Veratramine (T3D4084)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:04:53 UTC
Update Date2014-12-24 20:26:38 UTC
Accession NumberT3D4084
Identification
Common NameVeratramine
ClassSmall Molecule
DescriptionVeratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum.
Compound Type
  • Amine
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
(3beta,23beta)-14,15,16,17-Tetradehydroveratraman-3,23-diol
Chemical FormulaC27H39NO2
Average Molecular Mass409.604 g/mol
Monoisotopic Mass409.298 g/mol
CAS Registry Number60-70-8
IUPAC Name(2S,3R,5S)-2-[(1S)-1-[(1S,2R,5S,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-7,11(16),12,14-tetraen-14-yl]ethyl]-5-methylpiperidin-3-ol
Traditional Nameveratramine
SMILES[H][C@](C)(C1=C(C)C2=C(C=C1)[C@]1([H])CC=C3C[C@@]([H])(O)CC[C@]3(C)[C@@]1([H])C2)[C@]1([H])NC[C@@]([H])(C)C[C@@]1([H])O
InChI IdentifierInChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1
InChI KeyInChIKey=MALFODICFSIXPO-KFKQDBFTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassFluorenes
Sub ClassNot Available
Direct ParentFluorenes
Alternative Parents
Substituents
  • Fluorene
  • Indane
  • Aralkylamine
  • Piperidine
  • Cyclic alcohol
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • 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 Solubility0.0008 g/LALOGPS
logP4.57ALOGPS
logP4.41ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)14.57ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity124.09 m³·mol⁻¹ChemAxon
Polarizability49.66 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0006-0009200000-ec5dca7319fd201804922016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-1009000000-6e277f23d48e4caef0892016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2397000000-9702c3c9564aafaa86842016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0004900000-386171edb4cefa097aca2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-5219500000-844961e46c4ea9d3d3542016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dm-9201000000-d82d38207055f9bd67292016-08-04View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityVeratramine produces a characteristic excitatory action on the central nervous system, producing both tremor and a characteristic "struggling" behavior. This behavioral excitation is accompanied by changes in serotonin content in hypothalamus. The central serotonin agonist methysergide in doses of 5--15 mg per kg produces a dose-dependent inhibition of veratramine's action, while parachlorophenylalanine has no effect. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesVeratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum.
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 ID6070
ChEMBL IDCHEMBL464724
ChemSpider ID5845
KEGG IDC10829
UniProt IDNot Available
OMIM ID
ChEBI IDCHEBI:9951
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. Izumi K, Butterworth RF, Tunnicliff G, Gonce M, Barbeau A: Possible serotonin-agonist action of veratramine. Brain Res Bull. 1978 May-Jun;3(3):237-10. [213177 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available