Record Information
Version1.0
Creation date2010-04-08 22:13:23 UTC
Update date2019-11-26 03:15:26 UTC
Primary IDFDB017920
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBrevifolincarboxylic acid
DescriptionBrevifolincarboxylic acid belongs to isocoumarins and derivatives class of compounds. Those are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Brevifolincarboxylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Brevifolincarboxylic acid can be found in pomegranate, which makes brevifolincarboxylic acid a potential biomarker for the consumption of this food product.
CAS Number18490-95-4
Structure
Thumb
Synonyms
SynonymSource
7,8,9-Trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylateGenerator
BrevifolincarboxylateGenerator
1,2,3,5-Tetrahydro-7,8,9-trihydroxy-3,5-dioxocyclopenta[c][2]benzopyran-1-carboxylic acid, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility2.96 g/LALOGPS
logP1.38ALOGPS
logP0.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.03 m³·mol⁻¹ChemAxon
Polarizability25.3 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H8O8
IUPAC name7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylic acid
InChI IdentifierInChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19)
InChI KeyJFJWMFPFMLRLMI-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1CC(=O)C2=C1C1=C(C=C(O)C(O)=C1O)C(=O)O2
Average Molecular Weight292.1978
Monoisotopic Molecular Weight292.021917232
Classification
Description Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsocoumarins and derivatives
Sub ClassNot Available
Direct ParentIsocoumarins and derivatives
Alternative Parents
Substituents
  • Isocoumarin
  • Benzopyran
  • 2-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Ketone
  • Lactone
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.44%; H 2.76%; O 43.80%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]13D -3 (c, 0.4 in Me2CO aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-cd6aa32eaf9d781d35d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0090000000-4cde1c4215e89f9a84982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ns-0490000000-6174a5c8838ac2ebf1ba2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0090000000-f21cea4ae3fdd3aef3422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-0090000000-d65709c1294d2858e81b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v4i-9780000000-9936ba5327bf9afed16b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0090000000-3cd18dc695d7c34ba3062021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002g-0090000000-3025667ae85facff20d42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0290000000-b500d211f8e61fd40bc92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-7c929db8e418c0ef17802021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-8e37fba5799256353f592021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06y9-0960000000-dad569be1c17f3e250fb2021-10-21View 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 IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDLBT56-H:LBT56-H
EAFUS IDNot Available
Dr. Duke IDBREVIFOLIN-CARBOXYLIC-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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Navindra P. Seeram et al., “Section 1, Chapter 1 – Pomegranate Phytochemicals,” in Pomegranates: ancient roots to modern medicine (CRC Press, 2006), 3-30. [Structure]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).