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Also known as: Lithocolic acid, Lithocholate, 3alpha-hydroxy-5beta-cholan-24-oic acid, 3alpha-hydroxy-5beta-cholanic acid, 3alpha-hydroxycholanic acid, 3-alpha-hydroxycholanic acid

Molecular Formula

C₂₄H₄₀O₃

Molecular Weight

376.6 g/mol

InChI Key

SMEROWZSTRWXGI-HVATVPOCSA-N

FDA UNII

5QU0I8393U

A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.

1 2D Structure

Lithocholic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid

2.1.2 InChI

InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1

2.1.3 InChI Key

SMEROWZSTRWXGI-HVATVPOCSA-N

2.1.4 Canonical SMILES

CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C

2.1.5 Isomeric SMILES

C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C

2.2 Other Identifiers

2.2.1 UNII

5QU0I8393U

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Isolithocholic

2. Acid, Lithocholic

3. Isolithocholic Acid

4. Lithocholate

2.3.2 Depositor-Supplied Synonyms

1. Lithocolic Acid

2. Lithocholate

3. 3alpha-hydroxy-5beta-cholan-24-oic Acid

4. 3alpha-hydroxy-5beta-cholanic Acid

5. 3alpha-hydroxycholanic Acid

6. 3-alpha-hydroxycholanic Acid

7. 5beta-cholanic Acid-3alpha-ol

8. 3

9. A-hydroxy-5

10. A-cholanic Acid

11. Nci-c03861

12. 3-hydroxycholan-24-oic Acid

13. 3alpha-hydroxy-5beta-cholanoic Acid

14. (3alpha,5beta)-3-hydroxycholan-24-oic Acid

15. 3-alpha-hydroxy-5-beta-cholanic Acid

16. 3alpha-hydroxy-5beta-cholanate

17. 5-beta-cholanic Acid, 3-alpha-hydroxy-

18. Cholan-24-oic Acid, 3-hydroxy-, (3alpha,5beta)-

19. 5beta-cholan-24-oic Acid, 3alpha-hydroxy-

20. Nsc683770

21. (3-alpha,5-beta)-3-hydroxycholan-24-oic Acid

22. (4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoic Acid

23. Chembl1478

24. 17beta-(1-methyl-3-carboxypropyl)etiocholan-3alpha-ol

25. 3.alpha.-hydroxycholanic Acid

26. 17-beta-(1-methyl-3-carboxypropyl)ethiocholan-3-alpha-ol

27. Chebi:16325

28. 5-beta-cholan-24-oic Acid, 3-alpha-hydroxy-

29. Cholan-24-oic Acid, 3-hydroxy-, (3a,5b)-

30. 5qu0i8393u

31. Nsc-683770

32. Dsstox_cid_779

33. Dsstox_rid_75786

34. Dsstox_gsid_20779

35. Lca

36. Litocholic Acid

37. (3beta,5beta,14beta,17alpha)-3-hydroxycholan-24-oic Acid

38. Mfcd00003682

39. (r)-4-((3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

40. Ccris 363

41. Lithocholicacid

42. Hsdb 4113

43. Sr-05000000450

44. Einecs 207-099-1

45. Nsc 657956

46. Brn 3217757

47. Cholan-24-oic Acid, 3-hydroxy-, (3.alpha.,5.beta.)-

48. Unii-5qu0i8393u

49. Lithocholic-acid

50. Nsc657956

51. Nsc-657956

52. Prestwick_88

53. 4oa

54. 5beta-cholan-24-oic Acid-3alpha-ol

55. Nsc 683770

56. Lithocholic Acid,(s)

57. 4q0a

58. St069335

59. Prestwick0_000796

60. Prestwick1_000796

61. Prestwick2_000796

62. Prestwick3_000796

63. Spectrum5_002021

64. Bmse000686

65. Upcmld-dp153

66. Cid_9903

67. Lithocholic Acid, >=95%

68. Bidd:pxr0054

69. Schembl28449

70. 3a-hydroxy-5b-cholanic Acid

71. Bspbio_000932

72. Gtpl611

73. 4-10-00-00785 (beilstein Handbook Reference)

74. Mls002154006

75. 3a-hydroxy-5ss-cholanic Acid

76. Lithocholic Acid [mi]

77. Spbio_002871

78. Bpbio1_001026

79. Cholan-24-oic Acid, 3-hydroxy-, (3-alpha,5-beta)-

80. 3a-hydroxy-5b-cholan-24-oate

81. Lithocholic Acid [hsdb]

82. Dtxsid6020779

83. Upcmld-dp153:001

84. 5ss--cholan-24-oic Acid-3a-ol

85. Hms1570o14

86. Hms2097o14

87. Hms2269c14

88. Hms3714o14

89. 3a-hydroxy-5b-cholan-24-oic Acid

90. Hy-b0172

91. Zinc3918156

92. Tox21_201868

93. Tox21_302791

94. 3a-hydroxy-5ss-cholan-24-oic Acid

95. 5.beta.-cholanic Acid-3.alpha.-ol

96. Bdbm50236238

97. Lmst04010003

98. S4003

99. (3a,5b)-3-hydroxy-cholan-24-oate

100. Akos016010251

101. Lithocholic Acid [ep Impurity]

102. Ccg-220796

103. Cs-2049

104. Ds-3878

105. 3.alpha.-hydroxy-5.beta.-cholanic Acid

106. Ncgc00091272-01

107. Ncgc00091272-04

108. Ncgc00091272-06

109. Ncgc00091272-07

110. Ncgc00091272-08

111. Ncgc00256451-01

112. Ncgc00259417-01

113. (3a,5b)-3-hydroxy-cholan-24-oic Acid

114. (4s)-4-((1s,2s,11s,5r,7r,10r,14r,15r)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0. 0<2,7>.0<11,15>]heptadec-14-yl)pentanoic Acid

115. 3.alpha.-hydroxy-5.beta.-cholanoic Acid

116. Nci60_028903

117. Nci60_030095

118. Smr000112168

119. 5.beta.-cholan-24-oic Acid-3.alpha.-ol

120. L0089

121. 5-.beta.-cholanic Acid, 3-.alpha.-hydroxy-

122. 3.alpha.-hydroxy-5.beta.-cholan-24-oic Acid

123. C03990

124. 5.beta.-cholan-24-oic Acid, 3.alpha.-hydroxy-

125. A872700

126. Q3323035

127. Sr-05000000450-2

128. Sr-05000000450-4

129. Sr-05000000450-5

130. Ursodeoxycholic Acid Impurity C [ep Impurity]

131. 17-.beta.-(1-methyl-3-carboxypropyl)ethiocholan-3-.alpha.-ol

132. 3alpha-hydroxy-5beta-cholan-24-oic Acid (lithocholic Acid)

133. Cholan-24-oic Acid, 3-hydroxy-, (3-.alpha., 5-.beta.)-

134. Cholan-24-oic Acid, 3-hydroxy-, (3-alpha,5-beta)- (9ci)

135. 17.beta.-(1-methyl-3-carboxypropyl)etiocholan-3.alpha.-ol

136. Lithocholic Acid, European Pharmacopoeia (ep) Reference Standard

137. Ac268b61-0548-4391-90e9-546636926870

138. Lithocholic Acid, 50 Mug/ml In Methanol, Certified Reference Material

139. (4r)-4-((3r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

140. 3alpha-hydroxy-5beta-cholan-24-oic Acid 3alpha-hydroxy-5beta-cholanic Acid 3alpha-hydroxycholanic Acid 3-hydroxycholanic Acid 5beta-cholan-24-oic Acid-3alpha-ol 5beta-cholan-24-oic Acid-3a-ol 5beta-cholanic Acid-3alpha-ol Beta-cholanic Acid-3-alpha-ol Hydroycholanic Acid

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₄₀O₃
Molecular Weight	376.6 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	376.29774513 g/mol
Monoisotopic Mass	376.29774513 g/mol
Topological Polar Surface Area	57.5 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	574
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
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 MeSH Pharmacological Classification

Detergents

Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties. (See all compounds classified as Detergents.)

4.2 Metabolism/Metabolites

LITHOCHOLIC ACID (24)C(14) IS CONVERTED BY RAT LIVER HOMOGENATE INTO 3ALPHA-6BETA-DIHYDROXY-5BETA-CHOLANIC ACID, 7SIGMA-HYDROXYLATION OCCURS, HYDROXYLATION CONJUGATION WITH TAURINE & FORMATION OF 3-SULFATE ESTER CAN BE DEMONSTRATED.

BACK P, SCHERNAU-POTZI L; NAUNYN-SCHMIEDEBERG'S ARCH PHARMACOL 275 (2): 135 (1972)

LABELED LITHOCHOLATE WAS INJECTED INTO GALLSTONE PATIENTS & HEALTHY VOLUNTEERS, MAJORITY OF RADIOACTIVITY IN BILE (50-60%) WAS PRESENT AS SULFATED CONJUGATES. DEGREE OF SULFATION WAS GREATER FOR GLYCINE THAN TAURINE CONJUGATES, WHICH SUGGESTED PREFERENTIAL SULFATION OF GLYCINE CONJUGATES.

PMID:955496 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1411124 ALLAN RN ET AL; GUT 17 (6): 413 (1976)

Lithocholic Acid has known human metabolites that include 6alpha-Hydroxylithocholic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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