Record Information
Version1.0
Creation date2010-04-08 22:09:37 UTC
Update date2019-11-26 03:04:52 UTC
Primary IDFDB011384
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthoplanine
DescriptionXanthoplanine 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. Xanthoplanine is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthoplanine has been detected, but not quantified in, fruits. This could make xanthoplanine a potential biomarker for the consumption of these foods.
CAS Number6872-88-4
Structure
Thumb
Synonyms
SynonymSource
(+)-XanthoplanineHMDB
Xanthoplaninedb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H26NO4
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
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(O)C=C2CC3C4=C(C(OC)=C(OC)C=C4CC[N+]3(C)C)C2=C1
Average Molecular Weight356.4354
Monoisotopic Molecular Weight356.186183325
Classification
Description 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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.76%; H 7.35%; N 3.93%; O 17.95%DFC
Melting PointMp 207-209° (as iodide)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]21D +62 (c, 0.83 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthoplanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dm-0059000000-ed10d7d3ace3fb12f1efSpectrum
Predicted GC-MSXanthoplanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03e9-1019400000-2038dcbeb0a02ced68f3Spectrum
Predicted GC-MSXanthoplanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-46ab60beb28e30448d52Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vi-0039000000-9cb5c8b800d60f13465dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-0391000000-853a42bfdd91e96a1800Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-f75a89c806438ef55160Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-5447ea9e08c504ac62b9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05be-0098000000-139d2b67098e67c6b883Spectrum
NMRNot Available
ChemSpider ID4474684
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5315336
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33356
CRC / DFC (Dictionary of Food Compounds) IDCDG65-P:GNS33-W
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00027170
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference