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Record Information
Version1.0
Created at2022-04-28 20:22:37 UTC
Updated at2022-04-28 20:22:37 UTC
NP-MRD IDNP0075061
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-Hydroxycanthin-6-one
Description9-Hydroxycanthin-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. 9-Hydroxycanthin-6-one is found in Eurycoma harmandiana , Eurycoma longifolia and Eurycoma longifolida. It was first documented in 1991 (PMID: 1800638). 9-Hydroxycanthin-6-one is a strong basic compound (based on its pKa) (PMID: 11249106) (PMID: 21569213).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H8N2O2
Average Mass236.2300 Da
Monoisotopic Mass236.05858 Da
IUPAC Name13-hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one
Traditional Name13-hydroxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10(15),11,13-heptaen-2-one
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(C=C1)C1=C3N2C(=O)C=CC3=NC=C1
InChI Identifier
InChI=1S/C14H8N2O2/c17-8-1-2-9-10-5-6-15-11-3-4-13(18)16(14(10)11)12(9)7-8/h1-7,17H
InChI KeyJHPIJMUNSMWWAA-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
Eurycoma harmandianaPlant
Eurycoma longifoliaLOTUS Database
Eurycoma longifolidaPlant
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
  • Hydroxyindole
  • Indole
  • Indole or derivatives
  • Indolizine
  • Pyrrolopyridine
  • Pyridinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • 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
logP2.41ALOGPS
logP1.51ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.12 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.48 m³·mol⁻¹ChemAxon
Polarizability23.81 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID66041
Good Scents IDNot Available
References
General References
  1. Kanchanapoom T, Kasai R, Chumsri P, Hiraga Y, Yamasaki K: Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana. Phytochemistry. 2001 Feb;56(4):383-6. doi: 10.1016/s0031-9422(00)00363-0. [PubMed:11249106 ]
  2. Kardono LB, Angerhofer CK, Tsauri S, Padmawinata K, Pezzuto JM, Kinghorn AD: Cytotoxic and antimalarial constituents of the roots of Eurycoma longifolia. J Nat Prod. 1991 Sep-Oct;54(5):1360-7. doi: 10.1021/np50077a020. [PubMed:1800638 ]
  3. Chiou WF, Wu TS: 9-hydroxycanthin-6-one induces penile erection and delays ejaculation. J Sex Med. 2012 Apr;9(4):1027-36. doi: 10.1111/j.1743-6109.2011.02296.x. Epub 2011 May 13. [PubMed:21569213 ]