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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:05:29 UTC
Update Date2022-03-07 02:56:37 UTC
HMDB IDHMDB0040533
Secondary Accession Numbers
  • HMDB40533
Metabolite Identification
Common NameArtomunoxanthentrione epoxide
DescriptionArtomunoxanthentrione epoxide belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Artomunoxanthentrione epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, artomunoxanthentrione epoxide has been detected, but not quantified in, fruits. This could make artomunoxanthentrione epoxide a potential biomarker for the consumption of these foods.
Structure
Data?1563863560
SynonymsNot Available
Chemical FormulaC26H22O8
Average Molecular Weight462.4481
Monoisotopic Molecular Weight462.13146768
IUPAC Name12-hydroxy-20-methoxy-8,8-dimethyl-17-(prop-1-en-2-yl)-3,9,23-trioxahexacyclo[13.7.1.0¹,¹⁸.0²,¹⁵.0⁴,¹³.0⁵,¹⁰]tricosa-4(13),5(10),6,11,16,20-hexaene-14,19,22-trione
Traditional Name12-hydroxy-20-methoxy-8,8-dimethyl-17-(prop-1-en-2-yl)-3,9,23-trioxahexacyclo[13.7.1.0¹,¹⁸.0²,¹⁵.0⁴,¹³.0⁵,¹⁰]tricosa-4(13),5(10),6,11,16,20-hexaene-14,19,22-trione
CAS Registry Number143522-33-2
SMILES
COC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O
InChI Identifier
InChI=1S/C26H22O8/c1-11(2)13-10-25-22(30)18-14(27)8-15-12(6-7-24(3,4)33-15)21(18)32-23(25)26(34-25)17(28)9-16(31-5)20(29)19(13)26/h6-10,19,23,27H,1H2,2-5H3
InChI KeyNDLOJOBMSNOREU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentPyranoxanthones
Alternative Parents
Substituents
  • Pyranoxanthone
  • Naphthopyran
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Naphthalene
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Cyclohexenone
  • Pyran
  • Benzenoid
  • Vinylogous ester
  • Vinylogous acid
  • Oxetane
  • Ketone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point248 - 251 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP3.39ALOGPS
logP3.53ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.88ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area108.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity122.53 m³·mol⁻¹ChemAxon
Polarizability47.05 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-234.70130932474
DeepCCS[M+Na]+209.94830932474
AllCCS[M+H]+208.732859911
AllCCS[M+H-H2O]+206.432859911
AllCCS[M+NH4]+210.832859911
AllCCS[M+Na]+211.432859911
AllCCS[M-H]-214.932859911
AllCCS[M+Na-2H]-215.532859911
AllCCS[M+HCOO]-216.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Artomunoxanthentrione epoxideCOC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O4937.8Standard polar33892256
Artomunoxanthentrione epoxideCOC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O3446.1Standard non polar33892256
Artomunoxanthentrione epoxideCOC1=CC(=O)C23OC4(C=C(C2C1=O)C(C)=C)C3OC1=C(C(O)=CC2=C1C=CC(C)(C)O2)C4=O3482.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artomunoxanthentrione epoxide,1TMS,isomer #1C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(=O)C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C)=C1C3=O3535.0Semi standard non polar33892256
Artomunoxanthentrione epoxide,1TMS,isomer #2C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O)=C1C3=O3411.5Semi standard non polar33892256
Artomunoxanthentrione epoxide,2TMS,isomer #1C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C)=C1C3=O3367.0Semi standard non polar33892256
Artomunoxanthentrione epoxide,2TMS,isomer #1C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C)=C1C3=O3463.7Standard non polar33892256
Artomunoxanthentrione epoxide,1TBDMS,isomer #1C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(=O)C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C1C3=O3763.8Semi standard non polar33892256
Artomunoxanthentrione epoxide,1TBDMS,isomer #2C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O)=C1C3=O3644.2Semi standard non polar33892256
Artomunoxanthentrione epoxide,2TBDMS,isomer #1C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C1C3=O3785.1Semi standard non polar33892256
Artomunoxanthentrione epoxide,2TBDMS,isomer #1C=C(C)C1=CC23OC4(C(=O)C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C14)C2OC1=C2C=CC(C)(C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C1C3=O3858.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artomunoxanthentrione epoxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qd-7301900000-165ae9f61b9b20029be32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artomunoxanthentrione epoxide GC-MS (1 TMS) - 70eV, Positivesplash10-0aor-9330260000-21f600558731b5655e7d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artomunoxanthentrione epoxide 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 - Artomunoxanthentrione epoxide 10V, Positive-QTOFsplash10-03di-0000900000-135522ccc3af3d7886972017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Positive-QTOFsplash10-0301-2061900000-16ccd0301666c1e7a6f22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Positive-QTOFsplash10-016r-5940000000-8df62234e783b8adbbf52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 10V, Negative-QTOFsplash10-03di-0010900000-aff4b3d70741e2832fbb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Negative-QTOFsplash10-03di-1011900000-f2ea2049b93995a8bf8a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Negative-QTOFsplash10-0aru-6982000000-8a748a350724c38b44cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 10V, Positive-QTOFsplash10-03di-0000900000-9208e3ee3180b8cb41df2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Positive-QTOFsplash10-03di-0000900000-4df73206b8b8faa7de442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Positive-QTOFsplash10-03k9-1001900000-cbea8bae195f2e91da522021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 10V, Negative-QTOFsplash10-03di-0000900000-9a0269f6702280e746682021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 20V, Negative-QTOFsplash10-03di-0000900000-9e56d292e999e4a8eb142021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artomunoxanthentrione epoxide 40V, Negative-QTOFsplash10-014i-1012900000-0e2dbe2dc18ec4f370982021-09-25Wishart 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 IDFDB020301
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752846
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.. .