Lithocholic Acid

Details

• Internal ID: 93ed9c95-b8af-48b5-8586-835a9d5d2558
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Monohydroxy bile acids, alcohols and derivatives
• 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
• 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
• InChI Key: SMEROWZSTRWXGI-HVATVPOCSA-N
• Popularity: 3,694 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₀O₃
• Molecular Weight: 376.60 g/mol
• Exact Mass: 376.29774513 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 5.51
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 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
• CHEBI:16325
• 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
• 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
• MFCD00003682
• 5beta-Cholanic acid-3alpha-ol
• 3-Hydroxycholan-24-oic acid
• (3alpha,5beta)-3-hydroxycholan-24-oic acid
• 3-alpha-Hydroxy-5-beta-cholanic acid
• NSC683770
• (3-alpha,5-beta)-3-Hydroxycholan-24-oic acid
• CHEMBL1478
• 3.alpha.-Hydroxycholanic acid
• 5beta-Cholan-24-oic acid-3alpha-ol
• ST069335
• 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
• NSC 683770
• 4q0a
• 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
• 3a-hydroxy-5b-cholan-24-oate
• LITHOCHOLIC ACID [HSDB]
• UPCMLD-DP153:001
• 5ss--Cholan-24-oic acid-3a-ol
• 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
• LMST04010003
• s4003
• SBB012598
• (3a,5b)-3-hydroxy-cholan-24-oate
• AKOS016010251
• LITHOCHOLIC ACID [EP IMPURITY]
• CCG-220796
• CS-2049
• DS-3878
• FL24913
• ST 24:1;O3
• 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
• 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
• 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
• 2,8-DIAMINO-9-[3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-1H-PURIN-6-ONE
• (3a,5b)-3-Hydroxycholan-24-oic acid;17b-(1-Methyl-3-carboxypropyl)etiocholan-3a-ol;3-Hydroxycholan-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
• (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
• (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	-	0.5908	59.08%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7788	77.88%
OATP2B1 inhibitior	-	0.6025	60.25%
OATP1B1 inhibitior	-	0.7737	77.37%
OATP1B3 inhibitior	+	0.9623	96.23%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8329	83.29%
P-glycoprotein inhibitior	+	0.8036	80.36%
P-glycoprotein substrate	-	0.6387	63.87%
CYP3A4 substrate	+	0.7544	75.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8413	84.13%
CYP3A4 inhibition	-	0.8665	86.65%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9596	95.96%
CYP2D6 inhibition	-	0.9787	97.87%
CYP1A2 inhibition	-	0.9125	91.25%
CYP2C8 inhibition	-	0.8823	88.23%
CYP inhibitory promiscuity	-	0.9435	94.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6997	69.97%
Eye corrosion	-	0.9959	99.59%
Eye irritation	-	0.8462	84.62%
Skin irritation	+	0.7403	74.03%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5863	58.63%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5315	53.15%
skin sensitisation	-	0.7386	73.86%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8933	89.33%
Acute Oral Toxicity (c)	III	0.7072	70.72%
Estrogen receptor binding	+	0.5563	55.63%
Androgen receptor binding	+	0.7988	79.88%
Thyroid receptor binding	+	0.6705	67.05%
Glucocorticoid receptor binding	+	0.9238	92.38%
Aromatase binding	+	0.7161	71.61%
PPAR gamma	+	0.6102	61.02%
Honey bee toxicity	-	0.7854	78.54%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9812	98.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	15 nM	Ki	via Super-PRED
CHEMBL2047	Q96RI1	Bile acid receptor FXR	18.3 nM	IC50	PMID: 24775917
CHEMBL1293237	P54132	Bloom syndrome protein	39810.7 nM	Potency	via CMAUP
CHEMBL5990	P38398	Breast cancer type 1 susceptibility protein	39810.7 nM	Potency	via CMAUP
CHEMBL1795098	Q9GZU7	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	4823 nM	IC50	via CMAUP
CHEMBL3468	P55210	Caspase-7	12589.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	680 nM; 580 nM; 730 nM; 580 nM	EC50; EC50; EC50; EC50	PMID: 25735208; PMID: 18307294; PMID: 24900622; via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM	Potency	via CMAUP
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	12740 nM	IC50	PMID: 23067554
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	20450 nM	IC50	PMID: 23067554
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	44668.4 nM	Potency	via CMAUP
CHEMBL1977	P11473	Vitamin D receptor	46700 nM; 13600 nM	IC50; IC50	PMID: 26774929; PMID: 26774929

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.02%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	97.27%	90.17%
CHEMBL237	P41145	Kappa opioid receptor	94.60%	98.10%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.02%	97.25%
CHEMBL238	Q01959	Dopamine transporter	90.10%	95.88%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.93%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.49%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.11%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.97%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.61%	98.95%
CHEMBL2179	P04062	Beta-glucocerebrosidase	87.38%	85.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.36%	90.71%
CHEMBL274	P51681	C-C chemokine receptor type 5	87.31%	98.77%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.03%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.65%	89.05%
CHEMBL340	P08684	Cytochrome P450 3A4	86.58%	91.19%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	85.54%	96.03%
CHEMBL236	P41143	Delta opioid receptor	84.70%	99.35%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.63%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.45%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.16%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.83%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.81%	93.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.47%	93.00%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.61%	97.86%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.30%	96.47%
CHEMBL220	P22303	Acetylcholinesterase	82.13%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.66%	99.17%
CHEMBL2514	O95665	Neurotensin receptor 2	80.66%	100.00%

Plants that contains it

• Cephalotaxus fortunei

Cross-Links

• PubChem: 9903
• NPASS: NPC280026
• ChEMBL: CHEMBL1478