C-Curarine (T3D4068)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:02:02 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4068
Identification
Common NameC-Curarine
ClassSmall Molecule
DescriptionC-Curarine is a Curare alkaloid that is structurally similar to D-tubocurarine. Curare is a non-depolarizing muscle relaxant that blocks the nicotinic acetylcholine receptor (nAChR), one of the two types of acetylcholine (ACh) receptors, at the neuromuscular junction. The main toxin of curare, D-tubocurarine, occupies the same position on the receptor as ACh with an equal or greater affinity making it a competitive antagonist.
Compound Type
  • Amine
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
C-Curarine I
Chemical FormulaC40H44N4O
Average Molecular Mass596.803 g/mol
Monoisotopic Mass596.350 g/mol
CAS Registry Number7168-64-1
IUPAC Name(30Z,38Z)-30,38-diethylidene-16,32-dimethyl-10-oxa-8,16,26,32-tetraazadodecacyclo[27.5.2.2¹³,¹⁶.1⁸,¹².0¹,⁹.0²,⁷.0⁹,²⁸.0¹¹,¹⁹.0¹¹,²⁶.0¹⁵,¹⁹.0²⁰,²⁵.0³²,³⁵]nonatriaconta-2,4,6,12(39),20,22,24,27-octaene-16,32-diium
Traditional Name(30Z,38Z)-30,38-diethylidene-16,32-dimethyl-10-oxa-8,16,26,32-tetraazadodecacyclo[27.5.2.2¹³,¹⁶.1⁸,¹².0¹,⁹.0²,⁷.0⁹,²⁸.0¹¹,¹⁹.0¹¹,²⁶.0¹⁵,¹⁹.0²⁰,²⁵.0³²,³⁵]nonatriaconta-2,4,6,12(39),20,22,24,27-octaene-16,32-diium
SMILES[H]\C(C)=C1\C[N+]2(C)CCC34C2CC1C1=CN2C5=CC=CC=C5C56CC[N+]7(C)C\C(=C(\[H])C)C(CC57)C5=CN(C7=CC=CC=C37)C41OC265
InChI IdentifierInChI=1/C40H44N4O/c1-5-25-23-43(3)17-15-37-29-11-7-10-14-34(29)42-22-32-28-20-36-38(16-18-44(36,4)24-26(28)6-2)30-12-8-9-13-33(30)41-21-31(27(25)19-35(37)43)39(37,42)45-40(32,38)41/h5-14,21-22,27-28,35-36H,15-20,23-24H2,1-4H3/q+2/b25-5+,26-6+
InChI KeyInChIKey=DWELRYDMYVJVSL-GQBJSJAWNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassStrychnos alkaloids
Sub ClassNot Available
Direct ParentStrychnos alkaloids
Alternative Parents
Substituents
  • Strychnan skeleton
  • Akuammicine-skeleton
  • Stemmadenine-skeleton
  • Curan skeleton
  • Carbazole
  • Indolizidine
  • Indole or derivatives
  • Aralkylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Piperidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Pyrrolidine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Enamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Plasma 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 PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00018 g/LALOGPS
logP2.11ALOGPS
logP-2.4ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.71 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity204.19 m³·mol⁻¹ChemAxon
Polarizability68.75 ųChemAxon
Number of Rings12ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityIt has been prpoposed that surarine speeds up destruction of chemical transmitter, and raises the threshold point at which excess of the transmitter is able to exert its depressant power. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThe main toxin of curare, D-tubocurarine, occupies the same position on the receptor as ACh with an equal or greater affinity making it a competitive antagonist.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6391813
ChEMBL IDNot Available
ChemSpider ID16735754
KEGG IDC09144
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
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. Briscoe G: The antagonism between curarine and acetylcholine. J Physiol. 1936 Sep 8;87(4):425-8. [16994803 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available