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Also known as: 434-13-9, Lithocolic acid, Lithocholate, 3alpha-hydroxy-5beta-cholan-24-oic acid, 3alpha-hydroxy-5beta-cholanic acid, 3alpha-hydroxycholanic acid
Molecular Formula
C24H40O3
Molecular Weight
376.6  g/mol
InChI Key
SMEROWZSTRWXGI-HVATVPOCSA-N
FDA UNII
5QU0I8393U

CAS 434-13-9
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

CAS 434-13-9

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. 434-13-9

2. Lithocolic Acid

3. Lithocholate

4. 3alpha-hydroxy-5beta-cholan-24-oic Acid

5. 3alpha-hydroxy-5beta-cholanic Acid

6. 3alpha-hydroxycholanic Acid

7. Lithocholicacid

8. 3-alpha-hydroxycholanic Acid

9. 5beta-cholanic Acid-3alpha-ol

10. 3

11. A-hydroxy-5

12. A-cholanic Acid

13. Nci-c03861

14. 3-hydroxycholan-24-oic Acid

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

16. (3alpha,5beta)-3-hydroxycholan-24-oic Acid

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

18. 3alpha-hydroxy-5beta-cholanate

19. 5-beta-cholanic Acid, 3-alpha-hydroxy-

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

21. 5beta-cholan-24-oic Acid, 3alpha-hydroxy-

22. Nsc683770

23. (3-alpha,5-beta)-3-hydroxycholan-24-oic Acid

24. Chembl1478

25. 17beta-(1-methyl-3-carboxypropyl)etiocholan-3alpha-ol

26. 3.alpha.-hydroxycholanic Acid

27. 17-beta-(1-methyl-3-carboxypropyl)ethiocholan-3-alpha-ol

28. (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

29. Chebi:16325

30. 5-beta-cholan-24-oic Acid, 3-alpha-hydroxy-

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

32. 5qu0i8393u

33. Nsc-683770

34. Lca

35. Litocholic Acid

36. (3beta,5beta,14beta,17alpha)-3-hydroxycholan-24-oic Acid

37. Mfcd00003682

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

39. Ccris 363

40. Hsdb 4113

41. Sr-05000000450

42. Einecs 207-099-1

43. Nsc 657956

44. Brn 3217757

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

46. Unii-5qu0i8393u

47. Lithocholic-acid

48. Nsc657956

49. Nsc-657956

50. Prestwick_88

51. 4oa

52. Cas-434-13-9

53. 5beta-cholan-24-oic Acid-3alpha-ol

54. Nsc 683770

55. Lithocholic Acid,(s)

56. 4q0a

57. St069335

58. Prestwick0_000796

59. Prestwick1_000796

60. Prestwick2_000796

61. Prestwick3_000796

62. Spectrum5_002021

63. Bmse000686

64. Upcmld-dp153

65. Cid_9903

66. Lithocholic Acid, >=95%

67. Bidd:pxr0054

68. Schembl28449

69. 3a-hydroxy-5b-cholanic Acid

70. Bspbio_000932

71. Gtpl611

72. 4-10-00-00785 (beilstein Handbook Reference)

73. Mls002154006

74. 3a-hydroxy-5ss-cholanic Acid

75. Lithocholic Acid [mi]

76. Spbio_002871

77. Bpbio1_001026

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

79. 3a-hydroxy-5b-cholan-24-oate

80. Lithocholic Acid [hsdb]

81. Dtxsid6020779

82. Upcmld-dp153:001

83. 5ss--cholan-24-oic Acid-3a-ol

84. Hms1570o14

85. Hms2097o14

86. Hms2269c14

87. Hms3714o14

88. 3a-hydroxy-5b-cholan-24-oic Acid

89. Hy-b0172

90. Zinc3918156

91. Tox21_201868

92. Tox21_302791

93. 3a-hydroxy-5ss-cholan-24-oic Acid

94. 5.beta.-cholanic Acid-3.alpha.-ol

95. Bdbm50236238

96. Lmst04010003

97. S4003

98. (3a,5b)-3-hydroxy-cholan-24-oate

99. Akos016010251

100. Lithocholic Acid [ep Impurity]

101. Ccg-220796

102. Cs-2049

103. Ds-3878

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

105. Ncgc00091272-01

106. Ncgc00091272-04

107. Ncgc00091272-06

108. Ncgc00091272-07

109. Ncgc00091272-08

110. Ncgc00256451-01

111. Ncgc00259417-01

112. (3a,5b)-3-hydroxy-cholan-24-oic Acid

113. (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

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

115. Nci60_028903

116. Nci60_030095

117. Smr000112168

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

119. L0089

120. 5-.beta.-cholanic Acid, 3-.alpha.-hydroxy-

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

122. C03990

123. En300-393802

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. Z2216887942

132. 17-.beta.-(1-methyl-3-carboxypropyl)ethiocholan-3-.alpha.-ol

133. 3alpha-hydroxy-5beta-cholan-24-oic Acid (lithocholic Acid)

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

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

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

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

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

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

140. (4r)-4-((3r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)pentanoic Acid

141. (4r)-4-[(1r,3as,3br,5ar,7r,9as,9bs,11ar)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-1-yl]pentanoic Acid

142. (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]pentanoicacid

143. 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

2.3.3 Other Synonyms

1. Cas 434-13-9

2. 434-13-9

3. Cas-434-13-9

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 376.6 g/mol
Molecular Formula C24H40O3
XLogP36.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area57.5
Heavy Atom Count27
Formal Charge0
Complexity574
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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


BUILDING BLOCK

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