Protoveratrine A (CHEM003081)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:20:51 UTC
Update Date2026-05-20 20:12:38 UTC
Accession NumberCHEM003081
Identification
Common NameProtoveratrine A
ClassSmall Molecule
DescriptionProtoveratrine A 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 B (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)-2-hydroxy-2-methylbutanoic acidGenerator
PROTALBAChEMBL, MeSH
CryptenamineMeSH
NeoprotoveratrinMeSH
ProtoveratrinesMeSH
ProtoverinMeSH
TensatrinMeSH
VeralbaMeSH
VeratetrinMeSH
(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)-2-hydroxy-2-methylbutanoic acidGenerator
Chemical FormulaC41H63NO14
Average Molecular Mass793.937 g/mol
Monoisotopic Mass793.425 g/mol
CAS Registry Number143-57-7
IUPAC NameNot Available
Traditional Nameprotoveratrine
SMILES[H][C@@](C)(CC)C(=O)O[C@@]1([H])[C@]([H])(O)[C@@]2([H])[C@@]([H])(CN3C[C@@]([H])(C)CC[C@@]3([H])[C@@]2(C)O)[C@]2([H])C[C@@]34O[C@@]5(O)[C@@]([H])([C@@]([H])(OC(C)=O)[C@@]([H])(OC(C)=O)[C@@]3([H])[C@]12O)[C@]4(C)CC[C@]5([H])OC(=O)[C@@](C)(O)CC
InChI IdentifierInChI=1S/C41H63NO14/c1-10-20(4)34(46)55-33-28(45)27-23(18-42-17-19(3)12-13-25(42)38(27,9)49)24-16-39-32(40(24,33)50)30(53-22(6)44)29(52-21(5)43)31-36(39,7)15-14-26(41(31,51)56-39)54-35(47)37(8,48)11-2/h19-20,23-33,45,48-51H,10-18H2,1-9H3/t19-,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37-,38+,39+,40-,41+/m0/s1
InChI KeyHYTGGNIMZXFORS-MGYKWWNKSA-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
  • Synaptic Vesicle
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 Solubility0.81 g/LALOGPS
logP2.13ALOGPS
logP1.84ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)10.79ChemAxon
pKa (Strongest Basic)7.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area218.82 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity194.82 m³·mol⁻¹ChemAxon
Polarizability84.59 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, Positivesplash10-0059-2000003900-1a7651616b3d0055054cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0540-5100001900-9a676a39fe5fe95f466dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kar-9100015000-da93716da9e65950020eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fdo-3100002900-e12c82c28e5b1c256ef1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-9400006800-d07d0952263601ae680eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zmi-9400002000-90a869140ae2843e2744Spectrum
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 A 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 B (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 IDC00002256
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC10815
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available