L-Hypoglycin A (CHEM002984)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 04:49:23 UTC
Update Date2016-11-09 01:09:01 UTC
Accession NumberCHEM002984
Identification
Common NameL-Hypoglycin A
ClassSmall Molecule
DescriptionHypoglycin is toxic if ingested and is the causative agent of Jamaican vomiting sickness. It is an amino acid and chemically related to lysine.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amine
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Hypoglycin aKegg
Hypoglycine aKegg
L-HypoglycinKegg
Hypoglycin, (S)-isomerMeSH
HypoglycinMeSH
Hypoglycin, carboxy-(14)C-labeledMeSH
Chemical FormulaC7H11NO2
Average Molecular Mass141.168 g/mol
Monoisotopic Mass141.079 g/mol
CAS Registry Number156-56-9
IUPAC Name(2S)-2-amino-3-[(1S)-2-methylidenecyclopropyl]propanoic acid
Traditional Namehypoglycin
SMILES[H][C@](N)(C[C@]1([H])CC1=C)C(O)=O
InChI IdentifierInChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)/t5-,6-/m0/s1
InChI KeyOOJZCXFXPZGUBJ-WDSKDSINSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Carbocyclic fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Insulin secretionNot Availablemap04911
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 Solubility101 g/LALOGPS
logP-2.2ALOGPS
logP-2.1ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)9.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.69 m³·mol⁻¹ChemAxon
Polarizability14.6 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-9700000000-88f654ad511bd615f974Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-a638d182cec2d0f2e025Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-bf3e574de9d48c765285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-0947306f5db224c96483Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-8900000000-f72f90f16257f62431a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-762784d2a97818f41e95Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityGenerally, hypoglycin is an amino acid and chemically related to lysine. It competitively binds to enzymes used in the catabolism of lysine and is the reason why it and its metabolitemethylene cyclopropyl acetic acid (MCPA) are toxic. The metabolite MCPA also is a potent inhibitor of acyl CoA dehydrogenase, preventing the metabolism of fatty acids. It has been shown that oxidation of leucine is inhibited by hypoglycin A. In contrast, oxidation of valine and isoleucine are not significantly inhibited by this compound. However, the specific step in the pathway of leucine metabolism that is inhibited by hypoglycin A has not been precisely identified. Hypoglycemia and depletion of glycogen were due to the decreased gluconeogenesis resulting from impairment of long chain fatty acid metabolism after injection of hypoglycin A. Hypoglycin A or its metabolite, methylenecyclopropylacetic acid, and also 4-pentenoic acid (4-PE) were shown to inhibit long-chain fatty acid oxidation; whereas oxidation of straight short chain fatty acids including butyrate, hexanoate, and octanoate was not inhibited. Hypolglycin A inhibits dehydrogenation of isovaleryl-CoA and alpha-methylbutyryl-CoA by liver slices in vitro, and that it induces isovaleric and alpha-methylbutyric acidemias in experimental animals in vivo. (PMID: 4636318; PMID:5276292)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
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 IDC00001372
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHypoglycin A
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID441451
Kegg Compound IDC08287
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available