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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 of ORNITHINE PHENYLACETATE

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
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

Curator's Comment: Known to be CNS active in mouse. Human data not available.

Originator

Curator's Comment: Krebs, H.A. and Henseleit, K. Z. Physiol. Chem. 1932; 210: 33-66

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q5T6X5
Gene ID: 222545.0
Gene Symbol: GPRC6A
Target Organism: Homo sapiens (Human)
112.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
L-Ornithine

Approved Use

Used for nutritional supplementation, also for treating dietary shortage or imbalance.
PubMed

PubMed

TitleDatePubMed
The genome of Mycobacterium leprae: a minimal mycobacterial gene set.
2001
Cancer chemopreventive activities of S-3-1, a synthetic derivative of danshinone.
2001
Conservation of the binding site for the arginine repressor in all bacterial lineages.
2001
Possible implications of arginase and diamine oxidase in prostatic carcinoma.
2001
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
Transgenic manipulation of the metabolism of polyamines in poplar cells.
2001 Apr
Effects of dietary L-arginine on structure and function of flow-restricted vein grafts.
2001 Apr
Ornithine transcarbamylase deficiency unmasked because of gastrointestinal bleeding.
2001 Apr
Glutamine supplementation promotes anaplerosis but not oxidative energy delivery in human skeletal muscle.
2001 Apr
Effects of dietary salt intake on plasma arginine.
2001 Apr
Derivatization and chromatographic behavior of the o-phthaldialdehyde amino acid derivatives obtained with various SH-group-containing additives.
2001 Apr 13
CCAAT/enhancer-binding protein beta is required for activation of genes for ornithine cycle enzymes by glucocorticoids and glucagon in primary-cultured hepatocytes.
2001 Apr 6
Hyperornithinemia associated with gyrate atrophy of the choroid and retina in a child with myopia.
2001 Aug
The potential mechanism for glutamine-induced collagen biosynthesis in cultured human skin fibroblasts.
2001 Aug
A bridge between the RNA and protein worlds? Accelerating delivery of chemical reactivity to RNA and DNA by a specific short peptide (AAKK)(4).
2001 Feb
Plasma levels of amino acids and hypermetabolism in patients with chronic obstructive pulmonary disease.
2001 Feb
Nitric oxide generation by hemocytes of the mussel Mytilus galloprovincialis.
2001 Feb
Macrophage arginase promotes tumor cell growth and suppresses nitric oxide-mediated tumor cytotoxicity.
2001 Feb 1
Arginine catabolism by Thermanaerovibrio acidaminovorans.
2001 Feb 20
Synthesis of a conformationally restricted substrate analogue of siderophore biosynthetases.
2001 Feb 22
Synthesis and biological activity of novel macrocyclic antifungals: acylated conjugates of the ornithine moiety of the lipopeptidolactone FR901469.
2001 Feb 26
Transforming growth factor-beta(1) stimulates L-arginine transport and metabolism in vascular smooth muscle cells: role in polyamine and collagen synthesis.
2001 Feb 27
Ornithinimicrobium humiphilum gen. nov., sp. nov., a novel soil actinomycete with L-ornithine in the peptidoglycan.
2001 Jan
Urea flux in beef steers: effects of forage species and nitrogen fertilization.
2001 Jul
Antifungal activity of three spermidine conjugates.
2001 Jul 24
Abnormal elution behavior of ornitine derivatized with 1-fluoro-2,4-dinitrophenyl-5-leucinamide in advanced Marfey's method.
2001 Jul 6
Sustained oral lysine supplementation in ornithine delta-aminotransferase deficiency.
2001 Jun
Formation pathways for lysine-arginine cross-links derived from hexoses and pentoses by Maillard processes: unraveling the structure of a pentosidine precursor.
2001 Jun 29
Tryptic hydrolysis of hGH-RH(1-29)-NH2 analogues containing Lys or Orn in positions 12 and 21.
2001 Mar
Plasma levels of arginine, ornithine, and urea and growth performance of broilers fed supplemental L-arginine during cool temperature exposure.
2001 Mar
Clinicopathological study on eyes from cases of Fukuyama type congenital muscular dystrophy.
2001 Mar
Chromatographic quantification of argpyrimidine, a methylglyoxal-derived product in tissue proteins: comparison with pentosidine.
2001 Mar
Alterations in arginine metabolic enzymes in trauma.
2001 Mar
Nitric oxide synthase isoform expression in a porcine model of granulation tissue formation.
2001 Mar
In vivo confocal Raman microspectroscopy of the skin: noninvasive determination of molecular concentration profiles.
2001 Mar
Arginase I expression and activity in human mononuclear cells after injury.
2001 Mar
Induction of arginases I and II in cornea during herpes simplex virus infection.
2001 Mar
Mechanistic and metabolic inferences from the binding of substrate analogues and products to arginase.
2001 Mar 6
Gastrectomized patients are in a state of chronic protein malnutrition analyses of 23 amino acids.
2001 Mar-Apr
Facilitatory and neurotoxic effects of intravitreal ornithine on the electroretinographic responses of albino rats.
2001 Mar-Apr
Adverse effects of excess lysine in calves.
2001 May
Significance of arginase and ornithine in malignant tumors of the human skin.
2001 May
Biogenic amines in wines: role of lactic acid bacteria.
2001 May 15
Synthesis and antifungal activities of novel 1,3-beta-D-glucan synthase inhibitors. Part 2.
2001 May 21
Crystallographic studies on endothelial nitric oxide synthase complexed with nitric oxide and mechanism-based inhibitors.
2001 May 8
Localization of amino acid neurotransmitters following in vitro ischemia and anoxia in the rat retina.
2001 May-Jun
Effect of L-arginine on the course of experimental colitis.
2001 Oct
SREA is involved in regulation of siderophore biosynthesis, utilization and uptake in Aspergillus nidulans.
2001 Sep
Clinical and molecular findings in hyperornithinemia-hyperammonemia-homocitrullinuria syndrome.
2001 Sep 11
Allosteric control of the oligomerization of carbamoyl phosphate synthetase from Escherichia coli.
2001 Sep 18
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
USAN   WHO-DD  
USAN  
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
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
EU-Orphan Drug EU/3/11/945
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
Code System Code Type Description
FDA UNII
9D6YZ105SN
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
PUBCHEM
44247677
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
USAN
XX-162
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
SMS_ID
100000177166
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
CAS
952154-79-9
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
NCI_THESAURUS
C175179
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID90241788
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
MESH
C572232
Created by admin on Fri Dec 15 18:51:04 GMT 2023 , Edited by admin on Fri Dec 15 18:51:04 GMT 2023
PRIMARY
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ACTIVE MOIETY