Sakuranetin (CHEM023758)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:16:35 UTC
Update Date2016-11-09 01:17:46 UTC
Accession NumberCHEM023758
Identification
Common NameSakuranetin
ClassSmall Molecule
DescriptionA flavonoid phytoalexin that is (S)-naringenin in which the hydroxy group at position 7 is replaced by a methoxy group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC16H14O5
Average Molecular Mass286.279 g/mol
Monoisotopic Mass286.084 g/mol
CAS Registry Number2957-21-3
IUPAC Name(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namesakuranetin
SMILES[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gdr-1950300000-a48312953ffcce6caa36Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-056r-2951400000-d20272b440111f7a94e8Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gdr-1950300000-a48312953ffcce6caa36Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-056r-2951400000-d20272b440111f7a94e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1490000000-64eb4f6a24c41e1fbefaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-06di-7948800000-c577b426dfaff9381d6bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 20V, positivesplash10-014j-0900000000-54b50a99fb1941ecf021Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 20V, positivesplash10-014j-0900000000-4702d57aa6a61bd59567Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-9cf4fa799bfdc4e4130bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-a8ce07e74597351565e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0980000000-ad4f98ec1505fcea7278Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-2ac9f17f26389e03f793Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00kf-9700000000-7510c0e1f415ab13f395Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00kf-8900000000-890610439b8c00d535b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-662e43a055eea0b8da6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00kf-8900000000-30c9f7d08bfa3bac40b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-ff261837f1c0ee877f44Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0980000000-2156366d1516097a79e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kr-0980000000-dd5a370f9941d2861b69Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-72ef3a1b0a3a8e98b306Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-9c1d1e5a9b35f8821e91Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0890000000-cf1b6b4990b6fefcaf01Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-e2d490f2b12fa6f624a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kf-8900000000-bfd5bf6ff85e42769eb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0900000000-4fadcc8d663cfc88b52bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0290000000-5751ae9cb3dcf7cec01cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0890000000-32592494194e58ee1224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ba-3910000000-cb744b8c05b1a8820085Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-1a79d429ac0d0568bc14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0290000000-3868b08e8e2294ef0348Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5940000000-e495c14f115c39f42faeSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB08517
HMDB IDHMDB0030090
FooDB IDFDB001472
Phenol Explorer IDNot Available
KNApSAcK IDC00000999
BiGG IDNot Available
BioCyc IDCPD-7079
METLIN IDNot Available
PDB IDSAK
Wikipedia LinkSakuranetin
Chemspider ID66249
ChEBI ID28927
PubChem Compound ID73571
Kegg Compound IDC09833
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18522800
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22148193
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22512738
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22895058
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23170811
6. Kim BG, Jung BR, Lee Y, Hur HG, Lim Y, Ahn JH: Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli. J Agric Food Chem. 2006 Feb 8;54(3):823-8.
7. Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.