Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:47:03 UTC
Update Date2022-03-07 02:53:57 UTC
HMDB IDHMDB0034009
Secondary Accession Numbers
  • HMDB34009
Metabolite Identification
Common NameTrifolian
DescriptionTrifolian belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, trifolian is considered to be a flavonoid. Trifolian has been detected, but not quantified in, several different foods, such as herbal tea, black tea, herbs and spices, red tea, and green tea. This could make trifolian a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Trifolian.
Structure
Data?1563862494
Synonyms
ValueSource
1,3-Dihydroxy-2-methoxy-8,9-methylenedioxypterocarpanHMDB
Chemical FormulaC17H14O7
Average Molecular Weight330.2889
Monoisotopic Molecular Weight330.073952802
IUPAC Name15-methoxy-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaene-14,16-diol
Traditional Nametrifolian
CAS Registry Number73520-83-9
SMILES
COC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O
InChI Identifier
InChI=1S/C17H14O7/c1-20-17-9(18)3-13-14(15(17)19)16-8(5-21-13)7-2-11-12(23-6-22-11)4-10(7)24-16/h2-4,8,16,18-19H,5-6H2,1H3
InChI KeyPCVFSIAOIHIYNK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Pterocarpan
  • Isoflavanol
  • Isoflavan
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Coumaran
  • Benzodioxole
  • Benzofuran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point132 - 134 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility46.86 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.73 g/LALOGPS
logP2.2ALOGPS
logP1.83ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity80.81 m³·mol⁻¹ChemAxon
Polarizability32.57 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.47831661259
DarkChem[M-H]-176.25631661259
DeepCCS[M-2H]-207.63130932474
DeepCCS[M+Na]+182.85830932474
AllCCS[M+H]+175.932859911
AllCCS[M+H-H2O]+172.632859911
AllCCS[M+NH4]+179.132859911
AllCCS[M+Na]+180.032859911
AllCCS[M-H]-179.232859911
AllCCS[M+Na-2H]-178.432859911
AllCCS[M+HCOO]-177.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrifolianCOC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O4381.1Standard polar33892256
TrifolianCOC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O2802.9Standard non polar33892256
TrifolianCOC1=C(O)C2=C(OCC3C2OC2=CC4=C(OCO4)C=C32)C=C1O2977.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trifolian,1TMS,isomer #1COC1=C(O)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C)OCO53006.1Semi standard non polar33892256
Trifolian,1TMS,isomer #2COC1=C(O[Si](C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O)OCO53008.7Semi standard non polar33892256
Trifolian,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C)OCO53015.0Semi standard non polar33892256
Trifolian,1TBDMS,isomer #1COC1=C(O)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C(C)(C)C)OCO53260.0Semi standard non polar33892256
Trifolian,1TBDMS,isomer #2COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O)OCO53249.6Semi standard non polar33892256
Trifolian,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OCC3C4=CC5=C(C=C4OC3C2=C1O[Si](C)(C)C(C)(C)C)OCO53480.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trifolian GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-0469000000-140934f14ddf25c3bc832017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trifolian GC-MS (2 TMS) - 70eV, Positivesplash10-0r6r-3302900000-08b1ba9de58a9d76c5bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trifolian GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trifolian GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 10V, Positive-QTOFsplash10-001i-0009000000-6e8e7d679d840cad72fc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 20V, Positive-QTOFsplash10-001i-0119000000-a38e216c2ea4d5c5ffca2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 40V, Positive-QTOFsplash10-0fml-5891000000-92963a5fbd83082e701a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 10V, Negative-QTOFsplash10-004i-0009000000-d2032607a11eb21f8c832015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 20V, Negative-QTOFsplash10-004i-0069000000-86069b5084e79ad6918e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 40V, Negative-QTOFsplash10-05i0-3391000000-efcc5867c523c74ec4c42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 10V, Negative-QTOFsplash10-004i-0009000000-8e9d1a384717180cd0e22021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 20V, Negative-QTOFsplash10-004i-0019000000-3631fa029ef4aa6e4a312021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 40V, Negative-QTOFsplash10-00os-0391000000-dd2b2a9883903bc246722021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 10V, Positive-QTOFsplash10-001i-0009000000-931b28fcfeb1b8f804fe2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 20V, Positive-QTOFsplash10-001i-0009000000-da625d60a25b903108a42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trifolian 40V, Positive-QTOFsplash10-0pdi-0295000000-220779a38e51fc28188f2021-09-25Wishart LabView Spectrum
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 IDFDB012245
KNApSAcK IDC00009632
Chemspider ID24843036
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257476
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1839761
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.. .