Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:43:52 UTC
Update Date2022-03-07 03:17:53 UTC
HMDB IDHMDB0062330
Secondary Accession Numbers
  • HMDB62330
Metabolite Identification
Common NameN-Arachidonoyl GABA
Description4-{[(8Z,11Z,14Z)-1-hydroxyicosa-5,8,11,14-tetraen-1-ylidene]amino}butanoic 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. 4-{[(8Z,11Z,14Z)-1-hydroxyicosa-5,8,11,14-tetraen-1-ylidene]amino}butanoic acid is a very strong basic compound (based on its pKa).
Structure
Data?1563866296
Synonyms
ValueSource
4-{[(8Z,11Z,14Z)-1-hydroxyicosa-5,8,11,14-tetraen-1-ylidene]amino}butanoateGenerator
ElmirateHMDB
Elmiric acidHMDB
N-Arachidonoyl-g-aminobutanoateHMDB
N-Arachidonoyl-g-aminobutanoic acidHMDB
N-Arachidonoyl-gamma-aminobutanoateHMDB
N-Arachidonoyl-gamma-aminobutanoic acidHMDB
N-Arachidonoyl-γ-aminobutanoateHMDB
N-Arachidonoyl-γ-aminobutanoic acidHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-g-aminobutanoateHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-g-aminobutanoic acidHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-g-aminobutyrateHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-g-aminobutyric acidHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-gamma-aminobutanoateHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-gamma-aminobutanoic acidHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-gamma-aminobutyrateHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-gamma-aminobutyric acidHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-γ-aminobutanoateHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-γ-aminobutanoic acidHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-γ-aminobutyrateHMDB
N-[(5Z,8Z,11Z,14Z)-Eicosatetraenoyl]-γ-aminobutyric acidHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-g-aminobutanoateHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-g-aminobutanoic acidHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-g-aminobutyrateHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-g-aminobutyric acidHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-gamma-aminobutanoateHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-gamma-aminobutanoic acidHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-gamma-aminobutyrateHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-gamma-aminobutyric acidHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-γ-aminobutanoateHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-γ-aminobutanoic acidHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-γ-aminobutyrateHMDB
N-[(5Z,8Z,11Z,14Z)-Icosatetraenoyl]-γ-aminobutyric acidHMDB
NAGABAHMDB
Chemical FormulaC24H39NO3
Average Molecular Weight389.58
Monoisotopic Molecular Weight389.29299412
IUPAC Name4-{[(8Z,11Z,14Z)-1-hydroxyicosa-5,8,11,14-tetraen-1-ylidene]amino}butanoic acid
Traditional Name4-{[(8Z,11Z,14Z)-1-hydroxyicosa-5,8,11,14-tetraen-1-ylidene]amino}butanoic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCCC(O)=NCCCC(O)=O
InChI Identifier
InChI=1S/C24H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-23(26)25-22-19-21-24(27)28/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-22H2,1H3,(H,25,26)(H,27,28)/b7-6-,10-9-,13-12-,16-15?
InChI KeyJKUDIEXTAYKJNX-CDIMZWLNSA-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
  • Straight chain fatty acid
  • Fatty acyl
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00027 g/lALOGPS
LogP6.58ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.76ALOGPS
logP5.47ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity122.73 m³·mol⁻¹ChemAxon
Polarizability48.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+206.33231661259
DarkChem[M-H]-202.48831661259
DeepCCS[M+H]+218.330932474
DeepCCS[M-H]-216.40430932474
DeepCCS[M-2H]-249.64830932474
DeepCCS[M+Na]+224.03430932474
AllCCS[M+H]+203.832859911
AllCCS[M+H-H2O]+201.532859911
AllCCS[M+NH4]+205.932859911
AllCCS[M+Na]+206.532859911
AllCCS[M-H]-200.032859911
AllCCS[M+Na-2H]-202.732859911
AllCCS[M+HCOO]-205.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Arachidonoyl GABA[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCCC(O)=NCCCC(O)=O4687.2Standard polar33892256
N-Arachidonoyl GABA[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCCC(O)=NCCCC(O)=O2703.9Standard non polar33892256
N-Arachidonoyl GABA[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CC([H])=C([H])CCCC(O)=NCCCC(O)=O3169.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Arachidonoyl GABA,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC=CCCCC(=NCCCC(=O)O)O[Si](C)(C)C3112.8Semi standard non polar33892256
N-Arachidonoyl GABA,1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CC=CCCCC(O)=NCCCC(=O)O[Si](C)(C)C3063.1Semi standard non polar33892256
N-Arachidonoyl GABA,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC=CCCCC(=NCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3042.9Semi standard non polar33892256
N-Arachidonoyl GABA,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC=CCCCC(=NCCCC(=O)O)O[Si](C)(C)C(C)(C)C3348.5Semi standard non polar33892256
N-Arachidonoyl GABA,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\CC=CCCCC(O)=NCCCC(=O)O[Si](C)(C)C(C)(C)C3313.0Semi standard non polar33892256
N-Arachidonoyl GABA,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\CC=CCCCC(=NCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3534.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Arachidonoyl GABA GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fuu-9578000000-526d488bb421786e06de2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Arachidonoyl GABA GC-MS (2 TMS) - 70eV, Positivesplash10-01bi-9563560000-18a8f1de3a5e8fc3e4862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Arachidonoyl GABA GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Arachidonoyl GABA 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 - N-Arachidonoyl GABA 10V, Positive-QTOFsplash10-0fkc-4419000000-e4c64ae0b0edcd5e1be32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 20V, Positive-QTOFsplash10-0zg0-9511000000-850d4e7acd2544b28fba2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 40V, Positive-QTOFsplash10-0zfu-9410000000-5b7711bc3cefa3e294142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 10V, Negative-QTOFsplash10-000i-0009000000-c11751d6483c98cee22f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 20V, Negative-QTOFsplash10-0fe0-2229000000-289cf376830a828ad49e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 40V, Negative-QTOFsplash10-0006-9121000000-813d0e25d3fc110154cf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 10V, Positive-QTOFsplash10-0f6x-4429000000-7665674069a2b161180e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 20V, Positive-QTOFsplash10-0f8i-9523000000-d9605c51b113673f88912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 40V, Positive-QTOFsplash10-0f89-7910000000-af40ca6d4fd2315701622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 10V, Negative-QTOFsplash10-0079-0009000000-3d39a6cbe8d7d8cb15b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 20V, Negative-QTOFsplash10-000i-4339000000-9e459848a5a1146eed062021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoyl GABA 40V, Negative-QTOFsplash10-0uei-9542000000-cbeb493aeee59d9f3a232021-09-25Wishart 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ReferencesNot Available