Lasiocarpine (T3D4078)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 05:03:36 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4078
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.
Compound Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(-)-Lasiocarpine
7-Angelyl-9-lasiocarpylheliotridine
7-Angelyleuropine
Europine 7-angelate
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 KeyInChIKey=QHOZSLCIKHUPSU-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
LogPNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5669600000-8dc53d41a71bd0a11d352016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9422000000-a2fdff0d399db753ec682016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9400000000-9fd967dcd80dc852a4742016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gvt-4914300000-82d2984b4a8f2d78e2032016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-7957100000-81ccafaf05d6f2ad57092016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-5900000000-0efd2526369fff81035d2016-08-03View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6321388
ChEMBL IDNot Available
ChemSpider ID4884873
KEGG IDC10341
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
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. Armstrong SJ, Zuckerman AJ: The effects of lasiocarpine, retrorsine and retronecine pyrrole on human embryo lung and liver cells in culture. Br J Exp Pathol. 1972 Apr;53(2):138-44. [5032089 ]
  2. Rogers AE, Newberne PM: Lasiocarpine: factors influencing its toxicity and effects on liver cell division. Toxicol Appl Pharmacol. 1971 Feb;18(2):356-66. [4105574 ]
  3. Svoboda D, Reddy J, Bunyaratvej S: Hepatic megalocytosis in chronic lasiocarpine poisoning. Some functional studies. Am J Pathol. 1971 Nov;65(2):399-409. [5134890 ]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available