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MolPort-001-780-113

MolPort-001-780-113

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Also known as: Pentanoic acid, N-valeric acid, 109-52-4, N-pentanoic acid, Valerianic acid, 1-butanecarboxylic acid

Molecular Formula

C₅H₁₀O₂

Molecular Weight

102.13 g/mol

InChI Key

NQPDZGIKBAWPEJ-UHFFFAOYSA-N

FDA UNII

GZK92PJM7B

Pentanoic acid is a metabolite found in or produced by Saccharomyces cerevisiae.

1 2D Structure

MolPort-001-780-113

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

pentanoic acid

2.1.2 InChI

InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)

2.1.3 InChI Key

NQPDZGIKBAWPEJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

GZK92PJM7B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lithium Pentanoate

2. N-pentanoic Acid

3. N-pentanoic Acid, 11c-labeled

4. N-pentanoic Acid, 11c-labeled Sodium Salt

5. N-pentanoic Acid, Ammonium Salt

6. N-pentanoic Acid, Maganese (+2) Salt

7. N-pentanoic Acid, Potassium Salt

8. N-pentanoic Acid, Sodium Salt

9. N-pentanoic Acid, Zinc Salt

2.3.2 Depositor-Supplied Synonyms

1. Pentanoic Acid

2. N-valeric Acid

3. 109-52-4

4. N-pentanoic Acid

5. Valerianic Acid

6. 1-butanecarboxylic Acid

7. Propylacetic Acid

8. Butanecarboxylic Acid

9. Pentoic Acid

10. Kyselina Valerova

11. Valeric Acid, N-

12. Valeric Acid, Normal

13. N-pentanoate

14. Kyselina Valerova [czech]

15. Valerate

16. Fema No. 3101

17. Valeriansaeure

18. N-valerate

19. 1-pentanoic Acid

20. Nsc 406833

21. N-c4h9cooh

22. Gzk92pjm7b

23. Ch3-[ch2]3-cooh

24. Chebi:17418

25. Nsc-406833

26. 64118-37-2

27. Ncgc00183281-01

28. C5:0

29. Dsstox_cid_1655

30. Dsstox_rid_76267

31. Dsstox_gsid_21655

32. Valericacid

33. Cas-109-52-4

34. Shf

35. Hsdb 5390

36. Butane-1-carboxylic Acid

37. Einecs 203-677-2

38. Unii-gzk92pjm7b

39. Mfcd00004413

40. Brn 0969454

41. Pentoate

42. Propylacetate

43. Valerianate

44. Valeriansaure

45. Ai3-08657

46. Butanecarboxylate

47. 1-pentanoate

48. 1ylv

49. 1-butanecarboxylate

50. Valeric Acid Normal

51. N-bucooh

52. 1173023-05-6

53. Valeric Acid, 99%

54. Valeric Acid, >=99%

55. Bmse000345

56. Ec 203-677-2

57. Pentanoic Acid Valeric Acid

58. Schembl5886

59. Valeric Acid [fcc]

60. Wln: Qv4

61. Valeric Acid [fhfi]

62. N-valeric Acid [mi]

63. 4-02-00-00868 (beilstein Handbook Reference)

64. Mls001066335

65. Pentanoic Acid [hsdb]

66. Valeric Acid [mart.]

67. Pentanoic Acid (valeric Acid)

68. Chembl268736

69. Gtpl1061

70. Dtxsid7021655

71. Valeric Acid ( Pentanoic Acid )

72. Valeric Acid, Analytical Standard

73. Hms2267a03

74. Valeric Acid-[3,4,5-13c3]

75. Hy-n6056

76. Tox21_113414

77. Tox21_201561

78. Tox21_303030

79. Lmfa01010005

80. Nsc406833

81. Stl169350

82. Valeric Acid, >=99%, Fcc, Fg

83. Zinc31500905

84. Akos000118960

85. Db02406

86. Ncgc00183281-02

87. Ncgc00183281-03

88. Ncgc00256597-01

89. Ncgc00259110-01

90. Bs-42203

91. Smr000471834

92. Cs-0032261

93. Ft-0651620

94. Ft-0694066

95. V0003

96. Valeric Acid, Pharmaceutical Impurity Standard

97. C00803

98. Valproic Acid Impurity A [ep Impurity]

99. Q407796

100. J-002298

101. F2191-0105

102. Z955123768

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₅H₁₀O₂
Molecular Weight	102.13 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
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	59.1
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 Metabolism/Metabolites

It is metabolized by splitting into acetic acid and pyruvic acid.

Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1782

Labeled valeric acid was incubated with mixed culture of cellulolytic rumen bacteria resulting in the labeling of lipids. The distribution of radioactivity indicated that 1-(14)C-labeled valeric acid was not utilized directly for biosynthesis of higher fatty acids with odd number of carbon atoms by the addition of 2 C, but it was probably degraded into 1-(14)C-labeled acetic acid and into propionic acid.

HIDIROGLOU M, LEPAGE M; CAN J BIOCHEM 45 (12): 1789 (1967)

Valeric acid is formed by rumen microorganisms during the metabolism of proline, leucine, isoleucine, norleucine, and several intermediates of carbohydrate metabolism.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:713

Valeic acid is rapidly metabolized in rat liver to acetate and propionate, giving rise to both glycogen and ketone bodies. This same route of metabolism also predominates in rumen microorganisms.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:714

For more Metabolism/Metabolites (Complete) data for n-PENTANOIC ACID (6 total), please visit the HSDB record page.

4.2 Mechanism of Action

... Pentanoate was metabolized to a greater extent than octanoate and did not inhibit growth. Pentanoate inhibited acetate utilization in both the inner mitochondrial and peroxisomal compartments as indicated by a reduction in the incorporation of label from [1-14-C]acetate into lipids and into CO2, but there was no difference in oxidation of [2-14-C]pyruvate when pentanoate was the fatty acid substrate as compared to octanoate. Glyconeogenesis was inhibited when pentanoate was substituted for octanoate. ... The effects of 4-pentenoic acid were essentially the same whether octanoate or pentanoate was the fatty acid substrate, i.e. inhibition of glyconeogenesis from all labeled substrates and inhibition of [2-14-C]pyruvate oxidation.

Raugi GJ; J Biol Chem 250 (11): 4067-72 (1975)