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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:55:13 UTC
Update Date2022-03-07 02:53:59 UTC
HMDB IDHMDB0034124
Secondary Accession Numbers
  • HMDB34124
Metabolite Identification
Common NameFonsecin
DescriptionFonsecin 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. Fonsecin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Fonsecin.
Structure
Data?1563862514
Synonyms
ValueSource
2,3-dihydro-2,5,8-Trihydroxy-6-methoxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one, 9ciHMDB
Antibiotic TMC 256b1HMDB
O8-Demethylfonsecin bHMDB
TMC 256b1HMDB
Chemical FormulaC15H14O6
Average Molecular Weight290.2681
Monoisotopic Molecular Weight290.07903818
IUPAC Name2,5,8-trihydroxy-6-methoxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one
Traditional Name2,5,8-trihydroxy-6-methoxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one
CAS Registry Number3748-39-8
SMILES
COC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C1
InChI Identifier
InChI=1S/C15H14O6/c1-15(19)6-9(17)13-11(21-15)4-7-3-8(16)5-10(20-2)12(7)14(13)18/h3-5,16,18-19H,6H2,1-2H3
InChI KeyFKCYENFBFZUSDP-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
  • Naphthopyranone
  • Benzochromone
  • 2-naphthol
  • 1-naphthol
  • Chromone
  • Naphthalene
  • Benzopyran
  • 1-benzopyran
  • Chromane
  • Anisole
  • Aryl ketone
  • Aryl alkyl ketone
  • Pyranone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Hemiacetal
  • Ketone
  • Oxacycle
  • Polyol
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point198 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP1.6ALOGPS
logP2.07ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.68ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.99 m³·mol⁻¹ChemAxon
Polarizability28.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.28131661259
DarkChem[M-H]-166.9431661259
DeepCCS[M+H]+174.19630932474
DeepCCS[M-H]-171.83830932474
DeepCCS[M-2H]-204.72430932474
DeepCCS[M+Na]+180.28930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FonsecinCOC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C14082.0Standard polar33892256
FonsecinCOC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C12701.5Standard non polar33892256
FonsecinCOC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C12823.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fonsecin,1TMS,isomer #1COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C)=C122576.2Semi standard non polar33892256
Fonsecin,1TMS,isomer #2COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O)=C122571.2Semi standard non polar33892256
Fonsecin,1TMS,isomer #3COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O)=C122682.3Semi standard non polar33892256
Fonsecin,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C)=C122669.6Semi standard non polar33892256
Fonsecin,2TMS,isomer #2COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O[Si](C)(C)C)=C122586.0Semi standard non polar33892256
Fonsecin,2TMS,isomer #3COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O)=C122626.7Semi standard non polar33892256
Fonsecin,3TMS,isomer #1COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O[Si](C)(C)C)=C122664.3Semi standard non polar33892256
Fonsecin,1TBDMS,isomer #1COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C(C)(C)C)=C122818.4Semi standard non polar33892256
Fonsecin,1TBDMS,isomer #2COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O)=C122823.5Semi standard non polar33892256
Fonsecin,1TBDMS,isomer #3COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O)=C122915.8Semi standard non polar33892256
Fonsecin,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C(C)(C)C)=C123121.2Semi standard non polar33892256
Fonsecin,2TBDMS,isomer #2COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O[Si](C)(C)C(C)(C)C)=C123049.9Semi standard non polar33892256
Fonsecin,2TBDMS,isomer #3COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O)=C123104.8Semi standard non polar33892256
Fonsecin,3TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O[Si](C)(C)C(C)(C)C)=C123315.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fonsecin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ff1-1190000000-9f32839fa860a8f53a3b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fonsecin GC-MS (3 TMS) - 70eV, Positivesplash10-007o-3003900000-a0481e8670fc5a42371c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fonsecin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fonsecin LC-ESI-qTof , Positive-QTOFsplash10-0159-0890000000-1870c63ea48978d827432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fonsecin , positive-QTOFsplash10-0159-0890000000-1870c63ea48978d827432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fonsecin , positive-QTOFsplash10-001i-0390000000-864a85c4e93db9f756f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fonsecin , positive-QTOFsplash10-0a4i-0190000000-f52e6d795651410047692017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 10V, Positive-QTOFsplash10-0006-0090000000-8698fa82be4165228c8f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 20V, Positive-QTOFsplash10-006x-1090000000-dec5fb573943e34a68992015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 40V, Positive-QTOFsplash10-0ue9-0190000000-c8fcaf793d80a22f301c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 10V, Negative-QTOFsplash10-000i-0090000000-1d309636cbe4d6d7b4782015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 20V, Negative-QTOFsplash10-052r-0090000000-bd992c02ee453436b5692015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 40V, Negative-QTOFsplash10-0a59-4390000000-621bb98153ac85cae2d72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 10V, Negative-QTOFsplash10-000i-0090000000-4a89100bf019d25eb21a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 20V, Negative-QTOFsplash10-0a5i-0090000000-6fd94ee6fc378b9527262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 40V, Negative-QTOFsplash10-000x-2090000000-4f9de4f27c3a166ba5072021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 10V, Positive-QTOFsplash10-0006-0090000000-9a08772e651d55df45c32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 20V, Positive-QTOFsplash10-000x-0090000000-2d9c01b86f47e30e9a7f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fonsecin 40V, Positive-QTOFsplash10-0012-0590000000-34ac37097cfe3a1895652021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012396
KNApSAcK IDC00000559
Chemspider ID187517
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound216328
PDB IDNot Available
ChEBI ID64543
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .