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Isovaleric Acid

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Also known as: 3-methylbutanoic acid, 503-74-2, Isopentanoic acid, 3-methylbutyric acid, Delphinic acid, Butanoic acid, 3-methyl-

Molecular Formula

C₅H₁₀O₂

Molecular Weight

102.13 g/mol

InChI Key

GWYFCOCPABKNJV-UHFFFAOYSA-N

FDA UNII

1BR7X184L5

3-Methylbutanoic acid is a metabolite found in or produced by Saccharomyces cerevisiae.

1 2D Structure

Isovaleric Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-methylbutanoic acid

2.1.2 InChI

InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)

2.1.3 InChI Key

GWYFCOCPABKNJV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)CC(=O)O

2.2 Other Identifiers

2.2.1 UNII

1BR7X184L5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-methylbutyrate

2. 3-methylbutyric Acid

2.3.2 Depositor-Supplied Synonyms

1. 3-methylbutanoic Acid

2. 503-74-2

3. Isopentanoic Acid

4. 3-methylbutyric Acid

5. Delphinic Acid

6. Butanoic Acid, 3-methyl-

7. Isopropylacetic Acid

8. Isovalerianic Acid

9. Isobutylformic Acid

10. 3-methylbutyrate

11. Beta-methylbutyric Acid

12. Isovalerianic

13. Acetic Acid, Isopropyl-

14. Butyric Acid, 3-methyl-

15. 3-methyl-butanoic Acid

16. Isovalerate

17. Kyselina Isovalerova

18. 3-methyl Butyric Acid

19. 3-methyl-butyric Acid

20. Fema No. 3102

21. 3-methyl-n-butyric Acid

22. Isovaleriansaeure

23. .beta.-methylbutyric Acid

24. Mfcd00002726

25. Nsc 62783

26. 3-methylbuttersaeure

27. B-methylbutyric Acid

28. 3,4-diisovaleryl Adrenaline

29. Chebi:28484

30. 1br7x184l5

31. Butanoic Acid, 3-methyl-, (r)-

32. Isopropylacetate

33. Nsc-62783

34. Iva

35. Isobutyl Formic Acid

36. Isovaleric Acid (natural)

37. Fema Number: 3102

38. Kyselina Isovalerova [czech]

39. Methyl Butanoic Acid

40. Hsdb 629

41. Einecs 207-975-3

42. Methylbutanoic Acid

43. Brn 1098522

44. Unii-1br7x184l5

45. Ai3-24132

46. B-methylbutyrate

47. Iso-valeric Acid

48. 3-methylbutanoicacid

49. Delphinic-acid

50. Iso-c4h9cooh

51. Isovaleric Acid, 99%

52. Dsstox_cid_9182

53. Bmse000373

54. Na 1760 (related)

55. Ec 207-975-3

56. Dsstox_rid_78698

57. Dsstox_gsid_29182

58. Schembl43436

59. Isovaleric Acid [mi]

60. 4-02-00-00895 (beilstein Handbook Reference)

61. Isovaleric Acid [fcc]

62. Methylbutanoic Acid (related)

63. Natural Isovaleric Acid

64. Isopropyl Acetic Acid, Natural

65. Isovaleric Acid [fhfi]

66. Isovaleric Acid [hsdb]

67. Chembl568737

68. Wln: Qv1y1&1

69. Dtxsid5029182

70. Isovaleric Acid [mart.]

71. Isovaleric Acid [who-dd]

72. Zinc388188

73. Amy40214

74. Bcp32116

75. Nsc62783

76. Str08356

77. Isovaleric Acid, Analytical Standard

78. Tox21_201604

79. Bbl027399

80. Lmfa01020181

81. S6287

82. Stl146358

83. Akos000119861

84. Isovaleric Acid, >=99%, Fcc, Fg

85. Cs-w013696

86. Db03750

87. Hy-w012980

88. 3-methylbutyric Acid: Isopropyl-acetate

89. Isovaleric Acid Sodium Salt (salt/mix)

90. Isovaleric Acid, Natural, >=98%, Fg

91. Ncgc00249082-01

92. Ncgc00259153-01

93. 35915-22-1

94. Cas-503-74-2

95. 3-methylbutyric Acid: Isopropyl-acetic Acid

96. Ft-0627533

97. M0182

98. C08262

99. D78213

100. Q415536

101. J-522594

102. F2191-0067

103. Z955123492

104. 3-methylbutanoic Acid;3-methylbutyric Acid;isopentanoic Acid

105. 92634-50-9

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₅H₁₀O₂
Molecular Weight	102.13 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	102.068079557 g/mol
Monoisotopic Mass	102.068079557 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	7
Formal Charge	0
Complexity	66.5
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 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

It is readily absorbed from the gastrointestinal tract in man.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3545

4.2 Metabolism/Metabolites

In contrast to valeric acid, isovaleric acid is ketogenic. ...Is metabolized by the liver to give two- and three-carbon fragments. The isopropyl fragment of isovaleric acid is readily converted to acetoacetate and is an efficient source of carbon atoms for fatty acid and cholesterol synthesis. Isovaleric acid ... has been identified in the fermentative organs of ruminant animals.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3545

Isovaleric acid is an intermediate in leucine metabolism. High blood concentrations of isovaleric acid occur in patients with the clinical disorder "isovaleric acidemia." This is a genetic defect of leucine metabolism in which the enzyme isovaleryl-coenzyme A dehydrogenase is inhibited or absent. The disease is characterized by episodic acidosis, slight mental retardation, and an unpleasant body odor.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3545

RATS RECEIVING LABELED ISOVALERIC ACID EXCRETED NONRADIOACTIVE ISOVALTHINE.

PMID:4225844 KODAMA H ET AL; ACTA MED OKAYAMA 20 (3): 107-13 (1966)

Isovalerate given iv to normal rats was rapidly metabolized, with a 50% decr in plasma concn after 11 min, and this time was shortened to 5 min by the simultaneous admin of glycine. The hypoglycin metabolite methylenecyclopropylacetate-CoA inhibited butyryl-CoA dehydrogenase and isovaleryl-CoA dehydrogenase in liver.

PMID:7317076 Al-Bassam SS, Sherratt HSA; Biochem Pharmacol 30 (20): 2817-24 (1981)

Gas chromatographic and mass spectrometric parameters of isovaleryl-beta-D-glucuronide, a new metabolite in the urine of patients with isovaleric acidemia, were presented. The significance of this metabolite for the detoxication of isovalerate in isovaleric acid media is discussed.

PMID:6652913 Dorland L et al; Clin Chim Acta 134 (1-2): 77-83 (1983)

4.3 Mechanism of Action

(14)C-LABELED ISOVALERIC ACID ADMIN ORALLY TO RATS SHOWED ISOPROPYL GROUP WAS MORE EFFICIENTLY UTILIZED FOR CHOLESTEROL SYNTH THAN CARBOXYL GROUPS, & ALSO MORE EFFICIENTLY UTILIZED THAN FATTY ACID SYNTH. CLEAVAGE OF ACID INTO 2 FRAGMENTS OCCURS BEFORE CHOLESTEROL SYNTH. (14)C-LABELED ISOVALERIC ACID ADMIN ORALLY TO RATS APPEARS TO ENHANCE THE INCORPORATION OF CARBON DIOXIDE INTO CHOLESTEROL.

PMID:4225844 KODAMA H ET AL; ACTA MED OKAYAMA 20 (3): 107-13 (1966)

All liver mitochondrial preparations were affected by 1.19 mM isovalerate. Isovaleryl CoA is a potent inhibitor of succinate:CoA ligase (SCL) with positive cooperativity and half-maximal inhibition at 273 +/-11 uM isovaleryl CoA. The investigators suggested that inhibition of the citric acid cycle at the SCL step may be a general mechanism of organic acid toxicity to mitochondria.

PMID:7082321 Bergen BJ et al; Biochem Med 27 (2): 154-60 (1982)