Livestock Metabolome Database: Showing metabocard for N-Acetylglutamic acid (LMDB00299)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:47 UTC

Update Date

2016-07-20 20:59:41 UTC

Lmdb

LMDB00299

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetylglutamic acid

Description

N-acetylglutamic acid is an acetylated amino acid. N-Acetylglutamic acid (abbreviated NAcGlu) is biosynthesized from glutamic acid and acetyl-CoA by the enzyme N-acetylglutamate synthase (NAGS). NAcGlu activates carbamoyl phosphate synthetase in the urea cycle. A deficiency in N-Acetyl Glutamate Synthase or a genetic mutation in the gene coding for the enzyme, will lead to urea cycle failure in which ammonia is not converted to urea, but rather accumulated in blood leading to the condition called Type I Hyperammonemia. This is a severe neonatal disorder with fatal consequences, if not detected immediately upon birth.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-2-(Acetylamino)pentanedioic acid	ChEBI
Ac-glu-OH	ChEBI
Acetyl-L-glutamic acid	ChEBI
Acetylglutamic acid	ChEBI
L-N-Acetylglutamic acid	ChEBI
N-Ac-glu-OH	ChEBI
N-ACETYL-L-glutamATE	ChEBI
N-Acetylglutamic acid	ChEBI
(S)-2-(Acetylamino)pentanedioate	Generator
Acetyl-L-glutamate	Generator
Acetylglutamate	Generator
L-N-Acetylglutamate	Generator
N-Acetylglutamate	Generator
N-Acetylglutamic acid semialdehyde	HMDB
N-Acetylglutamate, potassium salt, (L)-isomer	HMDB
N-Acetylglutamate, (D)-isomer	HMDB
N-Acetylglutamate, calcium salt (1:1), (L)-isomer	HMDB
N-Acetylglutamate, dipotassium salt, (L)-isomer	HMDB
N-Acetylglutamate, disodium salt, (L)-isomer	HMDB
N-Acetylglutamate, calcium salt, (L)-isomer	HMDB
N-Acetylglutamate, magnesium salt, (L)-isomer	HMDB
Sodium N-acetylglutamate	HMDB
N-Acetylglutamate, (DL)-isomer	HMDB
N-Acetylglutamate, monosodium salt, (L)-isomer	HMDB
N-Acetyl-L-glutaminic acid	HMDB
alpha-(N-Acetyl)-L-glutamic acid	HMDB
Α-(N-acetyl)-L-glutamic acid	HMDB
NAcGlu	HMDB
N-Acetyl-L-glutamic acid	Generator, KEGG

Chemical Formula

C₇H₁₁NO₅

Average Molecular Weight

189.1659

Monoisotopic Molecular Weight

189.063722467

IUPAC Name

(2S)-2-acetamidopentanedioic acid

Traditional Name

N-acetyl-L-glutamate

CAS Registry Number

1188-37-0

SMILES

CC(=O)NC(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)

InChI Key

RFMMMVDNIPUKGG-UHFFFAOYSA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic 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 Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:17533 )
N-acyl-L-glutamic acid (CHEBI:17533 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.67	ALOGPS
logP	-1.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.73 m³·mol⁻¹	ChemAxon
Polarizability	17.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0a4i-1940000000-78ee4843d1eab79c7ca3	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0api-3930000000-e499004b087e5d741b02	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4j-0920000000-2d39b0eff0ff23756843	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aor-1920000000-a2fe62d19e50f9db103f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4j-0920000000-546571923f012476b58b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ap0-1910000000-d18f7c4035b189c1f4b6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4r-1900000000-fc8347700abd012bf349	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-cdb488a97c5bf1952810	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-1f9f80a37aa4e37ee878	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fb9-0900000000-5423b76f7eb4b2a17fac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-2900000000-38410c884a2999611065	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0zfr-9700000000-85acd9611312dd7df0db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0pb9-9100000000-0d780e23d772cf133da2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0ufr-1900000000-7a57de84cf9c6671cfc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-7b58c7204405ece93fca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-1900000000-515b33cc5674fc8985c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9300000000-b379a6e4d794e810c478	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-2ce098bb9e1b35433878	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-8e7d8abde262b7d5cb45	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-1900000000-a3bdc3627857c5f47f4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0ufr-2900000000-b074eaccd0b3864766b3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0fb9-0900000000-54faa7b7182f5cceca84	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-6900000000-0f14d0a7c8fb67a381b2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-9000000000-333b6aa44450dbd0c754	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-adf2d3645b4231cbddc3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-d7df112ff7af7e076d70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9000000000-d70c37086adaa1636750	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0900000000-88345aaf9776c7fb8676	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udl-2900000000-5fca3bd987ebf6b42946	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udj-9500000000-be58124b136b37456414	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a56ffb8d475d132443a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004v-2900000000-c32612499c0a2ceb8298	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9300000000-75dbbc130d00cfec5880	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details