Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2019-11-26 02:56:32 UTC
Primary IDFDB001504
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXylopine
DescriptionXylopine, also known as (-)-xylopine, is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Xylopine is practically insoluble (in water) and a very strong basic compound (based on its pKa). Xylopine can be found in cherimoya and custard apple, which makes xylopine a potential biomarker for the consumption of these food products. Xylopine is an antimicrobial benzylisoquinoline alkaloid .
CAS Number517-71-5
Structure
Thumb
Synonyms
SynonymSource
(-)-XylopineChEMBL
6abeta-Noraporphine, 9-methoxy-1,2-(methylenedioxy)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP2.11ALOGPS
logP2.78ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area39.72 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.96 m³·mol⁻¹ChemAxon
Polarizability32.34 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H17NO3
IUPAC name(12R)-16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene
InChI IdentifierInChI=1S/C18H17NO3/c1-20-12-2-3-13-11(6-12)7-14-16-10(4-5-19-14)8-15-18(17(13)16)22-9-21-15/h2-3,6,8,14,19H,4-5,7,9H2,1H3/t14-/m1/s1
InChI KeyRFWCCZDSXIZJMF-CQSZACIVSA-N
Isomeric SMILESCOC1=CC=C2C(C[C@H]3NCCC4=CC5=C(OCO5)C2=C34)=C1
Average Molecular Weight295.3325
Monoisotopic Molecular Weight295.120843415
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 Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Organoheterocyclic compound
  • Azacycle
  • Secondary amine
  • Oxacycle
  • Acetal
  • Ether
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-2f05a9287c8f61681e5bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-047b0b05686c6f93889eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-0390000000-193a1e3b8c54d1c49587Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-b637672f1416623d1d58Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-96200255e20b71b78965Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1190000000-231196c8222c33bb2efeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-807fb2619769e9d71665Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-807fb2619769e9d71665Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0390000000-83cc85f11a4db6331f53Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-617cac9c409742842799Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-2b719eb619faa1b40824Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r6-0090000000-4a358b74722d9c82121bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09670
Pubchem Compound ID160503
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001928
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.