Veratrine (CHEM042897)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 10:24:18 UTC
Update Date2016-11-09 01:22:49 UTC
Accession NumberCHEM042897
Identification
Common NameVeratrine
ClassSmall Molecule
DescriptionVeratridine is a steroidal alkaloid found in plants of the lily family, specifically the genera Veratrum and Schoenocaulon. Upon absorption through the skin or mucous membranes, it acts as a neurotoxin by binding to and preventing the inactivation of voltage-gated sodium ion channels in heart, nerve, and skeletal muscle cell membranes. Veratridine increases nerve excitability and intracellular Ca2+ concentrations.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
CevadineMeSH
VeratrineMeSH
(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,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 (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC32H49NO9
Average Molecular Mass591.742 g/mol
Monoisotopic Mass591.341 g/mol
CAS Registry Number62-59-9
IUPAC Name(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-22-yl (2Z)-2-methylbut-2-enoate
Traditional Name(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-22-yl (2Z)-2-methylbut-2-enoate
SMILES[H]\C(C)=C(/C)C(=O)O[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])[C@]5(O)C[C@]([H])(O)[C@@]6(O)[C@@]([H])(CN7C[C@@]([H])(C)CC[C@@]7([H])[C@@]6(C)O)[C@]5(O)C[C@]24O[C@]13O
InChI IdentifierInChI=1S/C32H49NO9/c1-6-18(3)25(35)41-24-11-12-26(4)19-8-9-20-28(37)13-23(34)31(39)21(29(28,38)16-30(20,26)42-32(19,24)40)15-33-14-17(2)7-10-22(33)27(31,5)36/h6,17,19-24,34,36-40H,7-16H2,1-5H3/b18-6-/t17-,19-,20-,21-,22-,23-,24-,26-,27+,28+,29+,30+,31-,32-/m0/s1
InChI KeyDBUCFOVFALNEOO-HWBIYQLFSA-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
  • Quinolizidine
  • Alkaloid or derivatives
  • Oxepane
  • Fatty acid ester
  • Piperidine
  • Fatty acyl
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid ester
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility1.78 g/LALOGPS
logP1.04ALOGPS
logP0.86ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.88ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area160.15 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity151.59 m³·mol⁻¹ChemAxon
Polarizability64.04 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2000290000-1daeee68b69aa4cffd49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05al-9000150000-402d1ab5b8393dcb2920Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9000310000-ecb641a36881388fb137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1000090000-7a7498c3448adb2921ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052e-9110360000-aa5ba6e225f70cfcc532Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9002000000-6bfe44c34e55ccb75889Spectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVeratridine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5380394
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available