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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:56:04 UTC
Update Date2019-07-23 06:15:17 UTC
HMDB IDHMDB0034139
Secondary Accession Numbers
  • HMDB34139
Metabolite Identification
Common NameTrifoliol
DescriptionTrifoliol 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. Thus, trifoliol is considered to be a flavonoid lipid molecule. Trifoliol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Trifoliol has been detected, but not quantified in, several different foods, such as alfalfa, green vegetables, herbs and spices, pulses, and tea. This could make trifoliol a potential biomarker for the consumption of these foods.
Structure
Data?1563862517
Synonyms
ValueSource
3,7-Dihydroxy-9-methoxycoumestanHMDB
7,10-Dihydroxy-12-methoxycoumestanHMDB
Chemical FormulaC16H10O6
Average Molecular Weight298.247
Monoisotopic Molecular Weight298.047738052
IUPAC Name5,12-dihydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Nametrifoliol
CAS Registry Number1857-26-7
SMILES
COC1=CC(O)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1
InChI Identifier
InChI=1S/C16H10O6/c1-20-8-5-10(18)13-12(6-8)21-15-9-3-2-7(17)4-11(9)22-16(19)14(13)15/h2-6,17-18H,1H3
InChI KeyYFVNQUXNYCREJW-UHFFFAOYSA-N
Chemical Taxonomy
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 Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point332 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.5ALOGPS
logP2.24ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.08ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.08 m³·mol⁻¹ChemAxon
Polarizability29.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00sj-0090000000-df8f664ac0e17dc464aeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ur-2619400000-1b9aa84dbc60e18c71a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-c92bdeecc53adf4c130fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-a1bb6f82879248140c64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-0090000000-3b49f0557f326ebea97aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-e29c1d4cf2cb4c86f35eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-1b28a987b752c154092aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h3r-0090000000-47b60f160152f4ae4264Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012414
KNApSAcK IDC00009762
Chemspider ID4589482
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5487671
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Trifoliol → 3,4,5-trihydroxy-6-({5-hydroxy-14-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-12-yl}oxy)oxane-2-carboxylic aciddetails
Trifoliol → 3,4,5-trihydroxy-6-({12-hydroxy-14-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl}oxy)oxane-2-carboxylic aciddetails