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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:47:45 UTC
Update Date2022-03-07 02:53:57 UTC
HMDB IDHMDB0034021
Secondary Accession Numbers
  • HMDB34021
Metabolite Identification
Common NameArtobiloxanthone
DescriptionArtobiloxanthone 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. Based on a literature review a significant number of articles have been published on Artobiloxanthone.
Structure
Data?1563862496
Synonyms
ValueSource
8,9-dihydro-6,10,11,13-Tetrahydroxy-3,3-dimethyl-9-(1-methylethenyl)-3H,7H-benzo[c]pyrano[3,2-H]xanthen-7-one, 9ciHMDB
KB 1HMDB
ArtobiloxanthoneMeSH
Chemical FormulaC25H22O7
Average Molecular Weight434.438
Monoisotopic Molecular Weight434.136553058
IUPAC Name11,18,19,21-tetrahydroxy-7,7-dimethyl-16-(prop-1-en-2-yl)-2,8-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one
Traditional Name11,18,19,21-tetrahydroxy-7,7-dimethyl-16-(prop-1-en-2-yl)-2,8-dioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁷,²²]docosa-1(14),3(12),4(9),5,10,17(22),18,20-octaen-13-one
CAS Registry Number121748-25-2
SMILES
CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O
InChI Identifier
InChI=1S/C25H22O7/c1-10(2)12-7-13-21(29)20-15(27)9-17-11(5-6-25(3,4)32-17)23(20)31-24(13)19-14(26)8-16(28)22(30)18(12)19/h5-6,8-9,12,26-28,30H,1,7H2,2-4H3
InChI KeyZIYAGIMFLYOZDS-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
  • Naphthopyranone
  • Naphthopyran
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • 1-naphthol
  • Naphthalene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Oxacycle
  • Ether
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Point162 - 164 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP4.31ALOGPS
logP4.42ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.26ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity120.36 m³·mol⁻¹ChemAxon
Polarizability45.43 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]+200.35931661259
DarkChem[M-H]-197.27131661259
DeepCCS[M+H]+200.91930932474
DeepCCS[M-H]-198.52330932474
DeepCCS[M-2H]-231.40730932474
DeepCCS[M+Na]+207.12130932474
AllCCS[M+H]+204.032859911
AllCCS[M+H-H2O]+201.432859911
AllCCS[M+NH4]+206.432859911
AllCCS[M+Na]+207.132859911
AllCCS[M-H]-204.732859911
AllCCS[M+Na-2H]-204.532859911
AllCCS[M+HCOO]-204.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ArtobiloxanthoneCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O5291.4Standard polar33892256
ArtobiloxanthoneCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O3862.8Standard non polar33892256
ArtobiloxanthoneCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C(O)C=C2O4026.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artobiloxanthone,1TMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O)=C213745.6Semi standard non polar33892256
Artobiloxanthone,1TMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C)=C213734.6Semi standard non polar33892256
Artobiloxanthone,1TMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O)=C213778.0Semi standard non polar33892256
Artobiloxanthone,1TMS,isomer #4C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O)=C213762.8Semi standard non polar33892256
Artobiloxanthone,2TMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O)=C213659.7Semi standard non polar33892256
Artobiloxanthone,2TMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O)=C213687.2Semi standard non polar33892256
Artobiloxanthone,2TMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C)=C213627.4Semi standard non polar33892256
Artobiloxanthone,2TMS,isomer #4C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O[Si](C)(C)C)=C213669.3Semi standard non polar33892256
Artobiloxanthone,2TMS,isomer #5C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C213627.6Semi standard non polar33892256
Artobiloxanthone,2TMS,isomer #6C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O)=C213687.0Semi standard non polar33892256
Artobiloxanthone,3TMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O)=C213666.7Semi standard non polar33892256
Artobiloxanthone,3TMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O)C(O[Si](C)(C)C)=C213631.6Semi standard non polar33892256
Artobiloxanthone,3TMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C213581.0Semi standard non polar33892256
Artobiloxanthone,3TMS,isomer #4C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C213603.2Semi standard non polar33892256
Artobiloxanthone,4TMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C213597.4Semi standard non polar33892256
Artobiloxanthone,1TBDMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O)=C213974.9Semi standard non polar33892256
Artobiloxanthone,1TBDMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C213950.7Semi standard non polar33892256
Artobiloxanthone,1TBDMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C214009.6Semi standard non polar33892256
Artobiloxanthone,1TBDMS,isomer #4C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O)=C213987.1Semi standard non polar33892256
Artobiloxanthone,2TBDMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O)=C214086.1Semi standard non polar33892256
Artobiloxanthone,2TBDMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C214136.6Semi standard non polar33892256
Artobiloxanthone,2TBDMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C214059.7Semi standard non polar33892256
Artobiloxanthone,2TBDMS,isomer #4C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C214091.2Semi standard non polar33892256
Artobiloxanthone,2TBDMS,isomer #5C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C214065.0Semi standard non polar33892256
Artobiloxanthone,2TBDMS,isomer #6C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C214133.5Semi standard non polar33892256
Artobiloxanthone,3TBDMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C214257.8Semi standard non polar33892256
Artobiloxanthone,3TBDMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C214225.2Semi standard non polar33892256
Artobiloxanthone,3TBDMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C214165.6Semi standard non polar33892256
Artobiloxanthone,3TBDMS,isomer #4C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C214180.5Semi standard non polar33892256
Artobiloxanthone,4TBDMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C214323.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artobiloxanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-066u-1232900000-e84a9cfc02616843c8d72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artobiloxanthone GC-MS (3 TMS) - 70eV, Positivesplash10-000i-1020139000-67d942d2ab4cee2e2bdd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artobiloxanthone 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 - Artobiloxanthone 10V, Positive-QTOFsplash10-000i-0003900000-668be1310d0d6fcb62852015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Positive-QTOFsplash10-00p0-1109400000-39bbf898fd245c31f0b62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Positive-QTOFsplash10-02vi-4019000000-5c30c4c85f0d9c4feaf12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 10V, Negative-QTOFsplash10-001i-0000900000-c0372ac112ace47c91562015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Negative-QTOFsplash10-001i-0004900000-d71552c889e74c89b61b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Negative-QTOFsplash10-002b-0029100000-ac17fcf0d204d9708d442015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 10V, Positive-QTOFsplash10-000i-0000900000-8c5edb9d93203123adad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Positive-QTOFsplash10-000i-0000900000-8c5edb9d93203123adad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Positive-QTOFsplash10-014r-0092500000-0f680dca4ab4f1c8f6b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 10V, Negative-QTOFsplash10-001i-0000900000-81a03ca7359d4e6c5e6c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 20V, Negative-QTOFsplash10-001i-0000900000-81a03ca7359d4e6c5e6c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artobiloxanthone 40V, Negative-QTOFsplash10-0api-0190200000-eca206f39d98b7f654e82021-09-24Wishart 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 IDNot Available
KNApSAcK IDC00004104
Chemspider ID24673270
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46887866
PDB IDNot Available
ChEBI ID172673
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.. .