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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:53:16 UTC
Update Date2022-03-07 02:53:59 UTC
HMDB IDHMDB0034095
Secondary Accession Numbers
  • HMDB34095
Metabolite Identification
Common NameGambogic acid
DescriptionGambogic acid, also known as gambogate or b-guttiferin, 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. Gambogic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gambogic acid is a xanthonoid that is derived from the brownish or orange resin from Garcinia hanburyi. Outside of the human body, gambogic acid has been detected, but not quantified in, fruits and herbs and spices. This could make gambogic acid a potential biomarker for the consumption of these foods. At the highest level of 120 mg/kg the primary toxic target organs were the liver and kidneys. For the same length of exposure, the higher the concentration of gambogic acid that was administered, the greater the effect on inhibiting cell growth. The ratio of relative tumor volume (RTV) for the treated group of mice to the control group indicates the gambogic acid was having an impact on tumor size while having no adverse effects on body weight or mortality.
Structure
Data?1563862509
Synonyms
ValueSource
GambogateGenerator
a-Gambogic acidHMDB
b-GuttiferinHMDB
b-GuttilactoneHMDB
Guttatic acidHMDB
Guttic acidHMDB
Gamboge acidHMDB
Gambogoic acidHMDB
(2Z)-4-[12-Hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoateGenerator
Gambogic acidMeSH
Chemical FormulaC38H44O8
Average Molecular Weight628.7512
Monoisotopic Molecular Weight628.303618384
IUPAC Name(2Z)-4-[12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid
Traditional Name(2Z)-4-[12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid
CAS Registry Number2752-65-0
SMILES
CC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C
InChI Identifier
InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-
InChI KeyGEZHEQNLKAOMCA-XKZIYDEJSA-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
  • Pyranochromene
  • Chromone
  • Aromatic monoterpenoid
  • Monoterpenoid
  • Aryl ketone
  • Alkyl aryl ether
  • Cyclohexenone
  • Oxepane
  • Benzenoid
  • Vinylogous acid
  • Tetrahydrofuran
  • Ketone
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • 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 Point86 - 91 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00071 g/LALOGPS
logP5.57ALOGPS
logP7.78ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity179.16 m³·mol⁻¹ChemAxon
Polarizability68.1 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+240.67931661259
DarkChem[M-H]-232.49731661259
DeepCCS[M-2H]-277.64930932474
DeepCCS[M+Na]+251.83830932474
AllCCS[M+H]+246.032859911
AllCCS[M+H-H2O]+244.832859911
AllCCS[M+NH4]+247.132859911
AllCCS[M+Na]+247.432859911
AllCCS[M-H]-248.532859911
AllCCS[M+Na-2H]-251.832859911
AllCCS[M+HCOO]-255.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gambogic acidCC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C6134.6Standard polar33892256
Gambogic acidCC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C4227.5Standard non polar33892256
Gambogic acidCC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C4305.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gambogic acid,1TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O)C5=O)C(=O)C1=C2O[Si](C)(C)C4379.1Semi standard non polar33892256
Gambogic acid,1TMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C)C5=O)C(=O)C1=C2O4324.7Semi standard non polar33892256
Gambogic acid,1TMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O4252.4Semi standard non polar33892256
Gambogic acid,2TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C)C5=O)C(=O)C1=C2O[Si](C)(C)C4266.3Semi standard non polar33892256
Gambogic acid,2TMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C4191.7Semi standard non polar33892256
Gambogic acid,2TMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O4148.5Semi standard non polar33892256
Gambogic acid,3TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C4112.2Semi standard non polar33892256
Gambogic acid,3TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C4212.5Standard non polar33892256
Gambogic acid,1TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O)C5=O)C(=O)C1=C2O[Si](C)(C)C(C)(C)C4630.9Semi standard non polar33892256
Gambogic acid,1TBDMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)C5=O)C(=O)C1=C2O4576.8Semi standard non polar33892256
Gambogic acid,1TBDMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O4503.1Semi standard non polar33892256
Gambogic acid,2TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5CC3C(C)(C)OC4(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)C5=O)C(=O)C1=C2O[Si](C)(C)C(C)(C)C4707.6Semi standard non polar33892256
Gambogic acid,2TBDMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O)OC(C)(C)C4C5)C(=O)C1=C2O[Si](C)(C)C(C)(C)C4637.3Semi standard non polar33892256
Gambogic acid,2TBDMS,isomer #3CC(C)=CCCC1(C)C=CC2=C(O1)C(CC=C(C)C)=C1OC34C(=CC5=C(O[Si](C)(C)C(C)(C)C)C3(C/C=C(/C)C(=O)O[Si](C)(C)C(C)(C)C)OC(C)(C)C4C5)C(=O)C1=C2O4588.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000057000-19abde6d758101a01ef72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gambogic acid GC-MS ("Gambogic acid,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 10V, Positive-QTOFsplash10-01t9-0000096000-e56a0ec531207df34ab62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 20V, Positive-QTOFsplash10-0o6r-3001591000-411cf0af71ea4c9389ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 40V, Positive-QTOFsplash10-016r-7153941000-92579129327c5702bfb82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 10V, Negative-QTOFsplash10-004i-1001039000-9c55dff29165d33866d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 20V, Negative-QTOFsplash10-057i-1014095000-77a8e0d8dca00f9672ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 40V, Negative-QTOFsplash10-0ab9-2794313000-d45dab05ad38be7aee922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 10V, Negative-QTOFsplash10-004i-0000009000-312b00b9e28384b5d53e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 20V, Negative-QTOFsplash10-004i-0000059000-d354ba3ab7fc6d3f14622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 40V, Negative-QTOFsplash10-02t9-2100391000-dcdb58e0da6ce0fbbe962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 10V, Positive-QTOFsplash10-004i-0000079000-d5501837c889acaa50342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 20V, Positive-QTOFsplash10-004r-0000093000-23942b0217f9c03ee8782021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gambogic acid 40V, Positive-QTOFsplash10-00kg-2000951000-5ee22b87ea31bfe4e09e2021-09-24Wishart 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 IDFDB012358
KNApSAcK IDC00002950
Chemspider ID4510165
KEGG Compound IDC10062
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGambogic acid
METLIN IDNot Available
PubChem Compound5353639
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.. .