Showing Compound Card for N-Acetyl-L-glutamic acid (CDB004885)

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Record Information
Version1.0
Created at2020-04-17 18:46:53 UTC
Updated at2020-11-18 16:38:55 UTC
CannabisDB IDCDB004885
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameN-Acetyl-L-glutamic acid
DescriptionN-Acetyl-L-glutamic acid, also known as acetylglutamate or ac-glu-OH, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. An N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group. N-Acetyl-L-glutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-L-glutamic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, N-Acetyl-L-glutamic acid has been detected, but not quantified in, several different foods, such as roselles, horned melons, tarragons, jostaberries, and cocoa beans. This could make N-acetyl-L-glutamic acid a potential biomarker for the consumption of these foods. N-Acetyl-L-glutamic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-2-(Acetylamino)pentanedioic acidChEBI
Ac-glu-OHChEBI
Acetyl-L-glutamic acidChEBI
Acetylglutamic acidChEBI
L-N-Acetylglutamic acidChEBI
N-Ac-glu-OHChEBI
N-ACETYL-L-glutamATEChEBI
N-Acetylglutamic acidChEBI
(S)-2-(Acetylamino)pentanedioateGenerator
Acetyl-L-glutamateGenerator
AcetylglutamateGenerator
L-N-AcetylglutamateGenerator
N-AcetylglutamateGenerator
N-Acetylglutamic acid semialdehydeHMDB
N-Acetylglutamate, potassium salt, (L)-isomerHMDB
N-Acetylglutamate, (D)-isomerHMDB
N-Acetylglutamate, calcium salt (1:1), (L)-isomerHMDB
N-Acetylglutamate, dipotassium salt, (L)-isomerHMDB
N-Acetylglutamate, disodium salt, (L)-isomerHMDB
N-Acetylglutamate, calcium salt, (L)-isomerHMDB
N-Acetylglutamate, magnesium salt, (L)-isomerHMDB
Sodium N-acetylglutamateHMDB
N-Acetylglutamate, (DL)-isomerHMDB
N-Acetylglutamate, monosodium salt, (L)-isomerHMDB
N-Acetyl-L-glutaminic acidHMDB
alpha-(N-Acetyl)-L-glutamic acidHMDB
Α-(N-acetyl)-L-glutamic acidHMDB
NAcGluHMDB
N-Acetyl-L-glutamic acidGenerator, KEGG
Chemical FormulaC7H11NO5
Average Molecular Weight189.17
Monoisotopic Molecular Weight189.0637
IUPAC Name(2S)-2-acetamidopentanedioic acid
Traditional NameN-acetyl-L-glutamate
CAS Registry Number1188-37-0
SMILES
CC(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1
InChI KeyRFMMMVDNIPUKGG-YFKPBYRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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 ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • 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
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point199 - 201 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility52 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.67ALOGPS
logP-1.1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.73 m³·mol⁻¹ChemAxon
Polarizability17.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSN-Acetyl-L-glutamic acid, 3 TMS, GC-MS Spectrumsplash10-0a4i-1940000000-78ee4843d1eab79c7ca3Spectrum
GC-MSN-Acetyl-L-glutamic acid, 2 TMS, GC-MS Spectrumsplash10-0api-3930000000-e499004b087e5d741b02Spectrum
GC-MSN-Acetyl-L-glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0a4j-0920000000-2d39b0eff0ff23756843Spectrum
GC-MSN-Acetyl-L-glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0aor-1920000000-a2fe62d19e50f9db103fSpectrum
GC-MSN-Acetyl-L-glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0a4j-0920000000-546571923f012476b58bSpectrum
GC-MSN-Acetyl-L-glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0ap0-1910000000-d18f7c4035b189c1f4b6Spectrum
GC-MSN-Acetyl-L-glutamic acid, non-derivatized, GC-MS Spectrumsplash10-0a4r-1900000000-fc8347700abd012bf349Spectrum
Predicted GC-MSN-Acetyl-L-glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9500000000-cdb488a97c5bf1952810Spectrum
Predicted GC-MSN-Acetyl-L-glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Acetyl-L-glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-1f9f80a37aa4e37ee8782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-0900000000-5423b76f7eb4b2a17fac2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-2900000000-38410c884a29996110652017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0zfr-9700000000-85acd9611312dd7df0db2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-9100000000-0d780e23d772cf133da22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0ufr-1900000000-7a57de84cf9c6671cfc22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-7b58c7204405ece93fca2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-515b33cc5674fc8985c82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-b379a6e4d794e810c4782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-2ce098bb9e1b354338782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8e7d8abde262b7d5cb452017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1900000000-a3bdc3627857c5f47f4b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-2900000000-b074eaccd0b3864766b32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0fb9-0900000000-54faa7b7182f5cceca842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-6900000000-0f14d0a7c8fb67a381b22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-053r-9000000000-333b6aa44450dbd0c7542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-adf2d3645b4231cbddc32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-d7df112ff7af7e076d702021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0536-9000000000-d70c37086adaa16367502021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-88345aaf9776c7fb86762016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-2900000000-5fca3bd987ebf6b429462016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9500000000-be58124b136b374564142016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a56ffb8d475d132443a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004v-2900000000-c32612499c0a2ceb82982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-75dbbc130d00cfec58802016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Carbamoyl-phosphate synthase [ammonia], mitochondrialCPS12q35P31327 details
N-acetylglutamate synthase, mitochondrialNAGS17q21.31Q8N159 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001138
DrugBank IDDB04075
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031019
KNApSAcK IDNot Available
Chemspider ID64077
KEGG Compound IDC00624
BioCyc IDACETYL-GLU
BiGG IDNot Available
Wikipedia LinkN-Acetylglutamic_acid
METLIN IDNot Available
PubChem Compound70914
PDB IDNot Available
ChEBI ID17533
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Carbamoyl-phosphate synthase [ammonia], mitochondrial
General function:
Involved in catalytic activity
Specific function:
Involved in the urea cycle of ureotelic animals where the enzyme plays an important role in removing excess ammonia from the cell.
Gene Name:
CPS1
Uniprot ID:
P31327
Molecular weight:
165649.075
Enzyme Details
2. N-acetylglutamate synthase, mitochondrial
General function:
Involved in N-acetyltransferase activity
Specific function:
Plays a role in the regulation of ureagenesis by producing variable amounts of N-acetylglutamate (NAG), thus modulating carbamoylphosphate synthase I (CPSI) activity.
Gene Name:
NAGS
Uniprot ID:
Q8N159
Molecular weight:
58155.835