ECMDB: N-Acetylornithine (ECMDB03357) (M2MDB000493)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (930)

Record Information

Version

2.0

Creation Date

2012-05-31 13:58:41 -0600

Update Date

2015-06-03 15:54:22 -0600

Secondary Accession Numbers

ECMDB03357

Identification

Name:

N-Acetylornithine

Description

N-Acetylornithine is a intermediate in arginine and proline metabolism pathway. It is converted to ornithine via acetylornithine deacetylase (EC:3.5.1.16). (KEGG)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2S)-2-acetamido-5-aminopentanoate
(2S)-2-acetamido-5-aminopentanoic acid
N-α-acetylornithine
N-acetylornithine
N²-acetyl-L-ornithine
N²-acetyl-ornithine
Acetyl-Ornithine
Acetylornithine
AOR
N(2)-Acetyl-L-ornithine
n-α-acetylornithine
N-a-Acetylornithine
N-AcOrn
N-alpha-Acetylornithine
N-α-Acetylornithine
N2-Acetyl-L-ornithine
N2-acetyl-ornithine

Chemical Formula:

C₇H₁₄N₂O₃

Weight:

Average: 174.1977
Monoisotopic: 174.100442324

InChI Key:

JRLGPAXAGHMNOL-LURJTMIESA-N

InChI:

InChI=1S/C7H14N2O3/c1-5(10)9-6(7(11)12)3-2-4-8/h6H,2-4,8H2,1H3,(H,9,10)(H,11,12)/t6-/m0/s1

CAS number:

Not Available

IUPAC Name:

(2S)-5-amino-2-acetamidopentanoic acid

Traditional IUPAC Name:

N(2)-acetyl-L-ornithine

SMILES:

CC(=O)N[C@@H](CCCN)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Monocarboxylic acid or derivatives
Carboxylic acid
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N2-acyl-L-ornithine (CHEBI:16543 )
acetylornithine (CHEBI:16543 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-0.896	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	37.8 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.6	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	9.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.65 m³·mol⁻¹	ChemAxon
Polarizability	17.94 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Lysine biosynthesis	PW000771
arginine metabolism	PW000790
ornithine metabolism	PW000791

KEGG Pathways:

Arginine and proline metabolism ec00330
Lysine biosynthesis ec00300
Metabolic pathways eco01100

EcoCyc Pathways:

ornithine biosynthesis GLUTORN-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
43± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
398± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
152± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
14± 0 uM	BW25113	48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco	Stationary Phase, glucose limited	Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h	37 oC	PMID: 17379776
0.61± 0.03 uM	BL21 DE3	Luria-Bertani (LB) media	Stationary phase cultures (overnight culture)	Shake flask	37 oC	Experimentally Determined Download Details

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0fk9-1930000000-28d5f476677a51e2f8ec	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-2900000000-092b404eaa0526439b15	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fk9-0930000000-6914c12040164b5148b0	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-0910000000-25d42f7fce94b1cb4b5c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fk9-1920000000-e1b66d25c11eafd0e0a9	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-0f0883367079e716da18	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fk9-1930000000-28d5f476677a51e2f8ec	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-2900000000-092b404eaa0526439b15	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9100000000-429f70cb44411bb90989	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fkc-9410000000-cee666cdbec55f97a0a0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-52f0d0fb8a9a849e95d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-0900000000-d83ff24b1fd0244f8e2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-2900000000-e708e107e9183bfe0f76	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-053r-9400000000-afb6a5b65f59f01dc761	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-4763dc8edae338a7f336	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-001i-0900000000-d157410f17955c8e0256	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-0900000000-52b9626c047fdc01fe7b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-c92081162e58f54cd2ec	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9200000000-476b94e0eacd5c51da0d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9000000000-e57c224e36a05f66f1b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-9000000000-44d1c5e14f69e175989a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-03fr-0900000000-5fe61be67a41d8d0facc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01b9-4900000000-624c1afbfd5d3b3b76cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01b9-4900000000-624c1afbfd5d3b3b76cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-310a7f3b3d4c1bf3af0b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-d0f88533afec85ff5c62	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-05r0-0900000000-f280065b578a1aa65149	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-8900000000-cf2ff97fd954fbc2ad67	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9000000000-ff059f4dd36bc1002fbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-1900000000-28d5e48c6fc3a56a4937	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06tr-4900000000-8aa79d29a3d89249bf78	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01vx-9200000000-2f866830ef23136853fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-9b37a30ee623b4f18e80	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0c30-4900000000-019d18f26e04ab2b397a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-b133fb2ce9e1a5eef782	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Armstrong MD: N-delta-acetylornithine and S-methylcysteine in blood plasma. Biochim Biophys Acta. 1979 Nov 1;587(4):638-42. Pubmed: 508804
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16543
HMDB ID	HMDB03357
Pubchem Compound ID	439232
Kegg ID	C00437
ChemSpider ID	388369
Wikipedia ID	Not Available
BioCyc ID	N-ALPHA-ACETYLORNITHINE
EcoCyc ID	N-ALPHA-ACETYLORNITHINE
Ligand Expo	AOR

Enzymes

Protein Details

1. Acetylornithine/succinyldiaminopimelate aminotransferase

General function:: Involved in transaminase activity
Specific function:: Involved in both the arginine and lysine biosynthetic pathways
Gene Name:: argD
Uniprot ID:: P18335
Molecular weight:: 43767

Reactions

N(2)-acetyl-L-ornithine + 2-oxoglutarate = N-acetyl-L-glutamate 5-semialdehyde + L-glutamate.
N-succinyl-L-2,6-diaminoheptanedioate + 2-oxoglutarate = N-succinyl-2-L-amino-6-oxoheptanedioate + L-glutamate.

Protein Details

2. Acetylornithine deacetylase

General function:: Involved in zinc ion binding
Specific function:: Displays a broad specificity and can also deacylate substrates such as acetylarginine, acetylhistidine or acetylglutamate semialdehyde
Gene Name:: argE
Uniprot ID:: P23908
Molecular weight:: 42347

Reactions

N(2)-acetyl-L-ornithine + H(2)O = acetate + L-ornithine.

Protein Details

3. Succinylornithine transaminase

General function:: Involved in transaminase activity
Specific function:: Catalyzes the transamination of N(2)-succinylornithine and alpha-ketoglutarate into N(2)-succinylglutamate semialdehyde and glutamate. Can also act as an acetylornithine aminotransferase
Gene Name:: astC
Uniprot ID:: P77581
Molecular weight:: 43665

Reactions

N(2)-succinyl-L-ornithine + 2-oxoglutarate = N-succinyl-L-glutamate 5-semialdehyde + L-glutamate.

N-Acetylornithine (ECMDB03357) (M2MDB000493)

Structure for #<Compound:0xad839958>

Enzymes

Reactions

Reactions

Reactions