Record Information
Version1.0
Creation date2010-04-08 22:05:27 UTC
Update date2020-02-24 19:10:34 UTC
Primary IDFDB002621
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGartanin
DescriptionGartanin belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Gartanin has been detected, but not quantified in, fruits and purple mangosteens (Garcinia mangostana). This could make gartanin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Gartanin.
CAS Number33390-42-0
Structure
Thumb
Synonyms
SynonymSource
1,3,5,8-Tetrahydroxy-2,4-diprenylxanthoneChEBI
1,3,5,8-Tetrahydroxy-2,4-bis(3-methyl-2-butenyl)xanthoneMeSH
1,3,5,8-Tetrahydroxy-2,4-bis(3-methyl-2-butenyl)-9H-xanthen-9-one, 9ciHMDB
GartininHMDB
1,3,5,8-Tetrahydroxy-2,4-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-onePhytoBank
1,3,5,8-Tetrahydroxy-2,4-bis(3-methyl-2-butenyl)-9H-xanthen-9-one, 9CIdb_source
Gartanindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP4.07ALOGPS
logP6.5ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity113.23 m³·mol⁻¹ChemAxon
Polarizability43.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H24O6
IUPAC name1,3,5,8-tetrahydroxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
InChI IdentifierInChI=1S/C23H24O6/c1-11(2)5-7-13-19(26)14(8-6-12(3)4)22-18(20(13)27)21(28)17-15(24)9-10-16(25)23(17)29-22/h5-6,9-10,24-27H,7-8H2,1-4H3
InChI KeyOJXQLGQIDIPMTE-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C(O)C(CC=C(C)C)=C2OC3=C(O)C=CC(O)=C3C(=O)C2=C1O
Average Molecular Weight396.4331
Monoisotopic Molecular Weight396.1572885
Classification
Description Belongs to the class of organic compounds known as 4-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 4-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent4-prenylated xanthones
Alternative Parents
Substituents
  • 2-prenylated xanthone
  • 4-prenylated xanthone
  • Chromone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.68%; H 6.10%; O 24.21%DFC
Melting PointMp 167°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data351 (e 11200) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGartanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-067l-1019000000-01a43ab7896e2a36d11aSpectrum
Predicted GC-MSGartanin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-1000019000-05b6ceaad1a9d0969229Spectrum
Predicted GC-MSGartanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGartanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-74eada288ff91c7554782015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-2019000000-6f9a7baa6f8f9259fc212015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-4093000000-cd9a0bcedd8cf3d8e2732015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-fa43c14e8cfae3cbb41b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0109000000-54e536f4bef3f9a91c7b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0699-1986000000-177a3051e6de070820cc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-a929cac834871923dca92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-fbdd852581d95085d6cf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-4339000000-7d510cf5fab9eb71673a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-0009000000-41b6109104d8373c25c02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0015-0049000000-c3b0d2ca7795d671999f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-0195000000-9631146a7d902845a7332021-09-25View Spectrum
NMRNot Available
ChemSpider ID4444952
ChEMBL IDCHEMBL487992
KEGG Compound IDC10063
Pubchem Compound ID5281633
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30700
CRC / DFC (Dictionary of Food Compounds) IDCMS44-B:CMS44-B
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002951
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.