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Showing Compound Acacetin (FDB002766)

Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-02-24 19:11:08 UTC
Primary IDFDB002766
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcacetin
Description5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one, also known as 4'-methoxy-5,7-dihydroxyflavone or acacetin, is a member of the class of compounds known as 4'-o-methylated flavonoids. 4'-o-methylated flavonoids are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one can be synthesized from apigenin. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, acacetin-7-O-beta-D-galactopyranoside, acacetin-8-C-neohesperidoside, and isoginkgetin. 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one can be found in ginkgo nuts, orange mint, and winter savory, which makes 5,7-dihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products.
CAS Number480-44-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4'-Methoxy-5,7-dihydroxyflavoneChEBI
5,7-Dihydroxy-2-(4-methoxyphenyl)-4-benzopyroneChEBI
AcacetinChEBI
LinarigeninChEBI
5,7-Dihydroxy-4'-methoxyflavoneKegg
5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Apigenin 4'-methyl etherdb_source
Buddleoflavonoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.056 g/LALOGPS
logP3.46ALOGPS
logP2.85ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.58ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.4 m³·mol⁻¹ChemAxon
Polarizability28.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O5
IUPAC name5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-8,17-18H,1H3
InChI KeyDANYIYRPLHHOCZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight284.2635
Monoisotopic Molecular Weight284.068473494
Classification
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
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.60%; H 4.25%; O 28.14%DFC
Melting PointNot Available
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-MSAcacetin, 1 TMS, GC-MS Spectrumsplash10-0a4r-7619000000-817802c448591650debaSpectrum
GC-MSAcacetin, 2 TMS, GC-MS Spectrumsplash10-03di-2733900000-3439dde28e0cc522d0d2Spectrum
Predicted GC-MSAcacetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08mi-5439700000-0c88005cfe5971080fe4Spectrum
Predicted GC-MSAcacetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05oc-0590000000-329b5fcd727ed303699bSpectrum
Predicted GC-MSAcacetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0190000000-f9171d6a3ce11fafc8dd2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090020000-dfe55f293e647f3301402017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0uxr-0940000000-73352417553e57b4bee22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-fbafd5ded7558cfda2302017-08-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-dc884c343b9a0499bc422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-2d6e86a23b7201fe960c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v09-2490000000-2328f6d9ee073d28b5622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-c1a5fd59543bc232e43d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-a047c9f433e7713707d92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-3590000000-64205560724c680d55952016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-aaff95cd19cd93fcb8d82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-139efeaa86e0903bbcb32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q9-0390000000-7b2e91829833aa7c385e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a8b9e5ba8bfe303a94182021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-fc15b98c0acb8f4ba8e02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0190000000-e42691aaeac33ae14a1c2021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01470
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID15335
Phenol-Explorer ID242
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNN51-J:CNN51-J
EAFUS IDNot Available
Dr. Duke IDAPIGENIN-4'-METHYL-ETHER|ACACETIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti mutagenicDUKE
aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
iodothyronine-deiodinase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
mutagenicDUKE
plasmodicideDUKE
protisticideDUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.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).