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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:04:14 UTC
Update Date2022-03-07 02:54:44 UTC
HMDB IDHMDB0036006
Secondary Accession Numbers
  • HMDB36006
Metabolite Identification
Common NameXanthopurpurin
DescriptionXanthopurpurin, also known as purpuroxanthin, belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Xanthopurpurin has been detected, but not quantified in, several different foods, such as herbal tea, black tea, red tea, beverages, and herbs and spices. This could make xanthopurpurin a potential biomarker for the consumption of these foods. Xanthopurpurin 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 Xanthopurpurin.
Structure
Data?1563862806
Synonyms
ValueSource
1,3-Dihydroxy-9,10-anthracenedioneChEBI
1,3-Dihydroxy-9,10-anthraquinoneChEBI
1,3-DihydroxyanthraquinoneChEBI
PurpuroxanthinChEBI
PurpuroxanthineChEBI
1,3-Dihydroxy-9,10-anthracenedione, 9ciHMDB
1,3-Dihydroxy-anthraquinoneHMDB
1,3-Dihydroxyanthracene-9,10-dioneHMDB
2-(Methoxymethyl)-1,3-dihydroxyanthraquinoneHMDB
9,10-Anthracenedione, 1,3-dihydroxy- (9ci)HMDB
Lucidin omega-methyl etherHMDB
PurpuroHMDB
PurpuroxathinHMDB
PurpuroxathineHMDB
XanthopurpinHMDB
Chemical FormulaC14H8O4
Average Molecular Weight240.2109
Monoisotopic Molecular Weight240.042258744
IUPAC Name1,3-dihydroxy-9,10-dihydroanthracene-9,10-dione
Traditional Namepurpuro
CAS Registry Number518-83-2
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1C2=O
InChI Identifier
InChI=1S/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H
InChI KeyWPWWKBNOXTZDQJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentHydroxyanthraquinones
Alternative Parents
Substituents
  • Hydroxyanthraquinone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point268 - 270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP3.01ALOGPS
logP2.96ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.43ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.11 m³·mol⁻¹ChemAxon
Polarizability23.38 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]+154.28131661259
DarkChem[M-H]-153.5431661259
DeepCCS[M+H]+150.64430932474
DeepCCS[M-H]-148.24830932474
DeepCCS[M-2H]-181.37630932474
DeepCCS[M+Na]+156.55630932474
AllCCS[M+H]+152.332859911
AllCCS[M+H-H2O]+148.332859911
AllCCS[M+NH4]+156.132859911
AllCCS[M+Na]+157.132859911
AllCCS[M-H]-153.232859911
AllCCS[M+Na-2H]-152.432859911
AllCCS[M+HCOO]-151.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthopurpurinOC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1C2=O3393.8Standard polar33892256
XanthopurpurinOC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1C2=O2146.7Standard non polar33892256
XanthopurpurinOC1=CC2=C(C(O)=C1)C(=O)C1=CC=CC=C1C2=O2498.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthopurpurin,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=C2C(=O)C3=CC=CC=C3C(=O)C2=C12511.4Semi standard non polar33892256
Xanthopurpurin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=CC=CC=C1C2=O2433.1Semi standard non polar33892256
Xanthopurpurin,2TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=CC=C3C(=O)C2=C12535.5Semi standard non polar33892256
Xanthopurpurin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C3=CC=CC=C3C(=O)C2=C12774.8Semi standard non polar33892256
Xanthopurpurin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C1=CC=CC=C1C2=O2703.6Semi standard non polar33892256
Xanthopurpurin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=CC=C3C(=O)C2=C13029.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanthopurpurin GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p6-1980000000-5567e2b30036f66ce1e82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthopurpurin GC-MS (2 TMS) - 70eV, Positivesplash10-02mi-5279000000-233f483632f78e0bb9722017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthopurpurin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthopurpurin LC-ESI-QFT , negative-QTOFsplash10-000i-0190000000-f0cb95627113225597cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthopurpurin 35V, Negative-QTOFsplash10-000i-0090000000-ead5dabaebc2e7aa8e8d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 10V, Positive-QTOFsplash10-0006-0090000000-371f0b8b1a8f6c68dc7f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 20V, Positive-QTOFsplash10-0006-0190000000-88ab080fba1d74a0a9f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 40V, Positive-QTOFsplash10-0pb9-6930000000-5608b6b548ed514bb0042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 10V, Negative-QTOFsplash10-000i-0090000000-a48f5c40958d95d8ebee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 20V, Negative-QTOFsplash10-000i-0090000000-7b0562276000db1fd5222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 40V, Negative-QTOFsplash10-0a4s-1940000000-55b7c66a281357c909022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 10V, Positive-QTOFsplash10-0006-0090000000-8c788adea9f79f33ff402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 20V, Positive-QTOFsplash10-0006-0090000000-8c788adea9f79f33ff402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 40V, Positive-QTOFsplash10-000i-4900000000-78e1972c7412716d13ab2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 10V, Negative-QTOFsplash10-000i-0090000000-ffc6344f48ef3652df862021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 20V, Negative-QTOFsplash10-000i-0090000000-ffc6344f48ef3652df862021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthopurpurin 40V, Negative-QTOFsplash10-0002-1920000000-2e73192d36c9f3aec40b2021-09-25Wishart 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 IDFDB014820
KNApSAcK IDC00032518
Chemspider ID170598
KEGG Compound IDC10370
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound196978
PDB IDNot Available
ChEBI ID37502
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.. .