| Common Name |
Cis-5-Caffeoylquinic acid
| Description |
Cis-5-Caffeoylquinic acid is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).Cis-5-Caffeoylquinic 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 HMDB29278 (Cis-5-Caffeoylquinic acid)
| Synonyms |
| Value |
Source |
5-O-(Z)-Caffeoylquinic acidChEBI
cis-5-O-Caffeoylquinic acidChEBI
cis-Chlorogenic acidChEBI
5-O-(Z)-CaffeoylquinateGenerator
cis-5-CaffeoylquinateGenerator
cis-5-O-CaffeoylquinateGenerator
cis-ChlorogenateGenerator
| Chemical Formlia |
C16H18O9
| Average Molecliar Weight |
354.3087
| Monoisotopic Molecliar Weight |
354.095082174
| IUPAC Name |
(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
| Traditional Name |
(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
| CAS Registry Number |
Not Available
| SMILES |
O[C@@H]1C[C@](O)(C[C@@H](OC(=O)C=C/C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O
| 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-/t11-,12-,14-,16+/m1/s1
| InChI Key |
CWVRJTMFETXNAD-XYXZIBEBSA-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
Styrenes
Catechols
1-hydroxy-2-unsubstituted benzenoids
1-hydroxy-4-unsubstituted benzenoids
Fatty acid esters
Cyclohexanols
Alpha hydroxy acids and derivatives
Dicarboxylic acids and derivatives
Tertiary alcohols
Enoate esters
Polyols
Carboxylic acids
Hydrocarbon derivatives
Carbonyl compounds
Organic oxides
| Substituents |
Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha-hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
cinnamate ester (CHEBI:75489 )
cyclitol carboxylic acid (CHEBI:75489 )
| 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 Solubility3.44 mg/mLALOGPS
logP0.17ALOGPS
logP-0.27ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.23 m3·mol-1ChemAxon
Polarizability31.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (6 TMS)splash10-0a4j-1897000000-09420d5c4ce1c849a2b5View 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 |
521
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000275
| 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 |
HMDB29278
| Metagene Link |
HMDB29278
| METLIN ID |
Not Available
| PubChem Compound |
1794425
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: PIM-447 (dihydrochloride)
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: 8627567
