ORNITHINE PHENYLACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H8O2.C5H12N2O2
Molecular Weight	268.3089
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@](N)(CCCN)C(O)=O.OC(=O)CC1=CC=CC=C1

InChI

InChIKey=LRSYFEZBIMVWRY-VWMHFEHESA-N

InChI=1S/C8H8O2.C5H12N2O2/c9-8(10)6-7-4-2-1-3-5-7;6-3-1-2-4(7)5(8)9/h1-5H,6H2,(H,9,10);4H,1-3,6-7H2,(H,8,9)/t;4-/m.0/s1

HIDE SMILES / InChI

Molecular Formula	C5H12N2O2
Molecular Weight	132.161
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C8H8O2
Molecular Weight	136.1479
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.hmdb.ca/metabolites/HMDB00214
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00129

Ornithine is an amino acid produced in the urea cycle by the splitting off of urea from arginine. It is a central part of the urea cycle, which allows for the disposal of excess nitrogen. Ornithine is also a precursor of citrulline and arginine. Arginine stimulates the pituitary release of growth hormone. Burns or other injuries affect the state of arginine in tissues throughout the body. As de novo synthesis of arginine during these conditions is usually not sufficient for normal immune function, nor for normal protein synthesis, ornithine may have immunomodulatory and wound-healing activities under these conditions (by virtue of its metabolism to arginine).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
G-protein coupled receptor family C group 6 member A 22 Target ID: Q5T6X5 Gene ID: 222545.0 Gene Symbol: GPRC6A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15576628	Agonist 2678		112.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dietary shortage or imbalance 9 Sources: https://www.drugbank.ca/drugs/DB00129	Primary		Approved 8429	L-Ornithine Approved Use Used for nutritional supplementation, also for treating dietary shortage or imbalance.

PubMed

Title	Date	PubMed
The genome of Mycobacterium leprae: a minimal mycobacterial gene set.	2001	11532219
[Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome].	2001	11462710
Effect of exercise on the metabolism of vitamin B6 and some PLP-dependent enzymes in young rats fed a restricted vitamin B6 diet.	2001 Apr	11508701
Effects of amino acid and trace element supplementation on pneumocandin production by Glarea lozoyensis: impact on titer, analogue levels, and the identification of new analogues of pneumocandin B(0).	2001 Apr	11464269
Analysis of amino acids in human serum by isocratic reversed-phase high-performance liquid chromatography with electrochemical detection.	2001 Apr 13	11355826
Hyperornithinemia associated with gyrate atrophy of the choroid and retina in a child with myopia.	2001 Aug	11521006
Is hyperprolinemia type I actually a benign trait? Report of a case with severe neurologic involvement and vigabatrin intolerance.	2001 Aug	11510941
Intrahepatic amino acid and glucose metabolism in a D-galactosamine-induced rat liver failure model.	2001 Aug	11481621
The potential mechanism for glutamine-induced collagen biosynthesis in cultured human skin fibroblasts.	2001 Aug	11470441
The Plasmodium falciparum bifunctional ornithine decarboxylase, S-adenosyl-L-methionine decarboxylase, enables a well balanced polyamine synthesis without domain-domain interaction.	2001 Aug 10	11390378
Amino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-proteinase: solid-phase synthesis of ornithine analogues.	2001 Aug 20	11514144
Synthesis of six novel N,N-dialkyl derivatives of spermidine and effects on growth of the fungal plant pathogen Pyrenophora avenae.	2001 Aug 21	11520618
Classical and slow-binding inhibitors of human type II arginase.	2001 Aug 7	11478904
Determination of amino acids by ion-exchange chromatography on filter paper spotted blood samples stored at different temperatures and for different periods: comparison with capillary and venous blood.	2001 Jul	11522278
Burkholderia ambifaria sp. nov., a novel member of the Burkholderia cepacia complex including biocontrol and cystic fibrosis-related isolates.	2001 Jul	11491349
Urea flux in beef steers: effects of forage species and nitrogen fertilization.	2001 Jul	11465382
Medical and surgical therapy of the cystine stone patient.	2001 Jul	11429493
Ornithine aminotransferase messenger RNA expression and enzymatic activity in fetal porcine intestine.	2001 Jul	11420426
Analysis of differentially expressed genes in human hepatocellular carcinoma using suppression subtractive hybridization.	2001 Jul 20	11461082
Antifungal activity of three spermidine conjugates.	2001 Jul 24	11470370
Structural requirements for conserved arginine of parathyroid hormone.	2001 Jul 31	11467957
Abnormal elution behavior of ornitine derivatized with 1-fluoro-2,4-dinitrophenyl-5-leucinamide in advanced Marfey's method.	2001 Jul 6	11471802
Experimental chronic arthritis and granulomatous inflammation induced by bifidobacterium cell walls.	2001 Jul-Aug	11439164
Metabolic effects of arginine addition to the enteral feeding of critically ill patients.	2001 Jul-Aug	11434648
The remarkable hydrophobic effect of a fatty acid side chain on the microbial growth promoting activity of a synthetic siderophore.	2001 Jun	11508848
Sustained oral lysine supplementation in ornithine delta-aminotransferase deficiency.	2001 Jun	11486915
Detection of neonatal argininosuccinate lyase deficiency by serum tandem mass spectrometry.	2001 Jun	11486903
Methohexital affects neutrophil (PMN) dynamic free amino acid pool and immune functions in vitro.	2001 Jun	11412289
HHH syndrome associated with callosal agenesis and disordered neuronal migration.	2001 Jun	11409836
Involvement of a transformylase enzyme in siderophore synthesis in Pseudomonas aeruginosa.	2001 Jun	11390682
Occupational lead exposure and amino acid profiles and liver function tests in industrial workers.	2001 Jun	11382350
Evidence for a spontaneous nitric oxide release from the rat median eminence: influence on gonadotropin-releasing hormone release.	2001 Jun	11356681
Regulation of loblolly pine (Pinus taeda L.) arginase in developing seedling tissue during germination and post-germinative growth.	2001 Mar	11414614
Gastrectomized patients are in a state of chronic protein malnutrition analyses of 23 amino acids.	2001 Mar-Apr	11379360
[Gyrate atrophy and craniopharyngioma: a case report].	2001 May	11397989
A new technique to elevate night time growth hormone release and a potential growth hormone feedback control loop.	2001 May	11388776
Adverse effects of excess lysine in calves.	2001 May	11374556
Expression, purification, and characterization of human type II arginase.	2001 May 1	11370664
Biogenic amines in wines: role of lactic acid bacteria.	2001 May 15	11356560
Synthesis and antifungal activities of novel 1,3-beta-D-glucan synthase inhibitors. Part 2.	2001 May 21	11392535
A new receptor molecule for lysine and histidine in water: strong binding of basic amino acid esters by a macrocyclic host.	2001 May 31	11405664
Convenient method for the determination of arginine and its related compounds in rumen fluid by reversed-phase high-performance liquid chromatography.	2001 May 5	11393720
Localization of amino acid neurotransmitters following in vitro ischemia and anoxia in the rat retina.	2001 May-Jun	11497418
Polyamine synthesis and interconversion by the Microsporidian Encephalitozoon cuniculi.	2001 May-Jun	11411847
Effect of L-arginine on the course of experimental colitis.	2001 Oct	11534936
SREA is involved in regulation of siderophore biosynthesis, utilization and uptake in Aspergillus nidulans.	2001 Sep	11555288
Induction of L-arginine transport is inhibited by atrial natriuretic peptide: a peptide hormone as a novel regulator of inducible nitric-oxide synthase substrate availability.	2001 Sep	11502871
Clinical and molecular findings in hyperornithinemia-hyperammonemia-homocitrullinuria syndrome.	2001 Sep 11	11552031
Interstrand side chain--side chain interactions in a designed beta-hairpin: significance of both lateral and diagonal pairings.	2001 Sep 12	11535071
Allosteric control of the oligomerization of carbamoyl phosphate synthetase from Escherichia coli.	2001 Sep 18	11551199

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Measurement of Ca2+-dependent chloride currents in Xenopus laevis oocytes facilitated the deorphanization of human family C G-protein-coupled receptor hGPRC6A/homologous goldfish 5.24 receptor chimeric construct (h6A/5.24) and identification of L-amino acids as agonists. The most active agonists were L-Arg, L-Lys, and L-ornithine, suggesting that these may function as endogenous signaling molecules (only L-Arg, L-Lys, and L-ornithine were able to activate h6A/5.24 at 10 uM concentration).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:51:04 GMT 2023` Edited by `admin` on `Fri Dec 15 18:51:04 GMT 2023`
Record UNII	9D6YZ105SN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ORNITHINE PHENYLACETATE

Official Name

English

L-ORNITHINE, BENZENEACETATE (1:1)

Common Name

English

(2S)-2,5-Diaminopentanoic acid phenylacetate (1:1)

Systematic Name

English

L-OP

Code

English

OCR-002

Code

English

ORNITHINE PHENYLACETATE [USAN]

Common Name

English

OP

Code

English

Ornithine phenylacetate [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

287309