gamma-Mangostin (CHEM029675)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:19:53 UTC
Update Date2016-11-09 01:18:55 UTC
Accession NumberCHEM029675
Identification
Common Namegamma-Mangostin
ClassSmall Molecule
DescriptionA member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3, 6 and 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antitumour activity.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
g-MangostinGenerator
Γ-mangostinGenerator
1,3,6,7-Tetrahydroxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one, 9ciHMDB
NormangostinHMDB
1,3,6,7-Tetrahydroxy-2,5-bis(3-methyl-2-butenyl)-9H-xanthen-9-oneMeSH
Chemical FormulaC23H24O6
Average Molecular Mass396.433 g/mol
Monoisotopic Mass396.157 g/mol
CAS Registry Number31271-07-5
IUPAC Name1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
Traditional Name1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-en-1-yl)xanthen-9-one
SMILESCC(C)=CCC1=C(O)C2=C(OC3=CC(O)=C(O)C(CC=C(C)C)=C3C2=O)C=C1O
InChI IdentifierInChI=1S/C23H24O6/c1-11(2)5-7-13-15(24)9-18-20(22(13)27)23(28)19-14(8-6-12(3)4)21(26)16(25)10-17(19)29-18/h5-6,9-10,24-27H,7-8H2,1-4H3
InChI KeyVEZXFTKZUMARDU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-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 Parent8-prenylated xanthones
Alternative Parents
Substituents
  • 2-prenylated xanthone
  • 8-prenylated xanthone
  • Chromone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0093 g/LALOGPS
logP4.1ALOGPS
logP5.85ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.15ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity113.23 m³·mol⁻¹ChemAxon
Polarizability43.18 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9x-1029000000-63942bea7e8631a7aaafSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-1001009000-1833b78f1ffe0e35221cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-0029000000-449d1e4e2a1d3d1864a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-052u-0093000000-e2463183b747e814560aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0019000000-fc4df9db3ce4d08a2aecSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0f89-0296000000-974dbc18c48306389b9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0049000000-8ec76b12f55e08a447ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-13ba15b795da5ddfe11bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0090000000-41bc771bbb15c7e9bbd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-838831fe934c834f57c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-faea1aebfd1d467a1143Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-2009000000-8634704a0ca49ed43d78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-8879000000-17811b777ab8f0801b56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-9357ddfeaf0bbb151111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0019000000-347316606972afa282e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-0966000000-e53a3d4ae68ae7a357c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-0039000000-4c4d4fabb5e22e025cb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0069000000-adb5b58aff95cde3016fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00e9-0091000000-c2949c6c40e7a4d5aa6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-a929cac834871923dca9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-6a1abd76b2102d4e8151Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1957000000-2a162ce5f09c7376f75eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0035795
FooDB IDFDB014545
Phenol Explorer IDNot Available
KNApSAcK IDC00030348
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4576523
ChEBI ID67548
PubChem Compound ID5464078
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1368866
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15322259
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21428375
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22759914
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23513467
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23866810
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=9535013
8. Matsumoto K, Akao Y, Ohguchi K, Ito T, Tanaka T, Iinuma M, Nozawa Y: Xanthones induce cell-cycle arrest and apoptosis in human colon cancer DLD-1 cells. Bioorg Med Chem. 2005 Nov 1;13(21):6064-9.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.