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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:04:20 UTC
Update Date2022-03-07 02:53:40 UTC
HMDB IDHMDB0033356
Secondary Accession Numbers
  • HMDB33356
Metabolite Identification
Common 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). Outside of the human body, xanthoplanine has been detected, but not quantified in, fruits. This could make xanthoplanine a potential biomarker for the consumption of these foods.
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
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point207 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.09731661259
DarkChem[M-H]-185.05231661259
DeepCCS[M+H]+190.70830932474
DeepCCS[M-H]-188.02730932474
DeepCCS[M-2H]-222.64230932474
DeepCCS[M+Na]+198.42630932474
AllCCS[M+H]+184.132859911
AllCCS[M+H-H2O]+181.332859911
AllCCS[M+NH4]+186.732859911
AllCCS[M+Na]+187.532859911
AllCCS[M-H]-194.332859911
AllCCS[M+Na-2H]-194.932859911
AllCCS[M+HCOO]-195.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthoplanineCOC1=C(O)C=C2CC3C4=C(C(OC)=C(OC)C=C4CC[N+]3(C)C)C2=C14287.3Standard polar33892256
XanthoplanineCOC1=C(O)C=C2CC3C4=C(C(OC)=C(OC)C=C4CC[N+]3(C)C)C2=C12533.5Standard non polar33892256
XanthoplanineCOC1=C(O)C=C2CC3C4=C(C(OC)=C(OC)C=C4CC[N+]3(C)C)C2=C12916.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthoplanine,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CC[N+]1(C)C2876.7Semi standard non polar33892256
Xanthoplanine,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(OC)=C23)CC[N+]1(C)C3090.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanthoplanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dm-0059000000-ed10d7d3ace3fb12f1ef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthoplanine GC-MS (1 TMS) - 70eV, Positivesplash10-03e9-1019400000-2038dcbeb0a02ced68f32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthoplanine 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 - Xanthoplanine 10V, Positive-QTOFsplash10-0a4i-0009000000-46ab60beb28e30448d522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoplanine 20V, Positive-QTOFsplash10-06vi-0039000000-9cb5c8b800d60f13465d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoplanine 40V, Positive-QTOFsplash10-02ai-0391000000-853a42bfdd91e96a18002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoplanine 10V, Positive-QTOFsplash10-0a4i-0009000000-f75a89c806438ef551602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoplanine 20V, Positive-QTOFsplash10-0a4i-0009000000-5447ea9e08c504ac62b92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoplanine 40V, Positive-QTOFsplash10-05be-0098000000-139d2b67098e67c6b8832021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
FooDB 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
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.. .