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Hypoglycin B (FDB000530)

Record Information
Version1.0
Creation date2010-04-08 22:04:36 UTC
Update date2020-02-24 19:10:09 UTC
Primary IDFDB000530
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHypoglycin B
DescriptionBiologically active component of Blighia sapida (akee apple) Hypoglycin 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. Hypoglycin B is found in many foods, some of which are jew's ear, black elderberry, rye, and root vegetables.
CAS Number502-37-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.1 g/LALOGPS
logP-2.7ALOGPS
logP-3.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity64.78 m³·mol⁻¹ChemAxon
Polarizability26.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H18N2O5
IUPAC name2-amino-4-{[1-carboxy-2-(2-methylidenecyclopropyl)ethyl]carbamoyl}butanoic acid
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)
InChI KeyUYDZYCPIQSRXKU-UHFFFAOYSA-N
Isomeric SMILESNC(CCC(=O)NC(CC1CC1=C)C(O)=O)C(O)=O
Average Molecular Weight270.2817
Monoisotopic Molecular Weight270.121571696
Classification
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
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Carbocyclic fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.33%; H 6.71%; N 10.36%; O 29.60%DFC
Melting PointMp 200-207° (200-204°) (double Mp)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 9.36DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHypoglycin B, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-9230000000-abf9f2628f7c6f3bf4c1Spectrum
Predicted GC-MSHypoglycin B, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0v4l-9114000000-381c08f28fd0085766f5Spectrum
Predicted GC-MSHypoglycin B, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHypoglycin B, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fi0-1390000000-264246a6ebc82408f8af2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056u-6970000000-7e42820d1c0dca3346532017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9200000000-81a366aa1fbda762e1d62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-1477a66ca40d6a5e22122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kxu-2790000000-b364e7c8f259fffd1a102017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9400000000-6aab591feaaac89bc93f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2390000000-514b84378308aa29dab62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-9310000000-6f7ee1b689a75066e0512021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-8bd6d39da96e91345c652021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gbc-1490000000-d146ac33ac4dde2ed7fb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00vl-4950000000-d04166d53bc496aa778d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-fb3a089478f48fb74cb52021-09-24View Spectrum
NMRNot Available
ChemSpider ID97200
ChEMBL IDNot Available
KEGG Compound IDC08280
Pubchem Compound ID108105
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29428
CRC / DFC (Dictionary of Food Compounds) IDBDG91-J:BDG91-J
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001360
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHypoglycin_B
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference