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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:42 UTC
Update Date2022-03-07 02:53:08 UTC
HMDB IDHMDB0031824
Secondary Accession Numbers
  • HMDB31824
Metabolite Identification
Common Name4',5,8-Trihydroxyflavanone
Description4',5,8-Trihydroxyflavanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, 4',5,8-trihydroxyflavanone is considered to be a flavonoid. 4',5,8-Trihydroxyflavanone has been detected, but not quantified in, green vegetables and spinaches (Spinacia oleracea). This could make 4',5,8-trihydroxyflavanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4',5,8-Trihydroxyflavanone.
Structure
Data?1563862176
Synonyms
ValueSource
3-Ethyl-7-(trifluoromethyl)-2-quinoxalinolHMDB
5,8,4'-TrihydroxyflavanoneHMDB
7-Trifluoromethyl-3-ethyl-2(1H)-quinoxalinoneHMDB
Chemical FormulaC15H12O5
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
IUPAC Name5,8-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number123067-25-4
SMILES
OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O1
InChI Identifier
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)14-10(17)5-6-11(18)15(14)20-13/h1-6,13,16-18H,7H2
InChI KeySMRHIFAZRRVAQZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 8-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavanone
  • Chromone
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point262 - 264 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility395.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP2.47ALOGPS
logP2.84ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.29 m³·mol⁻¹ChemAxon
Polarizability27.16 ųChemAxon
Number of Rings3ChemAxon
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]+163.02531661259
DarkChem[M-H]-162.31631661259
DeepCCS[M+H]+163.19930932474
DeepCCS[M-H]-160.84130932474
DeepCCS[M-2H]-193.72730932474
DeepCCS[M+Na]+169.29230932474
AllCCS[M+H]+163.132859911
AllCCS[M+H-H2O]+159.232859911
AllCCS[M+NH4]+166.732859911
AllCCS[M+Na]+167.732859911
AllCCS[M-H]-162.932859911
AllCCS[M+Na-2H]-162.332859911
AllCCS[M+HCOO]-161.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4',5,8-TrihydroxyflavanoneOC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O13874.4Standard polar33892256
4',5,8-TrihydroxyflavanoneOC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O12818.3Standard non polar33892256
4',5,8-TrihydroxyflavanoneOC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=CC(O)=C2O12729.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4',5,8-Trihydroxyflavanone,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O)=C3O2)C=C12784.5Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(O)C2=C1C(=O)CC(C1=CC=C(O)C=C1)O22794.4Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(O)C2=C1OC(C1=CC=C(O)C=C1)CC2=O2779.7Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C)C=CC(O)=C3O2)C=C12803.2Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O[Si](C)(C)C)=C3O2)C=C12801.0Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(O[Si](C)(C)C)C2=C1OC(C1=CC=C(O)C=C1)CC2=O2791.7Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C3O2)C=C12807.6Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O)=C3O2)C=C13048.4Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(O)C2=C1C(=O)CC(C1=CC=C(O)C=C1)O23060.2Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(O)C2=C1OC(C1=CC=C(O)C=C1)CC2=O3049.8Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C3O2)C=C13305.0Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C3O2)C=C13287.1Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(O[Si](C)(C)C(C)(C)C)C2=C1OC(C1=CC=C(O)C=C1)CC2=O3295.3Semi standard non polar33892256
4',5,8-Trihydroxyflavanone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C3O2)C=C13488.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,8-Trihydroxyflavanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1490000000-aab471b5b64975003a772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,8-Trihydroxyflavanone GC-MS (3 TMS) - 70eV, Positivesplash10-00b9-4922800000-e9d3f8c5da94bb79f83d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4',5,8-Trihydroxyflavanone 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 - 4',5,8-Trihydroxyflavanone 10V, Positive-QTOFsplash10-00di-0490000000-8a4c8b1f1cd45bd9d4df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Positive-QTOFsplash10-0kmi-0940000000-9146002fb44ad2244f022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Positive-QTOFsplash10-00xr-5900000000-45605c8fb550165fb1202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 10V, Negative-QTOFsplash10-00di-0190000000-b84e11e4da85266bccd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Negative-QTOFsplash10-00di-0890000000-e304ea692b0c5c88d10f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Negative-QTOFsplash10-0ap3-4900000000-ea6204221e88237530122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 10V, Negative-QTOFsplash10-00di-0090000000-ef3c85d68f246f25c9122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Negative-QTOFsplash10-0fk9-0790000000-a386e8bbaa9ae30462a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Negative-QTOFsplash10-014i-0900000000-09d69c292a81834ed9bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 10V, Positive-QTOFsplash10-00di-0090000000-105ebbdeec4c9fc3ae6f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 20V, Positive-QTOFsplash10-0uka-0940000000-c743726bc2bdef6b6f002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4',5,8-Trihydroxyflavanone 40V, Positive-QTOFsplash10-0udi-0900000000-c4390b819362ba19dc352021-09-24Wishart 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 IDFDB008502
KNApSAcK IDC00008392
Chemspider ID24846274
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14353343
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1828131
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
4',5,8-Trihydroxyflavanone → 3,4,5-trihydroxy-6-{[8-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
4',5,8-Trihydroxyflavanone → 6-[4-(5,8-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4',5,8-Trihydroxyflavanone → [4-(5,8-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic aciddetails