Hypoglycin B (T3D4025)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 04:49:24 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4025
Identification
Common NameHypoglycin B
ClassSmall Molecule
DescriptionHypoglycin B is a naturally occurring organic compound in the species Blighia sapida. It is particularly concentrated in the fruit of the plant especially in the seeds. Hypoglycin B is toxic if ingested and is a causative agent of Jamaican Vomiting Sickness. It is an amino acid and chemically related to lysine.
Compound Type
  • Amine
  • Food Toxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Hypoglycin b
Hypoglycine b
L-gamma-Glutamyl-L-hypoglycin
Chemical FormulaC12H18N2O5
Average Molecular Mass270.282 g/mol
Monoisotopic Mass270.122 g/mol
CAS Registry Number502-37-4
IUPAC Name(2S)-2-amino-4-{[(1S)-1-carboxy-2-[(1S)-2-methylidenecyclopropyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional Namehypoglycin B
SMILES[H][C@](N)(CCC(O)=N[C@@]([H])(C[C@]1([H])CC1=C)C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C12H18N2O5/c1-6-4-7(6)5-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h7-9H,1-5,13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-,9-/m0/s1
InChI KeyInChIKey=UYDZYCPIQSRXKU-CIUDSAMLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Alpha-amino acid
  • Carbocyclic fatty acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • N-acyl-amine
  • Fatty amide
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Mitochondrion
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolic PathwaysNot AvailableNot 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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP-2.7ALOGPS
logP-2.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity65.3 m³·mol⁻¹ChemAxon
Polarizability27.05 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-002f-2590000000-4a0778ebb6b64f6fa30a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-6940000000-ea2af9afb3dc58b10c172016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9300000000-30fc900f8671bb64f6352016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-2a07eedc109c9eaaf2fe2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05r0-2790000000-71922247b2d83ee1fe292016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9400000000-598fe281aab1c216971e2016-08-03View Spectrum
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.
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID441445
ChEMBL IDNot Available
ChemSpider ID390178
KEGG IDC08280
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkHypoglycin B
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available