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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:12 UTC
Update Date2022-03-07 02:52:38 UTC
HMDB IDHMDB0030655
Secondary Accession Numbers
  • HMDB30655
Metabolite Identification
Common NameCalabaxanthone
DescriptionCalabaxanthone 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 Calabaxanthone.
Structure
Data?1563862018
Synonyms
ValueSource
5-Hydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-b]xanthen-6-one, 9ciHMDB
Chemical FormulaC24H24O5
Average Molecular Weight392.4444
Monoisotopic Molecular Weight392.162373878
IUPAC Name5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2,6-dihydro-1,11-dioxatetracen-6-one
Traditional Name5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-1,11-dioxatetracen-6-one
CAS Registry Number39011-96-6
SMILES
COC1=C(CC=C(C)C)C2=C(OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C2=O)C=C1
InChI Identifier
InChI=1S/C24H24O5/c1-13(2)6-7-14-16(27-5)8-9-17-20(14)23(26)21-19(28-17)12-18-15(22(21)25)10-11-24(3,4)29-18/h6,8-12,25H,7H2,1-5H3
InChI KeyPLKQPRRVFTZBAE-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
  • Pyranoxanthone
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • 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
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point172 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.3e-05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP4.61ALOGPS
logP5.78ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.9 m³·mol⁻¹ChemAxon
Polarizability43.51 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]+191.50631661259
DarkChem[M-H]-195.64931661259
DeepCCS[M+H]+203.43230932474
DeepCCS[M-H]-201.07430932474
DeepCCS[M-2H]-233.95830932474
DeepCCS[M+Na]+209.52530932474
AllCCS[M+H]+195.932859911
AllCCS[M+H-H2O]+193.032859911
AllCCS[M+NH4]+198.632859911
AllCCS[M+Na]+199.332859911
AllCCS[M-H]-195.832859911
AllCCS[M+Na-2H]-195.432859911
AllCCS[M+HCOO]-195.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CalabaxanthoneCOC1=C(CC=C(C)C)C2=C(OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C2=O)C=C14337.9Standard polar33892256
CalabaxanthoneCOC1=C(CC=C(C)C)C2=C(OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C2=O)C=C13412.7Standard non polar33892256
CalabaxanthoneCOC1=C(CC=C(C)C)C2=C(OC3=C(C(O)=C4C=CC(C)(C)OC4=C3)C2=O)C=C13339.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Calabaxanthone,1TMS,isomer #1COC1=CC=C2OC3=CC4=C(C=CC(C)(C)O4)C(O[Si](C)(C)C)=C3C(=O)C2=C1CC=C(C)C3285.0Semi standard non polar33892256
Calabaxanthone,1TBDMS,isomer #1COC1=CC=C2OC3=CC4=C(C=CC(C)(C)O4)C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C2=C1CC=C(C)C3495.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Calabaxanthone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1139000000-64261dd98cdc627b930e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calabaxanthone GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3332900000-7f43da1e4214f57d90822017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calabaxanthone 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 - Calabaxanthone 10V, Positive-QTOFsplash10-0006-0009000000-eea98e514da5c455538a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 20V, Positive-QTOFsplash10-00ku-1009000000-95ed988baafc8ee54c442016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 40V, Positive-QTOFsplash10-014i-6249000000-c1bd74f0ae7494441cec2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 10V, Negative-QTOFsplash10-0006-0009000000-ea96a589666eb47803102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 20V, Negative-QTOFsplash10-0006-0009000000-8f7bb3608554d912eb0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 40V, Negative-QTOFsplash10-0a4i-1269000000-90a6120fb23fb1f1146c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 10V, Negative-QTOFsplash10-0006-0009000000-163f84c1fe290a9d7e8e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 20V, Negative-QTOFsplash10-0006-0009000000-19a1205ade170ac250cd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 40V, Negative-QTOFsplash10-02dj-0339000000-cc67f9a59f81e2ed89a12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 10V, Positive-QTOFsplash10-000f-0009000000-f55271e03c88f845566c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 20V, Positive-QTOFsplash10-000i-0009000000-d2b5dd3eb152c43b79692021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calabaxanthone 40V, Positive-QTOFsplash10-0006-2039000000-ab06d55b4b2baa4ec2762021-09-24Wishart 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 IDFDB002565
KNApSAcK IDC00055288
Chemspider ID302357
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound341188
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1821801
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.. .