L-(-)-Ornithine

HCID 6262CAS 25104-12-5

Basic information

Standard SMILES
NCCC[C@H](N)C(=O)O
InChIKey
AHLPHDHHMVZTML-BYPYZUCNSA-N
Molecular formula
C5H12N2O2
Average molar mass
132.16 g/mol
Monoisotopic mass
132.08987762

Overview

L-ornithine is an optically active form of ornithine having L-configuration. It has a role as a hepatoprotective agent, a mouse metabolite and an algal metabolite. It is an ornithine and a non-proteinogenic L-alpha-amino acid. It is a conjugate base of a L-ornithinium(1+). It is a conjugate acid of a L-ornithinate. It is an enantiomer of a D-ornithine.

Names & identifiers

Preferred name
L-(-)-Ornithine
IUPAC
(2S)-2,5-diaminopentanoic acid
English name
polyornithine
Molecular formula
C5H12N2O2
Molecular weight
132.16098

Names & synonyms

L-ornithineornithine70-26-8(S)-2,5-Diaminopentanoic acid(S)-Ornithine(S)-2,5-diaminovaleric acid(2S)-2,5-diaminopentanoic acid(S)-alpha,delta-Diaminovaleric acidOrnitina(+)-S-OrnithineOrnithinum(S)-2,5-Diaminopentanoate
Show more names
polyornithineL-Ornithine, homopolymer
L-(-)-OrnithineNSC-758894E524N2IXA3CHEBI:15729DTXSID00883219CHEBI:18257DTXSID00860383RefChem:856923

Database identifiers

CAS
25104-12-5、3184-13-2、70-26-8
PubChem CID
6262
DTXSID
DTXSID00883219
ChEMBL
CHEMBL446143
ChEBI
CHEBI:15729
UNII
E524N2IXA3
EC Number
200-731-7
Nikkaji
J9.177D

Properties

Computed structural properties

XLogP
-4.4
Topological polar surface area
89.3 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
9

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP-4.22
Solubility · 2 items

Appreciable

620 mg/mL

Physicochemical properties

EWG's Food Scores
1 · 1

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (6 of 6) of all reports.

Not Classified

Aggregated GHS information provided per 6 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: L-Ornithine

Status: Active Update: 13-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23820

L-Ornithine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - L-Ornithine: Environment tier I assessment
Hazard Classes and CategoriesNot Classified

Toxicology

Health Effects · 1 item

Chronically high levels of ornithine are associated with at least 9 inborn errors of metabolism including: Cystathionine Beta-Synthase Deficiency, Hyperornithinemia with gyrate atrophy, Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, Hyperprolinemia Type II, Lysinuric Protein Intolerance, Ornithine Aminotransferase Deficiency, Ornithine Transcarbamylase Deficiency and Prolinemia Type II.

Exposure RoutesAbsorbed from the small intestine via a sodium-dependent active transport process
Toxicity Summary · 1 item

L-Ornithine is metabolised to L-arginine. L-arginine stimulates the pituitary release of growth hormone. Burns or other injuries affect the state of L-arginine in tissues throughout the body. As De novo synthesis of L-arginine during these conditions is usually not sufficient for normal immune function, nor for normal protein synthesis, L-ornithine may have immunomodulatory and wound-healing activities under these conditions (by virtue of its metabolism to L-arginine).

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataOral, rat LD<sub>50</sub> = 10000 mg/kg

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

A non-essential and nonprotein amino acid, ornithine is critical for the production of the body's proteins, enzymes and muscle tissue. Ornithine plays a central role in the urea cycle and is important for the disposal of excess nitrogen (ammonia). Ornithine is the starting point for the synthesis of many polyamines such as putrescine and spermine. Ornithine supplements are claimed to enhance the release of growth hormone and to burn excess body fat. Ornithine is necessary for proper immune function and good liver function.

Mechanism of Action · 1 item

L-Ornithine is metabolised to L-arginine. L-arginine stimulates the pituitary release of growth hormone. Burns or other injuries affect the state of L-arginine in tissues throughout the body. As De novo synthesis of L-arginine during these conditions is usually not sufficient for normal immune function, nor for normal protein synthesis, L-ornithine may have immunomodulatory and wound-healing activities under these conditions (by virtue of its metabolism to L-arginine).

Metabolism/Metabolites · 2 items

Ornithine undergoes extensive metabolism in the liver to L-arginine, polyamines, and proline, and several other metabolites.

Ornithine undergoes extensive metabolism in the liver to L-arginine, polyamines, and proline, and several other metabolites.

Absorption, Distribution and ExcretionAbsorbed from the small intestine via a sodium-dependent active transport process
Tissue LocationsEpidermis
Cellular LocationsExtracellular

Uses & manufacturing

Uses · 3 items

A non-essential amino acid; Has been used in the treatment of hyperammonemia; [Merck Index]

Use (kg; approx.) in Germany (2009): >25000

Used for nutritional supplementation, also for treating dietary shortage or imbalance. It has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing.

Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationL-Ornithine: ACTIVE

Suppliers2 total

Additional notes · 1 item

DefinitionChEBI: L-ornithine is an optically active form of ornithine having L-configuration. It has a role as a hepatoprotective agent, an algal metabolite and a mouse metabolite. It is an ornithine and a non-proteinogenic L-alpha-amino acid. It is a conjugate base of a L-ornithinium(1+). It is a conjugate acid of a L-ornithinate. It is an enantiomer of a D-ornithine.

Related reactions

51 records

Linked notes

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