Record Information
Version1.0
Creation date2010-04-08 22:10:00 UTC
Update date2019-11-26 03:06:12 UTC
Primary IDFDB012108
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRubrofusarin
DescriptionRubrofusarin, also known as nsc 258316, is a member of the class of compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Rubrofusarin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Rubrofusarin can be found in mango, which makes rubrofusarin a potential biomarker for the consumption of this food product.
CAS Number3567-00-8
Structure
Thumb
Synonyms
SynonymSource
NSC 258316ChEBI
5,6-Dihydroxy-8-methoxy-2-methyl-4H-benzo(g)chromen-4-oneMeSH
5,6-dihydroxy-8-methoxy-2-methyl-4H-benzo[g]chromen-4-onebiospider
5,6-Dihydroxy-8-methoxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one, 9CIdb_source
5,6-Dihydroxy-8-methoxy-2-methyl-benzo[g]chromen-4-onebiospider
5,6-Dihydroxy-8-methoxy-2-methylbenzo[g]chromen-4-onedb_source
Rubrafusarinbiospider
Rubrofusarindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.9ALOGPS
logP2.75ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.82ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.98 m³·mol⁻¹ChemAxon
Polarizability27.53 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H12O5
IUPAC name5,6-dihydroxy-8-methoxy-2-methyl-4H-benzo[g]chromen-4-one
InChI IdentifierInChI=1S/C15H12O5/c1-7-3-10(16)14-12(20-7)5-8-4-9(19-2)6-11(17)13(8)15(14)18/h3-6,17-18H,1-2H3
InChI KeyFPNKCZKRICBAKG-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(O)=C2C(O)=C3C(=O)C=C(C)OC3=CC2=C1
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
Classification
Description belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • Chromone
  • 1-naphthol
  • Benzopyran
  • Naphthalene
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.17%; H 4.44%; O 29.38%DFC
Melting PointMp 210-211°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data415 (e 5200) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-0190000000-7a522176cb0801491646JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-cf4eca43e6fdbe9701dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-f8826a47f675a6e3f809JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pl9-1290000000-bc707d823f5a2d9cee22JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-0755533723b9e8cfd711JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-c92c4c60bdf3ed5cf066JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2940000000-bd75cef307d64460de2cJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID72537
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHDG37-L:HDG34-I
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002445
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.