5D5

2-{[(3alpha,5beta,7alpha,8alpha,14beta,17alpha)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid

Created:	2015-09-08
Last modified:	2016-04-13

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2 entries where 5D5 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	79
Chiral Atom Count	10
Bond Count	82
Aromatic Bond Count	0

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Chemical Component Summary
Name	2-{[(3alpha,5beta,7alpha,8alpha,14beta,17alpha)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid
Systematic Name (OpenEye OEToolkits)	2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-bis(oxidanyl)-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
Formula	C₂₆ H₄₅ N O₆ S
Molecular Weight	499.704
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	C1C4(C(CC(C1)O)CC(O)C3C2C(C(C(CCC(=O)NCCS(=O)(O)=O)C)CC2)(C)CCC34)C
SMILES	CACTVS	3.385	C[CH](CCC(=O)NCC[S](O)(=O)=O)[CH]1CC[CH]2[CH]3[CH](O)C[CH]4C[CH](O)CC[C]4(C)[CH]3CC[C]12C
SMILES	OpenEye OEToolkits	1.9.2	CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
Canonical SMILES	CACTVS	3.385	C[C@H](CCC(=O)NCC[S](O)(=O)=O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES	OpenEye OEToolkits	1.9.2	C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChI	InChI	1.03	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
InChIKey	InChI	1.03	BHTRKEVKTKCXOH-LBSADWJPSA-N

Drug Info: DrugBank

DrugBank ID	DB08834
Name	Tauroursodeoxycholic acid
Groups	approved investigational
Description	Tauroursodeoxycholic acid, also known as ursodoxicoltaurine, is a highly hydrophilic tertiary bile acid [A249070] that is produced in humans at a low concentration.[A249070] It is a taurine conjugate of [ursodeoxycholic acid] [A249065] with comparable therapeutic efficacy and safety,[A249070] but a much higher hydrophilicity.[A249060] Normally, hydrophilic bile acids regulates hydrophobic bile acids and their cytotoxic effects. Tauroursodeoxycholic acid can reduce the absorption of cholesterol in the small intestine, thereby reducing the body's intake of dietary cholesterol and the body cholesterol content.[A249080] Tauroursodeoxycholic acid is currently used in Europe to treat and prevent gallstones as a bile acid derivative.[L17040] Due to a range of its molecular properties - namely its anti-apoptotic effects - tauroursodeoxycholic acid has been examined in inflammatory metabolic diseases and neurodegenerative diseases.[A249065,A249070]
Synonyms	Ursodoxicoltaurine Tauroursodeoxycholic acid dihydrate Tauroursodeoxycholate Tauroursodesoxycholic acid Taurursodiol Ursodeoxycholyltaurine TUDCA Tauroursodeoxycholic acid
Brand Names	Relyvrio Albrioza
Indication	Tauroursodeoxycholic acid is used to prevent and treat gallstone formation.[L17040] Tauroursodeoxycholic acid is used in combination with [phenylbutyric acid] to treat amyotrophic lateral sclerosis (ALS) in adults.[L42105,L43473]
Categories	Bile Acids and Salts Cholagogues and Choleretics Cholanes Cholic Acids Gastrointestinal Agents Isomerism Sulfur Compounds Taurodeoxycholic Acid
CAS number	14605-22-2

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Integrin alpha-5	MGSRTPESPLHAVQLRWGPRRRPPLLPLLLLLLPPPPRVGGFNLDAEAPA...	unknown	activator
Cytochrome P450 3A1	MDLLSALTLETWVLLAVVLVLLYGFGTRTHGLFKKQGIPGPKPLPFFGTV...	unknown	inducer
Cytochrome P450 3A2	MDLLSALTLETWVLLAVILVLLYRLGTHRHGIFKKQGIPGPKPLPFLGTV...	unknown	inducer
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	substrate
Cystine/glutamate transporter	MVRKPVVSTISKGGYLQGNVNGRLPSLGNKEPPGQEKVQLKRKVTLLRGV...	unknown	substrate
ATP-binding cassette sub-family G member 5	MGDLSSLTPGGSMGLQVNRGSQSSLEGAPATAPEPHSLGILHASYSVSHR...	unknown	downregulator
ATP-binding cassette sub-family G member 8	MAGKAAEERGLPKGATPQDTSGLQDRLFSSESDNSLYFTYSGQPNTLEVR...	unknown	downregulator
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	regulator
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682