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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:34:41 UTC
Update Date2022-09-22 18:34:57 UTC
HMDB IDHMDB0030090
Secondary Accession Numbers
  • HMDB30090
Metabolite Identification
Common 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), black walnuts (Juglans nigra), wild carrots (Daucus carota), walnuts (Juglans), and prunus (cherry, plum). This could make sakuranetin a potential biomarker for the consumption of these foods. Sakuranetin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Sakuranetin.
Structure
Data?1563861935
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 Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namesakuranetin
CAS Registry Number2957-21-3
SMILES
[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point152 °CNot Available
Boiling Point555.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility109.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.370 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.51531661259
DarkChem[M-H]-169.15631661259
DeepCCS[M+H]+167.6530932474
DeepCCS[M-H]-165.29230932474
DeepCCS[M-2H]-199.4430932474
DeepCCS[M+Na]+174.6330932474
AllCCS[M+H]+167.232859911
AllCCS[M+H-H2O]+163.532859911
AllCCS[M+NH4]+170.732859911
AllCCS[M+Na]+171.732859911
AllCCS[M-H]-168.532859911
AllCCS[M+Na-2H]-167.932859911
AllCCS[M+HCOO]-167.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sakuranetin[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C13921.1Standard polar33892256
Sakuranetin[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C12839.3Standard non polar33892256
Sakuranetin[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C12820.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sakuranetin,1TMS,isomer #1COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C12750.6Semi standard non polar33892256
Sakuranetin,1TMS,isomer #2COC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C12808.7Semi standard non polar33892256
Sakuranetin,2TMS,isomer #1COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)O2)C(O[Si](C)(C)C)=C12800.3Semi standard non polar33892256
Sakuranetin,1TBDMS,isomer #1COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13007.9Semi standard non polar33892256
Sakuranetin,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C13072.0Semi standard non polar33892256
Sakuranetin,2TBDMS,isomer #1COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13268.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)splash10-0gdr-1950300000-a48312953ffcce6caa362017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)splash10-056r-2951400000-d20272b440111f7a94e82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)splash10-0gdr-1950300000-a48312953ffcce6caa362018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)splash10-056r-2951400000-d20272b440111f7a94e82018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sakuranetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1490000000-64eb4f6a24c41e1fbefa2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sakuranetin GC-MS (2 TMS) - 70eV, Positivesplash10-06di-7948800000-c577b426dfaff9381d6b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sakuranetin 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 - Sakuranetin LC-ESI-QFT 20V, positive-QTOFsplash10-014j-0900000000-54b50a99fb1941ecf0212020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin LC-ESI-IT 20V, positive-QTOFsplash10-014j-0900000000-4702d57aa6a61bd595672020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOFsplash10-000i-0090000000-9cf4fa799bfdc4e4130b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOFsplash10-014i-0900000000-a8ce07e74597351565e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOFsplash10-00kr-0980000000-ad4f98ec1505fcea72782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 30V, Positive-QTOFsplash10-014i-0900000000-2ac9f17f26389e03f7932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 50V, Positive-QTOFsplash10-00kf-9700000000-7510c0e1f415ab13f3952021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 50V, Positive-QTOFsplash10-00kf-8900000000-890610439b8c00d535b82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 30V, Positive-QTOFsplash10-014i-0900000000-662e43a055eea0b8da6d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 50V, Positive-QTOFsplash10-00kf-8900000000-30c9f7d08bfa3bac40b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 30V, Positive-QTOFsplash10-014i-0900000000-ff261837f1c0ee877f442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOFsplash10-00kr-0980000000-2156366d1516097a79e82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOFsplash10-00kr-0980000000-dd5a370f9941d2861b692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOFsplash10-000i-0090000000-72ef3a1b0a3a8e98b3062021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOFsplash10-014i-0900000000-9c1d1e5a9b35f8821e912021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOFsplash10-00kr-0890000000-cf1b6b4990b6fefcaf012021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOFsplash10-000i-0090000000-e2d490f2b12fa6f624a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOFsplash10-00kf-8900000000-bfd5bf6ff85e42769eb72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOFsplash10-014i-0900000000-4fadcc8d663cfc88b52b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOFsplash10-000i-0290000000-5751ae9cb3dcf7cec01c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sakuranetin 20V, Positive-QTOFsplash10-014r-0890000000-32592494194e58ee12242016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sakuranetin 40V, Positive-QTOFsplash10-01ba-3910000000-cb744b8c05b1a88200852016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sakuranetin 10V, Negative-QTOFsplash10-000i-0090000000-1a79d429ac0d0568bc142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sakuranetin 20V, Negative-QTOFsplash10-00kr-0290000000-3868b08e8e2294ef03482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sakuranetin 40V, Negative-QTOFsplash10-014i-5940000000-e495c14f115c39f42fae2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08517
Phenol Explorer Compound IDNot Available
FooDB IDFDB001472
KNApSAcK IDC00000999
Chemspider ID66249
KEGG Compound IDC09833
BioCyc IDCPD-7079
BiGG IDNot Available
Wikipedia LinkSakuranetin
METLIN IDNot Available
PubChem Compound73571
PDB IDSAK
ChEBI ID28927
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1588731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:16448189 ]
  2. (). 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.. .