| Common Name |
1,3-Dicaffeoylquinic acid
| Description |
1,3-Dicaffeoylquinic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).1,3-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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB29279 (1,3-Dicaffeoylquinic acid)
| Synonyms |
| Value |
Source |
15-O-trans-Dicaffeoylquinic acidChEMBL
15-O-trans-DicaffeoylquinateGenerator
1,3-DicaffeoylquinateGenerator
1,3-Di-O-caffeoylquinic acidHMDB
1,5-Dicaffeoylquinic acid?HMDB
CinarinMeSH
ListrocolMeSH
CynarexMeSH
CinarineMeSH
NivellipidMeSH
PhemocilMeSH
1,5-Dicaffeoylquinic acidMeSH
1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)MeSH
Cynarin, (1alpha,3alpha,4alpha,5beta)-isomerMeSH
ListricolMeSH
CinarinaMeSH
CynarinMeSH
CynarineMeSH
CynarixMeSH
| Chemical Formlia |
C25H24O12
| Average Molecliar Weight |
516.4509
| Monoisotopic Molecliar Weight |
516.126776232
| IUPAC Name |
(1S,3R,4R,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
| Traditional Name |
(1S,3R,4R,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid
| CAS Registry Number |
19870-46-3
| SMILES |
O[C@@H]1C[C@@](C[C@@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)[C@@H]1O)(OC(=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(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+/m1/s1
| InChI Key |
YDDUMTOHNYZQPO-PSEXTPKNSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as quinic acids and derivatives. These are compounds containing a quinic acid moiety (or a derivative thereof), which 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 |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic oxygen compounds
| Sub Class |
Organooxygen compounds
| Direct Parent |
Quinic acids and derivatives
| Alternative Parents |
Coumaric acids and derivatives
Cinnamic acid esters
Tricarboxylic acids and derivatives
Styrenes
Catechols
Fatty acid esters
Cyclohexanols
1-hydroxy-4-unsubstituted benzenoids
1-hydroxy-2-unsubstituted benzenoids
Enoate esters
1,2-diols
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| 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 Solubility0.14 mg/mLALOGPS
logP2.07ALOGPS
logP2.16ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.18ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.76 m3·mol-1ChemAxon
Polarizability49.62 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-03di-0900000000-bd90a1dbffd2fcf8b2d4View in MoNA
| 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 |
Cytoplasm
Extracellliar
| 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 |
526
| Phenol Explorer Metabolite ID |
526
| FoodDB ID |
FDB000278
| 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 |
HMDB29279
| Metagene Link |
HMDB29279
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Human growth hormone-releasing factor
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: 7984289
