MiMeDB: Showing metabocard for N-alpha-Acetyl-L-citrulline (MMDBc0000373)

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:22 UTC

Update Date

2024-10-11 01:43:04 UTC

Metabolite ID

MMDBc0000373

Metabolite Identification

Common Name

N-alpha-Acetyl-L-citrulline

Description

N-alpha-Acetyl-L-citrulline, also known as N-acetylcitrulline, is an N-acetylated metabolite of citrulline that is part of the arginine biosynthetic pathway. Arginine biosynthesis is notable for its complexity and variability at the genetic level, and by its connection with several other pathways, such as pyrimidine and polyamine biosynthesis, and certain degradative pathways. The initial steps of the arginine biosynthetic pathways proceed via N-acetylated intermediates. The presumed reason for this is that the acetylation prevents the spontaneous cyclization of glutamate derivatives, which leads to proline biosynthesis. N-acetyl-L-ornithine can be transcarbamylated directly by the enzyme acetylornithine transcarbamylase, resulting in N-acetyl-L-citrulline. The enzyme acetylornithine deacetylase can accept N-acetyl-L-citrulline as a substrate and can deacetylate it into citrulline. N-alpha-Acetyl-L-citrulline is found in cases of deficiency of the urea cycle enzyme argininosuccinate synthase (EC 6.3.4.5) that leads to increased concentrations of citrulline and N-acetylcitrulline in the urine (PMID: 14633929 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₈H₁₅N₃O₄

Average Mass

217.2224

Monoisotopic Mass

217.106255983

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)/t6-/m0/s1

InChI Key

WMQMIOYQXNRROC-LURJTMIESA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	499.7
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	499.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	369.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	369.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	49.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	49.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	240.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	240.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	276.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	276.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	256.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	256.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	408.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	408.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	832.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	832.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	608.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	608.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	152.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	152.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	517.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	517.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	166.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	166.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	51.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	51.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	377.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	377.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	750.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	750.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	51.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	51.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	225.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	225.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	729.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	729.7
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	572.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	572.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_1	CC(=O)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1520.54
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_2	CC(=O)N[C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2134.23
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_3	CC(=O)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	2070.34
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_4	CC(=O)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2149.73
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_5	CC(=O)N[C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1853.38
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_6	CC(=O)N([C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2302.98
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_7	CC(=O)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1740.03
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_8	CC(=O)N([C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	2074.94
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_9	CC(=O)N[C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2073.48
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_10	CC(=O)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1249.33
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_11	CC(=O)N([C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	1696.05
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_12	CC(=O)N([C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2178.24
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_13	CC(=O)N[C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1907.63
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_14	CC(=O)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2473.36
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_15	CC(=O)N([C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2049.66
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_16	CC(=O)N([C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	1980.47
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_17	CC(=O)N([C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	2237.74
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_18	CC(=O)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2245.94
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_19	CC(=O)N([C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1814.96
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_20	CC(=O)N([C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1496.27
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_21	CC(=O)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1368.6
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_22	CC(=O)N([C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	1859.02
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_23	CC(=O)N([C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1999.11
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_1	CC(=O)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1975.59
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_2	CC(=O)N[C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2333.6
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_3	CC(=O)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	2444.38
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_4	CC(=O)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2193.5
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_5	CC(=O)N[C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2265.57
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_6	CC(=O)N([C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1809.13
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_7	CC(=O)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2066.77
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_8	CC(=O)N([C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	2373.61
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_9	CC(=O)N[C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	1860.93
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_10	CC(=O)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2269.27
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_11	CC(=O)N([C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	2138.82
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_12	CC(=O)N([C@@H](CCCNC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2381.47
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_13	CC(=O)N[C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1974.37
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_14	CC(=O)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1821.42
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_15	CC(=O)N([C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2468.89
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_16	CC(=O)N([C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	1818.93
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_17	CC(=O)N([C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	2797.2
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_18	CC(=O)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	1591.71
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_19	CC(=O)N([C@@H](CCCN(C(=O)N[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1468.95
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_20	CC(=O)N([C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2279.11
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_21	CC(=O)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1944.42
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_22	CC(=O)N([C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	1970.61
Gas Chromatography	N-alpha-Acetyl-L-citrulline_TMS_23	CC(=O)N([C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2934.21

Biological Properties

Cellular Locations

Cytoplasm

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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/Eubacteria	Firmicutes	1	Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

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						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Engelke UF, Liebrand-van Sambeek ML, de Jong JG, Leroy JG, Morava E, Smeitink JA, Wevers RA: N-acetylated metabolites in urine: proton nuclear magnetic resonance spectroscopic study on patients with inborn errors of metabolism. Clin Chem. 2004 Jan;50(1):58-66. doi: 10.1373/clinchem.2003.020214. Epub 2003 Nov 18. [PubMed:14633929 ]

Showing metabocard for N-alpha-Acetyl-L-citrulline (MMDBc0000373)

MOL for #<Metabolite:0x00007f9ace7a08a8>

3D MOL for #<Metabolite:0x00007f9ace7a08a8>

3D SDF for #<Metabolite:0x00007f9ace7a08a8>

3D-SDF for #<Metabolite:0x00007f9ace7a08a8>

PDB for #<Metabolite:0x00007f9ace7a08a8>

3D PDB for #<Metabolite:0x00007f9ace7a08a8>

SMILES for #<Metabolite:0x00007f9ace7a08a8>

INCHI for #<Metabolite:0x00007f9ace7a08a8>

Structure for #<Metabolite:0x00007f9ace7a08a8>

3D Structure for #<Metabolite:0x00007f9ace7a08a8>