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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:57:11 UTC
Update Date2022-03-07 02:55:03 UTC
HMDB IDHMDB0036778
Secondary Accession Numbers
  • HMDB36778
Metabolite Identification
Common NameDiosbulbin C
DescriptionDiosbulbin C belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Diosbulbin C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, diosbulbin C has been detected, but not quantified in, root vegetables. This could make diosbulbin C a potential biomarker for the consumption of these foods.
Structure
Data?1563862925
Synonyms
ValueSource
3-(Furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.0¹,⁵.0⁶,¹¹]pentadecane-10-carboxylateGenerator
Chemical FormulaC19H22O7
Average Molecular Weight362.3738
Monoisotopic Molecular Weight362.136553058
IUPAC Name3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.0¹,⁵.0⁶,¹¹]pentadecane-10-carboxylic acid
Traditional Name3-(furan-3-yl)-8-hydroxy-5-methyl-14-oxo-2,13-dioxatetracyclo[10.2.1.0¹,⁵.0⁶,¹¹]pentadecane-10-carboxylic acid
CAS Registry Number20086-07-1
SMILES
CC12CC(OC11CC(OC1=O)C1C(CC(O)CC21)C(O)=O)C1=COC=C1
InChI Identifier
InChI=1S/C19H22O7/c1-18-6-13(9-2-3-24-8-9)26-19(18)7-14(25-17(19)23)15-11(16(21)22)4-10(20)5-12(15)18/h2-3,8,10-15,20H,4-7H2,1H3,(H,21,22)
InChI KeyUYALWPKCIMKALF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthofurans
Sub ClassNot Available
Direct ParentNaphthofurans
Alternative Parents
Substituents
  • Naphthofuran
  • Caprolactone
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Cyclic alcohol
  • Furan
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point247 - 250 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.57 g/LALOGPS
logP1.02ALOGPS
logP0.94ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area106.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity86.55 m³·mol⁻¹ChemAxon
Polarizability36.33 ųChemAxon
Number of Rings5ChemAxon
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]+180.44231661259
DarkChem[M-H]-174.99231661259
DeepCCS[M-2H]-218.62130932474
DeepCCS[M+Na]+194.27730932474
AllCCS[M+H]+185.332859911
AllCCS[M+H-H2O]+182.532859911
AllCCS[M+NH4]+187.932859911
AllCCS[M+Na]+188.632859911
AllCCS[M-H]-188.232859911
AllCCS[M+Na-2H]-187.932859911
AllCCS[M+HCOO]-187.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Diosbulbin CCC12CC(OC11CC(OC1=O)C1C(CC(O)CC21)C(O)=O)C1=COC=C14138.5Standard polar33892256
Diosbulbin CCC12CC(OC11CC(OC1=O)C1C(CC(O)CC21)C(O)=O)C1=COC=C12702.9Standard non polar33892256
Diosbulbin CCC12CC(OC11CC(OC1=O)C1C(CC(O)CC21)C(O)=O)C1=COC=C13187.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diosbulbin C,1TMS,isomer #1CC12CC(C3=COC=C3)OC13CC(OC3=O)C1C(C(=O)O)CC(O[Si](C)(C)C)CC123035.3Semi standard non polar33892256
Diosbulbin C,1TMS,isomer #2CC12CC(C3=COC=C3)OC13CC(OC3=O)C1C(C(=O)O[Si](C)(C)C)CC(O)CC122978.5Semi standard non polar33892256
Diosbulbin C,2TMS,isomer #1CC12CC(C3=COC=C3)OC13CC(OC3=O)C1C(C(=O)O[Si](C)(C)C)CC(O[Si](C)(C)C)CC122984.2Semi standard non polar33892256
Diosbulbin C,1TBDMS,isomer #1CC12CC(C3=COC=C3)OC13CC(OC3=O)C1C(C(=O)O)CC(O[Si](C)(C)C(C)(C)C)CC123275.7Semi standard non polar33892256
Diosbulbin C,1TBDMS,isomer #2CC12CC(C3=COC=C3)OC13CC(OC3=O)C1C(C(=O)O[Si](C)(C)C(C)(C)C)CC(O)CC123231.1Semi standard non polar33892256
Diosbulbin C,2TBDMS,isomer #1CC12CC(C3=COC=C3)OC13CC(OC3=O)C1C(C(=O)O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)CC123438.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diosbulbin C GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-6159000000-28fd56d0d30d4c3582782017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diosbulbin C GC-MS (2 TMS) - 70eV, Positivesplash10-01vw-6021900000-a55a9d36d54741ed1b162017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diosbulbin C 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 - Diosbulbin C 10V, Positive-QTOFsplash10-01ot-0029000000-05b80b17d2d890a1fe922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 20V, Positive-QTOFsplash10-00kb-1198000000-f3b8f7a77c7e93aa84952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 40V, Positive-QTOFsplash10-000b-7390000000-14a64054328ac75ab9822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 10V, Negative-QTOFsplash10-03xr-0019000000-73c899449e9b7224dce12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 20V, Negative-QTOFsplash10-014i-3049000000-a909bad5d773af8c32f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 40V, Negative-QTOFsplash10-05nr-2091000000-5288f7824cce04cd8dff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 10V, Negative-QTOFsplash10-03di-0009000000-ebe18b1008a99c90b1482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 20V, Negative-QTOFsplash10-014i-0029000000-34bd100acff98d3c0e8e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 40V, Negative-QTOFsplash10-014i-8097000000-4c867c54909b8ac5b7f92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 10V, Positive-QTOFsplash10-01ot-0009000000-d301b18e26b8c516b2a52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 20V, Positive-QTOFsplash10-01ot-0069000000-ad932b3fe00000c7b0292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diosbulbin C 40V, Positive-QTOFsplash10-014i-5289000000-5f1f94fb6c0d39f6153f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDFDB015720
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15559045
PDB IDNot Available
ChEBI IDNot Available
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.. .