Protoveratrine B (CHEM003082)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:21:21 UTC
Update Date2026-05-20 20:07:36 UTC
Accession NumberCHEM003082
Identification
Common NameProtoveratrine B
ClassSmall Molecule
DescriptionProtoveratrine B is a tetraester of the alkamine protoverine obtained from hellebores of the genus Veratrum (especially V. viride of North America and V. album of Europe) and used in the treatment of hypertension, along with protoveratrine A (1).
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Ester
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-Bis(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-{[(2R)-2-methylbutanoyl]oxy}-24-oxa-4-azaheptacyclo[12.12.0.0,.0,.0,.0,.0,]hexacosan-22-yl (2S,3R)-2,3-dihydroxy-2-methylbutanoic acidGenerator
(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-Bis(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-{[(2R)-2-methylbutanoyl]oxy}-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl (2S,3R)-2,3-dihydroxy-2-methylbutanoic acidGenerator
Chemical FormulaC41H63NO15
Average Molecular Mass809.937 g/mol
Monoisotopic Mass809.420 g/mol
CAS Registry Number124-97-0
IUPAC NameNot Available
Traditional Nameprotoveratrine B
SMILES[H][C@](C)(O)[C@](C)(O)C(=O)O[C@@]1([H])CC[C@@]2(C)[C@]3([H])[C@@]([H])(OC(C)=O)[C@@]([H])(OC(C)=O)[C@@]4([H])[C@@]5(O)[C@@]([H])(C[C@]24O[C@]13O)[C@]1([H])CN2C[C@@]([H])(C)CC[C@@]2([H])[C@@](C)(O)[C@@]1([H])[C@@]([H])(O)[C@]5([H])OC(=O)[C@]([H])(C)CC
InChI IdentifierInChI=1S/C41H63NO15/c1-10-19(3)34(47)56-33-28(46)27-23(17-42-16-18(2)11-12-25(42)38(27,9)50)24-15-39-32(40(24,33)51)30(54-22(6)45)29(53-21(5)44)31-36(39,7)14-13-26(41(31,52)57-39)55-35(48)37(8,49)20(4)43/h18-20,23-33,43,46,49-52H,10-17H2,1-9H3/t18-,19+,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37-,38+,39+,40-,41+/m0/s1
InChI KeyBFLXOMFFVWQPAZ-WLZWUCNJSA-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
  • Tetracarboxylic acid or derivatives
  • Quinolizidine
  • Alkaloid or derivatives
  • Oxepane
  • Fatty acid ester
  • Piperidine
  • Fatty acyl
  • Tertiary alcohol
  • Cyclic alcohol
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Tertiary amine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Hemiacetal
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
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
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP1.76ALOGPS
logP0.69ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.75ChemAxon
pKa (Strongest Basic)7.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area239.05 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity196.26 m³·mol⁻¹ChemAxon
Polarizability85.51 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0hg6-1000002910-80749808f5ead2d53625Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4r-4000000900-af867ff44f3fe579ca6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pys-9200016100-889e2843429d12e6edc4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ap4-4100002920-98435f9fb71898be8c7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-9300004700-563b6791e87cf70c8affSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-9300001000-dd21bb94c1954fec9f8aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesProtoveratrine B is a tetraester of the alkamine protoverine obtained from hellebores of the genus Veratrum (especially V. viride of North America and V. album of Europe) and used in the treatment of hypertension, along with protoveratrine A (1).
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 IDC00002257
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID442981
Kegg Compound IDC10816
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available