| Common Name |
Dicaffeoylquinic acid
| Description |
Dicaffeoylquinic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).Dicaffeoylquinic acid belongs to the family of Quinic Acids and Derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), whis is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29280 (Dicaffeoylquinic acid)
| Synonyms |
| Value |
Source |
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoateChEBI
3,5-DCQAChEBI
3,5-Dicaffeoylquinic acidChEBI
Isochlorogenic acid aChEBI
Quinic acid 3,5-di-O-caffeateChEBI
(1S,3R,4S,5R)-1,3,4,5-Tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoic acidGenerator
DicaffeoylquinateGenerator
3,5-DicaffeoylquinateGenerator
Isochlorogenate aGenerator
Quinate 3,5-di-O-caffeateGenerator
Quinic acid 3,5-di-O-caffeic acidGenerator
| Chemical Formlia |
C25H24O12
| Average Molecliar Weight |
516.4509
| Monoisotopic Molecliar Weight |
516.126776232
| IUPAC Name |
(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
| Traditional Name |
(1S,3R,4S,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid
| CAS Registry Number |
Not Available
| SMILES |
O[C@H]1[C@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)C[C@@](O)(C[C@H]1OC(=O)C=CC1=CC=C(O)C(O)=C1)C(=O)O
| InChI Identifier |
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
| InChI Key |
KRZBCHWVBQOTNZ-PSEXTPKNSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), whis is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1.
| Kingdom |
Organic compounds
| Super Class |
Organooxygen compounds
| Class |
Alcohols and polyols
| Sub Class |
Cyclic alcohols and derivatives
| Direct Parent |
Quinic acids and derivatives
| Alternative Parents |
Coumaric acids and derivatives
Cinnamic acid esters
Tricarboxylic acids and derivatives
Phenylpropenes
Styrenes
Catechols
Fatty acid esters
Cyclohexanols
Alpha hydroxy acids and derivatives
Tertiary alcohols
Enoate esters
Carboxylic acids
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Quinic acid
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Tricarboxylic acid or derivatives
Phenylpropene
Styrene
1,2-diphenol
Phenol
Fatty acid ester
Cyclohexanol
Fatty acyl
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
carboxylic ester (CHEBI:65751 )
cyclitol carboxylic acid (CHEBI:65751 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Membrane (predicted from logP)
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.12 mg/mLALOGPS
logP2.05ALOGPS
logP2.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.76 m3·mol-1ChemAxon
Polarizability49.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Membrane (predicted from logP)
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
528
| FoodDB ID |
FDB000279
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29280
| Metagene Link |
HMDB29280
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Porcine dynorphin A(1-13)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]
|
PMID: 3419539
