Compound: cholic acid
SMILES: O=C(O)CC[C@H]([C@@H]1[C@]2([C@@H](O)C[C@@H]3[C@@]4([C@@H](C[C@H](O)CC4)C[C@H]([C@H]3[C@@H]2CC1)O)C)C)C
InChIKey: BHQCQFFYRZLCQQ-OELDTZBJSA-N
Synonyms: cholic acid, 81-25-4, Cholalic acid, Colalin, Cholalin, Cholbam, Cholsaeure, cholicacid, NSC-6135, kolbam, orphacol, 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid, 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid, Cholic acid, 5beta-, 3,7,12-Trihydroxycholanic acid, (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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, G1JO7801AE, Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)-, DTXSID6040660, CHEBI:16359, 3-alpha,7-alpha,12-alpha-Trihydroxycholansaeure, 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3alpha,7alpha,12alpha-triol, 3,7,12-Trihydroxy-cholan-24-oic acid (3-alpha,5-beta,7-alpha,12-alpha), Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-alpha,5-beta,7-alpha,12-alpha)-, (4R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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, RefChem:54816, DTXCID4020660, Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-alpha, 5-beta, 7-alpha, 12-alpha)-, (4R)-4-((1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid, (4R)-4-((1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid, 201-337-8, MFCD00003672, Cholic acid [USAN], (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid, Cholan-24-oic acid, 3,7,12-trihydroxy-, (3a,5b,7a,12a)-, C24H40O5, HSDB 982, Ursodeoxycholic Acid EP Impurity B, CHEMBL205596, NSC6135, CHD, 3a,7a,12a-Trihydroxy-5b-cholanic acid, 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholan-24-oic acid, 5beta-Cholan-24-oic acid, 3alpha,7alpha,12alpha-trihydroxy-, 3,7,12-Trihydroxycholan-24-oic acid, (3alpha,5beta,7alpha,12alpha)-, Cholic acid (sodium), (4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid, 4-[(3R,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-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, (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid, 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic Acid (Cholic Acid), 4-((1S,2S,7S,11S,16S,5R,9R,10R,14R,15R)-5,9,16-trihydroxy-2,15-dimethyltetracy clo[8.7.0.0<2,7>.0<11,15>]heptadec-14-yl)pentanoic acid, SMR000112165, Colalin (VAN), Cholsaeure [German], 5beta-Cholanic acid-3alpha,7alpha,12alpha-triol, UNII-G1JO7801AE, Cholalate, OrphacolReg, cholic-acid, TERPENES AND TERPENOIDS, CCRIS 1626, (3alpha,5beta,7alpha,8xi,12alpha)-3,7,12-trihydroxycholan-24-oic acid, 5b-Cholate, 5b-Cholic acid, Cholic acid CRS, CholsA currencyure, Cholbam (TN), EINECS 201-337-8, 129874-08-4, Cholic acid (8CI), 5.beta.-Cholic acid, BRN 2822009, Spectrum5_002005, CHOLIC ACID [MI], 3alpha,7alpha,12alpha-Trihydroxycholanic acid, bmse000650, CHOLIC ACID [FCC], CHOLIC ACID [JAN], Cholic acid (JAN/USAN), EC 201-337-8, CHOLIC ACID [HSDB], BIDD:PXR0196, SCHEMBL27461, GTPL609, 3.alpha.,7.alpha.,12.alpha.-Trihydroxy-5.beta.-cholanic acid, 4-10-00-02072 (Beilstein Handbook Reference), MLS001066422, MLS002207051, CHOLIC ACID [USP-RS], CHOLIC ACID [WHO-DD], 3a,7a,12a-Trihydroxycholanate, 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanoic acid, orb1304796, orb3141025, CHOLIC ACID [EMA EPAR], BDBM21675, BDBM21680, 3-alpha,7-alpha,12-alpha-Trihydroxycholansaeure [German], MSK2328, CHOLIC ACID [EP IMPURITY], CHOLIC ACID [ORANGE BOOK], HMS2268L18, 3a,7a,12a-Trihydroxy-b-cholanate, 3a,7a,12a-Trihydroxycholanic acid, HY-N0324, 3a,7a,12a-Trihydroxy-5b-cholanate, 5b-Cholanic acid-3a,7a,12a-triol, BBL029799, EBC-08822, LMST04010001, s3742, STK801993, US11208418, Example Obeticholic, 3a,7a,12a-Trihydroxy-5b-cholanoate, 3a,7a,12a-Trihydroxy-beta-cholanate, AKOS005622502, 3a,7a,12a-Trihydroxy-b-cholanic acid, CCG-268746, CS-6608, DB02659, FC09616, US10208081, E6-ECDCA, US10266560, Example 6-ECDCA, 3,7,12-Trihydroxy-cholan-24-oic acid, 3a,7a,12a-Trihydroxy-5A-cholanic acid, NCGC00142384-03, 3a,7a,12a-Trihydroxy-5b-cholanoic acid, 3a,7a,12a-Trihydroxy-beta-cholanic acid, AS-69849, BP-30084, ST024722, SY012968, 3alpha,7alpha-dihydroxy-5beta-cholic acid, 3a,7a,12a-Trihydroxy-5b-cholan-24-oate, Cholic acid, Vetec(TM) reagent grade, 98%, NS00010900, Cholic acid, from ox or sheep bile, >=98%, 3a,7a,12a-Trihydroxy-5b-cholan-24-oic acid, C00695, D10699, EN300-6766788, Q287415, SR-01000765698, 3alpha,7alpha,12alpha-Trihydroxy-beta-cholanic acid, SR-01000765698-4, 3.alpha.,12.alpha.-Trihydroxy-5.beta.-cholanic acid, BRD-K43164539-001-11-5, URSODEOXYCHOLIC ACID IMPURITY B [EP IMPURITY], 3-.alpha.,7-.alpha.,12-.alpha.-Trihydroxycholansaeure, 3alpha, 7alpha, 12alpha-trihydroxy-5beta-cholanic acid, 3alpha, 7alpha, 12alpha-trihydroxy-5beta-cholanoic acid, Z1954806455, 3-&alpha,7-&alpha,12-&alpha-trihydroxy-5-&beta-cholanate, Cholic acid, British Pharmacopoeia (BP) Reference Standard, Cholic acid, European Pharmacopoeia (EP) Reference Standard, 17b-[1-Methyl-3-carboxypropyl]etiocholane-3a,7a,12a-triol, 5.beta.-Cholan-24-oic acid,7.alpha.,12.alpha.-trihydroxy-, 5beta-Cholanic acid, 3alpha,7alpha,12alpha-trihydroxy- (7CI), 5beta-Cholanic acid-3alpha,7alpha,12alpha-triol 5beta-Cholic acid, Cholic acid, 500 mug/mL in methanol, certified reference material, Cholic acid, United States Pharmacopeia (USP) Reference Standard, (3alpha,5beta,7alpha,8x,12alpha)-3,7,12-trihydroxycholan-24-oic acid, 17beta-[1-Methyl-3-carboxypropyl]etiocholane-3alpha,7alpha,12alpha-triol, 3-.alpha.,7-.alpha.,12-.alpha.-Trihydroxy-5-.beta.-cholan-24-oic acid, 5.beta.-Cholan-24-oic acid, 3.alpha.,7.alpha.,12.alpha.-trihydroxy-, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-3,7,12-Trihydroxycholan-24-oic acid sodium salt, (3alpha,5beta,7alpha,8alpha,12alpha,14beta,17alpha)-3,7,12-trihydroxycholan-24-oic acid, 17.beta.-(1-Methyl-3-carboxypropyl)etiocholane-3.alpha.,7.alpha.,12.alpha.-triol, 3,7,12-Trihydroxy-cholan-24-oic acid, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-, Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)- (9CI), Cholan-24-oic acid,7,12-trihydroxy-, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-, (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid, (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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, (R)-4-((3R,5S,7R,8R,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid, 10321-98-9
Theoretical properties:
molecular_formula: C24H40O5
molecular_weight: 408.6 g/mol
exact_mass: 408.28757437 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 4
heavy_atom_count: 29
topological_polar_surface_area: 98 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Plates from dilute acetic acid
color: Plates from dilute acetic acid
Descriptions:
pubchem: Cholic acid is a bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12. It has a role as a mouse metabolite and a human metabolite. It is a C24-steroid, a trihydroxy-5beta-cholanic acid, a bile acid, a 3alpha-hydroxy steroid, a 7alpha-hydroxy steroid and a 12alpha-hydroxy steroid. It is a conjugate acid of a cholate.
chebi: A bile acid that is 5β-cholan-24-oic acid bearing three α-hydroxy substituents at position 3, 7 and 12.
chembl: CHOLIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in alcohol and acetic acid),  it is a white crystalline substance.  Salts of cholic acid are called cholates.  Cholic acid, along with chenodeoxycholic acid, is one of the two major bile acids produced by the liver, where it is synthesized from cholesterol.  These two major bile acids are roughly equal in concentration in humans. Derivatives are made from cholyl-CoA, which exchanges its CoA with either glycine, or taurine, yielding glycocholic and taurocholic acid, respectively.
Cholic acid downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis), and cholesterol does the opposite.  This is why chenodeoxycholic acid, and not cholic acid, can be used to treat gallstones (because decreasing bile acid synthesis would supersaturate the stones even more).
Cholic acid and chenodeoxycholic acid are the most important human bile acids.  Other species may synthesize different bile acids as their predominant primary bile acids.