Taurodeoxycholic Acid

Details

• Internal ID: 1a6ef623-79ad-43b7-9d4a-c3fe6d57fadd
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Taurinated bile acids and derivatives
• IUPAC Name: 2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonic acid
• SMILES (Canonical): CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C
• SMILES (Isomeric): C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• InChI: InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1
• InChI Key: AWDRATDZQPNJFN-VAYUFCLWSA-N
• Popularity: 621 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₅NO₆S
• Molecular Weight: 499.70 g/mol
• Exact Mass: 499.29675933 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.40
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• Taurodeoxycholate
• Deoxycholyltaurine
• Tudcabil
• Taurodesoxycholic acid
• TAURODEOXYCHLOIC ACID
• 516-50-7
• CHEBI:9410
• CHEMBL412272
• HY209
• HY-209
• SODIUM TAURODEOXYCHOLATE
• J339.140J
• Sodium taurodeoxylate
• 2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoylamino]ethanesulfonic acid
• N-(3alpha,12alpha-dihydroxy-5beta-cholan-24-oyl)-taurine
• Taurodeoxycholic acid sodium salt
• Deoxytaurocholic acid
• TDCA
• 20668G0RPI
• Deoxy Cholate
• Deoxytaurocholate
• Taurodesoxycholate
• Taurodesoxycholsaure
• Spectrum5_002017
• Deoxycholyltaurine; Deoxytaurocholic acid; TDCA;Tudcabil
• SCHEMBL27304
• Taurodeoxycholic acid [WHO-DD]
• DTXSID00873418
• HY-B1899
• BDBM50375592
• LMST05040013
• MS-29280
• CS-0013959
• N-(3a,12a-dihydroxy-5b-cholan-24-oyl)-Taurine
• Q7688896
• W-204225
• BRD-K33572481-001-01-0
• 3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLANIC ACID-24-TAURINE
• TAURINE, N-(3.ALPHA.,12.ALPHA.-DIHYDROXY-5.BETA.-CHOLAN-24-OYL)-
• 2-[(3alpha,12alpha-dihydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid
• 2-(((3.ALPHA.,5.BETA.,12.ALPHA.)-3,12-DIHYDROXY-24-OXOCHOLAN-24-YL)AMINO)ETHANESULFONIC ACID
• 6SB

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7944	79.44%
Caco-2	-	0.9080	90.80%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4120	41.20%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	+	0.8440	84.40%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8064	80.64%
BSEP inhibitior	+	0.7775	77.75%
P-glycoprotein inhibitior	-	0.4417	44.17%
P-glycoprotein substrate	+	0.7769	77.69%
CYP3A4 substrate	+	0.7439	74.39%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.8239	82.39%
CYP3A4 inhibition	-	0.8612	86.12%
CYP2C9 inhibition	-	0.8625	86.25%
CYP2C19 inhibition	-	0.8426	84.26%
CYP2D6 inhibition	-	0.8685	86.85%
CYP1A2 inhibition	-	0.7814	78.14%
CYP2C8 inhibition	-	0.6144	61.44%
CYP inhibitory promiscuity	-	0.7175	71.75%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	+	0.6300	63.00%
Carcinogenicity (trinary)	Non-required	0.6284	62.84%
Eye corrosion	-	0.9710	97.10%
Eye irritation	-	0.9220	92.20%
Skin irritation	-	0.7668	76.68%
Skin corrosion	-	0.8836	88.36%
Ames mutagenesis	-	0.7081	70.81%
Human Ether-a-go-go-Related Gene inhibition	-	0.5295	52.95%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.6816	68.16%
skin sensitisation	-	0.8455	84.55%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8433	84.33%
Acute Oral Toxicity (c)	III	0.7688	76.88%
Estrogen receptor binding	+	0.5332	53.32%
Androgen receptor binding	+	0.7816	78.16%
Thyroid receptor binding	+	0.6452	64.52%
Glucocorticoid receptor binding	+	0.7727	77.27%
Aromatase binding	+	0.6121	61.21%
PPAR gamma	+	0.6129	61.29%
Honey bee toxicity	-	0.6652	66.52%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9449	94.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	680 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.25%	94.45%
CHEMBL2179	P04062	Beta-glucocerebrosidase	99.12%	85.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.21%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	96.34%	96.38%
CHEMBL2094135	Q96BI3	Gamma-secretase	96.15%	98.05%
CHEMBL2581	P07339	Cathepsin D	94.12%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	91.19%	95.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.99%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.91%	97.25%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	90.59%	95.34%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.83%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.49%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	89.45%	91.19%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.39%	96.77%
CHEMBL237	P41145	Kappa opioid receptor	89.02%	98.10%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.49%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.46%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.44%	99.23%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.37%	93.10%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.35%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.10%	97.09%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.89%	97.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.77%	98.75%
CHEMBL255	P29275	Adenosine A2b receptor	86.46%	98.59%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	86.15%	81.88%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	85.79%	96.25%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	85.57%	88.81%
CHEMBL1914	P06276	Butyrylcholinesterase	85.48%	95.00%
CHEMBL274	P51681	C-C chemokine receptor type 5	85.21%	98.77%
CHEMBL4588	P22894	Matrix metalloproteinase 8	85.12%	94.66%
CHEMBL238	Q01959	Dopamine transporter	84.63%	95.88%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.40%	91.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.39%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.05%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.94%	96.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.45%	91.24%
CHEMBL4302	P08183	P-glycoprotein 1	83.24%	92.98%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.24%	96.90%
CHEMBL221	P23219	Cyclooxygenase-1	82.98%	90.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.53%	95.83%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	82.12%	95.36%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.10%	93.04%
CHEMBL2514	O95665	Neurotensin receptor 2	81.42%	100.00%
CHEMBL3921	Q9Y251	Heparanase	81.19%	94.00%
CHEMBL5028	O14672	ADAM10	80.99%	97.50%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.96%	98.33%
CHEMBL5646	Q6L5J4	FML2_HUMAN	80.71%	100.00%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	80.62%	96.03%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	80.60%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.12%	94.45%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.01%	91.03%

Plants that contains it

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Cross-Links

• PubChem: 2733768
• LOTUS: LTS0152375
• wikiData: Q7688896