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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-07-01 14:27:27 UTC
NP-MRD IDNP0000119
Secondary Accession NumbersNone
Natural Product Identification
Common NameOrnithine
DescriptionOrnithine or L-ornithine, also known as (S)-2,5-diaminopentanoic acid is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-ornithine is soluble (in water) and a moderately basic compound. Ornithine is a non-proteinogenic amino acid that plays a role in the urea cycle. It is considered to be a non-essential amino acid. A non-essential amino acid is an amino acid that can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. L-Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea. Therefore, ornithine is a central part of the urea cycle, which allows for the disposal of excess nitrogen. Outside the human body, L-ornithine is abundant in a number of food items such as wild rice, brazil nuts, common oregano, and common grapes. L-ornithine can be found throughout most human tissues; and in most biofluids, some of which include blood, urine, cerebrospinal fluid (CSF), sweat, saliva, and feces. L-ornithine exists in all living species, from bacteria to plants to humans. L-Ornithine is also a precursor of citrulline and arginine. In order for ornithine that is 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 the enzyme known as 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 (PMID: 16256388 ). The pathophysiology of 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 ). In humans, L-ornithine is involved in a number of other metabolic disorders, some of which include, ornithine transcarbamylase deficiency (OTC deficiency), argininemia, and guanidinoacetate methyltransferase deficiency (GAMT deficiency). Ornithine is abnormally accumulated in the body in ornithine transcarbamylase deficiency. Moreover, Ornithine is found to be associated with cystinuria, hyperdibasic aminoaciduria I, and lysinuric protein intolerance, which are inborn errors of metabolism. It has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing.
Structure
Thumb
Synonyms
ValueSource
(S)-2,5-DiaminopentanoateChEBI
(S)-2,5-Diaminopentanoic acidChEBI
(S)-2,5-Diaminovaleric acidChEBI
(S)-alpha,delta-Diaminovaleric acidChEBI
(S)-OrnithineChEBI
(S)-2,5-DiaminovalerateGenerator
(S)-a,delta-DiaminovalerateGenerator
(S)-a,delta-Diaminovaleric acidGenerator
(S)-alpha,delta-DiaminovalerateGenerator
(S)-Α,δ-diaminovalerateGenerator
(S)-Α,δ-diaminovaleric acidGenerator
(S)-a,Δ-diaminovalerateHMDB
(S)-a,Δ-diaminovaleric acidHMDB
(+)-S-OrnithineHMDB
(S)-a,D-DiaminovalerateHMDB
(S)-a,D-Diaminovaleric acidHMDB
5-Amino-L-norvalineHMDB
L-(-)-OrnithineHMDB
L-OrnithineHMDB
2,5-Diaminopentanoic acidHMDB
Ornithine dihydrochloride, (L)-isomerHMDB
Ornithine hydrochloride, (D)-isomerHMDB
Ornithine, (D)-isomerHMDB
Ornithine, (L)-isomerHMDB
2,5 Diaminopentanoic acidHMDB
Ornithine monoacetate, (L)-isomerHMDB
Ornithine monohydrochloride, (D)-isomerHMDB
Ornithine monohydrochloride, (DL)-isomerHMDB
Ornithine phosphate (1:1), (L)-isomerHMDB
Ornithine sulfate (1:1), (L)-isomerHMDB
Ornithine hydrochloride, (DL)-isomerHMDB
Ornithine hydrochloride, (L)-isomerHMDB
Ornithine monohydrobromide, (L)-isomerHMDB
Ornithine, (DL)-isomerHMDB
Chemical FormulaC5H12N2O2
Average Mass132.1610 Da
Monoisotopic Mass132.08988 Da
IUPAC Name(2S)-2,5-diaminopentanoic acid
Traditional Nameornithine
CAS Registry Number3184-13-2
SMILES
NCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
InChI KeyAHLPHDHHMVZTML-BYPYZUCNSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-07-25View Spectrum
Species
Species of Origin
  • All
  • Chemical Taxonomy
    Description 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.
    KingdomOrganic compounds
    Super ClassOrganic acids and derivatives
    ClassCarboxylic acids and derivatives
    Sub ClassAmino acids, peptides, and analogues
    Direct ParentL-alpha-amino acids
    Alternative Parents
    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
    Molecular FrameworkAliphatic acyclic compounds
    External Descriptors
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point140 °CNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility620 mg/mLNot Available
    LogP-4.22SANGSTER (1994)
    Predicted Properties
    PropertyValueSource
    Water Solubility172 g/LALOGPS
    logP-3.6ALOGPS
    logP-3.7ChemAxon
    logS0.11ALOGPS
    pKa (Strongest Acidic)2.67ChemAxon
    pKa (Strongest Basic)10.29ChemAxon
    Physiological Charge1ChemAxon
    Hydrogen Acceptor Count4ChemAxon
    Hydrogen Donor Count3ChemAxon
    Polar Surface Area89.34 ŲChemAxon
    Rotatable Bond Count4ChemAxon
    Refractivity33.21 m³·mol⁻¹ChemAxon
    Polarizability13.85 ųChemAxon
    Number of Rings0ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0000214
    DrugBank IDDB00129
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB030969
    KNApSAcK IDC00001384
    Chemspider ID6026
    KEGG Compound IDC00077
    BioCyc IDL-ORNITHINE
    BiGG ID37976
    Wikipedia LinkOrnithine
    METLIN ID27
    PubChem Compound6262
    PDB IDNot Available
    ChEBI ID15729
    Good Scents IDNot Available
    References
    General References
    1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
    2. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
    3. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. [PubMed:6696735 ]
    4. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
    5. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
    6. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
    7. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
    8. Peters T, Thaete C, Wolf S, Popp A, Sedlmeier R, Grosse J, Nehls MC, Russ A, Schlueter V: A mouse model for cystinuria type I. Hum Mol Genet. 2003 Sep 1;12(17):2109-20. [PubMed:12923163 ]
    9. Mayer UM: [Hyperornithinaemia in patients with retinal dystrophy]. Ophthalmologe. 2003 Jan;100(1):55-61. [PubMed:12557027 ]
    10. Gray RG, Green A, Hall S, McKeown C: Prenatal exclusion of the HHH syndrome. Prenat Diagn. 1995 May;15(5):474-6. [PubMed:7644438 ]
    11. Jensen TG, Sullivan DM, Morgan RA, Taichman LB, Nussenblatt RB, Blaese RM, Csaky KG: Retrovirus-mediated gene transfer of ornithine-delta-aminotransferase into keratinocytes from gyrate atrophy patients. Hum Gene Ther. 1997 Nov 20;8(17):2125-32. [PubMed:9414260 ]
    12. Sell DR, Monnier VM: Ornithine is a novel amino acid and a marker of arginine damage by oxoaldehydes in senescent proteins. Ann N Y Acad Sci. 2005 Jun;1043:118-28. [PubMed:16037230 ]
    13. Stadler S, Gempel K, Bieger I, Pontz BF, Gerbitz KD, Bauer MF, Hofmann S: Detection of neonatal argininosuccinate lyase deficiency by serum tandem mass spectrometry. J Inherit Metab Dis. 2001 Jun;24(3):370-8. [PubMed:11486903 ]
    14. Gokmen SS, Aygit AC, Ayhan MS, Yorulmaz F, Gulen S: Significance of arginase and ornithine in malignant tumors of the human skin. J Lab Clin Med. 2001 May;137(5):340-4. [PubMed:11329531 ]
    15. Morizono H, Woolston JE, Colombini M, Tuchman M: The use of yeast mitochondria to study the properties of wild-type and mutant human mitochondrial ornithine transporter. Mol Genet Metab. 2005 Dec;86(4):431-40. Epub 2005 Oct 26. [PubMed:16256388 ]