Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2020-02-24 19:10:23 UTC
Primary IDFDB001472
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSakuranetin
DescriptionSakuranetin, also known as (2S)-sakuranetin, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, sakuranetin is considered to be a flavonoid lipid molecule. Sakuranetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sakuranetin is found, on average, in the highest concentration within mexican oregano. Sakuranetin has also been detected, but not quantified in, several different foods, such as prunus (cherry, plum), blackcurrants, walnuts, wild carrots, and carrots. This could make sakuranetin a potential biomarker for the consumption of these foods.
CAS Number2957-21-3
Structure
Thumb
Synonyms
SynonymSource
(2S)-SakuranetinChEBI
(S)-(-)-4',5-Dihydroxy-7-methoxyflavanoneChEBI
(S)-2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-oneChEBI
4',5-Dihydroxy-7-methoxyflavanoneChEBI
Naringenin 7-methyl etherChEBI
5,4'-Dihydroxy-7-methoxyflavanoneHMDB
7-O-MethylnaringeninHMDB
(S)-2,3-dihydro-5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-oneChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-chroman-4-onebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP2.86ALOGPS
logP2.98ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.77 m³·mol⁻¹ChemAxon
Polarizability29.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H14O5
IUPAC name(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
InChI KeyDJOJDHGQRNZXQQ-AWEZNQCLSA-N
Isomeric SMILES[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
Classification
Description belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • Flavanone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point152 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gdr-1950300000-a48312953ffcce6caa36JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-056r-2951400000-d20272b440111f7a94e8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gdr-1950300000-a48312953ffcce6caa36JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-056r-2951400000-d20272b440111f7a94e8JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1490000000-64eb4f6a24c41e1fbefaJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-06di-7948800000-c577b426dfaff9381d6bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 20V, positivesplash10-014j-0900000000-54b50a99fb1941ecf021JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 20V, positivesplash10-014j-0900000000-4702d57aa6a61bd59567JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0290000000-5751ae9cb3dcf7cec01cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0890000000-32592494194e58ee1224JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ba-3910000000-cb744b8c05b1a8820085JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-1a79d429ac0d0568bc14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0290000000-3868b08e8e2294ef0348JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5940000000-e495c14f115c39f42faeJSpectraViewer
ChemSpider ID66249
ChEMBL IDCHEMBL448297
KEGG Compound IDC09833
Pubchem Compound ID73571
Pubchem Substance IDNot Available
ChEBI ID28927
Phenol-Explorer ID226
DrugBank IDDB08517
HMDB IDHMDB30090
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSAKURANETIN
BIGG IDNot Available
KNApSAcK IDC00000999
HET IDSAK
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSakuranetin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.