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Showing Compound Isofraxidin (FDB000696)

Record Information
Version1.0
Creation date2010-04-08 22:04:40 UTC
Update date2025-11-18 22:21:14 UTC
Primary IDFDB000696
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsofraxidin
DescriptionIsofraxidin, also known as 6,8-dimethoxy-7-hydroxycoumarin or 7-hydroxy-6,8-dimethoxy-2h-1-benzopyran-2-one, is a member of the class of compounds known as 7-hydroxycoumarins. 7-hydroxycoumarins are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Isofraxidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isofraxidin can be found in muskmelon, tarragon, and watermelon, which makes isofraxidin a potential biomarker for the consumption of these food products. Isofraxidin is a chemical compound found in a variety of plants including Eleutherococcus senticosus .
CAS Number486-21-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
7-Hydroxy-6,8-dimethoxy-2H-1-benzopyran-2-oneKegg
6,8-Dimethoxy-7-hydroxycoumarinMeSH
Iso-fraxidinMeSH
6,8-Dimethoxy-7-hydroxy-coumarinMeSH
7-Hydroxy-6,8-dimethoxycoumarinMeSH
2H-1- Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-biospider
2H-1-Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-biospider
Calycanthogenoldb_source
Coumarin, 7-hydroxy-6,8-dimethoxy-biospider
Isofraxidindb_source
Phytodolordb_source
Umbelliferone, 6,8-dimethoxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility1.57 g/LALOGPS
logP1.8ALOGPS
logP1.16ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.46 m³·mol⁻¹ChemAxon
Polarizability21.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H10O5
IUPAC name7-hydroxy-6,8-dimethoxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)11(15-2)9(7)13/h3-5,13H,1-2H3
InChI KeyHOEVRHHMDJKUMZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(OC(=O)C=C2)C(OC)=C1O
Average Molecular Weight222.1941
Monoisotopic Molecular Weight222.05282343
Classification
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.46%; H 4.54%; O 36.00%DFC
Melting PointMp 148-149°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data342 (e ) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsofraxidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-0930000000-e502f8f83c7759190f00Spectrum
Predicted GC-MSIsofraxidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsofraxidin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsofraxidin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a4l-0690000000-e943de038d002660fa0f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-690afaa417170ba1dc1d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0390000000-212677f70322ad12af192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-06rl-0900000000-aa24d1c0fbf48a94421b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-08gi-0900000000-170edd53acb99b5615dc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-8900000000-d1b48951862a3a54844f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-08gi-0900000000-7292a28cd5c0fa5899ae2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-3587832a7955c218aa272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0390000000-2adfc1f5259aad53d77f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-0790000000-71b59713796325f7b5aa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0090000000-b22ff997dcc6cc2821432021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0bu0-0900000000-e5fcbf0f6a41ce9238dd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-0a4l-0790000000-418faebb7b1e5c97783a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0c03-0950000000-eb3e2d2d086710c39cea2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-004i-9200000000-fd65ec48652f5c770ac62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0090000000-22244300659ac6a1092a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-0690000000-dc953ef59eb04b6e4d6f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-004i-9710000000-50d65186813e327304682021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03du-0900000000-8d45cd1187b32be630bf2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-66689c72c7e98330efff2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-0406ea331c48a33ad2d62016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-0950000000-b9e71c15f1857b74f6982016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-0bbb60d8d4b11b95b03f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0390000000-57a9014b08f2bf03ccbf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvj-0910000000-0d7a54c1aec421e196112016-08-03View Spectrum
NMRNot Available
ChemSpider ID4477107
ChEMBL IDCHEMBL451518
KEGG Compound IDC17480
Pubchem Compound ID5318565
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFQ13-Z:BFQ16-C
EAFUS IDNot Available
Dr. Duke IDISOFRAXIDIN
BIGG IDNot Available
KNApSAcK IDC00030527
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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.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).