Compound: LITHOCHOLIC ACID
SMILES: O=C(O)CC[C@H]([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@@H](C[C@H](O)CC4)CC3)C)CC2)CC1)C)C
InChIKey: SMEROWZSTRWXGI-HVATVPOCSA-N
Synonyms: LITHOCHOLIC ACID, 434-13-9, 3alpha-Hydroxy-5beta-cholanic acid, 3alpha-Hydroxy-5beta-cholan-24-oic acid, 3alpha-Hydroxycholanic acid, 3-alpha-Hydroxycholanic acid, NCI-C03861, 3alpha-Hydroxy-5beta-cholanoic acid, 3alpha-Hydroxy-5beta-cholanate, 5-beta-Cholanic acid, 3-alpha-hydroxy-, 5beta-Cholan-24-oic acid, 3alpha-hydroxy-, DTXSID6020779, Cholan-24-oic acid, 3-hydroxy-, (3alpha,5beta)-, 17beta-(1-Methyl-3-carboxypropyl)etiocholan-3alpha-ol, 5QU0I8393U, 17-beta-(1-Methyl-3-carboxypropyl)ethiocholan-3-alpha-ol, 5-beta-Cholan-24-oic acid, 3-alpha-hydroxy-, (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, NSC-683770, DTXCID80779, CHEBI:16325, Cholan-24-oic acid, 3-hydroxy-, (3-alpha,5-beta)-, NSC-657956, Acid, Isolithocholic, Acid, Lithocholic, (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, RefChem:153789, (4R)-4-((2S,5R,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid, 207-099-1, Lithocolic acid, (3alpha,5beta)-3-hydroxycholan-24-oic acid, 3-Hydroxycholan-24-oic acid, 5beta-Cholanic acid-3alpha-ol, MFCD00003682, 3-alpha-Hydroxy-5-beta-cholanic acid, NSC683770, (3-alpha,5-beta)-3-Hydroxycholan-24-oic acid, CHEMBL1478, 3.alpha.-Hydroxycholanic acid, ST069335, (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid, LCA, Litocholic acid, LITHOCHOLICACID, (3beta,5beta,14beta,17alpha)-3-Hydroxycholan-24-Oic Acid, 3|A-Hydroxy-5|A-cholanic acid, (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, CCRIS 363, HSDB 4113, SR-05000000450, EINECS 207-099-1, NSC 657956, BRN 3217757, Cholan-24-oic acid, 3-hydroxy-, (3.alpha.,5.beta.)-, 3alpha-Hydroxy-5beta-cholan-24-oic Acid (Lithocholic Acid), UNII-5QU0I8393U, lithocholic-acid, NSC657956, Cholan-24-oic acid, 3-hydroxy-, (3a,5b)-, Prestwick_88, Ursodeoxycholic Acid EP Impurity C, 4OA, CAS-434-13-9, Lithocholic acid CRS, NSC 683770, 4q0a, (3|A,5|A)-3-Hydroxycholan-24-oic Acid, Prestwick0_000796, Prestwick1_000796, Prestwick2_000796, Prestwick3_000796, Spectrum5_002021, bmse000686, UPCMLD-DP153, 3-Hydroxy-5-cholanic acid, cid_9903, Lithocholic acid, >=95%, BIDD:PXR0054, SCHEMBL28449, BSPBio_000932, GTPL611, 4-10-00-00785 (Beilstein Handbook Reference), MLS002154006, 3a-Hydroxy-5ss-cholanic acid, LITHOCHOLIC ACID [MI], SPBio_002871, BPBio1_001026, orb1306119, orb3141027, 3a-hydroxy-5b-cholan-24-oate, LITHOCHOLIC ACID [HSDB], UPCMLD-DP153:001, 5ss--Cholan-24-oic acid-3a-ol, GLXC-08146, HMS1570O14, HMS2097O14, HMS2269C14, HMS3714O14, 3a-hydroxy-5b-cholan-24-oic acid, HY-B0172, MSK10393, Tox21_201868, Tox21_302791, 3a-Hydroxy-5ss-cholan-24-oic acid, 5.beta.-Cholanic acid-3.alpha.-ol, BDBM50236238, EBC-07670, LMST04010003, s4003, SBB012598, (3a,5b)-3-hydroxy-cholan-24-oate, 5beta-Cholan-24-oic acid-3alpha-ol, AKOS016010251, LITHOCHOLIC ACID [EP IMPURITY], CCG-220796, CS-2049, DS-3878, FL24913, ST 24:1;O3, (3a,5b)-3-Hydroxycholan-24-Oic acid, 3.alpha.-Hydroxy-5.beta.-cholanic acid, NCGC00091272-01, NCGC00091272-04, NCGC00091272-06, NCGC00091272-07, NCGC00091272-08, NCGC00256451-01, NCGC00259417-01, (3a,5b)-3-hydroxy-cholan-24-oic acid, (4R)-4-[(1R,3aS,3bR,5aR,7R,9aS,9bS,11aR)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid, 3.alpha.-Hydroxy-5.beta.-cholanoic acid, DA-75041, NCI60_028903, NCI60_030095, SMR000112168, SY105976, 5.beta.-Cholan-24-oic acid-3.alpha.-ol, L0089, NS00031340, 5-.beta.-Cholanic acid, 3-.alpha.-hydroxy-, 3.alpha.-Hydroxy-5.beta.-cholan-24-oic acid, C03990, EN300-393802, 17b-(1-Methyl-3-carboxypropyl)etiocholan-3a-ol, 5.beta.-Cholan-24-oic acid, 3.alpha.-hydroxy-, F241301, Q3323035, SR-05000000450-2, SR-05000000450-4, SR-05000000450-5, URSODEOXYCHOLIC ACID IMPURITY C [EP IMPURITY], Z2216887942, 17-.beta.-(1-Methyl-3-carboxypropyl)ethiocholan-3-.alpha.-ol, Cholan-24-oic acid, 3-hydroxy-, (3-.alpha., 5-.beta.)-, Cholan-24-oic acid, 3-hydroxy-, (3-alpha,5-beta)- (9CI), 17.BETA.-(1-METHYL-3-CARBOXYPROPYL)ETIOCHOLAN-3.ALPHA.-OL, Lithocholic acid, European Pharmacopoeia (EP) Reference Standard, AC268B61-0548-4391-90E9-546636926870, Lithocholic acid, 50 mug/mL in methanol, certified reference material, Ursodeoxycholic Acid EP Impurity C; Chenodeoxycholic Acid EP Impurity C, 2,8-DIAMINO-9-[3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-1H-PURIN-6-ONE, (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
Theoretical properties:
molecular_formula: C24H40O3
molecular_weight: 376.6 g/mol
exact_mass: 376.29774513 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 27
topological_polar_surface_area: 57.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: HEXAGONAL LEAFLETS FROM ALC, PRISMS FROM ACETIC ACID
color: HEXAGONAL LEAFLETS FROM ALC, PRISMS FROM ACETIC ACID
melting_point: 363 to 367 °F (NTP, 1992)
solubility: less than 1 mg/mL at 67.5 °F (NTP, 1992)
Descriptions:
pubchem: Lithocholic acid is a monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action. It has a role as a geroprotector, a mouse metabolite and a human metabolite. It is a C24-steroid, a bile acid and a monohydroxy-5beta-cholanic acid. It is a conjugate acid of a lithocholate.
chebi: A monohydroxy-5β-cholanic acid with a α-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.
chembl: LITHOCHOLIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Lithocholic acid, also known as 3α-hydroxy-5β-cholan-24-oic acid or LCA, is a bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces LCA from chenodeoxycholic acid by reduction of the hydroxyl functional group at carbon-7 in the "B" ring of the steroid framework.
It has been implicated in human and experimental animal carcinogenesis.
Dietary fiber can bind to lithocholic acid and aid in its excretion in stool; as such, fiber can protect against colon cancer.
LCA (and LCA acetate and LCA propionate) can activate the vitamin D receptor without raising calcium levels as much as vitamin D itself.
LCA binds with 20 μM affinity to the human membrane enzyme NAPE-PLD, enhancing dimer assembly and enabling catalysis. NAPE-PLD catalyzes the release of anandamide and other N-acylethanolamines (NAE) from the membrane precursor N-acylphosphatidylethanolamine (NAPE). NAPE-PLD facilitates crosstalk between bile acid signals and lipid amide signals.
LCA has been reported to have anti-aging effects in fruit flies, nematodes, and mice.