P. aeruginosa Metabolome Database: N-Acetylornithine (PAMDB000493)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000493

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 View Structure

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

Average Molecular Weight:

174.1977

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.

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-aliphatic-alpha amino acids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N2-acyl-L-ornithine (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 mg/mL	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:

N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
N-Acetylornithine + Water <> Acetic acid + Ornithine + L-Ornithine
N-Acetylornithine + Water <> Acetic acid + Ornithine
N-Acetylornithine + Oxoglutaric acid < N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
N-acetyl-L-glutamate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine
N-Acetylornithine + Water > Acetic acid + L-Ornithine monochlorohydrate/ornithine
N-Acetylornithine + Water > Ornithine + Acetic acid + Ornithine
N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine

Pathways:

Arginine and proline metabolism pae00330
Lysine biosynthesis pae00300
Metabolic pathways pae01100

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 - GC-MS	Not Available
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
1D NMR	13C NMR Spectrum	Not Available

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

N-Acetylornithine (PAMDB000493)

Structure for N-Acetylornithine (PAMDB000493)