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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:21 UTC
Update Date2022-03-07 02:52:09 UTC
HMDB IDHMDB0029427
Secondary Accession Numbers
  • HMDB29427
Metabolite Identification
Common NameL-Hypoglycin A
DescriptionL-Hypoglycin A belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). L-Hypoglycin A has been detected, but not quantified in, several different foods, such as european plums (Prunus domestica), opium poppies (Papaver somniferum), black crowberries (Empetrum nigrum), sorrels (Rumex acetosa), and alaska wild rhubarbs (Polygonum alpinum). This could make L-hypoglycin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on L-Hypoglycin A.
Structure
Data?1582753416
Synonyms
ValueSource
2-Amino-3-(2-methylenecyclopropyl)propionic acidChEBI
2-Amino-3-(2-methylenecyclopropyl)propionateGenerator
HypoglycinMeSH
Hypoglycin aMeSH
Hypoglycin, (S)-isomerMeSH
Hypoglycin, carboxy-(14)C-labeledMeSH
2-amino-4,5-Methylenehex-5-enoic acidHMDB
2-MethylenecyclopropanealanineHMDB
2-MethylenecyclopropanylalanineHMDB
2-MethyleneL-cyclopropanealanineHMDB
alpha-amino-2-Methylenecyclopropanepropanoic acidHMDB
alpha-amino-2-Methylenecyclopropanepropionic acidHMDB
alpha-amino-beta-(2-Methylenecyclopropyl)propionic acidHMDB
alpha-Aminomethylenecyclopropanepropionic acidHMDB
beta-(Methylenecyclopropyl)alanineHMDB
Hypoglycine aHMDB
L-alpha-amino-beta-Methylenecyclopropanepropionic acidHMDB
L-HypoglycinHMDB
2-Amino-3-(2-methylenecyclopropyl)propanoateGenerator
Chemical FormulaC7H11NO2
Average Molecular Weight141.1677
Monoisotopic Molecular Weight141.078978601
IUPAC Name2-amino-3-(2-methylidenecyclopropyl)propanoic acid
Traditional Namehypoglycine A
CAS Registry Number156-56-9
SMILES
NC(CC1CC1=C)C(O)=O
InChI Identifier
InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)
InChI KeyOOJZCXFXPZGUBJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Carbocyclic fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point280 - 284 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability14.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+131.01431661259
DarkChem[M-H]-125.88731661259
DeepCCS[M+H]+125.30230932474
DeepCCS[M-H]-122.17930932474
DeepCCS[M-2H]-159.05630932474
DeepCCS[M+Na]+133.96330932474
AllCCS[M+H]+132.232859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+136.232859911
AllCCS[M+Na]+137.332859911
AllCCS[M-H]-129.632859911
AllCCS[M+Na-2H]-131.332859911
AllCCS[M+HCOO]-133.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-Hypoglycin ANC(CC1CC1=C)C(O)=O2101.0Standard polar33892256
L-Hypoglycin ANC(CC1CC1=C)C(O)=O1251.8Standard non polar33892256
L-Hypoglycin ANC(CC1CC1=C)C(O)=O1502.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Hypoglycin A,1TMS,isomer #1C=C1CC1CC(N)C(=O)O[Si](C)(C)C1278.9Semi standard non polar33892256
L-Hypoglycin A,1TMS,isomer #2C=C1CC1CC(N[Si](C)(C)C)C(=O)O1377.1Semi standard non polar33892256
L-Hypoglycin A,2TMS,isomer #1C=C1CC1CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1406.9Semi standard non polar33892256
L-Hypoglycin A,2TMS,isomer #1C=C1CC1CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1458.7Standard non polar33892256
L-Hypoglycin A,2TMS,isomer #2C=C1CC1CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1588.4Semi standard non polar33892256
L-Hypoglycin A,2TMS,isomer #2C=C1CC1CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1520.2Standard non polar33892256
L-Hypoglycin A,3TMS,isomer #1C=C1CC1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1612.7Semi standard non polar33892256
L-Hypoglycin A,3TMS,isomer #1C=C1CC1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1594.3Standard non polar33892256
L-Hypoglycin A,1TBDMS,isomer #1C=C1CC1CC(N)C(=O)O[Si](C)(C)C(C)(C)C1505.6Semi standard non polar33892256
L-Hypoglycin A,1TBDMS,isomer #2C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O1637.1Semi standard non polar33892256
L-Hypoglycin A,2TBDMS,isomer #1C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1842.5Semi standard non polar33892256
L-Hypoglycin A,2TBDMS,isomer #1C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1898.4Standard non polar33892256
L-Hypoglycin A,2TBDMS,isomer #2C=C1CC1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2022.9Semi standard non polar33892256
L-Hypoglycin A,2TBDMS,isomer #2C=C1CC1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1967.5Standard non polar33892256
L-Hypoglycin A,3TBDMS,isomer #1C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2252.6Semi standard non polar33892256
L-Hypoglycin A,3TBDMS,isomer #1C=C1CC1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2240.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9000000000-1860e52823f730f633552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Hypoglycin A GC-MS (1 TMS) - 70eV, Positivesplash10-0ukj-9100000000-bb541e9f44219160c2c02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOFsplash10-0005-9800000000-a5171a1c4df83880eaf32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOFsplash10-0002-9100000000-e69156f7fafd560dd1242015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOFsplash10-0gb9-9000000000-d466aa46e7a29ca5ad5c2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOFsplash10-0005-9800000000-a5171a1c4df83880eaf32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOFsplash10-0002-9100000000-e69156f7fafd560dd1242015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOFsplash10-0gb9-9000000000-d466aa46e7a29ca5ad5c2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOFsplash10-0005-9800000000-a5171a1c4df83880eaf32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOFsplash10-0002-9100000000-e69156f7fafd560dd1242015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOFsplash10-0gb9-9000000000-d466aa46e7a29ca5ad5c2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOFsplash10-0005-9800000000-a5171a1c4df83880eaf32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOFsplash10-0002-9100000000-e69156f7fafd560dd1242015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOFsplash10-0gb9-9000000000-d466aa46e7a29ca5ad5c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOFsplash10-0006-1900000000-d9b471c4d83e3c6242d62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOFsplash10-00dl-7900000000-ea855029d5dfccb789a22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOFsplash10-00di-9000000000-30d74facc5bc53038ca72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOFsplash10-0006-1900000000-d9b471c4d83e3c6242d62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOFsplash10-00dl-7900000000-ea855029d5dfccb789a22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOFsplash10-00di-9000000000-30d74facc5bc53038ca72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOFsplash10-0006-1900000000-d9b471c4d83e3c6242d62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOFsplash10-00dl-7900000000-ea855029d5dfccb789a22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOFsplash10-00di-9000000000-30d74facc5bc53038ca72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOFsplash10-0006-1900000000-d9b471c4d83e3c6242d62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOFsplash10-00dl-7900000000-ea855029d5dfccb789a22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOFsplash10-00di-9000000000-30d74facc5bc53038ca72015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOFsplash10-0006-1900000000-23e6e4ddc37e52d215982021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000529
KNApSAcK IDC00001372
Chemspider ID8728
KEGG Compound IDC08287
BioCyc IDCPD-9699
BiGG IDNot Available
Wikipedia LinkHypoglycin A
METLIN IDNot Available
PubChem Compound9081
PDB IDNot Available
ChEBI ID136270
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .