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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:01 UTC
Update Date2022-03-07 02:52:23 UTC
HMDB IDHMDB0029989
Secondary Accession Numbers
  • HMDB29989
Metabolite Identification
Common NameDulciol B
DescriptionDulciol B 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. Based on a literature review very few articles have been published on Dulciol B.
Structure
Data?1563861921
Synonyms
ValueSource
7-(1,1-Dimethyl-2-propenyl)-2,3,5,8-tetrahydroxy-1,4-bis(3-methyl-2-butenyl)-9H-xanthen-9-oneHMDB
7-(1,1-Dimethyl-2-propenyl)-2,3,5,8-tetrahydroxy-1,4-diprenylxanthoneHMDB
Chemical FormulaC28H32O6
Average Molecular Weight464.5501
Monoisotopic Molecular Weight464.219888756
IUPAC Name2,3,5,8-tetrahydroxy-1,4-bis(3-methylbut-2-en-1-yl)-7-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one
Traditional Name2,3,5,8-tetrahydroxy-1,4-bis(3-methylbut-2-en-1-yl)-7-(2-methylbut-3-en-2-yl)xanthen-9-one
CAS Registry Number175617-24-0
SMILES
CC(C)=CCC1=C(O)C(O)=C(CC=C(C)C)C2=C1OC1=C(C(O)=C(C=C1O)C(C)(C)C=C)C2=O
InChI Identifier
InChI=1S/C28H32O6/c1-8-28(6,7)18-13-19(29)27-21(24(18)32)25(33)20-16(11-9-14(2)3)22(30)23(31)17(26(20)34-27)12-10-15(4)5/h8-10,13,29-32H,1,11-12H2,2-7H3
InChI KeyCLXFLUDZZDAVOS-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
  • 4-prenylated xanthone
  • 8-prenylated xanthone
  • Chromone
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point109 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.0e-06 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP5.23ALOGPS
logP7.54ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)7.26ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity136.54 m³·mol⁻¹ChemAxon
Polarizability51.07 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
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]+209.04531661259
DarkChem[M-H]-206.58131661259
DeepCCS[M+H]+208.56330932474
DeepCCS[M-H]-206.16830932474
DeepCCS[M-2H]-239.05130932474
DeepCCS[M+Na]+214.51930932474
AllCCS[M+H]+212.432859911
AllCCS[M+H-H2O]+210.232859911
AllCCS[M+NH4]+214.432859911
AllCCS[M+Na]+215.032859911
AllCCS[M-H]-208.332859911
AllCCS[M+Na-2H]-208.432859911
AllCCS[M+HCOO]-208.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dulciol BCC(C)=CCC1=C(O)C(O)=C(CC=C(C)C)C2=C1OC1=C(C(O)=C(C=C1O)C(C)(C)C=C)C2=O5217.3Standard polar33892256
Dulciol BCC(C)=CCC1=C(O)C(O)=C(CC=C(C)C)C2=C1OC1=C(C(O)=C(C=C1O)C(C)(C)C=C)C2=O3692.7Standard non polar33892256
Dulciol BCC(C)=CCC1=C(O)C(O)=C(CC=C(C)C)C2=C1OC1=C(C(O)=C(C=C1O)C(C)(C)C=C)C2=O3699.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dulciol B,1TMS,isomer #1C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O3639.8Semi standard non polar33892256
Dulciol B,1TMS,isomer #2C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O3644.7Semi standard non polar33892256
Dulciol B,1TMS,isomer #3C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3648.4Semi standard non polar33892256
Dulciol B,1TMS,isomer #4C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O3679.4Semi standard non polar33892256
Dulciol B,2TMS,isomer #1C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O3569.1Semi standard non polar33892256
Dulciol B,2TMS,isomer #2C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O3558.1Semi standard non polar33892256
Dulciol B,2TMS,isomer #3C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3526.2Semi standard non polar33892256
Dulciol B,2TMS,isomer #4C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O3575.9Semi standard non polar33892256
Dulciol B,2TMS,isomer #5C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3526.4Semi standard non polar33892256
Dulciol B,2TMS,isomer #6C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3598.9Semi standard non polar33892256
Dulciol B,3TMS,isomer #1C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O3513.0Semi standard non polar33892256
Dulciol B,3TMS,isomer #2C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3532.4Semi standard non polar33892256
Dulciol B,3TMS,isomer #3C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3483.9Semi standard non polar33892256
Dulciol B,3TMS,isomer #4C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3550.9Semi standard non polar33892256
Dulciol B,4TMS,isomer #1C=CC(C)(C)C1=CC(O[Si](C)(C)C)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C3515.1Semi standard non polar33892256
Dulciol B,1TBDMS,isomer #1C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O3883.4Semi standard non polar33892256
Dulciol B,1TBDMS,isomer #2C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O3891.9Semi standard non polar33892256
Dulciol B,1TBDMS,isomer #3C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C3889.7Semi standard non polar33892256
Dulciol B,1TBDMS,isomer #4C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O3909.2Semi standard non polar33892256
Dulciol B,2TBDMS,isomer #1C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O4028.9Semi standard non polar33892256
Dulciol B,2TBDMS,isomer #2C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O4007.6Semi standard non polar33892256
Dulciol B,2TBDMS,isomer #3C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C4007.1Semi standard non polar33892256
Dulciol B,2TBDMS,isomer #4C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O4036.6Semi standard non polar33892256
Dulciol B,2TBDMS,isomer #5C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C4008.2Semi standard non polar33892256
Dulciol B,2TBDMS,isomer #6C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C4040.8Semi standard non polar33892256
Dulciol B,3TBDMS,isomer #1C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O4115.5Semi standard non polar33892256
Dulciol B,3TBDMS,isomer #2C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C4179.4Semi standard non polar33892256
Dulciol B,3TBDMS,isomer #3C=CC(C)(C)C1=CC(O)=C2OC3=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C4090.1Semi standard non polar33892256
Dulciol B,3TBDMS,isomer #4C=CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C2OC3=C(CC=C(C)C)C(O)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3C(=O)C2=C1O[Si](C)(C)C(C)(C)C4198.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dulciol B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0072-1010900000-1b16c8ea0d0f40f0f91d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dulciol B GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1000009000-e403b812bfa11632161d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dulciol 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 - Dulciol B 10V, Negative-QTOFsplash10-03di-0000900000-6c57474ca976805a6d522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 20V, Negative-QTOFsplash10-03di-0004900000-0457fef072e8157c1ec52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 40V, Negative-QTOFsplash10-05mx-0294200000-ca7d55606a19de11dea52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 10V, Negative-QTOFsplash10-03di-0000900000-c2f336ffe0bfffbff6162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 20V, Negative-QTOFsplash10-03di-0000900000-8a2e2df7b3c1e72eebbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 40V, Negative-QTOFsplash10-004r-1009300000-db6ff0dd7f3f902058d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 10V, Positive-QTOFsplash10-014i-0000900000-e4b3f2423956f946ad202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 20V, Positive-QTOFsplash10-0aos-1003900000-e36d59b259917845ff892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 40V, Positive-QTOFsplash10-0159-4093200000-6b8d97fc32f634599ba52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 10V, Positive-QTOFsplash10-0pc0-0009700000-8519a1aba849353737a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 20V, Positive-QTOFsplash10-005c-0009100000-de4ae3ecb4f537bfbbb92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dulciol B 40V, Positive-QTOFsplash10-014i-4009000000-4c56b5f3a4c626ead3b82021-09-22Wishart 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 IDFDB001277
KNApSAcK IDC00037077
Chemspider ID8918118
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10742787
PDB IDNot Available
ChEBI ID172695
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1812811
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.. .