MiMeDB: Showing metabocard for N-Acetylglutamic acid (MMDBc0032843)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:01:55 UTC

Update Date

2022-08-31 21:44:20 UTC

Metabolite ID

MMDBc0032843

Metabolite Identification

Common Name

N-Acetylglutamic acid

Description

N-acetylglutamic acid is an acetylated amino acid. It is involved in arginine biosynthesis and is a substrate for both ArgA and ArgB in Pseudomonas aeruginosa.

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       9.240   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.930   6.668   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       9.240   5.335   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.540   5.335   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.470   4.001   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2    7    8                                                  
CONECT    6    3   10   11                                                  
CONECT    7    5   12   13                                                  
CONECT    8    4    5                                                       
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
N-Acetylglutamate	Generator
2-acetamido-L-Glutaraldehydate	HMDB
2-acetamido-L-Glutaraldehydic acid	HMDB
Ac-glu-OH	HMDB
Acetyl-glutamate	HMDB
Acetyl-L-glutamate	HMDB
Acetyl-L-glutamic acid	HMDB
Acetylglutamate	HMDB
Acetylglutamic acid	HMDB
DL-Acetylglutamate	HMDB
DL-Acetylglutamic acid	HMDB
N-Ac-glu-OH	HMDB
N-Acetyl L-glutamate	HMDB
N-Acetyl L-glutamic acid	HMDB
N-Acetyl-DL-glutamate	HMDB
N-Acetyl-DL-glutamic acid	HMDB
N-Acetyl-glutamate	HMDB
N-Acetyl-glutamic acid	HMDB
N-Acetyl-L-glutamate	HMDB
N-Acetyl-L-glutamic acid	HMDB
N-Acetyl-L-glutamic acid-gamma-semialdehyde	HMDB
N-Acetylglutamic gamma-semialdehyde	HMDB

Molecular Formula

C₇H₁₁NO₅

Average Mass

189.1659

Monoisotopic Mass

189.063722467

IUPAC Name

2-acetamidopentanedioic acid

Traditional Name

acetylglutamate

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
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.3 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-1.1	ChemAxon
logS	-1.6	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	17.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-560127f9ee4a85b68a72	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0076-9141000000-ec18a019a6d39fb1652a	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-006y-0900000000-253a2008e5434e261a26	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9600000000-784f477a051434e9ba82	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-053u-9000000000-3f296192137041b66c1a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-5900000000-9cc96458c06943e10820	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0ug0-0900000000-00353ebbdcea9aaf232d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0ug0-0900000000-00353ebbdcea9aaf232d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-5900000000-9cc96458c06943e10820	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0900000000-5972610ce36d009529ad	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ukc-1900000000-8fd7df51a003da81f9f5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ued-9400000000-685e49c4990fa86bc393	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-0900000000-9291a3ff223787dd1983	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kkm-1900000000-63c6f6cddf008161228d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-1c85f38f18966b628372	2017-09-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000180	Acetyl-CoA	N-Acetylglutamic acid	N-acetylglutamate synthase	N-Acteylglutamate Synthase, Mitochondrial	VMH	12459178
MMDBr0005772	N-Acetylglutamic acid	N-Acetylglutamic acid	Not Available	Transport of N-Acetyl-L-Glutamate, Diffusion	VMH	30371894
MMDBr0006811	N-Acetylglutamic acid	N-Acetylglutamic acid	Not Available	Transport of N-Acetyl-L-Glutamate, Mitochondrial	VMH	30371894
MMDBr0007042	N-Acetylglutamic acid	N-Acetyl-L-glutamyl 5-phosphate	Not Available	Acetylglutamate kinase	VMH	30371894
MMDBr0007043	Acetyl-CoA	N-Acetylglutamic acid	Not Available	N-acetylglutamate synthase	VMH	30371894
MMDBr0007130	N2-Acetylornithine	N-Acetylglutamic acid	Not Available	Ornithine transacetylase	VMH	30371894
MMDBr0013333	Adenosine triphosphate	ADP	Protein ARG5,6, mitochondrial	Phosphorylation	RHEA	34755880
MMDBr0013334	Adenosine triphosphate	ADP	Protein ARG5,6, mitochondrial		RHEA	34755880
MMDBr0013416	L-Glutamic acid	Ornithine	Arginine biosynthesis bifunctional protein ArgJ	Acetylation; Synthesis	RHEA	34755880
MMDBr0014436	Acetyl-CoA	CoA	Amino-acid acetyltransferase	Acetylation; Synthesis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	458	Human ; Human sputum; Human subgingival plaque; Human feces; Human unknown; Pig ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Dog ; Chicken	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	368	Pig ; Human feces; Human ; Human stool; Human pleural fluid plaque; Catfish ; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	156	Human feces; Human sputum; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	92	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	7	Human feces; Pig ; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Fusobacteria	10	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Tenericutes	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	62	Human feces; Human saliva; Human supragingival plaque
Bacteria	Cyanobacteria	29	Human
Bacteria	Acidobacteria	3
Bacteria	Aquificae	4
Archaea/Archaea	Euryarchaeota	21		Metabolic reconstruction
Bacteria	Chloroflexi	8
Bacteria	Chlorobi	8
Bacteria	Deinococcus-thermus	4
Bacteria	Elusimicrobia	1
Bacteria	Thermotogae	7
Bacteria	nah	1
Bacteria/NULL	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces; Human unknown; Pig ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Dog ; Chicken	Unknown; Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	7

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022447

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Acetylglutamic acid

METLIN ID

Not Available

PubChem Compound

185

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Caldovic L, Morizono H, Gracia Panglao M, Gallegos R, Yu X, Shi D, Malamy MH, Allewell NM, Tuchman M: Cloning and expression of the human N-acetylglutamate synthase gene. Biochem Biophys Res Commun. 2002 Dec 13;299(4):581-6. doi: 10.1016/s0006-291x(02)02696-7. [PubMed:12459178 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N-Acetylglutamic acid (MMDBc0032843)

MOL for #<Metabolite:0x000055c79c1e8020>

3D MOL for #<Metabolite:0x000055c79c1e8020>

3D SDF for #<Metabolite:0x000055c79c1e8020>

3D-SDF for #<Metabolite:0x000055c79c1e8020>

PDB for #<Metabolite:0x000055c79c1e8020>

3D PDB for #<Metabolite:0x000055c79c1e8020>

SMILES for #<Metabolite:0x000055c79c1e8020>

INCHI for #<Metabolite:0x000055c79c1e8020>

Structure for #<Metabolite:0x000055c79c1e8020>

3D Structure for #<Metabolite:0x000055c79c1e8020>