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Neochlorogenic acid (FDB002562)

Record Information
Version1.0
Creation date2010-04-08 22:05:25 UTC
Update date2019-11-26 02:57:37 UTC
Primary IDFDB002562
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNeochlorogenic acid
DescriptionNeochlorogenic acid, also known as neochlorogenate or 3-O-caffeoylquinic acid, belongs to quinic acids and derivatives class of compounds. Those 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. Neochlorogenic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Neochlorogenic acid can be found in a number of food items such as quince, chicory, white cabbage, and grape wine, which makes neochlorogenic acid a potential biomarker for the consumption of these food products. Neochlorogenic acid is a natural polyphenolic compound found in some types of dried fruits and a variety of other plant sources such as peaches. It is an isomer of chlorogenic acid .
CAS Number906-33-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.44 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.23 m³·mol⁻¹ChemAxon
Polarizability33.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H18O9
IUPAC name(1R,3R,4S,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
InChI IdentifierInChI=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 KeyCWVRJTMFETXNAD-NXLLHMKUSA-N
Isomeric SMILESO[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
Average Molecular Weight354.3087
Monoisotopic Molecular Weight354.095082174
Classification
Description Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentQuinic acids and derivatives
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Foods

Fruits and vegetables:

Beverages:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.24%; H 5.12%; O 40.64%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
GC-MSNeochlorogenic acid, 6 TMS, GC-MS Spectrumsplash10-0a4i-2779000000-05b2fc59f56f79049968Spectrum
Predicted GC-MSNeochlorogenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-000l-0900000000-5ab6455873264462bceb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000f-0900000000-cda19179fe6c6b526bab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-002f-0901000000-893cb76037debb93b2ad2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-002f-0900000000-ca261c56261936391ff52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-5de1931e7418f0c537ac2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-03dr-0900000000-de7078adddab10dc09ac2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-105a6e539cf0d57bb2562021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-1b705a6715ed1c6c3c4e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-0900000000-8c0991eea696d59be2f62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0900000000-06335c33e4d64583bd462021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0918000000-3ee17b66f5461b5349a22016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g3-0902000000-adb0080c9976132686562016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-837dabfad864902782242016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfu-0519000000-d321b79970ee8839fc242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vm-1922000000-410b2ca167dfdb9d0a542016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-090aec697972e64791aa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-0907000000-7552557c59dc3f71d17e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f76-0912000000-2007c2339d38311de1462021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-2901000000-8f60dc3d397918e40c712021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0905000000-558b49c195cd84c2bb622021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-a3bfaab2ee36f5805f062021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ib-2900000000-d93b9afe7d5384280f4d2021-09-23View 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 ID467
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCMK22-F:CMK22-F
EAFUS IDNot Available
Dr. Duke ID5-O-CAFFEOYLQUINIC-ACID|NEOCLOROGENIC-ACID|NEO-CHLOROGENIC-ACID
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 ID467
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
vulnerary73336 A drug used in treating and healing of wounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).