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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:49:07 UTC
Update Date2022-03-07 02:54:38 UTC
HMDB IDHMDB0035796
Secondary Accession Numbers
  • HMDB35796
Metabolite Identification
Common Namealpha-Mangostin
Descriptionalpha-Mangostin, also known as mangostin, 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. alpha-Mangostin has been detected, but not quantified in, fruits. This could make alpha-mangostin a potential biomarker for the consumption of these foods. alpha-Mangostin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on alpha-Mangostin.
Structure
Data?1563862773
Synonyms
ValueSource
1,3,6-Trihydroxy-7-methoxy-2,8-diprenylxanthoneChEBI
MangostinChEBI
a-MangostinGenerator
Α-mangostinGenerator
delta-MangostinMeSH
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-onePhytoBank
1,3,6-Trihydroxy-7-methoxy-2,8-bis(3,3-dimethylallyl)xanthonePhytoBank
1,3,6-Trihydroxy-7-methoxy-2,8-di(3-methyl-2-butenyl)xanthonePhytoBank
7-O-Methyl-4-desprenylcostatinPhytoBank
7-O-Methyl-gamma-mangostinPhytoBank
7-O-Methyl-γ-mangostinPhytoBank
alpha-MangostenPhytoBank
α-MangostenPhytoBank
alpha-MangostinPhytoBank
Chemical FormulaC24H26O6
Average Molecular Weight410.4596
Monoisotopic Molecular Weight410.172938564
IUPAC Name1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
Traditional Namemangostin
CAS Registry Number6147-11-1
SMILES
COC1=C(O)C=C2OC3=C(C(O)=C(CC=C(C)C)C(O)=C3)C(=O)C2=C1CC=C(C)C
InChI Identifier
InChI=1S/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3
InChI KeyGNRIZKKCNOBBMO-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
  • 8-prenylated xanthone
  • 2-prenylated xanthone
  • Chromone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Polyol
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 - 181 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0002 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available198.784http://allccs.zhulab.cn/database/detail?ID=AllCCS00001150
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0094 g/LALOGPS
logP4.41ALOGPS
logP6ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.24ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity117.71 m³·mol⁻¹ChemAxon
Polarizability45.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+202.80430932474
DeepCCS[M-H]-200.44630932474
DeepCCS[M-2H]-233.65330932474
DeepCCS[M+Na]+209.25430932474
AllCCS[M+H]+200.032859911
AllCCS[M+H-H2O]+197.432859911
AllCCS[M+NH4]+202.532859911
AllCCS[M+Na]+203.232859911
AllCCS[M-H]-200.532859911
AllCCS[M+Na-2H]-200.632859911
AllCCS[M+HCOO]-200.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-MangostinCOC1=C(O)C=C2OC3=C(C(O)=C(CC=C(C)C)C(O)=C3)C(=O)C2=C1CC=C(C)C5301.9Standard polar33892256
alpha-MangostinCOC1=C(O)C=C2OC3=C(C(O)=C(CC=C(C)C)C(O)=C3)C(=O)C2=C1CC=C(C)C3376.2Standard non polar33892256
alpha-MangostinCOC1=C(O)C=C2OC3=C(C(O)=C(CC=C(C)C)C(O)=C3)C(=O)C2=C1CC=C(C)C3556.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
alpha-Mangostin,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OC3=CC(O)=C(CC=C(C)C)C(O)=C3C(=O)C2=C1CC=C(C)C3450.1Semi standard non polar33892256
alpha-Mangostin,1TMS,isomer #2COC1=C(O)C=C2OC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C(=O)C2=C1CC=C(C)C3401.2Semi standard non polar33892256
alpha-Mangostin,1TMS,isomer #3COC1=C(O)C=C2OC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C(=O)C2=C1CC=C(C)C3447.6Semi standard non polar33892256
alpha-Mangostin,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O)=C3C(=O)C2=C1CC=C(C)C3354.5Semi standard non polar33892256
alpha-Mangostin,2TMS,isomer #2COC1=C(O[Si](C)(C)C)C=C2OC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C(=O)C2=C1CC=C(C)C3321.7Semi standard non polar33892256
alpha-Mangostin,2TMS,isomer #3COC1=C(O)C=C2OC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C(=O)C2=C1CC=C(C)C3370.1Semi standard non polar33892256
alpha-Mangostin,3TMS,isomer #1COC1=C(O[Si](C)(C)C)C=C2OC3=CC(O[Si](C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C)=C3C(=O)C2=C1CC=C(C)C3358.9Semi standard non polar33892256
alpha-Mangostin,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O)=C(CC=C(C)C)C(O)=C3C(=O)C2=C1CC=C(C)C3654.5Semi standard non polar33892256
alpha-Mangostin,1TBDMS,isomer #2COC1=C(O)C=C2OC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1CC=C(C)C3615.8Semi standard non polar33892256
alpha-Mangostin,1TBDMS,isomer #3COC1=C(O)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C(=O)C2=C1CC=C(C)C3656.5Semi standard non polar33892256
alpha-Mangostin,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O)=C3C(=O)C2=C1CC=C(C)C3800.9Semi standard non polar33892256
alpha-Mangostin,2TBDMS,isomer #2COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1CC=C(C)C3754.0Semi standard non polar33892256
alpha-Mangostin,2TBDMS,isomer #3COC1=C(O)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1CC=C(C)C3802.4Semi standard non polar33892256
alpha-Mangostin,3TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC3=CC(O[Si](C)(C)C(C)(C)C)=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1CC=C(C)C3964.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Mangostin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-1029000000-1f5de86672681aa1c1ad2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Mangostin GC-MS (3 TMS) - 70eV, Positivesplash10-03di-1010049000-bd703bc0125b88cf61192017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Mangostin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Mangostin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0002900000-9fe10fc927e3f564417b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin LC-ESI-QTOF , negative-QTOFsplash10-0a4i-0009400000-766493a9b0de25dca6a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin LC-ESI-QTOF , negative-QTOFsplash10-0udi-0029000000-d78e22a7f1e06b5d68dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0009100000-1d0c9b543c58884594102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 40V, Negative-QTOFsplash10-0udi-0029000000-d78e22a7f1e06b5d68dc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 20V, Negative-QTOFsplash10-0a4i-0009400000-766493a9b0de25dca6a52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 10V, Positive-QTOFsplash10-0a4i-0009100000-1d0c9b543c58884594102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 10V, Negative-QTOFsplash10-0a4i-0001900000-c5659645a789b65ec3692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 40V, Negative-QTOFsplash10-0udi-0019000000-a6e5a02e80b8c47ed8312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 20V, Negative-QTOFsplash10-0a4i-0009800000-dbdc5519f5cf95fd05902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 10V, Positive-QTOFsplash10-0a4i-0009400000-2bc6a3fe6db700e599522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 20V, Positive-QTOFsplash10-0a4i-0009000000-7492218023ef475692bc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 10V, Negative-QTOFsplash10-0a4i-0000900000-69c6dbcbc7e2020b1cdc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - alpha-Mangostin 40V, Positive-QTOFsplash10-006t-0093000000-25952350e4430a10772a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 10V, Positive-QTOFsplash10-03di-0009800000-ef2ac781d10f9aeeb2e02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 20V, Positive-QTOFsplash10-0cdi-2009100000-03c99065c50debccbeae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 40V, Positive-QTOFsplash10-00kr-5429000000-7e04558e502b49725cbb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 10V, Negative-QTOFsplash10-0a4i-0001900000-e652023559da770a8a012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 20V, Negative-QTOFsplash10-0a4i-0119800000-f5f14dafd0f7fac701e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 40V, Negative-QTOFsplash10-00b9-1967000000-0f3addd028fbb777973b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 10V, Negative-QTOFsplash10-0a4i-0000900000-d2c445cbedf3cebfa6b32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 20V, Negative-QTOFsplash10-0a4i-0007900000-0cfcf5aef061d62030262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 40V, Negative-QTOFsplash10-056r-1139200000-a4c7bc0b28ff86858e8f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 10V, Positive-QTOFsplash10-0a4i-0049300000-f0c54c4043c089a72e2c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Mangostin 20V, Positive-QTOFsplash10-0a4i-0029000000-8f8679eb3fbff8768cbf2021-09-24Wishart 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 IDFDB014546
KNApSAcK IDC00002963
Chemspider ID4444969
KEGG Compound IDC10080
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMangostin
METLIN IDNot Available
PubChem Compound5281650
PDB IDNot Available
ChEBI ID67547
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1751521
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.. .