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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:14:35 UTC
Update Date2019-07-23 06:32:55 UTC
HMDB IDHMDB0040671
Secondary Accession Numbers
  • HMDB40671
Metabolite Identification
Common NamePhysapruin B
DescriptionArtonin L belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Thus, artonin L is considered to be a flavonoid lipid molecule. Artonin L is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Artonin L has been detected, but not quantified in, fruits and jackfruits. This could make artonin L a potential biomarker for the consumption of these foods.
Structure
Data?1563863575
Synonyms
ValueSource
5a,6-Dihydro-3,8-dihydroxy-1,10-dimethoxy-5,5-dimethyl-5H,7H-benzofuro[3,4-BC]xanthen-7-oneHMDB
7-Butoxy-14-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-8-yl acetic acidGenerator
Chemical FormulaC34H50O9
Average Molecular Weight602.7554
Monoisotopic Molecular Weight602.345483198
IUPAC Name7-butoxy-14-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-8-yl acetate
Traditional Name7-butoxy-14-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-8-yl acetate
CAS Registry NumberNot Available
SMILES
CCCCOC12CC=CC(=O)C1(C)C1CCC3(C)C(O)(CCC3(O)C(C)(O)C3CC(C)=C(C)C(=O)O3)C1CC2OC(C)=O
InChI Identifier
InChI=1S/C34H50O9/c1-8-9-17-41-33-13-10-11-25(36)30(33,6)23-12-14-29(5)32(39,24(23)19-27(33)42-22(4)35)15-16-34(29,40)31(7,38)26-18-20(2)21(3)28(37)43-26/h10-11,23-24,26-27,38-40H,8-9,12-19H2,1-7H3
InChI KeyBUTLOLBCWDNVGA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthones
Alternative Parents
Substituents
  • Naphthopyranone
  • Xanthone
  • Naphthopyran
  • Chromone
  • Naphthalene
  • Coumaran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP2.97ALOGPS
logP3.94ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.59 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity159.7 m³·mol⁻¹ChemAxon
Polarizability65.51 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fai-5464970000-b16e08a952e8d769b6b1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0pdi-8406398000-d3b9c44ccaa3001a0821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-1000192000-2285b8961306b7c92f4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar3-7101290000-5388183c54f31674b1c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9001110000-891422cce6048117621eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-2000294000-4d71b7184c238de7cd05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3902350000-48a4edf8aac616b85b74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vi-9500230000-142f7bac9d671171fdecSpectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB020471
KNApSAcK IDC00013479
Chemspider ID24844321
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258662
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.