Back to Compounds

Showing Compound 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
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
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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).