Fonsecin B (CHEM028000)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:08:58 UTC
Update Date2016-11-09 01:18:35 UTC
Accession NumberCHEM028000
Identification
Common NameFonsecin B
ClassSmall Molecule
DescriptionA naphtho-gamma-pyrone that is fonsecin in which the hydroxy group at position 8 (meta to the methoxy group) has been converted to the corresponding methyl ether. Found in Aspergillus fonsecaeus.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2,5-Dihydroxy-6,8-dimethoxy-2-methyl-2,3-dihydro-4H-naphtho[2,3-b]pyran-4-oneChEBI
2,5-Dihydroxy-6,8-dimethoxy-2-methyl-2.3-dihydrobenzo[g]chromen-4-oneChEBI
Fonsecin monomethyl etherChEBI
TMC 256 b2ChEBI
TMC-256b2ChEBI
TMC256b2ChEBI
Antibiotic TMC 256b2HMDB
TMC 256b2HMDB
Chemical FormulaC16H16O6
Average Molecular Mass304.295 g/mol
Monoisotopic Mass304.095 g/mol
CAS Registry Number1856-95-7
IUPAC Name2,5-dihydroxy-6,8-dimethoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one
Traditional Name2,5-dihydroxy-6,8-dimethoxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one
SMILESCOC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=C1
InChI IdentifierInChI=1S/C16H16O6/c1-16(19)7-10(17)14-12(22-16)5-8-4-9(20-2)6-11(21-3)13(8)15(14)18/h4-6,18-19H,7H2,1-3H3
InChI KeyZYTKFYQKQVYVMW-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Benzochromone
  • Naphthopyranone
  • Chromone
  • 1-naphthol
  • Chromane
  • Benzopyran
  • Naphthalene
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Pyranone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Hemiacetal
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP1.47ALOGPS
logP2.22ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.47 m³·mol⁻¹ChemAxon
Polarizability30.66 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pa-1090000000-caf70b76d1736aca171bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-4009800000-3a30b25e7fdd1fc35e2dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0079000000-bf437d6e9b14ac7fcebbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-1094000000-91e1c9a018e78d4add49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-1290000000-0ce998f5b0b466a8d448Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0069000000-066645bde46f7ee064f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1094000000-8a4888711d69d6b7cc1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1390000000-ccb1eb485faeba81cc52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-aad98767acd0285db910Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0091000000-51789fb628e383733296Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-7090000000-cbc4700ed7afbb28b9b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0039000000-34cd6f4a45fe5457c8acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0096000000-46024f8a4eefd44cfe61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h01-0490000000-fb7e38ebbe11e4cd1448Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033866
FooDB IDFDB012050
Phenol Explorer IDNot Available
KNApSAcK IDC00034518
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID141119
ChEBI ID133825
PubChem Compound ID160596
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20383387
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22377027
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=4837062
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.