Lithocholic acid
Molecular FormulaC24H40O3
- 9 of 9 defined stereocentres
(3alpha,5beta)-3-Hydroxycholan-24-oic acid
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
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
SMEROWZSTRWXGI-HVATVPOCSA-N
(3a,5b)-3-hydroxycholan-24-oic acid
(3a,5b)-3-hydroxy-cholan-24-oic acid
(3α,5β)-3-Hydroxycholan-24-oic acid [ACD/IUPAC Name]
(3α,5β)-3-Hydroxycholan-24-säure [German] [ACD/IUPAC Name]
(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentansäure [German]
17b-(1-Methyl-3-carboxypropyl)etiocholan-3a-ol
3217757 [Beilstein]
3a-Hydroxy-5b-cholan-24-oic Acid
3a-Hydroxycholanic Acid
3α-hydroxy-5β-cholan-24-oic acid
3α-hydroxy-5β-cholanic acid
3-α-Hydroxy-5-β-cholanic acid
4-10-00-00785 [Beilstein]
5QU0I8393U
5β-Cholan-24-oic acid, 3α-hydroxy-
5-β-Cholan-24-oic acid, 3-α-hydroxy-
5β-Cholan-24-oic acid-3α-ol
Acide (3α,5β)-3-hydroxycholan-24-oïque [French] [ACD/IUPAC Name]
Acide (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-diméthylhexadécahydro-1H-cyclopenta[a]phénanthrén-17-yl]pentanoïque [French]
cholan-24-oic acid, 3-hydroxy-, (3a,5b)-
Cholan-24-oic acid, 3-hydroxy-, (3α,5β)- [ACD/Index Name]
Cholan-24-oic acid, 3-hydroxy-, (3α,5β)-
Cholan-24-oic acid, 3-hydroxy-, (3-α,5-β)- (9CI)
FZ2275000
Lithocholic acid [Wiki]
(3?,5?)-3-hydroxy-cholan-24-oic acid
(3a,5b)-3-hydroxy-cholan-24-oate
(3α,5β)-3-hydroxy-cholan-24-oic acid
(3α,5β)-3-hydroxy-cholan-24-oic acid
(3-α,5-β)-3-Hydroxycholan-24-oic acid
(3β,5β,14β,17α)-3-Hydroxycholan-24-Oic Acid
(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid
(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
(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]valeric acid
(4R)-4-[(3R,5R,8S,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
(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
(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
17-β-(1-Methyl-3-carboxypropyl)ethiocholan-3-α-ol
17β-(1-methyl-3-carboxypropyl)etiocholan-3α-ol
3?-hydroxycholanic acid
3a-hydroxy-5b-cholan-24-oate
3c-5β-cholan-24-oic acid
3α-hydroxy-5β-cholanoic acid
3α-hydroxycholanic acid
3-α-Hydroxycholanic acid
4OA
5-β-Cholanic acid, 3-α-hydroxy-
5β-cholanic acid-3α-ol
83701-16-0 [RN]
BPBio1_001026
BSPBio_000932
CHEMBL1478
Cholan-24-oic acid, 3-hydroxy-, (3-α, 5-β)-
lithocholic acid 95%
lithocholic acid, 98%
LITHOCHOLIC ACID[11,12-3H]
Lithocholic Acid|(3α,5β)-3-hydroxy-cholan-24-oic acid
Lithocholic acid-2,2,4,4-d4
lithocholic acld
Lithocholicacid
Lithocolic Acid
Prestwick2_000796
SBB012598
Spectrum5_002021
UNII:5QU0I8393U
UNII-5QU0I8393U
リトコール酸 [Japanese]
C03990 [DBID]
CCRIS 363 [DBID]
CHEBI:16325 [DBID]
L6250_SIGMA [DBID]
LMST04010003 [DBID]
NCGC00091272-01 [DBID]
NCI60_028903 [DBID]
NCI-C03861 [DBID]
Prestwick_88 [DBID]
Prestwick0_000796 [DBID]
SPBio_002871 [DBID]
UPCMLD-DP153:001 [DBID]
186 °C TCI L0089
Experimental Solubility:
10 mM in H2O MedChem Express HY-B0172
DMSO 75 mg/mL; Water <1 mg/mL; Ethanol 49 mg/mL MedChem Express HY-B0172
Predicted Physico-chemical Properties
Predicted Melting Point:
IRRITANT Matrix Scientific 099190
Target Organs:
Farnesoid X receptor;VD TargetMol T2202
Chemical Class:
A monohydroxy-5<stereo>beta</stereo>-cholanic acid with a <stereo>alpha</stereo>-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action. ChEBI CHEBI:16325
Therapeutical Effect:
Detergents Sean Ekins
Bio Activity:
FXR,PXR;VD receptor TargetMol T2202
Lithocholic acid is a toxic secondary bile acid, causes intrahepatic cholestasis, has tumor-promoting activity. MedChem Express
Lithocholic acid is a toxic secondary bile acid, causes intrahepatic cholestasis, has tumor-promoting activity.; Target: Others; Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. MedChem Express HY-B0172
Metabolism; Vitamin TargetMol T2202
Others MedChem Express HY-B0172
Boiling Point: 511.0±23.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.0 mmHg at 25°C
Flash Point: 276.9±19.1 °C
Molar Refractivity: 108.1±0.3 cm3
ACD/BCF (pH 5.5): 1457.92
ACD/BCF (pH 7.4): 23.29
Polar Surface Area: 58 Å2
MP  (exp database):  186 deg C
Water Solubility at 25 deg C (mg/L):  0.1784
Water Sol (Exper. database match) =  0.377 mg/L (20 deg C)
Wat Sol (v1.01 est) =  2.0157 mg/L
Wat Sol (Exper. database match) =  0.38
Neutral Organics-acid
Group Method:   8.48E-012  atm-m3/mole
Log Kaw used:  -7.802  (HenryWin est)
Mackay model           :  16.9
Octanol/air (Koa) model:  24.1
Fraction sorbed to airborne particulates (phi): 0.999 (Junge,Mackay)
Koc    :  1.362E+004
Henry LC:  8.48E-012 atm-m3/mole  (estimated by Group SAR Method)
Half-Life from Model River:  1.34E+008  hours   (5.583E+006 days)
Half-Life from Model Lake : 1.462E+009  hours   (6.09E+007 days)
Total sludge adsorption:    92.04  percent
Air       0.0157          5.86         1000
Water     2.85            900          1000
Soil      44              1.8e+003     1000
Sediment  53.2            8.1e+003     0
Persistence Time: 3.38e+003 hr