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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:10 UTC
Update Date2022-03-07 02:52:12 UTC
HMDB IDHMDB0029561
Secondary Accession Numbers
  • HMDB29561
Metabolite Identification
Common Name(+)-Calycanthine
Description(+)-Calycanthine 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. No indication of carcinogenicity to humans (not listed by IARC) (+)-Calycanthine is a very strong basic compound (based on its pKa). Outside of the human body, (+)-calycanthine has been detected, but not quantified in, herbs and spices. This could make (+)-calycanthine a potential biomarker for the consumption of these foods. The principal alkaloid of the family Calycanthaceae, calycanthine has long been recognized as a central convulsant (A) receptors expressed in Xenopus laevis oocytes but had no effect at 100 microM on human rho(1) GABA(c) receptors (+)-Calycanthine is a potentially toxic compound. 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, t-butylbicyclophosphorothionate. 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. 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). This effect appeared to be moderately selective since calycanthine at 100 microM had only a weak effect on the potassium-stimulated release of acetylcholine (15%) and no significant effects on the release of D-aspartate from hippocampal and cerebellar slices or the release of 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.
Structure
Data?1582753436
Synonyms
ValueSource
CalycanthineHMDB
Chemical FormulaC22H26N4
Average Molecular Weight346.4686
Monoisotopic Molecular Weight346.215746852
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
CAS Registry Number595-05-1
SMILES
CN1CCC23C4NC5=C(C=CC=C5)C2(CCN4C)C1NC1=C3C=CC=C1
InChI Identifier
InChI=1S/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 KeyXSYCDVWYEVUDKQ-UHFFFAOYSA-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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point250 - 251 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.61131661259
DarkChem[M-H]-178.8931661259
DeepCCS[M-2H]-218.26730932474
DeepCCS[M+Na]+193.59530932474
AllCCS[M+H]+185.232859911
AllCCS[M+H-H2O]+182.232859911
AllCCS[M+NH4]+188.132859911
AllCCS[M+Na]+188.932859911
AllCCS[M-H]-194.832859911
AllCCS[M+Na-2H]-194.332859911
AllCCS[M+HCOO]-193.932859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-Calycanthine,1TMS,isomer #1CN1CCC23C4=CC=CC=C4NC1C21CCN(C)C3N([Si](C)(C)C)C2=CC=CC=C212955.0Semi standard non polar33892256
(+)-Calycanthine,1TMS,isomer #1CN1CCC23C4=CC=CC=C4NC1C21CCN(C)C3N([Si](C)(C)C)C2=CC=CC=C213145.0Standard non polar33892256
(+)-Calycanthine,2TMS,isomer #1CN1CCC23C4=CC=CC=C4N([Si](C)(C)C)C1C21CCN(C)C3N([Si](C)(C)C)C2=CC=CC=C212933.0Semi standard non polar33892256
(+)-Calycanthine,2TMS,isomer #1CN1CCC23C4=CC=CC=C4N([Si](C)(C)C)C1C21CCN(C)C3N([Si](C)(C)C)C2=CC=CC=C213013.9Standard non polar33892256
(+)-Calycanthine,1TBDMS,isomer #1CN1CCC23C4=CC=CC=C4NC1C21CCN(C)C3N([Si](C)(C)C(C)(C)C)C2=CC=CC=C213175.9Semi standard non polar33892256
(+)-Calycanthine,1TBDMS,isomer #1CN1CCC23C4=CC=CC=C4NC1C21CCN(C)C3N([Si](C)(C)C(C)(C)C)C2=CC=CC=C213514.9Standard non polar33892256
(+)-Calycanthine,2TBDMS,isomer #1CN1CCC23C4=CC=CC=C4N([Si](C)(C)C(C)(C)C)C1C21CCN(C)C3N([Si](C)(C)C(C)(C)C)C2=CC=CC=C213315.6Semi standard non polar33892256
(+)-Calycanthine,2TBDMS,isomer #1CN1CCC23C4=CC=CC=C4N([Si](C)(C)C(C)(C)C)C1C21CCN(C)C3N([Si](C)(C)C(C)(C)C)C2=CC=CC=C213637.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Calycanthine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001s-0059000000-61886ab02401e72884bb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Calycanthine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-Calycanthine LC-ESI-qTof , Positive-QTOFsplash10-03di-0942100000-1ad329a52b02cd758c4e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-Calycanthine , positive-QTOFsplash10-008c-0981000000-04efdcee7a71719b9c4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-Calycanthine 6V, Positive-QTOFsplash10-0002-0479000000-a6439abec973403fdceb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-Calycanthine 6V, Positive-QTOFsplash10-0002-0469000000-efa6c307a636055178fc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 10V, Positive-QTOFsplash10-0002-0009000000-178c45fa30b5ed9f81b22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 20V, Positive-QTOFsplash10-0002-0009000000-a652df12fd59a565ae0a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 40V, Positive-QTOFsplash10-0f79-3094000000-347f18c27fa532cb36f32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 10V, Negative-QTOFsplash10-0002-0009000000-4fb8dca670aa9a67846b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 20V, Negative-QTOFsplash10-0002-1009000000-5cabbd0f8a7bccd6f2092015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 40V, Negative-QTOFsplash10-00p0-1059000000-e40b92e4cc6c670f550b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 10V, Positive-QTOFsplash10-0002-0009000000-37c95b847a9e45a225892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 20V, Positive-QTOFsplash10-0002-0009000000-37c95b847a9e45a225892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 40V, Positive-QTOFsplash10-0006-0092000000-b79d70f700d16f3fcfd32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 10V, Negative-QTOFsplash10-0002-0009000000-a5ed12fd7e24b3ac19f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 20V, Negative-QTOFsplash10-0002-0009000000-a5ed12fd7e24b3ac19f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Calycanthine 40V, Negative-QTOFsplash10-0f6t-0019000000-403fce3ed9ac9812dcbc2021-09-25Wishart 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 IDFDB000715
KNApSAcK IDC00002318
Chemspider ID232050
KEGG Compound IDC10573
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound264115
PDB IDNot Available
ChEBI ID95133
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. 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. [PubMed:7595588 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .