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Showing Compound 3-Feruloyl-4-caffeoylquinic acid (FDB010998)

Record Information
Version1.0
Creation date2010-04-08 22:09:25 UTC
Update date2019-11-26 03:04:27 UTC
Primary IDFDB010998
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Feruloyl-4-caffeoylquinic acid
Description4-O-Caffeoyl-3-O-feruloylquinic acid belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 4-O-Caffeoyl-3-O-feruloylquinic acid has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 4-O-caffeoyl-3-O-feruloylquinic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-O-Caffeoyl-3-O-feruloylquinic acid.
CAS Number96990-65-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4-O-Caffeoyl-3-O-feruloylquinateGenerator
4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3-dihydroxy-5-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylateGenerator
3-Feruloyl-4-caffeoylquinateGenerator
3-Feruloyl-4-caffeoylquinic acidmanual
4-Caffeoyl-3-feruloylquinic acidmanual
4-O-Caffeoyl-3-O-feruloylquinic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.065 g/LALOGPS
logP2.55ALOGPS
logP2.3ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area200.28 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity131.25 m³·mol⁻¹ChemAxon
Polarizability50.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H26O12
IUPAC name4-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3-dihydroxy-5-{[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
InChI IdentifierInChI=1S/C26H26O12/c1-36-20-11-15(3-7-17(20)28)5-8-22(31)37-21-13-26(35,25(33)34)12-19(30)24(21)38-23(32)9-4-14-2-6-16(27)18(29)10-14/h2-11,19,21,24,27-30,35H,12-13H2,1H3,(H,33,34)/b8-5-,9-4-
InChI KeySDMADMBVKYOYQN-QWUBYWPLSA-N
Isomeric SMILESCOC1=C(O)C=CC(\C=C/C(=O)OC2CC(O)(CC(O)C2OC(=O)\C=C/C2=CC(O)=C(O)C=C2)C(O)=O)=C1
Average Molecular Weight530.4774
Monoisotopic Molecular Weight530.142426296
Classification
Description Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Phenolic glycoside
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Glycosyl compound
  • C-glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Pyranone
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Dialkyl ether
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.87%; H 4.94%; O 36.19%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002r-5934410000-fa4562dfb106babec262Spectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0c0a-6560309000-a0ca9cafcb5f97c20bdeSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Feruloyl-4-caffeoylquinic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gr-0907360000-769b511076b1173447652016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0903010000-6ffb6afee902152407182016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-0911000000-c464ce10604f62fb3d682016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0809870000-1db13e4421b35b30c9862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0906200000-40622efe8b599839c7422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0902000000-ffc57b32badfbac8b42a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fb9-0108090000-4b6e51bf28a93afc3c4f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0709140000-48375a6751d5c03338602021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-0901320000-6ee40b165e07765c2ef32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01rt-0901150000-9be0e0599b1dfa25e33b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0900000000-38423c47cc34633425852021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1900000000-533ec0badb73fc0419112021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33008
CRC / DFC (Dictionary of Food Compounds) IDCMS81-K:FYB19-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference