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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:17 UTC
Update Date2022-03-07 02:53:06 UTC
HMDB IDHMDB0031760
Secondary Accession Numbers
  • HMDB31760
Metabolite Identification
Common NameGentisin
DescriptionGentisin, also known as gentianin or gentianic acid, 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. Gentisin 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 Gentisin.
Structure
Data?1601258508
Synonyms
ValueSource
1,7-Dihydroxy-3-methoxyxanthoneChEBI
1,7-Dihydroxy-3-methoxy-9H-xanthen-9-oneHMDB
1,7-Dihydroxy-3-methoxy-xanthen-9-oneHMDB
1,7-Dihydroxy-3-methoxyxanthen-9-oneHMDB
Gentianic acidHMDB
GentianinHMDB
Gentianin?HMDB
GentisineHMDB
Chemical FormulaC14H10O5
Average Molecular Weight258.2262
Monoisotopic Molecular Weight258.05282343
IUPAC Name1,7-dihydroxy-3-methoxy-9H-xanthen-9-one
Traditional Namegentisin
CAS Registry Number437-50-3
SMILES
COC1=CC(O)=C2C(=O)C3=CC(O)=CC=C3OC2=C1
InChI Identifier
InChI=1S/C14H10O5/c1-18-8-5-10(16)13-12(6-8)19-11-3-2-7(15)4-9(11)14(13)17/h2-6,15-16H,1H3
InChI KeyXOXYHGOIRWABTC-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
  • Xanthone
  • Chromone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point273 - 275 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.3 mg/mL at 16 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP2.8ALOGPS
logP2.84ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.26ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.24 m³·mol⁻¹ChemAxon
Polarizability25.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.96931661259
DarkChem[M-H]-161.58831661259
DeepCCS[M+H]+161.95630932474
DeepCCS[M-H]-159.59830932474
DeepCCS[M-2H]-192.48430932474
DeepCCS[M+Na]+168.04930932474
AllCCS[M+H]+156.932859911
AllCCS[M+H-H2O]+153.032859911
AllCCS[M+NH4]+160.632859911
AllCCS[M+Na]+161.732859911
AllCCS[M-H]-158.932859911
AllCCS[M+Na-2H]-158.232859911
AllCCS[M+HCOO]-157.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GentisinCOC1=CC(O)=C2C(=O)C3=CC(O)=CC=C3OC2=C14044.4Standard polar33892256
GentisinCOC1=CC(O)=C2C(=O)C3=CC(O)=CC=C3OC2=C12604.7Standard non polar33892256
GentisinCOC1=CC(O)=C2C(=O)C3=CC(O)=CC=C3OC2=C12639.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gentisin,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC(O)=CC=C3OC2=C12768.8Semi standard non polar33892256
Gentisin,1TMS,isomer #2COC1=CC(O)=C2C(=O)C3=CC(O[Si](C)(C)C)=CC=C3OC2=C12821.9Semi standard non polar33892256
Gentisin,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC(O[Si](C)(C)C)=CC=C3OC2=C12869.3Semi standard non polar33892256
Gentisin,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC(O)=CC=C3OC2=C13011.3Semi standard non polar33892256
Gentisin,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3OC2=C13022.7Semi standard non polar33892256
Gentisin,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3OC2=C13289.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gentisin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kcr-0690000000-2bbf6cbd52cc6e2f60152017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisin GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-4329000000-fdce50a515c2c215c9062017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gentisin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 10V, Positive-QTOFsplash10-0a4i-0090000000-f5fd12a26902f2c21dc72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 20V, Positive-QTOFsplash10-0a4i-0090000000-f5fd12a26902f2c21dc72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 40V, Positive-QTOFsplash10-0a6r-3890000000-1c8202ff47295eb82fdc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 10V, Negative-QTOFsplash10-0a4i-0090000000-6f3295d8b42fbe6db70c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 20V, Negative-QTOFsplash10-0a4i-0090000000-de58987fb8ac7f96cf512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 40V, Negative-QTOFsplash10-0ar0-2590000000-d340c5bb7527d832db6c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 10V, Negative-QTOFsplash10-0a4i-0090000000-5c99e00473c8f7c5ab032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 20V, Negative-QTOFsplash10-0a4i-0090000000-5c99e00473c8f7c5ab032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 40V, Negative-QTOFsplash10-0ue9-1950000000-b9181e023acf15e1a7192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 10V, Positive-QTOFsplash10-0a4i-0090000000-adb7dbccff647a6174612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 20V, Positive-QTOFsplash10-0a4i-0090000000-adb7dbccff647a6174612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gentisin 40V, Positive-QTOFsplash10-0pea-2490000000-75d431da9d2be7bedfca2021-09-22Wishart 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 IDFDB008432
KNApSAcK IDC00002954
Chemspider ID4444955
KEGG Compound IDC10066
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281636
PDB IDNot Available
ChEBI ID5324
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1827761
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.. .