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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:37 UTC
Update Date2023-02-21 17:19:36 UTC
HMDB IDHMDB0030409
Secondary Accession Numbers
  • HMDB30409
Metabolite Identification
Common Name4-Amino-2-methylenebutanoic acid
Description4-Amino-2-methylenebutanoic acid belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Based on a literature review very few articles have been published on 4-Amino-2-methylenebutanoic acid.
Structure
Data?1676999976
Synonyms
ValueSource
4-Amino-2-methylenebutanoateGenerator
g-Amino-a-methylenebutyric acidHMDB
4-Amino-2-methylidenebutanoateHMDB
Chemical FormulaC5H9NO2
Average Molecular Weight115.1305
Monoisotopic Molecular Weight115.063328537
IUPAC Name4-amino-2-methylidenebutanoic acid
Traditional Name4-amino-2-methylidenebutanoic acid
CAS Registry Number65370-67-4
SMILES
NCCC(=C)C(O)=O
InChI Identifier
InChI=1S/C5H9NO2/c1-4(2-3-6)5(7)8/h1-3,6H2,(H,7,8)
InChI KeyFTWHFXMUJQRNBK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Amino fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 - 179 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility164 g/LALOGPS
logP-2.6ALOGPS
logP-2.4ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)10.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.84 m³·mol⁻¹ChemAxon
Polarizability11.65 ųChemAxon
Number of Rings0ChemAxon
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]+123.34231661259
DarkChem[M-H]-118.16331661259
DeepCCS[M+H]+126.05830932474
DeepCCS[M-H]-123.25830932474
DeepCCS[M-2H]-159.56130932474
DeepCCS[M+Na]+134.16930932474
AllCCS[M+H]+128.832859911
AllCCS[M+H-H2O]+124.632859911
AllCCS[M+NH4]+132.732859911
AllCCS[M+Na]+133.932859911
AllCCS[M-H]-125.232859911
AllCCS[M+Na-2H]-128.532859911
AllCCS[M+HCOO]-132.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Amino-2-methylenebutanoic acidNCCC(=C)C(O)=O2014.9Standard polar33892256
4-Amino-2-methylenebutanoic acidNCCC(=C)C(O)=O1216.7Standard non polar33892256
4-Amino-2-methylenebutanoic acidNCCC(=C)C(O)=O1143.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Amino-2-methylenebutanoic acid,1TMS,isomer #1C=C(CCN)C(=O)O[Si](C)(C)C1188.5Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,1TMS,isomer #2C=C(CCN[Si](C)(C)C)C(=O)O1311.9Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #1C=C(CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C1353.0Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #1C=C(CCN[Si](C)(C)C)C(=O)O[Si](C)(C)C1432.2Standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #2C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1530.8Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TMS,isomer #2C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1445.3Standard non polar33892256
4-Amino-2-methylenebutanoic acid,3TMS,isomer #1C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1545.6Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,3TMS,isomer #1C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1557.4Standard non polar33892256
4-Amino-2-methylenebutanoic acid,1TBDMS,isomer #1C=C(CCN)C(=O)O[Si](C)(C)C(C)(C)C1402.8Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,1TBDMS,isomer #2C=C(CCN[Si](C)(C)C(C)(C)C)C(=O)O1560.4Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #1C=C(CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1798.1Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #1C=C(CCN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1811.9Standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #2C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O1962.8Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,2TBDMS,isomer #2C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O1865.6Standard non polar33892256
4-Amino-2-methylenebutanoic acid,3TBDMS,isomer #1C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2190.4Semi standard non polar33892256
4-Amino-2-methylenebutanoic acid,3TBDMS,isomer #1C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2155.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Amino-2-methylenebutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-5bce7376b76e0e5d734d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Amino-2-methylenebutanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9200000000-06aae0df20cb65cf4e952017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Amino-2-methylenebutanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 10V, Positive-QTOFsplash10-00kb-9300000000-87bbc6affbd5953b1b4a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Positive-QTOFsplash10-0f6t-9000000000-12225cc8d658dc7e98572015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Positive-QTOFsplash10-0udi-9000000000-86ded6c35c43a4b0ab472015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 10V, Negative-QTOFsplash10-03di-2900000000-69900af268e52fa5ad182015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Negative-QTOFsplash10-0229-9400000000-518b22bf53e4ba0abdb22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Negative-QTOFsplash10-0v4l-9000000000-1edce3c9adc88aaede622015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 10V, Positive-QTOFsplash10-0002-9100000000-ff1346c48908fbea15102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Positive-QTOFsplash10-0fdo-9000000000-efbda9f06b3632d2fc212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Positive-QTOFsplash10-0zfu-9000000000-2521a990ed07185cccfa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 10V, Negative-QTOFsplash10-01ot-9500000000-cfef122a5cd40b6ef7c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 20V, Negative-QTOFsplash10-00kb-9000000000-cee8ead2149daee5efed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Amino-2-methylenebutanoic acid 40V, Negative-QTOFsplash10-0gb9-9000000000-5bfd61203c81eb2c616b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX 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 IDFDB002271
KNApSAcK IDC00054452
Chemspider ID4476652
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318003
PDB IDNot Available
ChEBI IDNot Available
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.. .