Ornithine
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Basic Info
| Common Name | Ornithine(F05342) |
| 2D Structure | |
| Description | 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. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine produced in the cytosol to be converted to citrulline, it must first cross the inner mitochondrial membrane into the mitochondrial matrix where it is carbamylated by ornithine transcarbamylase. This transfer is mediated by the mitochondrial ornithine transporter (SLC25A15; AF112968; ORNT1). Mutations in the mitochondrial ornithine transporter result in hyperammonemia, hyperornithinemia, homocitrullinuria (HHH) syndrome, a disorder of the urea cycle. The pathophysiology of thef the disease may involve diminished ornithine transport into mitochondria, resulting in ornithine accumulation in the cytoplasm and reduced ability to clear carbamoyl phosphate and ammonia loads. (OMIM 838970). (A3420). |
| FRCD ID | F05342 |
| CAS Number | 70-26-8 |
| PubChem CID | 6262 |
| Formula | C5H12N2O2 |
| IUPAC Name | (2S)-2,5-diaminopentanoic acid |
| InChI Key | AHLPHDHHMVZTML-BYPYZUCNSA-N |
| InChI | InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1 |
| Canonical SMILES | C(CC(C(=O)O)N)CN |
| Isomeric SMILES | C(C[C@@H](C(=O)O)N)CN |
| Wikipedia | Ornithine |
| Synonyms |
Ornithine [INN]
L-ornithine
ornithine
70-26-8
(S)-2,5-Diaminopentanoic acid
(S)-Ornithine
L-Norvaline, 5-amino-
(S)-alpha,delta-Diaminovaleric acid
Ornithinum [Latin]
Ornitina [Spanish]
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids |
| Direct Parent | L-alpha-amino acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | L-alpha-amino acid - Fatty acid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Primary aliphatic amine - Organic nitrogen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 132.163 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Complexity | 95 |
| Monoisotopic Mass | 132.09 |
| Exact Mass | 132.09 |
| XLogP | -4.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7613 |
| Human Intestinal Absorption | HIA+ | 0.8449 |
| Caco-2 Permeability | Caco2- | 0.7431 |
| P-glycoprotein Substrate | Non-substrate | 0.6568 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9856 |
| Non-inhibitor | 0.9681 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8847 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5690 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8464 |
| CYP450 2D6 Substrate | Non-substrate | 0.7517 |
| CYP450 3A4 Substrate | Non-substrate | 0.8238 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9653 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9639 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9786 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9659 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9327 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9931 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9771 |
| Non-inhibitor | 0.9663 | |
| AMES Toxicity | AMES toxic | 0.8541 |
| Carcinogens | Non-carcinogens | 0.8407 |
| Fish Toxicity | Low FHMT | 0.8832 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9936 |
| Honey Bee Toxicity | Low HBT | 0.7113 |
| Biodegradation | Ready biodegradable | 0.8711 |
| Acute Oral Toxicity | IV | 0.5561 |
| Carcinogenicity (Three-class) | Non-required | 0.7043 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.3771 | LogS |
| Caco-2 Permeability | 0.5088 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.0540 | LD50, mol/kg |
| Fish Toxicity | 3.1484 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.0739 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Novel photoluminescence enzyme immunoassay based on supramolecular host-guest recognition using L-arginine/6-aza-2-thiothymine-stabilized gold nanocluster. | Biosens Bioelectron | 2018 Jun 30 | 29529510 |
| Comprehensive Dissection of Metabolic Changes in Albino and Green Tea Cultivars. | J Agric Food Chem | 2018 Feb 28 | 29397711 |
| Transcriptome analysis shows activation of the arginine deiminase pathway inLactococcus lactis as a response to ethanol stress. | Int J Food Microbiol | 2017 Sep 18 | 28644989 |
| Safety of Lactobacillus plantarum ST8Sh and Its Bacteriocin. | Probiotics Antimicrob Proteins | 2017 Sep | 28233282 |
| Obesity-induced vascular dysfunction and arterial stiffening requires endothelialcell arginase 1. | Cardiovasc Res | 2017 Nov 1 | 29048462 |
| Rapid discrimination of strain-dependent fermentation characteristics amongLactobacillus strains by NMR-based metabolomics of fermented vegetable juice. | PLoS One | 2017 Jul 31 | 28759594 |
| Regulation of Botulinum Neurotoxin Synthesis and Toxin Complex Formation by Arginine and Glucose in Clostridium botulinum ATCC 3502. | Appl Environ Microbiol | 2017 Jul 1 | 28455330 |
| Exploring polyamine metabolism of Alternaria alternata to target new substances to control the fungal infection. | Food Microbiol | 2017 Aug | 28400003 |
| Dietary fibers influence the intestinal SCFAs and plasma metabolites profiling ingrowing pigs. | Food Funct | 2016 Nov 9 | 27754504 |
| Protein RS1 (RSC1A1) Downregulates the Exocytotic Pathway of Glucose Transporter SGLT1 at Low Intracellular Glucose via Inhibition of Ornithine Decarboxylase. | Mol Pharmacol | 2016 Nov | 27555600 |
| Cloning, expression, and characterization of a thermostable l-arginase fromGeobacillus thermodenitrificans NG80-2 for l-ornithine production. | Biotechnol Appl Biochem | 2016 May | 25908562 |
| Metabolic and clinical response to Escherichia coli lipopolysaccharide in layer pullets of different genetic backgrounds supplied with graded dietary L-arginine. | Poult Sci | 2016 Mar | 26740139 |
| Manganese-induced regulations in growth, yield formation, quality characters,rice aroma and enzyme involved in 2-acetyl-1-pyrroline biosynthesis in fragrantrice. | Plant Physiol Biochem | 2016 Jun | 26995311 |
| Changes in the metabolome of rats after exposure to arginine andN-carbamylglutamate in combination with diquat, a compound that causes oxidative stress, assessed by 1H NMR spectroscopy. | Food Funct | 2016 Feb | 26732548 |
| Effects of Fungicide Treatment on Free Amino Acid Concentration andAcrylamide-Forming Potential in Wheat. | J Agric Food Chem | 2016 Dec 28 | 27977182 |
| Analysis of Gambierdiscus transcriptome data supports ancient origins of mixotrophic pathways in dinoflagellates. | Environ Microbiol | 2016 Dec | 27485969 |
| Chemical Composition, Antioxidant, and Antibacterial Activity of Wood Vinegarfrom Litchi chinensis. | Molecules | 2016 Aug 30 | 27589711 |
| Gene expressions and metabolomic research on the effects of polyphenols from the involucres of Castanea mollissima Blume on heat-stressed broilers chicks. | Poult Sci | 2016 Aug 1 | 27209434 |
| Lysozyme affects the microbial catabolism of free arginine in raw-milk hardcheeses. | Food Microbiol | 2016 Aug | 27052697 |
| Isolation and Structural Elucidation of Brevibacillin, an AntimicrobialLipopeptide from Brevibacillus laterosporus That Combats Drug-ResistantGram-Positive Bacteria. | Appl Environ Microbiol | 2016 Apr 18 | 26921428 |
Targets
- General Function:
- Manganese ion binding
- Gene Name:
- ARG1
- Uniprot ID:
- P05089
- Molecular Weight:
- 34734.655 Da
References
- El Alami M, Dubois E, Oudjama Y, Tricot C, Wouters J, Stalon V, Messenguy F: Yeast epiarginase regulation, an enzyme-enzyme activity control: identification of residues of ornithine carbamoyltransferase and arginase responsible for enzyme catalytic and regulatory activities. J Biol Chem. 2003 Jun 13;278(24):21550-8. Epub 2003 Apr 4. [12679340 ]
- General Function:
- Glycine amidinotransferase activity
- Specific Function:
- Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
- Gene Name:
- GATM
- Uniprot ID:
- P50440
- Molecular Weight:
- 48455.01 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Phospholipid binding
- Gene Name:
- OTC
- Uniprot ID:
- P00480
- Molecular Weight:
- 39934.775 Da
References
- Morizono H, Cabrera-Luque J, Shi D, Gallegos R, Yamaguchi S, Yu X, Allewell NM, Malamy MH, Tuchman M: Acetylornithine transcarbamylase: a novel enzyme in arginine biosynthesis. J Bacteriol. 2006 Apr;188(8):2974-82. [16585758 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
- Gene Name:
- SLC7A3
- Uniprot ID:
- Q8WY07
- Molecular Weight:
- 67168.31 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor.
- Gene Name:
- SLC7A1
- Uniprot ID:
- P30825
- Molecular Weight:
- 67637.62 Da
References
- Cerec V, Piquet-Pellorce C, Aly HA, Touzalin AM, Jegou B, Bauche F: Multiple pathways for cationic amino acid transport in rat seminiferous tubule cells. Biol Reprod. 2007 Feb;76(2):241-9. Epub 2006 Oct 25. [17065601 ]
- Specific Function:
- Ornithine transport across inner mitochondrial membrane, from the cytoplasm to the matrix.
- Gene Name:
- SLC25A2
- Uniprot ID:
- Q9BXI2
- Molecular Weight:
- 32580.07 Da
References
- Camacho JA, Rioseco-Camacho N, Andrade D, Porter J, Kong J: Cloning and characterization of human ORNT2: a second mitochondrial ornithine transporter that can rescue a defective ORNT1 in patients with the hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, a urea cycle disorder. Mol Genet Metab. 2003 Aug;79(4):257-71. [12948741 ]
- General Function:
- Pyridoxal phosphate binding
- Gene Name:
- OAT
- Uniprot ID:
- P04181
- Molecular Weight:
- 48534.39 Da
References
- Levillain O, Balvay S, Peyrol S: Localization and differential expression of arginase II in the kidney of male and female mice. Pflugers Arch. 2005 Feb;449(5):491-503. Epub 2004 Dec 23. [15616821 ]
- General Function:
- Ornithine decarboxylase inhibitor activity
- Specific Function:
- Ornithine decarboxylase (ODC) antizyme protein that negatively regulates ODC activity and intracellular polyamine biosynthesis and uptake by binding to and targeting ODC1 for degradation (PubMed:17900240). Stabilizes AZIN2 by interfering with its ubiquitination. Also inhibits cellular uptake of polyamines by inactivating the polyamine uptake transporter. SMAD1/OAZ1/PSMB4 complex mediates the degradation of the CREBBP/EP300 repressor SNIP1. Involved in the translocation of AZNI2 from ER-Golgi intermediate compartment (ERGIC) to the cytosol.
- Gene Name:
- OAZ1
- Uniprot ID:
- P54368
- Molecular Weight:
- 25405.265 Da
References
- Janne J, Alhonen L, Pietila M, Keinanen TA: Genetic approaches to the cellular functions of polyamines in mammals. Eur J Biochem. 2004 Mar;271(5):877-94. [15009201 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Involved in the transport of the cationic amino acids (arginine, lysine and ornithine).
- Gene Name:
- SLC7A4
- Uniprot ID:
- O43246
- Molecular Weight:
- 68267.17 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Ornithine transport across inner mitochondrial membrane, from the cytoplasm to the matrix.
- Gene Name:
- SLC25A15
- Uniprot ID:
- Q9Y619
- Molecular Weight:
- 32735.96 Da
References
- Camacho JA, Mardach R, Rioseco-Camacho N, Ruiz-Pesini E, Derbeneva O, Andrade D, Zaldivar F, Qu Y, Cederbaum SD: Clinical and functional characterization of a human ORNT1 mutation (T32R) in the hyperornithinemia-hyperammonemia-homocitrullinuria (HHH) syndrome. Pediatr Res. 2006 Oct;60(4):423-9. Epub 2006 Aug 28. [16940241 ]
- General Function:
- Ornithine decarboxylase inhibitor activity
- Specific Function:
- Ornithine decarboxylase (ODC) antizyme protein that negatively regulates ODC activity and intracellular polyamine biosynthesis and uptake by binding to ODC1 without promoting its degradation (PubMed:17900240). Involved in the translocation of AZNI2 from ER-Golgi intermediate compartment (ERGIC) to the cytosol.
- Gene Name:
- OAZ2
- Uniprot ID:
- O95190
- Molecular Weight:
- 21010.94 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Putrescine transmembrane transporter activity
- Specific Function:
- Ornithine decarboxylase (ODC) antizyme protein that negatively regulates ODC activity and intracellular polyamine biosynthesis and uptake by binding to ODC1 without promoting its degradation (PubMed:17900240). Stabilizes AZIN2 by interfering with its ubiquitination. Involved in the translocation of AZNI2 from ER-Golgi intermediate compartment (ERGIC) to the cytosol. Probably plays a key role in spermatogenesis by regulating the intracellular concentration of polyamines in haploid germ cells.
- Gene Name:
- OAZ3
- Uniprot ID:
- Q9UMX2
- Molecular Weight:
- 27412.93 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Metal ion binding
- Specific Function:
- May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to NO synthase. Since NO synthase is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase II plays a role in both male and female sexual arousal. It is therefore a potential target for the treatment of male and female sexual arousal disorders.
- Gene Name:
- ARG2
- Uniprot ID:
- P78540
- Molecular Weight:
- 38577.515 Da
References
- Rodriguez PC, Zea AH, DeSalvo J, Culotta KS, Zabaleta J, Quiceno DG, Ochoa JB, Ochoa AC: L-arginine consumption by macrophages modulates the expression of CD3 zeta chain in T lymphocytes. J Immunol. 2003 Aug 1;171(3):1232-9. [12874210 ]
- General Function:
- Low-affinity l-arginine transmembrane transporter activity
- Specific Function:
- Functions as permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine); the affinity for its substrates differs between isoforms created by alternative splicing. Isoform 1 functions as permease that mediates the transport of the cationic amino acids (arginine, lysine and ornithine), and it has much higher affinity for arginine than isoform 2. Isoform 2 functions as low-affinity, high capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) (PubMed:9174363). May play a role in classical or alternative activation of macrophages via its role in arginine transport.
- Gene Name:
- SLC7A2
- Uniprot ID:
- P52569
- Molecular Weight:
- 71672.175 Da
References
- Cerec V, Piquet-Pellorce C, Aly HA, Touzalin AM, Jegou B, Bauche F: Multiple pathways for cationic amino acid transport in rat seminiferous tubule cells. Biol Reprod. 2007 Feb;76(2):241-9. Epub 2006 Oct 25. [17065601 ]