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Record Information
Version2.0
Created at2022-04-27 22:15:25 UTC
Updated at2022-04-27 22:15:25 UTC
NP-MRD IDNP0050847
Secondary Accession NumbersNone
Natural Product Identification
Common NameCanthin-6-one
DescriptionCanthin-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. Canthin-6-one is a strong basic compound (based on its pKa). Canthin-6-one is found in Ailanthus altissima, Ailanthus altissima , Ailanthus malabarica , Ailanthus triphysa, Allium neapolitanum , Brucea antidysenterica, Brucea javanica, Brucea mollis, Eurycoma longifolia , Eurycoma longifolida, Fagaropsis angolensis, Hannoa chlorantha, Hibiscus syriacus, Pentaceras australis, Phellodendron amurense , Phellodendron chinense , Picrasma crenata, Picrasma excelsa, Picrasma quassioides , Pierreodendron africanum, Pulveroboletus curtisii, Quassia africana, Simaba orinocensis, Simaba polyphylla, Simarouba glauca, Zanthoxylum belizense, Zanthoxylum chiloperone var. angustifolium, Zanthoxylum dipetalum, Zanthoxylum ekmanii, Zanthoxylum elephantiasis, Zanthoxylum integrifoliolum, Zanthoxylum mayu, Zanthoxylum ovalifolium, Zanthoxylum piasezkii, Zanthoxylum suberosum, Zanthoxylum viride and Zanthoxylum zanthoxyloides. Canthin-6-one was first documented in 2009 (PMID: 19325221). An indole alkaloid that is 6H-indolonaphthyridine substituted by an oxo group at position 6 (PMID: 21134431) (PMID: 21236329).
Structure
Thumb
Synonyms
ValueSource
6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-oneChEBI
Chemical FormulaC14H8N2O
Average Mass220.2310 Da
Monoisotopic Mass220.06366 Da
IUPAC Name1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one
Traditional Namecanthin-6-one
CAS Registry NumberNot Available
SMILES
O=C1C=CC2=NC=CC3=C2N1C1=C3C=CC=C1
InChI Identifier
InChI=1S/C14H8N2O/c17-13-6-5-11-14-10(7-8-15-11)9-3-1-2-4-12(9)16(13)14/h1-8H
InChI KeyZERVJPYNQLONEK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ailanthus altissimaLOTUS Database
Ailanthus altissimusPlant
Ailanthus malabaricaPlant
Ailanthus triphysusLOTUS Database
Allium neapolitanumPlant
Brucea antidysentericaLOTUS Database
Brucea javanicaLOTUS Database
Brucea mollisLOTUS Database
Eurycoma longifoliaPlant
Eurycoma longifolidaPlant
Fagaropsis angolensisLOTUS Database
Hannoa chloranthaLOTUS Database
Hibiscus syriacusLOTUS Database
Pentaceras australisPlant
Phellodendron amurensePlant
Phellodendron chinensePlant
Picrasma crenataPlant
Picrasma excelsaLOTUS Database
Picrasma quassioidesPlant
Pierreodendron africanumLOTUS Database
Pulveroboletus curtisiiLOTUS Database
Quassia africanaLOTUS Database
Simaba orinocensisLOTUS Database
Simaba polyphyllaLOTUS Database
Simarouba glaucaLOTUS Database
Zanthoxylum belizensePlant
Zanthoxylum chiloperone var. angustifoliumPlant
Zanthoxylum dipetalumPlant
Zanthoxylum ekmaniiLOTUS Database
Zanthoxylum elephantiasisPlant
Zanthoxylum integrifoliolumPlant
Zanthoxylum mayuLOTUS Database
Zanthoxylum ovalifoliumPlant
Zanthoxylum piasezkiiLOTUS Database
Zanthoxylum suberosumPlant
Zanthoxylum virideLOTUS Database
Zanthoxylum zanthoxyloidesLOTUS Database
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
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.55ALOGPS
logP1.81ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)3.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64.5 m³·mol⁻¹ChemAxon
Polarizability22.75 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001701
Chemspider IDNot Available
KEGG Compound IDC09098
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound97176
PDB IDNot Available
ChEBI ID3363
Good Scents IDNot Available
References
General References
  1. Tada A, Sugimoto N, Sato K, Akiyama T, Asanoma M, Yun YS, Yamazaki T, Tanamoto K: [Examination of original plant of Jamaica quassia extract, a natural bittering agent, based on composition of the constituents]. Shokuhin Eiseigaku Zasshi. 2009 Feb;50(1):16-21. doi: 10.3358/shokueishi.50.16. [PubMed:19325221 ]
  2. Ferreira ME, Cebrian-Torrejon G, Corrales AS, Vera de Bilbao N, Rolon M, Gomez CV, Leblanc K, Yaluf G, Schinini A, Torres S, Serna E, Rojas de Arias A, Poupon E, Fournet A: Zanthoxylum chiloperone leaves extract: first sustainable Chagas disease treatment. J Ethnopharmacol. 2011 Feb 16;133(3):986-93. doi: 10.1016/j.jep.2010.11.032. Epub 2010 Dec 4. [PubMed:21134431 ]
  3. de Souza Almeida ES, Filho VC, Niero R, Clasen BK, Balogun SO, de Oliveira Martins DT: Pharmacological mechanisms underlying the anti-ulcer activity of methanol extract and canthin-6-one of Simaba ferruginea A. St-Hil. in animal models. J Ethnopharmacol. 2011 Apr 12;134(3):630-6. doi: 10.1016/j.jep.2011.01.009. Epub 2011 Jan 12. [PubMed:21236329 ]