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    Lithocholic Acid

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 104Xls

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    2D Structure
    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

    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. 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 Weight 376.6 g/mol
    Molecular Formula C24H40O3
    XLogP36.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass376.29774513 g/mol
    Monoisotopic Mass376.29774513 g/mol
    Topological Polar Surface Area57.5 Ų
    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