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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:26 UTC
Update Date2022-03-07 02:53:27 UTC
HMDB IDHMDB0032729
Secondary Accession Numbers
  • HMDB32729
Metabolite Identification
Common NameDulxanthone B
DescriptionDulxanthone B 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. Dulxanthone B has been detected, but not quantified in, fruits. This could make dulxanthone b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dulxanthone B.
Structure
Data?1563862298
Synonyms
ValueSource
1,5,6-Trihydroxy-3-methoxy-2,4-diprenylxanthoneHMDB
Chemical FormulaC24H26O6
Average Molecular Weight410.4596
Monoisotopic Molecular Weight410.172938564
IUPAC Name1,5,6-trihydroxy-3-methoxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
Traditional Name1,5,6-trihydroxy-3-methoxy-2,4-bis(3-methylbut-2-en-1-yl)xanthen-9-one
CAS Registry Number197447-28-2
SMILES
COC1=C(CC=C(C)C)C2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=C(O)C=C1
InChI Identifier
InChI=1S/C24H26O6/c1-12(2)6-8-14-19(26)18-20(27)15-10-11-17(25)21(28)24(15)30-23(18)16(22(14)29-5)9-7-13(3)4/h6-7,10-11,25-26,28H,8-9H2,1-5H3
InChI KeySGSSJGOWXOYJNC-UHFFFAOYSA-N
Chemical Taxonomy
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
  • 4-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00012 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0092 g/LALOGPS
logP4.44ALOGPS
logP6ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)7.54ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity117.71 m³·mol⁻¹ChemAxon
Polarizability45.06 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
DarkChem[M+H]+196.74731661259
DarkChem[M-H]-198.08831661259
DeepCCS[M+H]+205.6130932474
DeepCCS[M-H]-203.25230932474
DeepCCS[M-2H]-236.13830932474
DeepCCS[M+Na]+212.32230932474
AllCCS[M+H]+198.432859911
AllCCS[M+H-H2O]+195.732859911
AllCCS[M+NH4]+200.832859911
AllCCS[M+Na]+201.532859911
AllCCS[M-H]-198.532859911
AllCCS[M+Na-2H]-198.132859911
AllCCS[M+HCOO]-197.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dulxanthone BCOC1=C(CC=C(C)C)C2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=C(O)C=C14959.0Standard polar33892256
Dulxanthone BCOC1=C(CC=C(C)C)C2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=C(O)C=C13671.6Standard non polar33892256
Dulxanthone BCOC1=C(CC=C(C)C)C2=C(C(O)=C1CC=C(C)C)C(=O)C1=C(O2)C(O)=C(O)C=C13489.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dulxanthone B,1TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O)C(O)=C3OC2=C1CC=C(C)C3441.1Semi standard non polar33892256
Dulxanthone B,1TMS,isomer #2COC1=C(CC=C(C)C)C(O)=C2C(=O)C3=CC=C(O)C(O[Si](C)(C)C)=C3OC2=C1CC=C(C)C3419.6Semi standard non polar33892256
Dulxanthone B,1TMS,isomer #3COC1=C(CC=C(C)C)C(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C(O)=C3OC2=C1CC=C(C)C3446.7Semi standard non polar33892256
Dulxanthone B,2TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C(O)=C3OC2=C1CC=C(C)C3364.8Semi standard non polar33892256
Dulxanthone B,2TMS,isomer #2COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O)C(O[Si](C)(C)C)=C3OC2=C1CC=C(C)C3343.1Semi standard non polar33892256
Dulxanthone B,2TMS,isomer #3COC1=C(CC=C(C)C)C(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3OC2=C1CC=C(C)C3357.5Semi standard non polar33892256
Dulxanthone B,3TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3OC2=C1CC=C(C)C3339.1Semi standard non polar33892256
Dulxanthone B,1TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O)C(O)=C3OC2=C1CC=C(C)C3655.8Semi standard non polar33892256
Dulxanthone B,1TBDMS,isomer #2COC1=C(CC=C(C)C)C(O)=C2C(=O)C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3OC2=C1CC=C(C)C3630.5Semi standard non polar33892256
Dulxanthone B,1TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3OC2=C1CC=C(C)C3669.5Semi standard non polar33892256
Dulxanthone B,2TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3OC2=C1CC=C(C)C3815.4Semi standard non polar33892256
Dulxanthone B,2TBDMS,isomer #2COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3OC2=C1CC=C(C)C3780.2Semi standard non polar33892256
Dulxanthone B,2TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3OC2=C1CC=C(C)C3792.2Semi standard non polar33892256
Dulxanthone B,3TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3OC2=C1CC=C(C)C3910.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dulxanthone B GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-1019000000-44a0a84a112e8f6f052c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dulxanthone B GC-MS (3 TMS) - 70eV, Positivesplash10-03di-1000059000-94ae89d17b3595ba831c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dulxanthone B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dulxanthone B 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 - Dulxanthone B 10V, Positive-QTOFsplash10-03di-0009800000-effb2f953ccd2882d1972015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 20V, Positive-QTOFsplash10-07vi-2009100000-086133e98f1173ce9a872015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 40V, Positive-QTOFsplash10-014s-7169000000-97131dc9801ba91125752015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 10V, Negative-QTOFsplash10-0a4i-0001900000-f51ada7389a9927c02262015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 20V, Negative-QTOFsplash10-0a4i-0009700000-06f11f5500bb6ff402d02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 40V, Negative-QTOFsplash10-0a6r-0947000000-60776b8477de042d5e7f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 10V, Negative-QTOFsplash10-0a4i-0000900000-d2c445cbedf3cebfa6b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 20V, Negative-QTOFsplash10-0a4i-0009600000-051e0613158927ed7e7d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 40V, Negative-QTOFsplash10-0a4i-0019400000-b837c5b613c8981122b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 10V, Positive-QTOFsplash10-08fr-0005900000-77e0d1d81784997beadb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 20V, Positive-QTOFsplash10-0a4i-0009100000-4c34afec06fbc1e647a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulxanthone B 40V, Positive-QTOFsplash10-0a4i-0039100000-0a1edb26d257eafbabc92021-09-23Wishart 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 IDFDB010690
KNApSAcK IDC00030162
Chemspider ID8963019
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10787706
PDB IDNot Available
ChEBI ID175288
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1831141
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.. .