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Chemistry

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Also known as: 2-ketoglutaric acid, 2-oxopentanedioic acid, 328-50-7, Alpha-ketoglutaric acid, Alpha-ketoglutarate, 2-oxoglutarate

Molecular Formula

C₅H₆O₅

Molecular Weight

146.10 g/mol

InChI Key

KPGXRSRHYNQIFN-UHFFFAOYSA-N

FDA UNII

8ID597Z82X

A family of compounds containing an oxo group with the general structure of 1,5-pentanedioic acid. (From Lehninger, Principles of Biochemistry, 1982, p442)

1 2D Structure

CAS 328-50-7

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-oxopentanedioic acid

2.1.2 InChI

InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

2.1.3 InChI Key

KPGXRSRHYNQIFN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C(CC(=O)O)C(=O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

8ID597Z82X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2 Ketoglutarate

2. 2 Ketoglutaric Acid

3. 2 Oxoglutarate

4. 2 Oxoglutaric Acid

5. 2-ketoglutarate

6. 2-ketoglutaric Acid

7. 2-oxoglutarate

8. Alpha Ketoglutarate

9. Alpha Ketoglutaric Acid

10. Alpha Ketoglutaric Acid, Diammonium Salt

11. Alpha Ketoglutaric Acid, Dipotassium Salt

12. Alpha Ketoglutaric Acid, Disodium Salt

13. Alpha Ketoglutaric Acid, Monopotassium Salt

14. Alpha Ketoglutaric Acid, Monosodium Salt

15. Alpha Ketoglutaric Acid, Potassium Salt

16. Alpha Ketoglutaric Acid, Sodium Salt

17. Alpha Oxoglutarate

18. Alpha-ketoglutarate

19. Alpha-ketoglutarate, Calcium

20. Alpha-ketoglutaric Acid

21. Alpha-ketoglutaric Acid, Calcium Salt (2:1)

22. Alpha-ketoglutaric Acid, Diammonium Salt

23. Alpha-ketoglutaric Acid, Dipotassium Salt

24. Alpha-ketoglutaric Acid, Disodium Salt

25. Alpha-ketoglutaric Acid, Monopotassium Salt

26. Alpha-ketoglutaric Acid, Monosodium Salt

27. Alpha-ketoglutaric Acid, Potassium Salt

28. Alpha-ketoglutaric Acid, Sodium Salt

29. Alpha-oxoglutarate

30. Calcium Alpha Ketoglutarate

31. Calcium Alpha-ketoglutarate

32. Calcium Ketoglutarate

33. Ketoglutaric Acid

34. Ketoglutaric Acids

35. Oxogluric Acid

36. Oxoglutarates

2.3.2 Depositor-Supplied Synonyms

1. 2-ketoglutaric Acid

2. 2-oxopentanedioic Acid

3. 328-50-7

4. Alpha-ketoglutaric Acid

5. Alpha-ketoglutarate

6. 2-oxoglutarate

7. Oxoglutaric Acid

8. Alpha Ketoglutarate

9. Oxoglutarate

10. 2-oxo-1,5-pentanedioic Acid

11. Pentanedioic Acid, 2-oxo-

12. Alphaketoglutaric Acid

13. Alpha-oxoglutaric Acid

14. Oxoglurate

15. Glutaric Acid, 2-oxo-

16. Oxogluric Acid

17. Glutaric Acid, Alpha Keto

18. 2-ketoglutarate

19. Pentanedioic Acid, Oxo-

20. A-ketoglutaric Acid

21. Ketoglutaric Acid

22. Bis(l-arginin)-2-oxoglutarat

23. Oxoglurate [inn]

24. Alpha Ketoglutaric Acid

25. .alpha.-ketoglutaric Acid

26. Ai3-26938

27. Mfcd00004165

28. Nsc 17391

29. Alpha-ketoglutaric Acid Alpha

30. 17091-15-5

31. 2-oxo-pentanedioic Acid

32. Alpha-keto-glutaric Acid

33. Nsc17391

34. .alpha.-oxoglutaric Acid

35. Nsc-17391

36. 378-50-7

37. Chembl1686

38. Chebi:30915

39. Glutaric Acid, 2-oxo- (8ci)

40. 8id597z82x

41. 2-oxopentanedioate

42. 2-oxo-glutaric Acid

43. 2-oxopentanedionate

44. 2-ketoglutaricacid

45. Dsstox_cid_13179

46. Dsstox_rid_79054

47. Dsstox_gsid_33179

48. Pentanedioic Acid, 2-oxo-, Sodium Salt

49. Ketoglutaric Acids

50. Cas-328-50-7

51. Akg

52. Einecs 206-330-3

53. Alpha-ketoglutaricum Acidum

54. Unii-8id597z82x

55. 3ouj

56. 4nro

57. 4oct

58. 4qkd

59. 4usi

60. Keto Glutaric Acid

61. 2-oxoglutaric-acid

62. .alpha.-ketoglutarate

63. 2-oxo-pentanedioicaci

64. 34410-46-3

65. Alpha-oxo-glutaric Acid

66. Alpha -ketoglutaric Acid

67. Alpha-oxopentanedioic Acid

68. 2-oxo-1,5-pentanedioate

69. Bmse000064

70. Bmse000801

71. Bmse000937

72. Schembl7400

73. Ncistruc1_001710

74. Ncistruc2_000215

75. Alfa-ketoglutaric Acid

76. A-ketoglutaricum Acidum

77. Glutaric Acid, .alpha.-keto-

78. Gtpl3636

79. Oxogluric Acid [mart.]

80. Dtxsid5033179

81. Ketoglutaric Acid [inci]

82. Oxogluric Acid [who-dd]

83. Nci17391

84. Pentanedioic Acid, 2-oxo- (9ci)

85. Zinc1532519

86. Tox21_110016

87. Tox21_200918

88. Bbl010614

89. Bdbm50303766

90. Ccg-37641

91. Ncgc00013225

92. S6237

93. Stk002174

94. 2-oxopentanedioic Acid [fhfi]

95. A-ketoglutaricum Acidum [hpus]

96. Akos000120908

97. Cs-w014352

98. Db02926

99. Db03806

100. Db08845

101. Hy-w013636

102. .alpha.-ketoglutaric Acid [mi]

103. Ncgc00013225-01

104. Ncgc00013225-02

105. Ncgc00013225-03

106. Ncgc00013225-04

107. Ncgc00013225-05

108. Ncgc00013225-06

109. Ncgc00090946-01

110. Ncgc00090946-02

111. Ncgc00258472-01

112. Alpha-ketoglutaric Acid, >=99.0% (t)

113. As-12579

114. Nci60_001411

115. Sy004310

116. Db-048280

117. Am20090486

118. Ft-0612734

119. Ft-0670633

120. K0005

121. C00026

122. D70548

123. K-2400

124. Ab00640269-03

125. A855282

126. Q306140

127. Alpha-ketoglutaric Acid, >=98.5% (naoh, Titration)

128. Z57127547

129. F2191-0182

130. 15118487-024f-412c-9995-24e8e6ca72ef

131. Alpha-ketoglutaric Acid, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₅H₆O₅
Molecular Weight	146.10 g/mol
XLogP3	-0.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	146.02152329 g/mol
Monoisotopic Mass	146.02152329 g/mol
Topological Polar Surface Area	91.7 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	171
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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

--Ketoglutarate is not approved for any indication in the world but is an investigational drug in the United States. The potential indications for -Ketoglutarate are in patients with the metabolic disorder propionic acidemia and in trauma patients with muscle loss.

5 Pharmacology and Biochemistry

5.1 Pharmacology

All of the physiological roles of alpha-ketoglutarate have not been determined. What is known is that alpha-keotglutarate is involved in the Krebs cycle, transamination reactions, and promotes muscle synthesis.

5.2 Mechanism of Action

The exact mechanisms of action for -Ketoglutarate have not yet been elucidated. Some of -Ketoglutarates actions include acting in the Krebs cycle as an intermediate, transamination reactions during the metabolism of amino acids, forming glutamic acid by combining with ammonia, and reducing nitrogen by combining with it as well. Concerning -Ketoglutarates actions with ammonia, it is proposed that -Ketoglutarate can help patients with propionic academia who have high levels of ammonia and low levels of glutamine/glutamate in their blood. Because endogenous glutamate/glutamine is produced from -Ketoglutarate, propionic acidemia patients have impaired production of -Ketoglutarate and supplementation of -Ketoglutarate should improve the condition of these patients. Several other experimental studies have also shown that administration of -Ketoglutarate in parenteral nutrition given to post-operative patients helped attenuate the decreased synthesis of muscle protein that is often seen after a surgery. This decreased muscle synthesis is speculated to be due to too low -Ketoglutarate levels.

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