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Record Information
Version1.0
Created at2019-05-20 17:30:31 UTC
Updated at2020-09-02 17:33:11 UTC
NP-MRD IDNP0000001
Secondary Accession NumbersNone
Natural Product Identification
Common NameStrychnine
DescriptionStrychnine 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. A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position. Strychnine is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
StrychninChEBI
Strychnine nitrateMeSH
Nitrate, strychnineMeSH
(-)-StrychnineNP-MRD
StrychnineNP-MRD
Chemical FormulaC21H22N2O2
Average Molecular Weight334.4116
Monoisotopic Molecular Weight334.168127958
IUPAC Name(1R,11S,18S,20R,21R,22S)-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one
Traditional Name(1R,11S,18S,20R,21R,22S)-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one
CAS Registry Number57-24-9
SMILES
[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C7=CC=CC=C7[C@@]1(CCN2C4)[C@]6([H])[C@@]35[H]
InChI Identifier
InChI=1S/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+/m0/s1
InChI KeyQMGVPVSNSZLJIA-FVWCLLPLSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
Species of Origin
Species
Species NameSourceReference
Strychnos nux-vomica L.Seed
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
  • Carbazole
  • Quinolidine
  • Indole or derivatives
  • Indolizidine
  • Aralkylamine
  • Piperidinone
  • Delta-lactam
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxamide group
  • Amino acid or derivatives
  • Lactam
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • 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
logP1.68ALOGPS
logP0.93ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)17.24ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.51 m³·mol⁻¹ChemAxon
Polarizability35.88 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00025213
Chemspider IDNot Available
KEGG Compound IDC06522
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStrychnine
METLIN IDNot Available
PubChem Compound441071
PDB IDNot Available
ChEBI ID28973
References
General References
  1. Parker AJ, Lee JB, Redman J, Jolliffe L: Strychnine poisoning: gone but not forgotten. Emerg Med J. 2011 Jan;28(1):84. doi: 10.1136/emj.2009.080879. Epub 2010 Sep 1. [PubMed:20810461 ]