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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:52:50 UTC
Update Date2022-03-07 02:56:34 UTC
HMDB IDHMDB0040350
Secondary Accession Numbers
  • HMDB40350
Metabolite Identification
Common Name6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one
Description6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 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. 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one has been detected, but not quantified in, fruits. This could make 6,11-dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one.
Structure
Data?1563863541
Synonyms
ValueSource
Xanthone 4HMDB
Chemical FormulaC23H22O5
Average Molecular Weight378.4178
Monoisotopic Molecular Weight378.146723814
IUPAC Name6,11-dihydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2,10-dihydro-1,5-dioxatetraphen-10-one
Traditional Name6,11-dihydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-1,5-dioxatetraphen-10-one
CAS Registry Number35338-77-3
SMILES
CC(C)=CCCC1(C)OC2=C(C=C1)C1=C(C(O)=C2)C(=O)C2=C(O1)C(O)=CC=C2
InChI Identifier
InChI=1S/C23H22O5/c1-13(2)6-5-10-23(3)11-9-14-18(28-23)12-17(25)19-20(26)15-7-4-8-16(24)21(15)27-22(14)19/h4,6-9,11-12,24-25H,5,10H2,1-3H3
InChI KeyLVANTWLBTIEHSX-UHFFFAOYSA-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
  • 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
  • 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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 - 141 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0049 g/LALOGPS
logP5.07ALOGPS
logP5.64ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.9 m³·mol⁻¹ChemAxon
Polarizability41.28 ųChemAxon
Number of Rings4ChemAxon
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]+191.35231661259
DarkChem[M-H]-188.8831661259
DeepCCS[M+H]+191.00230932474
DeepCCS[M-H]-188.64430932474
DeepCCS[M-2H]-222.22230932474
DeepCCS[M+Na]+197.4530932474
AllCCS[M+H]+194.832859911
AllCCS[M+H-H2O]+191.832859911
AllCCS[M+NH4]+197.732859911
AllCCS[M+Na]+198.532859911
AllCCS[M-H]-191.132859911
AllCCS[M+Na-2H]-190.832859911
AllCCS[M+HCOO]-190.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-oneCC(C)=CCCC1(C)OC2=C(C=C1)C1=C(C(O)=C2)C(=O)C2=C(O1)C(O)=CC=C24508.2Standard polar33892256
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-oneCC(C)=CCCC1(C)OC2=C(C=C1)C1=C(C(O)=C2)C(=O)C2=C(O1)C(O)=CC=C23157.3Standard non polar33892256
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-oneCC(C)=CCCC1(C)OC2=C(C=C1)C1=C(C(O)=C2)C(=O)C2=C(O1)C(O)=CC=C23391.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one,1TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC2=C(O)C=CC=C2C3=O)O13383.8Semi standard non polar33892256
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one,1TMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(C=C(O)C3=C2OC2=C(O[Si](C)(C)C)C=CC=C2C3=O)O13357.1Semi standard non polar33892256
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one,2TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(C=C(O[Si](C)(C)C)C3=C2OC2=C(O[Si](C)(C)C)C=CC=C2C3=O)O13341.9Semi standard non polar33892256
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one,1TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC2=C(O)C=CC=C2C3=O)O13586.1Semi standard non polar33892256
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one,1TBDMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(C=C(O)C3=C2OC2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2C3=O)O13561.2Semi standard non polar33892256
6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one,2TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(C=C(O[Si](C)(C)C(C)(C)C)C3=C2OC2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2C3=O)O13765.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-9118000000-4016e26a53664b1ffb482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-8000690000-27217de1e3a4873fdda82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 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 - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 10V, Positive-QTOFsplash10-004i-0029000000-c010cd6679faebcb599d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 20V, Positive-QTOFsplash10-0a6r-4094000000-aed0987474bbe87d5b302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 40V, Positive-QTOFsplash10-066r-9260000000-ca50ea067b37335314382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 10V, Negative-QTOFsplash10-004i-0009000000-941e38660ca5144ea7a22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 20V, Negative-QTOFsplash10-004i-0029000000-b3ca0a3be9f68b34ba1c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 40V, Negative-QTOFsplash10-054x-1493000000-0c7fe6cd2e167746e56a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 10V, Positive-QTOFsplash10-004i-0009000000-913f6daceb13d08af49e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 20V, Positive-QTOFsplash10-004i-0129000000-122824fa4a2d1d374c002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 40V, Positive-QTOFsplash10-014m-2092000000-334ff4ee57771e392e072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 10V, Negative-QTOFsplash10-004i-0009000000-396e5f6c5ce1bbacff872021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 20V, Negative-QTOFsplash10-004i-0049000000-9651bff63b45f40016822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,11-Dihydroxy-3-methyl-3-(4-methyl-3-pentenyl)-3H,7H-pyrano[2,3-c]xanthen-7-one 40V, Negative-QTOFsplash10-0ktf-2492000000-a078475e07f8898ea2482021-09-23Wishart 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 IDFDB020076
KNApSAcK IDNot Available
Chemspider ID4577158
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5465516
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.. .