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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:47 UTC
Update Date2022-03-07 02:52:41 UTC
HMDB IDHMDB0030746
Secondary Accession Numbers
  • HMDB30746
Metabolite Identification
Common Name5,7,3'-Trihydroxy-4'-methoxyflavanone
Description5,7,3'-Trihydroxy-4'-methoxyflavanone belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Based on a literature review a small amount of articles have been published on 5,7,3'-Trihydroxy-4'-methoxyflavanone.
Structure
Data?1563862031
SynonymsNot Available
Chemical FormulaC16H14O6
Average Molecular Weight302.282
Monoisotopic Molecular Weight302.079038171
IUPAC Name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namehesperetine
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3
InChI KeyAIONOLUJZLIMTK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • Flavanone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Flavan
  • Chromone
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Methoxybenzene
  • Phenoxy compound
  • Aryl alkyl ketone
  • Anisole
  • Phenol ether
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.52ALOGPS
logP2.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.75 m³·mol⁻¹ChemAxon
Polarizability30.32 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]+170.82531661259
DarkChem[M-H]-173.16131661259
DeepCCS[M+H]+173.0430932474
DeepCCS[M-H]-170.68230932474
DeepCCS[M-2H]-203.92130932474
DeepCCS[M+Na]+179.14730932474
AllCCS[M+H]+170.632859911
AllCCS[M+H-H2O]+167.032859911
AllCCS[M+NH4]+173.932859911
AllCCS[M+Na]+174.932859911
AllCCS[M-H]-170.832859911
AllCCS[M+Na-2H]-170.332859911
AllCCS[M+HCOO]-169.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,7,3'-Trihydroxy-4'-methoxyflavanoneCOC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O14274.3Standard polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanoneCOC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O13013.0Standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanoneCOC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O12995.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TMS,isomer #1COC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C2962.5Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TMS,isomer #2COC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O2990.2Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TMS,isomer #3COC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O3002.5Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TMS,isomer #1COC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C2926.1Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TMS,isomer #2COC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C2949.2Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TMS,isomer #3COC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O2953.2Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,3TMS,isomer #1COC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C2934.3Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TBDMS,isomer #1COC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3232.6Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TBDMS,isomer #2COC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O3255.8Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TBDMS,isomer #3COC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O3270.0Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TBDMS,isomer #1COC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O[Si](C)(C)C(C)(C)C3429.5Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TBDMS,isomer #2COC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C3449.2Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TBDMS,isomer #3COC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O3448.8Semi standard non polar33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,3TBDMS,isomer #1COC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O[Si](C)(C)C(C)(C)C3593.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)splash10-052f-1971000000-56754303127301d1b2ea2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)splash10-000l-2971100000-c6ded90239807f8bb8982017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)splash10-0a4l-1890100000-d023765b6d478c3463882017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)splash10-052f-1971000000-56754303127301d1b2ea2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)splash10-000l-2971100000-c6ded90239807f8bb8982018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)splash10-0a4l-1890100000-d023765b6d478c3463882018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0792000000-043d1ca82d47023493412017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-MS (3 TMS) - 70eV, Positivesplash10-0udj-3860980000-a1715e067e13bbdada3e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone DI-ESI-qTof , Negative-QTOFsplash10-0udi-0498000000-93e6bf74ac9acf6199dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone DI-ESI-qTof , Positive-QTOFsplash10-0udi-0900000000-3155fa8cf11cb598c7b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-qTof , Positive-QTOFsplash10-0udi-0910000000-950b0c394b2535d33d8e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , negative-QTOFsplash10-0udi-0009000000-e068a12319d0bfd192f12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , negative-QTOFsplash10-0udi-0693000000-4d820f1d6dcf9d80fc412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , negative-QTOFsplash10-0a4r-0910000000-3ba63f0018fc2d3146ed2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone Linear Ion Trap , negative-QTOFsplash10-000l-0190000000-5929a6a017c13b7d93e62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone Linear Ion Trap , negative-QTOFsplash10-000i-0190000000-eb01c4ad53e16b476f092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOFsplash10-0udi-0169000000-5d9b7fba914d229018a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOFsplash10-053i-0920000000-b6ab2fed21176a341b282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOFsplash10-0udi-0009000000-32f8b49c4bc1df10782a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOFsplash10-0iki-0930000000-20176d350f94ae4a84ed2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , positive-QTOFsplash10-0udi-0907000000-36605ac798a9e373e56c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , positive-QTOFsplash10-0ufr-0900000000-de657b62f36904fa4d9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , positive-QTOFsplash10-0udi-0900000000-aca6930de1cdc2b44ee32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone Linear Ion Trap , positive-QTOFsplash10-004i-0950000000-3910d5d1943ed6685f2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone , positive-QTOFsplash10-0udi-0910000000-950b0c394b2535d33d8e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone , positive-QTOFsplash10-0udi-0901000000-21943a0770755ae8ec602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 6V, Positive-QTOFsplash10-0udi-0859000000-8990f8b07e70df4050b52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 10V, Positive-QTOFsplash10-0udi-0329000000-4364410cdc5a65b920322016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 20V, Positive-QTOFsplash10-0udr-0944000000-edd7b755d11b9331e6c92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 40V, Positive-QTOFsplash10-0uki-3910000000-9e449d46da8305c0b7942016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 10V, Negative-QTOFsplash10-0udi-0109000000-21473197ac3beced46282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 20V, Negative-QTOFsplash10-0udi-0569000000-1e4d2574c341d9d9124f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 40V, Negative-QTOFsplash10-0pbl-4940000000-c9a717aa36bf4402e6c72016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002676
KNApSAcK IDC00014343
Chemspider ID3467
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3593
PDB IDNot Available
ChEBI ID244674
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barreca D, Lagana G, Tellone E, Ficarra S, Leuzzi U, Galtieri A, Bellocco E: Influences of flavonoids on erythrocyte membrane and metabolic implication through anionic exchange modulation. J Membr Biol. 2009 Aug;230(3):163-71. doi: 10.1007/s00232-009-9197-x. [PubMed:19727922 ]
  2. Choi EJ: Hesperetin induced G1-phase cell cycle arrest in human breast cancer MCF-7 cells: involvement of CDK4 and p21. Nutr Cancer. 2007;59(1):115-9. [PubMed:17927510 ]
  3. De Clercq E: Potential antivirals and antiviral strategies against SARS coronavirus infections. Expert Rev Anti Infect Ther. 2006 Apr;4(2):291-302. [PubMed:16597209 ]
  4. Jin YR, Han XH, Zhang YH, Lee JJ, Lim Y, Chung JH, Yun YP: Antiplatelet activity of hesperetin, a bioflavonoid, is mainly mediated by inhibition of PLC-gamma2 phosphorylation and cyclooxygenase-1 activity. Atherosclerosis. 2007 Sep;194(1):144-52. Epub 2006 Nov 7. [PubMed:17092506 ]
  5. Kuppusamy UR, Das NP: Antilipolytic action of hesperetin in rat adipocytes. Planta Med. 1993 Dec;59(6):508-12. [PubMed:8302948 ]
  6. (). 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
5,7,3'-Trihydroxy-4'-methoxyflavanone → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails
5,7,3'-Trihydroxy-4'-methoxyflavanone → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
5,7,3'-Trihydroxy-4'-methoxyflavanone → 6-[5-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)-2-methoxyphenoxy]-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
5,7,3'-Trihydroxy-4'-methoxyflavanone → hesperetin 3'-O-sulfatedetails