(-)-Chimonanthine (CHEM024305)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:37:21 UTC
Update Date2016-11-09 01:17:52 UTC
Accession NumberCHEM024305
Identification
Common Name(-)-Chimonanthine
ClassSmall Molecule
DescriptionA ring assembly that is 2,2',3,3',8,8',8a,8a'-octahydro-1H,1'H-3a,3a'-bipyrrolo[2,3-b]indole substituted by methyl groups at positions 1 and 1'.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Demethyl-calycanthidineHMDB
1-DemethylcalycanthidineHMDB
ChimonanthinHMDB
ChimonanthineHMDB
L-ChimonanthineHMDB
Chemical FormulaC22H26N4
Average Molecular Mass346.469 g/mol
Monoisotopic Mass346.216 g/mol
CAS Registry Number5545-89-1
IUPAC Name1-methyl-3a-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole
Traditional Namechimonanthine
SMILESCN1CCC2(C1NC1=C2C=CC=C1)C12CCN(C)C1NC1=C2C=CC=C1
InChI IdentifierInChI=1S/C22H26N4/c1-25-13-11-21(15-7-3-5-9-17(15)23-19(21)25)22-12-14-26(2)20(22)24-18-10-6-4-8-16(18)22/h3-10,19-20,23-24H,11-14H2,1-2H3
InChI KeyHOYXPMHLHJOGHD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Indole
  • Dihydroindole
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrole
  • Pyrrolidine
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.51ALOGPS
logP2.85ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.86ChemAxon
pKa (Strongest Basic)7.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area30.54 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity107.91 m³·mol⁻¹ChemAxon
Polarizability38.58 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fz9-0839000000-e6dc51fe7686225cb76eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-ede6dda140966de044baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1009000000-5fc4e48dea2309927723Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-6094000000-72a46e04248bd284193cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0209000000-f04b1a47b3ee880c297dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1109000000-036750f7127d1ff0f027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-2934000000-45e537f8de9ae517804dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-37c95b847a9e45a22589Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0019000000-5f6508ee1c8e805d7483Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdx-2695000000-2bc392ec5723c1849154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-a5ed12fd7e24b3ac19f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-a5ed12fd7e24b3ac19f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0902000000-eaebb7fc5a7a7f5c48bfSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030280
FooDB IDFDB002115
Phenol Explorer IDNot Available
KNApSAcK IDC00026840
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID520787
ChEBI ID38955
PubChem Compound ID599086
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.