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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:33 UTC
Update Date2022-03-07 02:52:28 UTC
HMDB IDHMDB0030227
Secondary Accession Numbers
  • HMDB30227
Metabolite Identification
Common Name5-Methoxycanthin-6-one
Description5-Methoxycanthin-6-one belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.g. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. 5-Methoxycanthin-6-one is a strong basic compound (based on its pKa). Alkaloid from the wood of Picrasma excelsa (Jamaican quassiawood).
Structure
Data?1563861956
Synonyms
ValueSource
5-Methoxy-6H-indolo(3,2,1-de)(1,5)naphthyridin-6-oneHMDB
5-Methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-oneHMDB
5-Methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one, 9ciHMDB
5-Methoxy-canthin-6-oneHMDB
5-Methoxycanthin-6-oneMeSH
Chemical FormulaC15H10N2O2
Average Molecular Weight250.2521
Monoisotopic Molecular Weight250.074227574
IUPAC Name3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one
Traditional Name3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one
CAS Registry Number15071-56-4
SMILES
COC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O
InChI Identifier
InChI=1S/C15H10N2O2/c1-19-13-8-11-14-10(6-7-16-11)9-4-2-3-5-12(9)17(14)15(13)18/h2-8H,1H3
InChI KeyTXEFUSAHPIYZHD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassIndolonaphthyridine alkaloids
Sub ClassNot Available
Direct ParentIndolonaphthyridine alkaloids
Alternative Parents
Substituents
  • Indolo[3,2-1de][1,5]naphthyridine
  • Beta-carboline
  • Pyridoindole
  • Diazanaphthalene
  • Naphthyridine
  • Indole
  • Indole or derivatives
  • Indolizine
  • Pyrrolopyridine
  • Pyridinone
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Lactam
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point243 - 244 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.72ALOGPS
logP1.68ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)3.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.22 m³·mol⁻¹ChemAxon
Polarizability25.87 ųChemAxon
Number of Rings4ChemAxon
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]+157.25731661259
DarkChem[M-H]-156.50331661259
DeepCCS[M-2H]-190.23530932474
DeepCCS[M+Na]+165.830932474
AllCCS[M+H]+154.632859911
AllCCS[M+H-H2O]+150.532859911
AllCCS[M+NH4]+158.532859911
AllCCS[M+Na]+159.632859911
AllCCS[M-H]-160.432859911
AllCCS[M+Na-2H]-159.432859911
AllCCS[M+HCOO]-158.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Methoxycanthin-6-oneCOC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O3366.6Standard polar33892256
5-Methoxycanthin-6-oneCOC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O2459.1Standard non polar33892256
5-Methoxycanthin-6-oneCOC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O2535.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxycanthin-6-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0490000000-f1860259b35079360f072017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxycanthin-6-one 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 - 5-Methoxycanthin-6-one 10V, Positive-QTOFsplash10-0udi-0090000000-087c85fcbf011bb838ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Positive-QTOFsplash10-0udi-0090000000-51012159796bca1ea8d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Positive-QTOFsplash10-00di-0390000000-8d27d5f34a9d9340e8002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 10V, Negative-QTOFsplash10-0002-0090000000-53e7b115923dfd043f332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Negative-QTOFsplash10-0002-0090000000-2d114b98cc00ff75b9b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Negative-QTOFsplash10-014i-0390000000-2ddc80db905851cc2b6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 10V, Positive-QTOFsplash10-0udi-0090000000-01844139d9a1e29fbe912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Positive-QTOFsplash10-0udi-0090000000-01844139d9a1e29fbe912021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Positive-QTOFsplash10-0umi-0890000000-806cddf1b93a105cce4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 10V, Negative-QTOFsplash10-0002-0090000000-6971a302c8bdd54e58342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Negative-QTOFsplash10-0002-0090000000-6971a302c8bdd54e58342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Negative-QTOFsplash10-016r-0590000000-2c58456b19a8c665fb262021-09-24Wishart 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 IDFDB002046
KNApSAcK IDNot Available
Chemspider ID227523
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound259218
PDB IDNot Available
ChEBI ID544162
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.. .