDDUMTOHNYZQPO-AOHQRWFOSA-N
InChI Identifier
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20?,23?,25?/m0/s1
SMILES
O[C@H]1CC(CC(OC(=O)\C=C\C2=CC=C(O)C(O)=C2)C1O)(OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O
Structure

Calculated Properties

Solubility (ALOGPS)
1.37e-01 g/l
LogS (ALOGPS)
-3.58
LogP (ALOGPS)
2.07
Hydrogen Acceptors
10
Hydrogen Donors
7
Rotatable Bond Count
9
Polar Surface Area
211.27999999999997
Refractivity
126.76419999999997
Polarizability
49.80468596797699
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-3.23256292481747
pKa (strongest acidic)
3.184533116763618
Number of Rings
3
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

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 PhytochemicalFamilyClassSub-class
1,5-Dicaffeoylquinic acidPolyphenolsPhenolic acidsHydroxycinnamic acidsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Organooxygen compounds
Super-class
Organic oxygen compounds
Sub-class
Alcohols and polyols
Direct Parent Name
Quinic acids and derivatives
Alternative Parent Names
["1,2-diols", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Cinnamic acid esters", "Coumaric acids and derivatives", "Cyclohexanols", "Enoate esters", "Fatty acid esters", "Hydrocarbon derivatives", "Organic oxides", "Styrenes", "Tricarboxylic acids and derivatives"]
External Descriptor Annotations
Not Available
Substituent Names
["1,2-diol", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Alpha,beta-unsaturated carboxylic ester", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Catechol", "Cinnamic acid ester", "Cinnamic acid or derivatives", "Coumaric acid or derivatives", "Cyclohexanol", "Enoate ester", "Fatty acid ester", "Fatty acyl", "Hydrocarbon derivative", "Hydroxycinnamic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Phenol", "Quinic acid", "Secondary alcohol", "Styrene", "Tricarboxylic acid or derivatives"]

Spectra from Online Resources

No spectra information available

Food Sources

NameGroup
Globe artichokeVegetables, Other vegetables PublicationsShow

Food Sources of its Food Phytochemical(s)

Food PhytochemicalFood SourceFood Source Group
1,5-Dicaffeoylquinic acidGlobe artichokeVegetables, Other vegetables PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
1,5-Dicaffeoylquinic acid 1,5-Dicaffeoylquinic acidhumanplasmaunchanged1h-3h50-200 nmol/LNot AvailableC25H24O12516.126776213 Detailed Intervention Studies Publications
1,5-Dicaffeoylquinic acid 1,5-Diferuloylquinic acidNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableNot Available Detailed Intervention Studies

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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