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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:06 UTC
Update Date2022-03-07 02:52:34 UTC
HMDB IDHMDB0030489
Secondary Accession Numbers
  • HMDB30489
Metabolite Identification
Common NameArtonol C
DescriptionArtonol C 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. Thus, artonol C is considered to be a flavonoid lipid molecule. Artonol C is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, artonol C has been detected, but not quantified in, breadfruits and fruits. This could make artonol C a potential biomarker for the consumption of these foods.
Structure
Data?1563861992
Synonyms
ValueSource
9,12-Dihydro-6,10,15-trihydroxy-3,3,12,12-tetramethyl-9-(1-methylethenyl)-3H,7H,8H-[1]benzopyrano[7,6-c]pyrano[3,2-H]xanthen-7-oneHMDB
Chemical FormulaC30H28O7
Average Molecular Weight500.5391
Monoisotopic Molecular Weight500.18350325
IUPAC Name3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one
Traditional Name3,10,17-trihydroxy-7,7,21,21-tetramethyl-12-(prop-1-en-2-yl)-8,20,26-trioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁶,²⁵.0¹⁹,²⁴]hexacosa-1(14),2(11),3,5,9,16(25),17,19(24),22-nonaen-15-one
CAS Registry Number186824-59-9
SMILES
CC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O
InChI Identifier
InChI=1S/C30H28O7/c1-13(2)16-11-17-24(33)21-18(31)12-19-14(7-9-29(3,4)36-19)26(21)35-27(17)22-20(16)25(34)28-15(23(22)32)8-10-30(5,6)37-28/h7-10,12,16,31-32,34H,1,11H2,2-6H3
InChI KeyJVLAUHJNDLMVDW-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
  • Pyranone
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Polyol
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point182 - 184 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP5ALOGPS
logP5.62ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)8.35ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity142.77 m³·mol⁻¹ChemAxon
Polarizability54.37 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+214.44631661259
DarkChem[M-H]-212.96731661259
DeepCCS[M+H]+216.35430932474
DeepCCS[M-H]-213.95930932474
DeepCCS[M-2H]-247.00330932474
DeepCCS[M+Na]+222.26730932474
AllCCS[M+H]+222.232859911
AllCCS[M+H-H2O]+220.132859911
AllCCS[M+NH4]+224.232859911
AllCCS[M+Na]+224.732859911
AllCCS[M-H]-218.432859911
AllCCS[M+Na-2H]-219.032859911
AllCCS[M+HCOO]-220.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Artonol CCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O5406.6Standard polar33892256
Artonol CCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O3844.9Standard non polar33892256
Artonol CCC(=C)C1CC2=C(OC3=C(C(O)=CC4=C3C=CC(C)(C)O4)C2=O)C2=C1C(O)=C1OC(C)(C)C=CC1=C2O4210.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Artonol C,1TMS,isomer #1C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O)=C213956.6Semi standard non polar33892256
Artonol C,1TMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C213908.9Semi standard non polar33892256
Artonol C,1TMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C3=C(OC(C)(C)C=C3)C(O)=C213948.8Semi standard non polar33892256
Artonol C,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)C3=C(OC(C)(C)C=C3)C(O)=C213835.5Semi standard non polar33892256
Artonol C,2TMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O[Si](C)(C)C)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C213797.6Semi standard non polar33892256
Artonol C,2TMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C213814.0Semi standard non polar33892256
Artonol C,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)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C)=C213776.3Semi standard non polar33892256
Artonol C,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)C3=C(OC(C)(C)C=C3)C(O)=C214186.0Semi standard non polar33892256
Artonol C,1TBDMS,isomer #2C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C214117.1Semi standard non polar33892256
Artonol C,1TBDMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(OC(C)(C)C=C3)C(O)=C214159.3Semi standard non polar33892256
Artonol C,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)C3=C(OC(C)(C)C=C3)C(O)=C214251.6Semi standard non polar33892256
Artonol C,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)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C214193.6Semi standard non polar33892256
Artonol C,2TBDMS,isomer #3C=C(C)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C214202.5Semi standard non polar33892256
Artonol C,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)C3=C(OC(C)(C)C=C3)C(O[Si](C)(C)C(C)(C)C)=C214333.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Artonol C GC-MS (Non-derivatized) - 70eV, Positivesplash10-052r-0002900000-4804490c18510294e1a12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Artonol C GC-MS (2 TMS) - 70eV, Positivesplash10-00c0-2100329000-c0707026fa8bdc9396262017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 10V, Positive-QTOFsplash10-0udi-1000790000-4a8c8253d87b4cfa16782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 20V, Positive-QTOFsplash10-0f6x-0000910000-fae61f07f304d732689c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 40V, Positive-QTOFsplash10-014r-6005900000-c7eef290eb9c469b04b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 10V, Negative-QTOFsplash10-0002-0000900000-b2fd9fadad15c043aa252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 20V, Negative-QTOFsplash10-0002-0000900000-7c50a43d54579fdb3a1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 40V, Negative-QTOFsplash10-00lr-0006900000-d61cc44e173ffd6f88542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 10V, Positive-QTOFsplash10-0udi-0000090000-cf99df1bcf26156d9ad02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 20V, Positive-QTOFsplash10-0udi-0000090000-cf99df1bcf26156d9ad02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 40V, Positive-QTOFsplash10-0uxr-0090250000-c029941dbf22259df5b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 10V, Negative-QTOFsplash10-0002-0000900000-ae7e5a7ce68f4f846e432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 20V, Negative-QTOFsplash10-0002-0000900000-ae7e5a7ce68f4f846e432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Artonol C 40V, Negative-QTOFsplash10-00di-0249200000-823163c4501e82eabb6a2021-09-23Wishart 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 IDFDB002358
KNApSAcK IDC00013492
Chemspider ID9014400
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10839101
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.. .