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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:24:01 UTC
Update Date2022-03-07 02:53:48 UTC
HMDB IDHMDB0033649
Secondary Accession Numbers
  • HMDB33649
Metabolite Identification
Common NameO-Demethylfonsecin
DescriptionO-Demethylfonsecin 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. O-Demethylfonsecin 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 significant number of articles have been published on O-Demethylfonsecin.
Structure
Data?1563862438
Synonyms
ValueSource
DemethylfonsecinChEBI
DesmethylfonsecinChEBI
De-O-methylfonsecinHMDB
YWA 1HMDB
O-DemethylfonsecinChEBI
Chemical FormulaC14H12O6
Average Molecular Weight276.2415
Monoisotopic Molecular Weight276.063388116
IUPAC Name2,5,6,8-tetrahydroxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one
Traditional Name2,5,6,8-tetrahydroxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one
CAS Registry NumberNot Available
SMILES
CC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1
InChI Identifier
InChI=1S/C14H12O6/c1-14(19)5-9(17)12-10(20-14)3-6-2-7(15)4-8(16)11(6)13(12)18/h2-4,15-16,18-19H,5H2,1H3
InChI KeyRTYDQIKVNMHQMZ-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
  • 2-naphthol
  • 1-naphthol
  • Chromane
  • Benzopyran
  • Naphthalene
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Ketone
  • Hemiacetal
  • Polyol
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP0.93ALOGPS
logP1.92ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.25ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.51 m³·mol⁻¹ChemAxon
Polarizability26.59 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]+164.07631661259
DarkChem[M-H]-164.09931661259
DeepCCS[M+H]+166.15930932474
DeepCCS[M-H]-163.80130932474
DeepCCS[M-2H]-196.68730932474
DeepCCS[M+Na]+172.25330932474
AllCCS[M+H]+162.132859911
AllCCS[M+H-H2O]+158.332859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.632859911
AllCCS[M-H]-162.732859911
AllCCS[M+Na-2H]-162.232859911
AllCCS[M+HCOO]-161.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
O-DemethylfonsecinCC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O14273.3Standard polar33892256
O-DemethylfonsecinCC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O12705.3Standard non polar33892256
O-DemethylfonsecinCC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O12834.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
O-Demethylfonsecin,1TMS,isomer #1CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O)O12628.8Semi standard non polar33892256
O-Demethylfonsecin,1TMS,isomer #2CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C)O12610.8Semi standard non polar33892256
O-Demethylfonsecin,1TMS,isomer #3CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O)O12607.8Semi standard non polar33892256
O-Demethylfonsecin,1TMS,isomer #4CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O)O12655.9Semi standard non polar33892256
O-Demethylfonsecin,2TMS,isomer #1CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O)O12606.7Semi standard non polar33892256
O-Demethylfonsecin,2TMS,isomer #2CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O)O12596.8Semi standard non polar33892256
O-Demethylfonsecin,2TMS,isomer #3CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C)O12624.1Semi standard non polar33892256
O-Demethylfonsecin,2TMS,isomer #4CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O[Si](C)(C)C)O12598.2Semi standard non polar33892256
O-Demethylfonsecin,2TMS,isomer #5CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O12585.0Semi standard non polar33892256
O-Demethylfonsecin,2TMS,isomer #6CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O)O12649.5Semi standard non polar33892256
O-Demethylfonsecin,3TMS,isomer #1CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O)O12624.3Semi standard non polar33892256
O-Demethylfonsecin,3TMS,isomer #2CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O[Si](C)(C)C)O12606.7Semi standard non polar33892256
O-Demethylfonsecin,3TMS,isomer #3CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O12609.5Semi standard non polar33892256
O-Demethylfonsecin,3TMS,isomer #4CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O12643.9Semi standard non polar33892256
O-Demethylfonsecin,4TMS,isomer #1CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O12687.8Semi standard non polar33892256
O-Demethylfonsecin,1TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O)O12900.6Semi standard non polar33892256
O-Demethylfonsecin,1TBDMS,isomer #2CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O12882.4Semi standard non polar33892256
O-Demethylfonsecin,1TBDMS,isomer #3CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O12864.1Semi standard non polar33892256
O-Demethylfonsecin,1TBDMS,isomer #4CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O)O12907.6Semi standard non polar33892256
O-Demethylfonsecin,2TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O)O13118.4Semi standard non polar33892256
O-Demethylfonsecin,2TBDMS,isomer #2CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O13081.8Semi standard non polar33892256
O-Demethylfonsecin,2TBDMS,isomer #3CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O13112.2Semi standard non polar33892256
O-Demethylfonsecin,2TBDMS,isomer #4CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O13105.7Semi standard non polar33892256
O-Demethylfonsecin,2TBDMS,isomer #5CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O13065.7Semi standard non polar33892256
O-Demethylfonsecin,2TBDMS,isomer #6CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O13139.1Semi standard non polar33892256
O-Demethylfonsecin,3TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O13341.8Semi standard non polar33892256
O-Demethylfonsecin,3TBDMS,isomer #2CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O13309.7Semi standard non polar33892256
O-Demethylfonsecin,3TBDMS,isomer #3CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O13268.3Semi standard non polar33892256
O-Demethylfonsecin,3TBDMS,isomer #4CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O13320.8Semi standard non polar33892256
O-Demethylfonsecin,4TBDMS,isomer #1CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O13524.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O-Demethylfonsecin GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-2190000000-92067630613a090a62682017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - O-Demethylfonsecin GC-MS (4 TMS) - 70eV, Positivesplash10-00rg-9100740000-883c543f5e40f4da387c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - O-Demethylfonsecin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 10V, Positive-QTOFsplash10-056r-0090000000-d4ed37b50af2d0f4561c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Positive-QTOFsplash10-0a6r-1090000000-57b3333d9a3ed94892392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Positive-QTOFsplash10-0gdi-1890000000-95593eff745cf0e039692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 10V, Negative-QTOFsplash10-004i-0390000000-e0861a6bb40d34035f292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Negative-QTOFsplash10-056r-0490000000-745be75b0f78defaf2262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Negative-QTOFsplash10-00xr-1930000000-85766bd5d383df5fa4af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 10V, Negative-QTOFsplash10-004i-0090000000-fdefbfcb4d27fe320d4b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Negative-QTOFsplash10-004i-0090000000-34fc5131036b1ec5e26f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Negative-QTOFsplash10-0aou-3290000000-3468e25876a93af9e7302021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 10V, Positive-QTOFsplash10-004i-0090000000-9f46e36098b5d5b4738d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Positive-QTOFsplash10-056r-0090000000-f42f9726e3904deb0d4b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Positive-QTOFsplash10-05mo-5290000000-38b1ad796f7ab20886532021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart 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 IDFDB011751
KNApSAcK IDNot Available
Chemspider ID35013649
KEGG Compound IDNot Available
BioCyc IDCPD-18255
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100923872
PDB IDNot Available
ChEBI ID133763
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.. .