Record Information
Version1.0
Creation date2010-04-08 22:11:41 UTC
Update date2019-11-26 03:11:14 UTC
Primary IDFDB015173
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsotrifoliol
DescriptionIsotrifoliol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Isotrifoliol is an extremely weak basic (essentially neutral) compound (based on its pKa). Isotrifoliol has been detected, but not quantified in, herbs and spices. This could make isotrifoliol a potential biomarker for the consumption of these foods.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
3,9-Dihydroxy-1-methoxycoumestanHMDB
IsotrifoliolMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP2.54ALOGPS
logP2.24ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.21ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.08 m³·mol⁻¹ChemAxon
Polarizability29.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H10O6
IUPAC name5,14-dihydroxy-3-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one
InChI IdentifierInChI=1S/C16H10O6/c1-20-11-5-8(18)6-12-14(11)15-13(16(19)22-12)9-3-2-7(17)4-10(9)21-15/h2-6,17-18H,1H3
InChI KeyOVLUQDOJWGTPHA-UHFFFAOYSA-N
Isomeric SMILESCOC1=C2C3=C(C4=C(O3)C=C(O)C=C4)C(=O)OC2=CC(O)=C1
Average Molecular Weight298.247
Monoisotopic Molecular Weight298.047738052
Classification
Description Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.43%; H 3.38%; O 32.19%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 Data361 (sh) () (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsotrifoliol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00sj-0190000000-97e135336bc2f4ee0092Spectrum
Predicted GC-MSIsotrifoliol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i1-4249500000-f771aa9c2acd65afb780Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-3a1c73a243f500d29415Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-a4db415efa2c378cc979Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-0190000000-3617bac350efb170dbf5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-4f72c19c40413a4bee27Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-12af3276a21593dee63bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u0-0490000000-b377712d4067c24811d2Spectrum
NMRNot Available
ChemSpider ID4477198
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5318679
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36305
CRC / DFC (Dictionary of Food Compounds) IDKWC15-T:JYK01-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00018990
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