Echimidine (CHEM003037)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:03:27 UTC
Update Date2026-05-20 18:28:01 UTC
Accession NumberCHEM003037
Identification
Common NameEchimidine
ClassSmall Molecule
DescriptionEchimidine is a major hepatotoxic dehydropyrrolizidine alkaloid toxin produced by Echium plantagineum. It can be detected in honey produced by bees foraging on Echium plantagineum
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-Angelyl-9-echimidinylretronecineKegg
(1R,7AR)-7-({[(2R)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC20H31NO7
Average Molecular Mass397.463 g/mol
Monoisotopic Mass397.210 g/mol
CAS Registry Number520-68-3
IUPAC NameNot Available
Traditional Nameechimidine
SMILES[H]\C(C)=C(/C)C(=O)O[C@]1([H])CCN2CC=C(COC(=O)[C@@](O)([C@]([H])(C)O)C(C)(C)O)[C@]12[H]
InChI IdentifierInChI=1S/C20H31NO7/c1-6-12(2)17(23)28-15-8-10-21-9-7-14(16(15)21)11-27-18(24)20(26,13(3)22)19(4,5)25/h6-7,13,15-16,22,25-26H,8-11H2,1-5H3/b12-6-/t13-,15+,16+,20-/m0/s1
InChI KeyHRSGCYGUWHGOPY-LYHHMGRNSA-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
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • N-alkylpyrrolidine
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Pyrrolidine
  • Pyrroline
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Amine
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen 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 Solubility2.24 g/LALOGPS
logP0.98ALOGPS
logP0.68ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.55ChemAxon
pKa (Strongest Basic)7.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.53 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity103.38 m³·mol⁻¹ChemAxon
Polarizability41.66 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, Positivesplash10-000t-3469000000-2a942cbf62285dae7a32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gi-9661000000-eff7e94f3c54b459689aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06si-9700000000-50859f76237646135f8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001s-3918000000-f25593039e484dd85d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-5968000000-c8d07fb75db71d3a811cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-fcb19756d734f41d92cdSpectrum
MSMass Spectrum (Electron Ionization)splash10-00dl-9740000000-9beac8e8a27e12816531Spectrum
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/SourcesEchimidine is a major hepatotoxic dehydropyrrolizidine alkaloid toxin produced by Echium plantagineum. It can be detected in honey produced by bees foraging on Echium plantagineum.
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 IDC00002085
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5281729
Kegg Compound IDC10299
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available