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    CAS-434-13-9

    BUILDING BLOCK

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    2D Structure
    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
    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

    2D Structure

    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