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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:35 UTC
Update Date2022-03-07 02:52:35 UTC
HMDB IDHMDB0030552
Secondary Accession Numbers
  • HMDB30552
Metabolite Identification
Common NameThelephoric acid
DescriptionThelephoric acid, also known as thelephate, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Thelephoric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is derived from atromentin, and its precusor can be from cyclovariegatin. Outside of the human body, thelephoric acid has been detected, but not quantified in, mushrooms. This could make thelephoric acid a potential biomarker for the consumption of these foods. Fragmentation patterns have suggested that polymers of thelephoric acid exists. Chemicals that inhibit prolyl endopeptidase have attracted research interest due to their potential therapeutic effects. Thelephoric acid has been shown to inhibit prolyl endopeptidase, an enzyme that has a role in processing proteins (specifically, amyloid precursor protein) in Alzheimer's disease.
Structure
Data?1563862003
Synonyms
ValueSource
ThelephateGenerator
Thelephic acidGenerator
2,3,8,9-Tetrahydroxybenzo[1,2-b:4,5-b']bisbenzofuran-6,12-dione, 9ciHMDB
Chemical FormulaC18H8O8
Average Molecular Weight352.2513
Monoisotopic Molecular Weight352.021917232
IUPAC Name6,7,16,17-tetrahydroxy-10,20-dioxapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁴,¹⁹]icosa-1(13),3(11),4(9),5,7,14(19),15,17-octaene-2,12-dione
Traditional Name6,7,16,17-tetrahydroxy-10,20-dioxapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁴,¹⁹]icosa-1(13),3(11),4(9),5,7,14(19),15,17-octaene-2,12-dione
CAS Registry Number479-64-1
SMILES
OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O
InChI Identifier
InChI=1S/C18H8O8/c19-7-1-5-11(3-9(7)21)25-17-13(5)15(23)18-14(16(17)24)6-2-8(20)10(22)4-12(6)26-18/h1-4,19-22H
InChI KeyPDICCECAPKBDBB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.71ALOGPS
logP1.86ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.81ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.34 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.51 m³·mol⁻¹ChemAxon
Polarizability33.98 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]+178.47931661259
DarkChem[M-H]-178.1731661259
DeepCCS[M+H]+181.30130932474
DeepCCS[M-H]-178.94430932474
DeepCCS[M-2H]-212.54430932474
DeepCCS[M+Na]+187.77230932474
AllCCS[M+H]+180.332859911
AllCCS[M+H-H2O]+177.032859911
AllCCS[M+NH4]+183.332859911
AllCCS[M+Na]+184.232859911
AllCCS[M-H]-178.432859911
AllCCS[M+Na-2H]-177.332859911
AllCCS[M+HCOO]-176.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Thelephoric acidOC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O4541.6Standard polar33892256
Thelephoric acidOC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O3326.8Standard non polar33892256
Thelephoric acidOC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=C2C=C(O)C(O)=C3)C1=O3782.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thelephoric acid,1TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O)=C(O)C=C23)C1=O3738.8Semi standard non polar33892256
Thelephoric acid,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O23740.7Semi standard non polar33892256
Thelephoric acid,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C1=C(O2)C(=O)C2=C(OC3=CC(O)=C(O)C=C23)C1=O3599.4Semi standard non polar33892256
Thelephoric acid,2TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O[Si](C)(C)C)=C(O)C=C23)C1=O3769.6Semi standard non polar33892256
Thelephoric acid,2TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O)=C(O[Si](C)(C)C)C=C23)C1=O3779.9Semi standard non polar33892256
Thelephoric acid,2TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O)C=C1O23791.7Semi standard non polar33892256
Thelephoric acid,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C23)C1=O3665.7Semi standard non polar33892256
Thelephoric acid,3TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C1O23690.6Semi standard non polar33892256
Thelephoric acid,4TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C1=C(O2)C(=O)C2=C(OC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C23)C1=O3596.6Semi standard non polar33892256
Thelephoric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O)=C(O)C=C23)C1=O3967.8Semi standard non polar33892256
Thelephoric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C2=C(C1=O)C1=CC(O)=C(O)C=C1O23966.4Semi standard non polar33892256
Thelephoric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1=C(O2)C(=O)C2=C(OC3=CC(O)=C(O)C=C23)C1=O4063.6Semi standard non polar33892256
Thelephoric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C23)C1=O4234.4Semi standard non polar33892256
Thelephoric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C23)C1=O4237.6Semi standard non polar33892256
Thelephoric acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C1O24239.8Semi standard non polar33892256
Thelephoric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C1=C(O2)C(=O)C2=C(OC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C23)C1=O4359.6Semi standard non polar33892256
Thelephoric acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C2C(=O)C2=C(C1=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C1O24365.7Semi standard non polar33892256
Thelephoric acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1=C(O2)C(=O)C2=C(OC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C23)C1=O4460.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thelephoric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-0916000000-7c389e87839964c21ff82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thelephoric acid GC-MS (4 TMS) - 70eV, Positivesplash10-0100-5211094000-c6b240f55f0857542d1b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thelephoric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thelephoric acid 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 - Thelephoric acid 10V, Positive-QTOFsplash10-0udi-0009000000-321dd4770cf689e709662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 20V, Positive-QTOFsplash10-0udi-0109000000-a5a30582fb6b06abe7e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 40V, Positive-QTOFsplash10-002s-0978000000-94dd6908cacb3a9ec1ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 10V, Negative-QTOFsplash10-0udi-0009000000-1dfe9fcaecc93f43ba452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 20V, Negative-QTOFsplash10-0udi-0109000000-93414176177ee7a5422e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 40V, Negative-QTOFsplash10-004j-0955000000-c713b2f39ff8be10b6932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 10V, Negative-QTOFsplash10-0udi-0009000000-353eccd1de879c2990422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 20V, Negative-QTOFsplash10-0udi-0009000000-353eccd1de879c2990422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 40V, Negative-QTOFsplash10-05o3-0194000000-e7ab38bea41feb6d3dd52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 10V, Positive-QTOFsplash10-0udi-0009000000-00812e694c0cd96d91912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 20V, Positive-QTOFsplash10-0udi-0009000000-00812e694c0cd96d91912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thelephoric acid 40V, Positive-QTOFsplash10-0041-0596000000-5147b9d01c215f6c52642021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB002428
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThelephoric acid
METLIN IDNot Available
PubChem Compound135464206
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.. .