U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ORNITHINE

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
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
Possible implications of arginase and diamine oxidase in prostatic carcinoma.
2001
Agmatine deiminase from maize shoots: purification and properties.
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
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
Intrahepatic amino acid and glucose metabolism in a D-galactosamine-induced rat liver failure model.
2001 Aug
The potential mechanism for glutamine-induced collagen biosynthesis in cultured human skin fibroblasts.
2001 Aug
The Plasmodium falciparum bifunctional ornithine decarboxylase, S-adenosyl-L-methionine decarboxylase, enables a well balanced polyamine synthesis without domain-domain interaction.
2001 Aug 10
Amino acid derived sulfonamide hydroxamates as inhibitors of procollagen C-proteinase: solid-phase synthesis of ornithine analogues.
2001 Aug 20
Classical and slow-binding inhibitors of human type II arginase.
2001 Aug 7
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
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 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
Analysis of differentially expressed genes in human hepatocellular carcinoma using suppression subtractive hybridization.
2001 Jul 20
An invariant threonine is involved in self-catalyzed cleavage of the precursor protein for ornithine acetyltransferase.
2001 Jul 6
Metabolic effects of arginine addition to the enteral feeding of critically ill patients.
2001 Jul-Aug
Detection of neonatal argininosuccinate lyase deficiency by serum tandem mass spectrometry.
2001 Jun
Methohexital affects neutrophil (PMN) dynamic free amino acid pool and immune functions in vitro.
2001 Jun
HHH syndrome associated with callosal agenesis and disordered neuronal migration.
2001 Jun
Filobacillus milensis gen. nov., sp. nov., a new halophilic spore-forming bacterium with Orn-D-Glu-type peptidoglycan.
2001 Mar
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
Mechanistic and metabolic inferences from the binding of substrate analogues and products to arginase.
2001 Mar 6
Facilitatory and neurotoxic effects of intravitreal ornithine on the electroretinographic responses of albino rats.
2001 Mar-Apr
[Gyrate atrophy and craniopharyngioma: a case report].
2001 May
A new technique to elevate night time growth hormone release and a potential growth hormone feedback control loop.
2001 May
Significance of arginase and ornithine in malignant tumors of the human skin.
2001 May
Argpyrimidine, a blue fluorophore in human lens proteins: high levels in brunescent cataractous lenses.
2001 May
Biogenic amines in wines: role of lactic acid bacteria.
2001 May 15
A new receptor molecule for lysine and histidine in water: strong binding of basic amino acid esters by a macrocyclic host.
2001 May 31
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
Polyamine synthesis and interconversion by the Microsporidian Encephalitozoon cuniculi.
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
Interstrand side chain--side chain interactions in a designed beta-hairpin: significance of both lateral and diagonal pairings.
2001 Sep 12
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 15:10:01 UTC 2023
Edited
by admin
on Fri Dec 15 15:10:01 UTC 2023
Record UNII
E524N2IXA3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORNITHINE
INCI   INN   MART.   MI   WHO-DD  
INCI   INN  
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
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LOINC 2674-0
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NCI_THESAURUS C29596
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LOINC 44344-0
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LOINC 53395-0
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LOINC 32261-0
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DSLD 170 (Number of products:81)
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LOINC 15133-2
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LOINC 13408-0
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LOINC 47714-1
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LOINC 53396-8
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LOINC 2679-9
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LOINC 22725-6
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LOINC 27335-9
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LOINC 2681-5
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LOINC 13786-9
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LOINC 30049-1
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LOINC 17389-8
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NCI_THESAURUS C68442
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LOINC 27219-5
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LOINC 75215-4
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LOINC 25965-5
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DSLD 1819 (Number of products:212)
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LOINC 75214-7
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LOINC 2675-7
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LOINC 53155-8
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LOINC 2678-1
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LOINC 2680-7
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LOINC 20652-4
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LOINC 22682-9
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LOINC 32260-2
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LOINC 25491-2
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LOINC 25966-3
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LOINC 57011-9
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Code System Code Type Description
DRUG BANK
DB00129
Created by admin on Fri Dec 15 15:10:01 UTC 2023 , Edited by admin on Fri Dec 15 15:10:01 UTC 2023
PRIMARY
DAILYMED
E524N2IXA3
Created by admin on Fri Dec 15 15:10:01 UTC 2023 , Edited by admin on Fri Dec 15 15:10:01 UTC 2023
PRIMARY
SMS_ID
100000083329
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PRIMARY
NCI_THESAURUS
C29611
Created by admin on Fri Dec 15 15:10:01 UTC 2023 , Edited by admin on Fri Dec 15 15:10:01 UTC 2023
PRIMARY
RXCUI
7704
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PRIMARY
CAS
70-26-8
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PRIMARY
MESH
D009952
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PRIMARY
EPA CompTox
DTXSID00883219
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PRIMARY
EVMPD
SUB09466MIG
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PRIMARY
CHEBI
44667
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PRIMARY
NSC
758894
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PRIMARY
FDA UNII
E524N2IXA3
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PRIMARY
CHEBI
18257
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PRIMARY
PUBCHEM
6262
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PRIMARY
MERCK INDEX
m8239
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PRIMARY Merck Index
INN
6167
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PRIMARY
RXCUI
314709
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ALTERNATIVE
ECHA (EC/EINECS)
200-731-7
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PRIMARY
CHEBI
46911
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PRIMARY
DRUG CENTRAL
3401
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PRIMARY
CHEBI
15729
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PRIMARY
ChEMBL
CHEMBL446143
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PRIMARY
WIKIPEDIA
ORNITHINE
Created by admin on Fri Dec 15 15:10:01 UTC 2023 , Edited by admin on Fri Dec 15 15:10:01 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
DEGRADENT -> PARENT
Precursor is Ornithine
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
ACTIVE MOIETY