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Record Information
Version2.0
Creation Date2014-08-29 05:00:13 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4061
Identification
Common NameVeratridine
ClassSmall Molecule
DescriptionVeratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by activating sodium ion channels. It is primarily obtained from the herb Veratrum and sabadilla seeds. It binds to intramembrane receptor site 2 and increases intracellular Ca2+ concentration. It acts by preferentially binding to activated Na+ channels causing persistent activation that leads to increased nerve excitability.
Compound Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(3•_,4alpha-,16•_)-4,12,14,16,17,20-hexahydroxy-4,9-epoxycevan-3-yl 3,4-dimethoxybenzoate
Chemical FormulaC36H51NO11
Average Molecular Mass673.790 g/mol
Monoisotopic Mass673.346 g/mol
CAS Registry Number71-62-5
IUPAC Name(1R,10R,11S,12S,14R,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 3,4-dimethoxybenzoate
Traditional Name(1R,10R,11S,12S,14R,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 3,4-dimethoxybenzoate
SMILES[H]C12CCC3([H])[C@]4(O)C[C@]([H])(O)[C@@]5(O)C([H])(CN6CC([H])(C)CCC6([H])[C@@]5(C)O)[C@]4(O)C[C@@]33O[C@]1(O)C([H])(CCC23C)OC(=O)C1=CC(OC)=C(OC)C=C1
InChI IdentifierInChI=1S/C36H51NO11/c1-19-6-11-26-31(3,40)35(43)25(17-37(26)16-19)33(42)18-34-24(32(33,41)15-27(35)38)10-9-23-30(34,2)13-12-28(36(23,44)48-34)47-29(39)20-7-8-21(45-4)22(14-20)46-5/h7-8,14,19,23-28,38,40-44H,6,9-13,15-18H2,1-5H3/t19?,23?,24?,25?,26?,27-,28?,30?,31+,32+,33+,34+,35-,36-/m0/s1
InChI KeyInChIKey=FVECELJHCSPHKY-UIHGVQCZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal alkaloids
Direct ParentCerveratrum-type alkaloids
Alternative Parents
Substituents
  • Cerveratrum-type alkaloid
  • Azasteroid
  • M-methoxybenzoic acid or derivatives
  • P-methoxybenzoic acid or derivatives
  • Benzoate ester
  • Quinolizidine
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Benzoic acid or derivatives
  • Alkaloid or derivatives
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Oxepane
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Monocyclic benzene moiety
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Tertiary amine
  • Secondary alcohol
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Hemiacetal
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Alcohol
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Cytoplasm
  • Cytosol
  • Endoplasmic reticulum
  • Endosome
  • Extracellular
  • Extracellular matrix
  • Lysosome
  • Membrane Fraction
  • Microtubule
  • Mitochondrial Matrix
  • Mitochondrial Membrane
  • Mitochondrion
  • Nerve Fiber
  • Perinuclear region
  • Plasma Membrane
  • Sarcoplasmic Reticulum
  • Secretory Granule
  • Secretory vesicle
  • Synaptic Vesicle
  • Tubulin
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Oxidative phosphorylationNot Availablemap00190
Insulin secretionNot Availablemap04911
Vascular smooth muscle contractionNot Availablemap04270
AnticonvulsantsNot AvailableNot Available
Cell cycleNot Availablemap04110
Pancreatic secretionNot Availablemap04972
PhenothiazinesNot AvailableNot Available
Long-term potentiationNot Availablemap04720
Antiarrhythmic DrugsNot AvailableNot Available
Fatty acid MetabolismSMP00051 map00071
EndocytosisNot Availablemap04144
EicosanoidsNot AvailableNot Available
ApplicationsNot Available
Biological Roles
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 Solubility1.16 g/LALOGPS
logP0.87ALOGPS
logP0.83ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.88ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area178.61 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity170.51 m³·mol⁻¹ChemAxon
Polarizability72.28 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000209000-3237a2bdd832d24442002016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0101109000-c5201e08ab9ba9b0ef482016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dm-5600619000-a48eade657a0b301a9ea2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0200009000-f87b37a1ff8901bf13662016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-0900116000-37885115e65f1290eac82016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-3056855f4ba192868e8d2016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityVeratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by abolishing inactivation of sodium ion channels. It binds to intramembrane receptor site 2 and increases intracellular Ca2+ concentration. It acts by preferentially binding to activated Na+ channels causing persistent activation that leads to increased nerve excitability. (Wikipedia) The activation of the action potential Na+ ionophore by veratridine is time- and concentrationdependent and completely reversible. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesVeratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by activating sodium ion channels.
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 ID441081
ChEMBL IDNot Available
ChemSpider ID5290571
KEGG IDC06544
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
MSDST3D4061.pdf
General References
  1. Catterall WA: Activation of the action potential Na+ ionophore of cultured neuroblastoma cells by veratridine and batrachotoxin. J Biol Chem. 1975 Jun 10;250(11):4053-9. [1168643 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available