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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-25 14:19:28 UTC
Update Date2020-02-26 21:25:45 UTC
HMDB IDHMDB0005096
Secondary Accession Numbers
  • HMDB0062617
  • HMDB05096
  • HMDB62617
Metabolite Identification
Common NameN-Arachidonoylglycine
DescriptionN-Arachidonoylglycine, also known as nagly or ema-1 20:4, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Thus, N-arachidonoylglycine is considered to be a fatty amide lipid molecule. N-Arachidonoylglycine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752345
Synonyms
ValueSource
N-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycineChEBI
N-Arachidonoyl glycineChEBI
NAGlyChEBI
N-Arachidonyl-L-glycineHMDB
N-ArachidonylglycineHMDB
EMA-1 20:4HMDB
NAGly amino acidHMDB
N-Arachidonoyl glycinateHMDB
N-ArachidonoylglycinateHMDB
N-[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-Eicosatetraen-1-yl]glycineHMDB
N-ArachidonoylglycineHMDB
Chemical FormulaC22H35NO3
Average Molecular Weight361.5182
Monoisotopic Molecular Weight361.261693991
IUPAC Name2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamido]acetic acid
Traditional Namenagly
CAS Registry Number179113-91-8
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C22H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(24)23-20-22(25)26/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-20H2,1H3,(H,23,24)(H,25,26)/b7-6-,10-9-,13-12-,16-15-
InChI KeyYLEARPUNMCCKMP-DOFZRALJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.043Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00036 g/LALOGPS
logP6.28ALOGPS
logP5.48ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity112.76 m³·mol⁻¹ChemAxon
Polarizability42.86 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]+199.19131661259
DarkChem[M-H]-198.06131661259
DeepCCS[M+H]+199.41530932474
DeepCCS[M+H]+191.25630932474
DeepCCS[M-H]-197.05730932474
DeepCCS[M-H]-188.89830932474
DeepCCS[M-2H]-229.94330932474
DeepCCS[M+Na]+205.50830932474
DeepCCS[M-2H]-221.78530932474
DeepCCS[M+Na]+197.3530932474
AllCCS[M+H]+196.132859911
AllCCS[M+H-H2O]+193.532859911
AllCCS[M+NH4]+198.432859911
AllCCS[M+Na]+199.132859911
AllCCS[M-H]-194.132859911
AllCCS[M+Na-2H]-196.332859911
AllCCS[M+HCOO]-198.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-ArachidonoylglycineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC(O)=O4026.9Standard polar33892256
N-ArachidonoylglycineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC(O)=O2437.7Standard non polar33892256
N-ArachidonoylglycineCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCC(O)=O2925.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Arachidonoylglycine,1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O[Si](C)(C)C2879.8Semi standard non polar33892256
N-Arachidonoylglycine,1TMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O)[Si](C)(C)C2971.1Semi standard non polar33892256
N-Arachidonoylglycine,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C2896.2Semi standard non polar33892256
N-Arachidonoylglycine,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C2932.7Standard non polar33892256
N-Arachidonoylglycine,2TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C3036.3Standard polar33892256
N-Arachidonoylglycine,1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C3142.4Semi standard non polar33892256
N-Arachidonoylglycine,1TBDMS,isomer #2CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C3213.4Semi standard non polar33892256
N-Arachidonoylglycine,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3392.8Semi standard non polar33892256
N-Arachidonoylglycine,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3282.6Standard non polar33892256
N-Arachidonoylglycine,2TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3079.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Arachidonoylglycine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fyc-7393000000-04b6b96f91829d5feefe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Arachidonoylglycine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9141100000-d5de221d0748b6c073222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Arachidonoylglycine 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-Arachidonoylglycine 10V, Positive-QTOFsplash10-0229-9015000000-2860195ca439964f027c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Positive-QTOFsplash10-00di-9011000000-6f824b09e6808edc46852016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Positive-QTOFsplash10-00di-9010000000-6846d3f3704692ffd2ca2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 10V, Negative-QTOFsplash10-03di-0019000000-c766b47b5693745260322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Negative-QTOFsplash10-03k9-4139000000-6be001e2e3c064731d712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Negative-QTOFsplash10-05fu-9120000000-24a924229e7f342b295f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 10V, Positive-QTOFsplash10-03fr-6119000000-3e536a637c2f6c3b9ffc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Positive-QTOFsplash10-004i-9221000000-51b37d44e7dae3812d5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Positive-QTOFsplash10-05qc-9600000000-87a70dd054c2e35516e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 10V, Negative-QTOFsplash10-03di-1009000000-ad572766b9cd41e2eda22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 20V, Negative-QTOFsplash10-00di-9002000000-58daec3d933739b930af2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Arachidonoylglycine 40V, Negative-QTOFsplash10-00di-9000000000-77d408cf5bc92e1b44fd2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.09 +/- 0.73 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023629
KNApSAcK IDNot Available
Chemspider ID4446510
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Arachidonylglycine
METLIN IDNot Available
PubChem Compound5283389
PDB IDNot Available
ChEBI ID58961
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. Lipid Maps (LMFA08020003) [Link]

Enzymes

General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055