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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:23:38 UTC
Update Date2021-09-14 15:25:43 UTC
HMDB IDHMDB0060477
Secondary Accession Numbers
  • HMDB60477
Metabolite Identification
Common Namegamma-Glutamyl-beta-aminopropiononitrile
Descriptiongamma-Glutamyl-beta-aminopropiononitrile belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). gamma-Glutamyl-beta-aminopropiononitrile is a very strong basic compound (based on its pKa). gamma-Glutamyl-beta-aminopropiononitrile exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1563866065
Synonyms
ValueSource
gamma-Glutamyl-3-aminopropiononitrileChEBI
g-Glutamyl-3-aminopropiononitrileGenerator
Γ-glutamyl-3-aminopropiononitrileGenerator
g-Glutamyl-b-aminopropiononitrileGenerator
Γ-glutamyl-β-aminopropiononitrileGenerator
Chemical FormulaC8H13N3O3
Average Molecular Weight199.2071
Monoisotopic Molecular Weight199.095691297
IUPAC Name(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid
Traditional Name(2S)-2-amino-4-[(2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CCC(O)=NCCC#N)C(O)=O
InChI Identifier
InChI=1S/C8H13N3O3/c9-4-1-5-11-7(12)3-2-6(10)8(13)14/h6H,1-3,5,10H2,(H,11,12)(H,13,14)/t6-/m0/s1
InChI KeyVQPVVWAFTIFKDD-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • N-acyl-amine
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.8 g/LALOGPS
logP10(-2.4) g/LALOGPS
logP10(-3.2) g/LChemAxon
logS10(-1.5) g/LALOGPS
pKa (Strongest Acidic)1.5ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.7 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.29 m³·mol⁻¹ChemAxon
Polarizability20.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.21431661259
DarkChem[M-H]-145.21131661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
gamma-Glutamyl-beta-aminopropiononitrile,1TMS,#1C[Si](C)(C)OC(CC[C@H](N)C(=O)O)=NCCC#N2072.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,1TMS,#2C[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=NCCC#N2018.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,1TMS,#3C[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O2104.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,#1C[Si](C)(C)OC(=O)[C@@H](N)CCC(=NCCC#N)O[Si](C)(C)C1995.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,#2C[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C)C(=O)O2116.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,#3C[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O[Si](C)(C)C2075.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TMS,#4C[Si](C)(C)N([C@@H](CCC(O)=NCCC#N)C(=O)O)[Si](C)(C)C2214.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(CC[C@H](N)C(=O)O)=NCCC#N2279.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(O)=NCCC#N2213.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,1TBDMS,#3CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O2308.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C2357.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,#2CC(C)(C)[Si](C)(C)N[C@@H](CCC(=NCCC#N)O[Si](C)(C)C(C)(C)C)C(=O)O2497.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,#3CC(C)(C)[Si](C)(C)N[C@@H](CCC(O)=NCCC#N)C(=O)O[Si](C)(C)C(C)(C)C2455.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
gamma-Glutamyl-beta-aminopropiononitrile,2TBDMS,#4CC(C)(C)[Si](C)(C)N([C@@H](CCC(O)=NCCC#N)C(=O)O)[Si](C)(C)C(C)(C)C2611.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uec-9200000000-f218d4c91166ca03ce382017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile GC-MS (2 TMS) - 70eV, Positivesplash10-004i-4290000000-3a1d60db995aff45ffa32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 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 - gamma-Glutamyl-beta-aminopropiononitrile 10V, Positive-QTOFsplash10-0gb9-9810000000-a233576842f26de131762015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Positive-QTOFsplash10-0gb9-9200000000-a6db4bf10b3c15dfd50f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Positive-QTOFsplash10-0uxr-9000000000-917dcb7053cf2f9907492015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 10V, Negative-QTOFsplash10-0002-0900000000-9d0a6c69667f7d6a86fd2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Negative-QTOFsplash10-00l2-4900000000-e2cc039bb0175e6b71612015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Negative-QTOFsplash10-0006-9100000000-cc0e7eb8ba343b858c492015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 10V, Positive-QTOFsplash10-0udi-4590000000-0a447d1b6cfc6063f94b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Positive-QTOFsplash10-000i-9400000000-c22ed552944f5df105f12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Positive-QTOFsplash10-0zg0-9000000000-97712e263528b70448322021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 10V, Negative-QTOFsplash10-001i-1900000000-496e5c0ed03ca00229a52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 20V, Negative-QTOFsplash10-00ur-9700000000-d3f6caee9c201874729a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Glutamyl-beta-aminopropiononitrile 40V, Negative-QTOFsplash10-00kf-9200000000-b077f442c50f547f73662021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID389750
KEGG Compound IDC06114
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440920
PDB IDNot Available
ChEBI ID28092
Food Biomarker OntologyNot Available
VMH IDHC01700
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
GGT5
Uniprot ID:
P36269
Molecular weight:
62331.75
Reactions
Beta-Aminopropionitrile + L-Glutamic acid → gamma-Glutamyl-beta-aminopropiononitrile + Waterdetails