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Record Information
Version2.0
Creation Date2014-08-29 04:49:25 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4026
Identification
Common Name(+)-Calycanthine
ClassSmall Molecule
Description(+)-Calycanthine is found in herbs and spices. (+)-Calycanthine is an alkaloid from Calycanthus floridus (Carolina allspice) and other Calycanthus species. (+)-Calycanthine belongs to the family of Naphthyridines. These are compounds containing a naphthyridine moeity, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.
Compound Type
  • Amine
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
Calycanthine
Chemical FormulaC22H26N4
Average Molecular Mass346.469 g/mol
Monoisotopic Mass346.216 g/mol
CAS Registry Number595-05-1
IUPAC Name21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3²,¹⁰.0¹,¹⁰.0⁴,⁹.0¹³,¹⁸]tetracosa-4(9),5,7,13(18),14,16-hexaene
Traditional Name21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3²,¹⁰.0¹,¹⁰.0⁴,⁹.0¹³,¹⁸]tetracosa-4(9),5,7,13(18),14,16-hexaene
SMILESCN1CCC23C4NC5=CC=CC=C5C2(CCN4C)C1NC1=CC=CC=C31
InChI IdentifierInChI=1/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3
InChI KeyInChIKey=XSYCDVWYEVUDKQ-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct ParentAminoquinolines and derivatives
Alternative Parents
Substituents
  • Aminoquinoline
  • Diazanaphthalene
  • Naphthyridine
  • Tetrahydroquinoline
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Piperidine
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point250 - 251°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP3.37ALOGPS
logP2.85ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.86ChemAxon
pKa (Strongest Basic)7.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area30.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity107.91 m³·mol⁻¹ChemAxon
Polarizability38.53 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001s-0059000000-61886ab02401e72884bbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0942100000-1ad329a52b02cd758c4eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-008c-0981000000-04efdcee7a71719b9c4fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0479000000-a6439abec973403fdcebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0469000000-efa6c307a636055178fcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-178c45fa30b5ed9f81b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-a652df12fd59a565ae0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-3094000000-347f18c27fa532cb36f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-4fb8dca670aa9a67846bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1009000000-5cabbd0f8a7bccd6f209JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00p0-1059000000-e40b92e4cc6c670f550bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-37c95b847a9e45a22589JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-37c95b847a9e45a22589JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0092000000-b79d70f700d16f3fcfd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-a5ed12fd7e24b3ac19f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-a5ed12fd7e24b3ac19f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6t-0019000000-403fce3ed9ac9812dcbcJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityThe principal alkaloid of the family Calycanthaceae, calycanthine has long been recognized as a central convulsant. Convulsant actions of calycanthine is mediated, at least in part, by blocking the postsynaptic action of GABA as indicated by its inhibitory effect onthe binding of the radiolabeled cage convulsant, [35S]t-butylbicyclophosphorothionate. The alkaloid inhibited the potassium-stimulated release of [(3)H]GABA from slices of rat hippocampus with an ED(50) of approximately 21 microM. This effect appeared to be moderately selective since calycanthine at 100 microM had only a weak effect on the potassium-stimulated release of [(3)H]acetylcholine (15%) and no significant effects on the release of [(3)H]D-aspartate from hippocampal and cerebellar slices or the release of [(3)H]glycine from spinal cord slices. Calycanthine blocked the L-type calcium currents with an IC(50) of approximately 42 microM and also weakly inhibited the N-type calcium currents (IC(50) > 100 microM) from neuroblastoma X glioma cells, suggesting voltage-dependent calcium channel blockade as a possible mechanism for its inhibition of GABA and ACh release. Calycanthine was also found to directly inhibit GABA-mediated currents (K(B) approximately 135 microM) from human alpha(1)beta(2)gamma(2L) GABA(A) receptors expressed in Xenopus laevis oocytes but had no effect at 100 microM on human rho(1) GABA(c) receptors. Calycanthine may mediate its convulsant action predominantly by inhibiting the release of the inhibitory neurotransmitter GABA as a result of interactions with L-type Ca(2+) channels and by inhibiting GABA-mediated chloride currents at GABA(A) receptors. The properties of this alkaloid have also been investigated on the genesis, conduction, and transmission of the nerve impulse, using giant axons of the cockroach (Periplaneta americana). Calycanthine hydrochloride (10(-5) M), which did not alter nervous conduction in pre- and post-synaptic fibers, significantly reduced the efficacy of the synaptic transmission. (PMID: 1653964; PMID: 12831783)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources(+)-Calycanthine is found in herbs and spices. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29561
PubChem Compound ID264115
ChEMBL IDCHEMBL464770
ChemSpider ID232050
KEGG IDC10573
UniProt IDNot Available
OMIM ID
ChEBI ID3333
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Kuke RK, Allan RD, Johnston GA, Mewett KN, Mitrovic AD, Duke CC, Hambley TW: Idiospermuline, a trimeric pyrrolidinoindoline alkaloid from the seed of Idiospermum australiense. J Nat Prod. 1995 Aug;58(8):1200-8. [7595588 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available