1,5-Dicaffeoylquinic acid
precursor
Showing entry for 1,5-Dicaffeoylquinic acid
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
External Links
No external links
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 | |
---|---|---|---|---|
1,5-Dicaffeoylquinic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show 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
Name | Group | |||
---|---|---|---|---|
Globe artichoke | Vegetables, Other vegetables | Publications | Show |
Food Sources of its Food Phytochemical(s)
Food Phytochemical | Food Source | Food Source Group | |||
---|---|---|---|---|---|
1,5-Dicaffeoylquinic acid | Globe artichoke | Vegetables, Other vegetables | 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 | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,5-Dicaffeoylquinic acid | 1,5-Dicaffeoylquinic acid | human | plasma | unchanged | 1h-3h | 50-200 nmol/L | Not Available | C25H24O12 | 516.126776213 | Detailed Intervention Studies | Publications | ||
1,5-Dicaffeoylquinic acid | 1,5-Diferuloylquinic acid | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | Detailed Intervention Studies |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value |
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