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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:04:20 UTC
Update Date2019-07-23 06:13:13 UTC
HMDB IDHMDB0033356
Secondary Accession Numbers
  • HMDB33356
Metabolite Identification
Common NameXanthoplanine
DescriptionXanthoplanine is found in fruits. Quaternary alkaloid from Litsea cubeba (mountain pepper).
Structure
Data?1563862393
Synonyms
ValueSource
(+)-XanthoplanineHMDB
Chemical FormulaC21H26NO4
Average Molecular Weight356.4354
Monoisotopic Molecular Weight356.186183325
IUPAC Name5-hydroxy-4,15,16-trimethoxy-10,10-dimethyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-10-ium
Traditional Name5-hydroxy-4,15,16-trimethoxy-10,10-dimethyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-10-ium
CAS Registry Number6872-88-4
SMILES
COC1=C(O)C=C2CC3C4=C(C(OC)=C(OC)C=C4CC[N+]3(C)C)C2=C1
InChI Identifier
InChI=1S/C21H25NO4/c1-22(2)7-6-12-10-18(25-4)21(26-5)20-14-11-17(24-3)16(23)9-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/p+1
InChI KeyFGUCOPALAZXICJ-UHFFFAOYSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic salt
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point207 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP0.8ALOGPS
logP-1.2ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)7.1ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity113.31 m³·mol⁻¹ChemAxon
Polarizability39.79 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dm-0059000000-ed10d7d3ace3fb12f1efJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03e9-1019400000-2038dcbeb0a02ced68f3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-46ab60beb28e30448d52JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vi-0039000000-9cb5c8b800d60f13465dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-0391000000-853a42bfdd91e96a1800JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB011384
KNApSAcK IDC00027170
Chemspider ID4474684
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5315336
PDB IDNot Available
ChEBI 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.. .