ORNITHINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H12N2O2
Molecular Weight	132.161
Optical Activity	( + )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCC[C@H](N)C(O)=O

InChI

InChIKey=AHLPHDHHMVZTML-BYPYZUCNSA-N

InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/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

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
Ophthalmologic heterogeneity in subjects with gyrate atrophy of choroid and retina harboring the L402P mutation of ornithine aminotransferase.	2001 Apr	11297489
Glutamine supplementation promotes anaplerosis but not oxidative energy delivery in human skeletal muscle.	2001 Apr	11254475
Analysis of amino acids in human serum by isocratic reversed-phase high-performance liquid chromatography with electrochemical detection.	2001 Apr 13	11355826
Derivatization and chromatographic behavior of the o-phthaldialdehyde amino acid derivatives obtained with various SH-group-containing additives.	2001 Apr 13	11355824
Is hyperprolinemia type I actually a benign trait? Report of a case with severe neurologic involvement and vigabatrin intolerance.	2001 Aug	11510941
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
Evidence for inducible nitric-oxide synthase expression and activity in vascular smooth muscle of streptozotocin-diabetic rats.	2001 Feb	11160605
Arginine catabolism by Thermanaerovibrio acidaminovorans.	2001 Feb 20	11179661
Synthesis of a conformationally restricted substrate analogue of siderophore biosynthetases.	2001 Feb 22	11178814
Synthesis and biological activity of novel macrocyclic antifungals: acylated conjugates of the ornithine moiety of the lipopeptidolactone FR901469.	2001 Feb 26	11229752
Antifungal activity of three spermidine conjugates.	2001 Jul 24	11470370
An invariant threonine is involved in self-catalyzed cleavage of the precursor protein for ornithine acetyltransferase.	2001 Jul 6	11320085
Methohexital affects neutrophil (PMN) dynamic free amino acid pool and immune functions in vitro.	2001 Jun	11412289
Evidence for a spontaneous nitric oxide release from the rat median eminence: influence on gonadotropin-releasing hormone release.	2001 Jun	11356681
Filobacillus milensis gen. nov., sp. nov., a new halophilic spore-forming bacterium with Orn-D-Glu-type peptidoglycan.	2001 Mar	11324591
Chromatographic quantification of argpyrimidine, a methylglyoxal-derived product in tissue proteins: comparison with pentosidine.	2001 Mar	11237339
Alterations in arginine metabolic enzymes in trauma.	2001 Mar	11236905
Nitric oxide synthase isoform expression in a porcine model of granulation tissue formation.	2001 Mar	11231463
In vivo confocal Raman microspectroscopy of the skin: noninvasive determination of molecular concentration profiles.	2001 Mar	11231318
Arginase I expression and activity in human mononuclear cells after injury.	2001 Mar	11224628
Rat colon ornithine and arginine metabolism: coordinated effects after proliferative stimuli.	2001 Mar	11171621
Mechanistic and metabolic inferences from the binding of substrate analogues and products to arginase.	2001 Mar 6	11258880
Adverse effects of excess lysine in calves.	2001 May	11374556
Significance of arginase and ornithine in malignant tumors of the human skin.	2001 May	11329531
Nitric oxide modulates cardiac performance in the heart of Anguilla anguilla.	2001 May	11316492
Expression, purification, and characterization of human type II arginase.	2001 May 1	11370664
Synthesis and antifungal activities of novel 1,3-beta-D-glucan synthase inhibitors. Part 2.	2001 May 21	11392535
Crystallographic studies on endothelial nitric oxide synthase complexed with nitric oxide and mechanism-based inhibitors.	2001 May 8	11331003
Polyamine synthesis and interconversion by the Microsporidian Encephalitozoon cuniculi.	2001 May-Jun	11411847
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

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 15:10:01 GMT 2023` Edited by `admin` on `Fri Dec 15 15:10:01 GMT 2023`
Record UNII	E524N2IXA3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ORNITHINE

Official Name

English

ORNITHINE [MART.]

Common Name

English

ORNITHINE [MI]

Common Name

English

L-ORNITHINE

Systematic Name

English

ORNITHINE [INCI]

Common Name

English

ornithine [INN]

Common Name

English

LYSINE ACETATE IMPURITY E [EP IMPURITY]

Common Name

English

(+)-S-ORNITHINE

Common Name

English

Ornithine [WHO-DD]

Common Name

English

ORNITHINE, (L)-ISOMER

Common Name

English

NSC-758894

Code

English

Classification Tree Code System Code

LOINC

13379-3