Jervine (CHEM003043)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-08-29 05:04:40 UTC
Update Date2026-03-31 17:48:22 UTC
Accession NumberCHEM003043
Identification
Common NameJervine
ClassSmall Molecule
DescriptionJervine is a steroidal alkaloid with molecular formula C27H39NO3 which is derived from the Veratrum plant genus. Similar to cyclopamine, which also occurs in the Veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Jervine, acetate, (3beta,23beta)-isomerMeSH
Chemical FormulaC27H39NO3
Average Molecular Mass425.604 g/mol
Monoisotopic Mass425.293 g/mol
CAS Registry Number469-59-0
IUPAC Name(1'S,2R,2'R,3R,3aS,5'S,6S,7aR,10'S,11'S)-5'-hydroxy-2',3,6,15'-tetramethyl-3a,4,5,6,7,7a-hexahydro-3H-spiro[furo[3,2-b]pyridine-2,14'-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadecane]-7',15'-dien-17'-one
Traditional Namejervine
SMILES[H][C@@]12C[C@]([H])(C)CN[C@@]1([H])[C@@]([H])(C)[C@@]1(CC[C@]3([H])C(C(=O)[C@@]4([H])[C@@]3([H])CC=C3C[C@@]([H])(O)CC[C@]43C)=C1C)O2
InChI IdentifierInChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1
InChI KeyCLEXYFLHGFJONT-DNMILWOZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as jerveratrum-type alkaloids. These are steroidal alkaloids with a structure that is based on the jervane ring system. Jerveratrum alkaloids have alkamines with 1-3 oxygen atoms, and occur as such or as monoglycosides.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal alkaloids
Direct ParentJerveratrum-type alkaloids
Alternative Parents
Substituents
  • Jerveratrum-type alkaloid
  • Azasteroid
  • Alkaloid or derivatives
  • Piperidine
  • Cyclic alcohol
  • Tetrahydrofuran
  • Ketone
  • Secondary alcohol
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Oxacycle
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular matrix
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
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 Solubility0.0063 g/LALOGPS
logP3.43ALOGPS
logP3.39ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity122.89 m³·mol⁻¹ChemAxon
Polarizability51.03 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0001900000-c6cd0e861335854cc21bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-3569600000-9f93284c65706877006eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-a471f5794d2332789cd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001900000-b3d40c10be62db944896Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0101900000-0d5d5c88891f8215ce04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v4j-9414100000-19933bc2b637e92427cfSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityJervine's biological activity is mediated via its interaction with the 7 pass trans membrane protein smoothened. Jervine binds with and inhibits smoothened, which is an integral part of the hedgehog signaling pathways. With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed. (Wikipedia) It is now known that the teratogenic effects of jervine and cyclopamine are due to their specific inhibition of vertebrate cellular responses to the Hedgehog (Hh) family of secreted growth factors. (1) In cultures with cyclopamine, jervine, or blocking antibody, fungiform papilla numbers doubled on the dorsal tongue with a distribution that essentially eliminated inter-papilla regions, compared with tongues in standard medium or solanidine. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesJervine is a steroidal alkaloid with molecular formula C27H39NO3 which is derived from the Veratrum plant genus.
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 IDC00002253
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkJervine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID10098
Kegg Compound IDC10811
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available