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Sakuranetin (FDB001472)

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. Sakuranetin is found, on average, in the highest concentration within mexican oreganos (Lippia graveolens). Sakuranetin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), prunus (cherry, plum), wild carrots (Daucus carota), walnuts (Juglans), and blackcurrants (Ribes nigrum). This could make sakuranetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Sakuranetin.
CAS Number2957-21-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSSakuranetin, non-derivatized, GC-MS Spectrumsplash10-0gdr-1950300000-a48312953ffcce6caa36Spectrum
GC-MSSakuranetin, non-derivatized, GC-MS Spectrumsplash10-056r-2951400000-d20272b440111f7a94e8Spectrum
GC-MSSakuranetin, non-derivatized, GC-MS Spectrumsplash10-0gdr-1950300000-a48312953ffcce6caa36Spectrum
GC-MSSakuranetin, non-derivatized, GC-MS Spectrumsplash10-056r-2951400000-d20272b440111f7a94e8Spectrum
Predicted GC-MSSakuranetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1490000000-64eb4f6a24c41e1fbefaSpectrum
Predicted GC-MSSakuranetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-7948800000-c577b426dfaff9381d6bSpectrum
Predicted GC-MSSakuranetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 20V, positivesplash10-014j-0900000000-54b50a99fb1941ecf0212020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 20V, positivesplash10-014j-0900000000-4702d57aa6a61bd595672020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-9cf4fa799bfdc4e4130b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-a8ce07e74597351565e22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0980000000-ad4f98ec1505fcea72782021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-2ac9f17f26389e03f7932021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00kf-9700000000-7510c0e1f415ab13f3952021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00kf-8900000000-890610439b8c00d535b82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-662e43a055eea0b8da6d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00kf-8900000000-30c9f7d08bfa3bac40b32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-ff261837f1c0ee877f442021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0980000000-2156366d1516097a79e82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kr-0980000000-dd5a370f9941d2861b692021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-72ef3a1b0a3a8e98b3062021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-9c1d1e5a9b35f8821e912021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0890000000-cf1b6b4990b6fefcaf012021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-e2d490f2b12fa6f624a72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kf-8900000000-bfd5bf6ff85e42769eb72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-4fadcc8d663cfc88b52b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0290000000-5751ae9cb3dcf7cec01c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0890000000-32592494194e58ee12242016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ba-3910000000-cb744b8c05b1a88200852016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-1a79d429ac0d0568bc142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0290000000-3868b08e8e2294ef03482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5940000000-e495c14f115c39f42fae2016-08-03View Spectrum
NMRNot Available
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.