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MolPort-001-792-339

MolPort-001-792-339

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Also known as: 537-55-3, Ac-tyr-oh, N-acetyl-tyrosine, Acetyl tyrosine, Acetyl-l-tyrosine, L-tyrosine, n-acetyl-

Molecular Formula

C₁₁H₁₃NO₄

Molecular Weight

223.22 g/mol

InChI Key

CAHKINHBCWCHCF-JTQLQIEISA-N

FDA UNII

DA8G610ZO5

N-acetyltyrosine, also referred to as N-acetyl-L-tyrosine, is used in place of as a tyrosine precursor. [DB00135] is a non-essential amino acid with a polar side group. N-acetyltyrosine is administered as parenteral nutrition or intravenous infusion due to its enhanced solubility compared to tyrosine. It is typically administered as a source of nutritional support where oral nutrition is inadequate or cannot be tolerated.

1 2D Structure

MolPort-001-792-339

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid

2.1.2 InChI

InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1

2.1.3 InChI Key

CAHKINHBCWCHCF-JTQLQIEISA-N

2.1.4 Canonical SMILES

CC(=O)NC(CC1=CC=C(C=C1)O)C(=O)O

2.1.5 Isomeric SMILES

CC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

DA8G610ZO5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acetyl-l-tyrosine

2. N-acetyltyrosine

3. N-acetyltyrosine, (d)-isomer

4. N-acetyltyrosine, (dl)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 537-55-3

2. Ac-tyr-oh

3. N-acetyl-tyrosine

4. Acetyl Tyrosine

5. Acetyl-l-tyrosine

6. L-tyrosine, N-acetyl-

7. L-n-acetyltyrosine

8. N-acetyltyrosin

9. Melanowhite-a

10. (2s)-2-acetamido-3-(4-hydroxyphenyl)propanoic Acid

11. Tyrosine, N-acetyl-

12. Chembl65543

13. Da8g610zo5

14. Chebi:21563

15. (s)-2-acetamido-3-(4-hydroxyphenyl)propanoic Acid

16. (2s)-2-acetylamino-3-(4-hydroxyphenyl)propanoic Acid

17. N-acetyltyrosine (n-acetyl-l-tyrosine)

18. Ncgc00159393-02

19. Ncgc00159393-03

20. Dsstox_cid_26045

21. Dsstox_rid_81305

22. Dsstox_gsid_46045

23. (+)-(2s)-2-(acetylamino)-3-(4-hydroxyphenyl)propanoic Acid

24. Mfcd00037190

25. Cas-537-55-3

26. N-aceyl-l-tyrosine

27. L-tyrosine, Acetyl-

28. Tyrosine, N-acetyl-, L-

29. N-acetyltyrosine (van)

30. Unii-da8g610zo5

31. Nsc-10853

32. N-acetyl Tyrosine

33. Einecs 208-671-3

34. Nsc 10853

35. L-n-acetyl-tyrosine

36. Tanogen Hb

37. Tyr-excel

38. Acetyl L-tyrosine

39. N-acetyl-l-tyrosine,(s)

40. L-tyrosine, N-acetyl

41. Schembl321220

42. Acetyl Tyrosine [inci]

43. (2s)-2-(acetylamino)-3-(4-hydroxyphenyl)propanoic Acid

44. Dtxsid7046045

45. N-acetyltyrosin [who-dd]

46. Zinc156395

47. Tox21_111630

48. Ac7826

49. Bdbm50043802

50. S6316

51. Akos010396311

52. Akos015841008

53. N-acetyl-l-tyrosine [usp-rs]

54. N-acetyl-l-tyrosine, >99% (tlc)

55. Tox21_111630_1

56. Am82306

57. Cs-w013098

58. Db11102

59. Hy-w012382

60. N-acetyltyrosine [ep Monograph]

61. Ac-13390

62. Ds-15166

63. (2s)-2-acetylamino-3-(4-hydroxyphenyl)propanoate

64. (s)-2-acetamido-3-(4-hydroxyphenyl)propanoicacid

65. 537a553

66. A829762

67. J-300276

68. N-acetyl-l-tyrosine 100 Microg/ml In Acetonitrile

69. Q-201443

70. A53ee723-a216-4295-8abe-c8c9ee26bbfc

71. Q27109405

72. (s)-2-acetylamino-3-(4-hydroxy-phenyl)-propionic Acid

73. 2-(s)-acetylamino-3-(4-hydroxy-phenyl)-propionic Acid

74. N-acetyltyrosine, European Pharmacopoeia (ep) Reference Standard

75. N-acetyl-l-tyrosine, United States Pharmacopeia (usp) Reference Standard

76. N-acetyl-l-tyrosine, Pharmaceutical Secondary Standard; Certified Reference Material

77. 3nf

78. N-acetyl-l-tyrosine, Pharmagrade, Ajinomoto, Ep, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

2.4 Create Date

2005-07-08

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₃NO₄
Molecular Weight	223.22 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	223.08445790 g/mol
Monoisotopic Mass	223.08445790 g/mol
Topological Polar Surface Area	86.6 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	259
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

N-acetyltyrosine is indicated, in combination with several other amino acids and dextrose, as a peripherally administered source of nitrogen for nutritional support in patients with adequate stores of body fat in whom, for short periods, oral administration cannot be tolerated, is undesirable, or inadequate. It is also indicated, with other amino acids, 5-10% dextrose, and fat emulsion, for parenteral nutrition to preserve protein and reduce catabolism in stress conditions where oral administration is inadequate. When administered with other amino acids and concentrated dextrose, it is indicated for central vein infusion to prevent or reverse negative nitrogen balance in patients where the alimentary tract by the oral, gastrostomy, or jejestomy routes cannot or should not be used or in patients in which gastrointestinal absorption of protein is impaired, metabolic requirements for protein are substantially increased, or morbidity and mortality may be reduced by replacing amino acids lost from tissue breakdown

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

N-acetyltyrosine is used as a high solubility precursor to [DB00135] used due to [DB00135]'s poor solubility. It is deacetylated to form [DB00135].

5.2 Absorption, Distribution and Excretion

Route of Elimination

N-acetyltyrosine is eliminated in the urine. The extent of urinary elimination versus utilization in the tissues appears to be related to the rapidity of infusion. When infused slowly in standard doses as in the clinical setting, about 35% is excreted unchanged in the urine. When larger doses are infused rapidly, much higher amounts are excreted reaching values up to 56%. In rat studies it was found that of the drug eliminated in the urine about 74% is present as unchanged N-acetyltyrosine and 23% is present as tyrosine.

5.3 Mechanism of Action

Used as a source of [DB00135]. See [DB00135] for more information on its role and pharmacology.