Taurochenodeoxycholic Acid

Details

• Internal ID: a95bd3e0-736b-4e12-abf3-3405c6d3e87c
• 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,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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
• InChI: InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1
• InChI Key: BHTRKEVKTKCXOH-BJLOMENOSA-N
• Popularity: 1,180 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

• 516-35-8
• Taurochenodeoxycholate
• Taurochenodesoxycholic acid
• Chenyltaurine
• Chenodeoxycholyltaurine
• 12-Deoxycholyltaurine
• Taurine chenodeoxycholate
• TCDCA
• Chenodeoxycholoyltaurine
• 12-Desoxycholyltaurine
• CHEMBL185878
• CHEBI:16525
• 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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
• 651KU15938
• N-(3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl)-taurine
• 2-[(3a,7a-dihydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonate
• C26H45NO6S
• Ursodeoxycholic acid;UDCA
• ST 24:1;O3;T
• TUD
• Taurochenodesoxycholate
• Taurochenodesoxycholicacid
• n-(3a,7a-dihydroxy-5b-cholan-24-oyl)-taurine
• SCHEMBL56780
• GTPL4747
• SCHEMBL20261728
• DTXSID101020121
• HMS3885A10
• UNII-651KU15938
• HY-N2027
• BDBM50375595
• LMST05040005
• MFCD00232922
• s3865
• AKOS025290383
• Taurochenodeoxycholic Acid-d5 (Major)
• CCG-269686
• CS-6329
• DB08833
• Ethanesulfonic acid, 2-(((3alpha,5beta,7alpha)-3,7-dihydroxy-24-oxocholan-24-yl)amino)-
• BS-16963
• NCI60_028900
• C05465
• Q7688892
• 3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide
• 2-([3alpha,7alpha-dihydroxy-24-oxo-5beta-cholan24-yl]amino)ethanesulfonic acid
• 2-[(3alpha,7alpha-dihydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid
• 3.ALPHA.,7.ALPHA.-DIHYDROXY-N-(2-SULFOETHYL)-5.BETA.-CHOLAN-24-AMIDE
• Taurochenodeoxycholate, TCDCA, 12-Deoxycholyltaurine, Chenodeoxycholyltaurine, Chenyltaurine
• 2-((R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)ethanesulfonic acid
• 2-((R)-4-((3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)ethanesulfonicacid
• 2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
• 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-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]ethanesulfonicacid
• 2-{[(3beta,5beta,7alpha,14beta,17alpha)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7944	79.44%
Caco-2	-	0.9009	90.09%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4120	41.20%
OATP2B1 inhibitior	+	0.5238	52.38%
OATP1B1 inhibitior	+	0.7241	72.41%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8064	80.64%
BSEP inhibitior	+	0.8773	87.73%
P-glycoprotein inhibitior	+	0.6071	60.71%
P-glycoprotein substrate	+	0.6996	69.96%
CYP3A4 substrate	+	0.7765	77.65%
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	-	0.7229	72.29%
CYP inhibitory promiscuity	-	0.7175	71.75%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	+	0.6300	63.00%
Carcinogenicity (trinary)	Non-required	0.6284	62.84%
Eye corrosion	-	0.9710	97.10%
Eye irritation	-	0.9510	95.10%
Skin irritation	-	0.7668	76.68%
Skin corrosion	-	0.8836	88.36%
Ames mutagenesis	-	0.5215	52.15%
Human Ether-a-go-go-Related Gene inhibition	-	0.4603	46.03%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.7782	77.82%
skin sensitisation	-	0.8455	84.55%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7100	71.00%
Acute Oral Toxicity (c)	III	0.7688	76.88%
Estrogen receptor binding	-	0.5292	52.92%
Androgen receptor binding	+	0.7225	72.25%
Thyroid receptor binding	+	0.6450	64.50%
Glucocorticoid receptor binding	+	0.7755	77.55%
Aromatase binding	+	0.6079	60.79%
PPAR gamma	+	0.6108	61.08%
Honey bee toxicity	-	0.7322	73.22%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9449	94.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2179	P04062	Beta-glucocerebrosidase	99.49%	85.31%
CHEMBL220	P22303	Acetylcholinesterase	99.34%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.13%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.99%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	95.00%	95.93%
CHEMBL2581	P07339	Cathepsin D	94.35%	98.95%
CHEMBL2094135	Q96BI3	Gamma-secretase	93.82%	98.05%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.73%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.32%	96.38%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	90.75%	95.34%
CHEMBL340	P08684	Cytochrome P450 3A4	90.57%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.57%	90.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.32%	82.69%
CHEMBL3055	P50613	Cyclin-dependent kinase 7	89.99%	81.88%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	89.16%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.89%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.49%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.11%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.02%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.82%	91.11%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	87.16%	93.10%
CHEMBL255	P29275	Adenosine A2b receptor	87.12%	98.59%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.67%	95.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.40%	96.90%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	86.24%	89.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.20%	96.00%
CHEMBL237	P41145	Kappa opioid receptor	86.01%	98.10%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.73%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.69%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.68%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.52%	93.04%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.28%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.08%	94.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.92%	96.61%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.75%	90.08%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.34%	91.24%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.24%	97.50%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	84.15%	96.03%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.02%	95.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.99%	91.38%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	83.55%	88.81%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.07%	90.24%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.61%	96.25%
CHEMBL2514	O95665	Neurotensin receptor 2	80.93%	100.00%
CHEMBL5646	Q6L5J4	FML2_HUMAN	80.77%	100.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.73%	98.33%
CHEMBL238	Q01959	Dopamine transporter	80.04%	95.88%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 387316
• LOTUS: LTS0017738
• wikiData: Q7688892