Lasiocarpine (CHEM003038)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:03:36 UTC
Update Date2026-04-05 10:23:51 UTC
Accession NumberCHEM003038
Identification
Common NameLasiocarpine
ClassSmall Molecule
DescriptionLasiocarpine is a pyrrolizidine alkaloid that is found in the seeds of Heliotropium lasiocarpum, Heliotropium europaeum, and several other plant species, all members of the family Boraginaceae. Lasiocarpine is carcinogenic and leads to hepatocellular tumors and hematopoietic tumors in rats.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 2B
  • T3DB toxins
Contaminant Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Lasiocarpine sulfate, (1S-(1alpha(Z),7(2S*,3R*),7aalpha))-isomerMeSH
Lasiocarpine hydrochloride, (1S-(1alpha(Z),7(2S*,3R*),7aalpha))-isomerMeSH
Chemical FormulaC21H33NO7
Average Molecular Mass411.489 g/mol
Monoisotopic Mass411.226 g/mol
CAS Registry Number303-34-4
IUPAC Name(1S,7aR)-7-({[(2S)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate
Traditional Name(1S,7aR)-7-({[(2S)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoate
SMILES[H]\C(C)=C(/C)C(=O)O[C@@]1([H])CCN2CC=C(COC(=O)[C@](O)([C@]([H])(C)OC)C(C)(C)O)[C@]12[H]
InChI IdentifierInChI=1S/C21H33NO7/c1-7-13(2)18(23)29-16-9-11-22-10-8-15(17(16)22)12-28-19(24)21(26,14(3)27-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7-/t14-,16-,17+,21+/m0/s1
InChI KeyQHOZSLCIKHUPSU-PNFBIMPKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Pyrrolizine
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • N-alkylpyrrolidine
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Pyrrolidine
  • Tertiary alcohol
  • Pyrroline
  • Amino acid or derivatives
  • Carboxylic acid ester
  • 1,2-diol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Organoheterocyclic compound
  • Ether
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Microsome
  • Peroxisome
Biofluid LocationsNot Available
Tissue Locations
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Rna polymeraseNot Availablemap03020
Cell cycleNot Availablemap04110
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 Solubility1.39 g/LALOGPS
logP1.95ALOGPS
logP1.33ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.54ChemAxon
pKa (Strongest Basic)7.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.13 m³·mol⁻¹ChemAxon
Polarizability43.35 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-03di-5669600000-8dc53d41a71bd0a11d35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9422000000-a2fdff0d399db753ec68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9400000000-9fd967dcd80dc852a474Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gvt-4914300000-82d2984b4a8f2d78e203Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-7957100000-81ccafaf05d6f2ad5709Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-5900000000-0efd2526369fff81035dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityLasiocarpine is toxic to liver cells but not to lung cells, which is unable to metabolize the pyrrolizidine alkaloids to pyrroles. The application of lasiocarpine to human liver cells in culture is followed by inhibition of DNA, RNA and protein synthesis; vacuolation of the cells, the prevention of mitosis and the formation of giant cells (“megalocytes”). (1) Effects on the liver include hemorrhagic necrosis of parenchymal cells, marked enlargement of parenchymal cells and of their nuclei and nucleoli, fibrosis or cirrhosis, depression of cell division, and possibly neoplasia. (2) The inducibility of tryptophan pyrrolase activity by hydrocortisone, in the livers of rats treated chronically with lasiocarpine is an indication that translational mechanisms are intact. However, the increased uptake of 3H-thymidine by megalocytes, in the absence of observable mitotic activity, suggests that these cells are in the process of hypertrophy. They may act as prolonged, potent inhibitors of mitosis in hepatocytes, they are mutagenic in Drosophila and cause chromosome breakage in leukocytes. One of the unusual results of chronic poisoning by lasiocarpine and other members of the pyrrolizidine alkaloids is progressive enlargement of liver cells to up to three times the normal diameter, with an accompanying proportionate increase in nuclear diameter. The term megalocytosis has been applied to this abnormality which may be associated with mild fibrosis of central veins and proliferation of bile ducts. The prominence of rough ER in enlarged hepatocytes is s a sign of increased metabolic activity. (3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesLasiocarpine is a pyrrolizidine alkaloid that is found in the seeds of Heliotropium lasiocarpum, Heliotropium europaeum, and several other plant species, all members of the family Boraginaceae.
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 LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6321388
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available