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Ornithine

Synopsis, Chemistry

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Also known as: Ornithine, 70-26-8, (s)-2,5-diaminopentanoic acid, (s)-ornithine, (s)-2,5-diaminovaleric acid, Ornithine [inn]

Molecular Formula

C₅H₁₂N₂O₂

Molecular Weight

132.16 g/mol

InChI Key

AHLPHDHHMVZTML-BYPYZUCNSA-N

FDA UNII

E524N2IXA3

An amino acid produced in the urea cycle by the splitting off of urea from arginine.

1 2D Structure

Ornithine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2,5-diaminopentanoic acid

2.1.2 InChI

InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1

2.1.3 InChI Key

AHLPHDHHMVZTML-BYPYZUCNSA-N

2.1.4 Canonical SMILES

C(CC(C(=O)O)N)CN

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

E524N2IXA3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,5 Diaminopentanoic Acid

2. 2,5-diaminopentanoic Acid

3. Ornithine

4. Ornithine Dihydrochloride, (l)-isomer

5. Ornithine Hydrochloride, (d)-isomer

6. Ornithine Hydrochloride, (dl)-isomer

7. Ornithine Hydrochloride, (l)-isomer

8. Ornithine Monoacetate, (l)-isomer

9. Ornithine Monohydrobromide, (l)-isomer

10. Ornithine Monohydrochloride, (d)-isomer

11. Ornithine Monohydrochloride, (dl)-isomer

12. Ornithine Phosphate (1:1), (l)-isomer

13. Ornithine Sulfate (1:1), (l)-isomer

14. Ornithine, (d)-isomer

15. Ornithine, (dl)-isomer

16. Ornithine, (l)-isomer

2.3.2 Depositor-Supplied Synonyms

1. Ornithine

2. 70-26-8

3. (s)-2,5-diaminopentanoic Acid

4. (s)-ornithine

5. (s)-2,5-diaminovaleric Acid

6. Ornithine [inn]

7. (2s)-2,5-diaminopentanoic Acid

8. L-norvaline, 5-amino-

9. (s)-alpha,delta-diaminovaleric Acid

10. Ornithinum [latin]

11. Ornitina [spanish]

12. Ornithine (van)

13. (+)-s-ornithine

14. (s)-2,5-diaminopentanoate

15. Ornithine, (l)-isomer

16. Pentanoic Acid, 2,5-diamino-, (s)-

17. Ornithine, L-

18. L-ornithine, Hcl

19. Brn 1722298

20. L-(-)-ornithine

21. Chebi:15729

22. Nsc-758894

23. E524n2ixa3

24. Ornithine (inn)

25. Polyornithine

26. Poly-l-ornithine

27. L( )-ornithine

28. 5-amino-l-norvaline

29. Ornithinum

30. Ornitina

31. L-ornithine, Homopolymer

32. Orn

33. L(-)-ornithine

34. Einecs 200-731-7

35. Unii-e524n2ixa3

36. Levo-ornithine

37. 1hqg

38. 1lah

39. 3jdw

40. 25104-12-5

41. L-ornithine (9ci)

42. 5-diaminopentanoic Acid

43. Ornithine [mi]

44. Ornithine [inci]

45. (s)-a,d-diaminovalerate

46. Ornithine, L- (8ci)

47. Bmse000162

48. Ornithine [mart.]

49. Ornithine [who-dd]

50. Schembl8579

51. Gtpl725

52. (s)-a,d-diaminovaleric Acid

53. 4-04-00-02644 (beilstein Handbook Reference)

54. Pentanoic Acid, 2,5-diamino

55. Chembl446143

56. Alpha, Delta-diaminovaleric Acid

57. Dtxsid00883219

58. L-ornithine2,5-diaminovalericacid

59. Pharmakon1600-01504524

60. Hy-b1352

61. Zinc1532530

62. (r,s)-2,5-diamino-pentanoic Acid

63. Bdbm50487430

64. L-ornithine;2,5-diaminovaleric Acid

65. Mfcd00242584

66. Nsc758894

67. S4857

68. Akos006239312

69. Cs-4817

70. Db00129

71. Nsc 758894

72. Smp2_000009

73. Ncgc00263569-01

74. Ac-13803

75. As-80993

76. (s)-2

77. S4653

78. C00077

79. D08302

80. Lysine Acetate Impurity E [ep Impurity]

81. 070o268

82. A866639

83. Q410198

84. W-104562

85. 8ab10027-4d34-488a-9f55-e86692ca2853

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₅H₁₂N₂O₂
Molecular Weight	132.16 g/mol
XLogP3	-4.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	132.089877630 g/mol
Monoisotopic Mass	132.089877630 g/mol
Topological Polar Surface Area	89.3 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	95
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

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.

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 Absorption, Distribution and Excretion

Absorption

Absorbed from the small intestine via a sodium-dependent active transport process

5.3 Metabolism/Metabolites

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

5.4 Mechanism of Action

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).