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Showing Compound 5,3',4'-Trihydroxy-3-methoxy-6,7-methylenedioxyflavone (FDB001548)

Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:35 UTC
Primary IDFDB001548
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5,3',4'-Trihydroxy-3-methoxy-6,7-methylenedioxyflavone
Description5,3',4'-trihydroxy-3-methoxy-6,7-methylenedioxyflavone is a member of the class of compounds known as 3-o-methylated flavonoids. 3-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, 5,3',4'-trihydroxy-3-methoxy-6,7-methylenedioxyflavone is considered to be a flavonoid lipid molecule. 5,3',4'-trihydroxy-3-methoxy-6,7-methylenedioxyflavone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,3',4'-trihydroxy-3-methoxy-6,7-methylenedioxyflavone can be found in spinach, which makes 5,3',4'-trihydroxy-3-methoxy-6,7-methylenedioxyflavone a potential biomarker for the consumption of this food product.
CAS Number36284-99-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.65ALOGPS
logP2.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.35ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.4 m³·mol⁻¹ChemAxon
Polarizability33.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H12O8
IUPAC name6-(3,4-dihydroxyphenyl)-9-hydroxy-7-methoxy-2H,8H-[1,3]dioxolo[4,5-g]chromen-8-one
InChI IdentifierInChI=1S/C17H12O8/c1-22-17-14(21)12-10(5-11-16(13(12)20)24-6-23-11)25-15(17)7-2-3-8(18)9(19)4-7/h2-5,18-20H,6H2,1H3
InChI KeyBBZORTSKYSEICL-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC=C(O)C(O)=C1
Average Molecular Weight344.2724
Monoisotopic Molecular Weight344.05321736
Classification
Description Belongs to the class of organic compounds known as 3-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • Flavone
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Benzodioxole
  • Catechol
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-eed85fb5835ad71f8add2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0119000000-05df6f5ac6d9a6dd0cc42016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aps-3891000000-2cc4c535aa4079ca7d592016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7d5b4f3b263e19ae7b342016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0029000000-7e3bf9e2d96b4a19b3d92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0400-4932000000-6c8b1f577de4e1d0a7882016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-3f68f407690ad3c91ed62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-108425f0323ef4d96a492021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ls-2933000000-7ec930a261ffcf61e4e82021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-830d07053efb41c3c3212021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0309000000-22356ebc5fe11cdaaa952021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-032c-1912000000-90c9bae5fdb0eeecb40f2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID388
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00005050
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
SpinachExpected but not quantifiedNot AvailableKNAPSACK
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Masakazu A, Kawasaki T: Three highly oxygenated flavone glucuronides in leaves of Spinacia oleracea. Phytochemistry. 1984 Aug;23(9):2043-47. Article [Structure] [No Pubmed ID]
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.