Ursodeoxycholic acid

Details

• Internal ID: f9d0ab6b-a106-4159-97e8-d3dd1ef6b893
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Bile acids, alcohols and derivatives > Hydroxy bile acids, alcohols and derivatives > Dihydroxy bile acids, alcohols and derivatives
• IUPAC Name: (4R)-4-[(3R,5S,7S,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]pentanoic acid
• SMILES (Canonical): CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• SMILES (Isomeric): C[C@H](CCC(=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=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
• InChI Key: RUDATBOHQWOJDD-UZVSRGJWSA-N
• Popularity: 11,154 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₀O₄
• Molecular Weight: 392.60 g/mol
• Exact Mass: 392.29265975 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• ursodiol
• 128-13-2
• Actigall
• ursodeoxycholate
• UDCA
• Ursofalk
• Ursolvan
• UrSO
• Delursan
• Ursodesoxycholic acid
• Urso Forte
• Destolit
• Ursochol
• Cholit-ursan
• Litursol
• Solutrat
• Ursobilin
• Ursodamor
• Arsacol
• Deursil
• Lyeton
• Ursacol
• Peptarom
• Urso DS
• UDCS
• 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid
• Ursosan
• Ursacholic Acid
• Urso 250
• Ursodiol [USAN]
• Deoxyursocholic Acid
• Antigall
• Urosiol
• 3-alpha,7-beta-Dioxycholanic acid
• 7-beta-Hydroxylithocholic acid
• Ursocholic acid, deoxy-
• Ursodeoxycholicacid
• 3-alpha,7-beta-Dihydroxycholanic acid
• Ursodexycholic Acid
• Acido ursodeossicolico [Italian]
• Acido ursodeoxicolico
• Acido ursodeossicolico
• Acido ursodeoxicolico [INN-Spanish]
• Acidum ursodeoxycholicum [INN-Latin]
• Acide ursodesoxycholique
• Acide ursodesoxycholique [INN-French]
• Acidum ursodeoxycholicum
• Ursonorm
• NSC 683769
• 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid
• Sodium Ursodeoxycholate
• (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
• Actigall (TN)
• Ursodiol (USP)
• NSC 657950
• BRN 3219888
• 3,7-Dihydroxycholan-24-oic acid
• CCRIS 5502
• (4R)-4-[(3R,5S,7S,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]pentanoic acid
• Urso (TN)
• Ursodiol [USAN:USP]
• EINECS 204-879-3
• Ursodeoxycholic acid [INN]
• ursocol
• CHEMBL1551
• UNII-724L30Y2QR
• MLS000028461
• CHEBI:9907
• 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol
• 724L30Y2QR
• 3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-oic Acid
• NSC-683769
• 5beta-Cholanic Acid-3alpha,7beta-diol
• SMR000058403
• Cholan-24-oic acid, 3,7-dihydroxy-, (3alpha,5beta,7beta)-
• 3alpha,7beta-Dihydroxy-5beta-cholanic acid
• U0030
• Cholan-24-oic acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.beta.)-
• EC 204-879-3
• U-9000
• (R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
• 4-10-00-01604 (Beilstein Handbook Reference)
• IU5
• 5-beta-Cholan-24-oic acid, 3-alpha,7-beta-dihydroxy-
• (3alpha,5beta,7beta,8xi)-3,7-dihydroxycholan-24-oic acid
• Cholan-24-oic acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-beta)-
• Dom-ursodiol c
• PHL-ursodiol c
• PMS-ursodiol c
• 7beta-Hydroxylithocholic acid
• SR-01000737091
• MFCD00003680
• Ursodexycholate
• Paptarom
• Udiliv
• Desol
• Urdes
• Urosdesoxycholate
• 5beta-Cholan-24-oic acid-3alpha,7beta-diol
• Ursodesoxycholicacid
• Ursodeoxycholoc acid
• Deursil (TN)
• Ursosan (TN)
• Urosdesoxycholic acid
• Urso Forte (TN)
• URSODIOL [INCI]
• URSODIOL [MI]
• Ursodiol (Actigal Urso)
• URSODIOL [VANDF]
• Prestwick0_000958
• Prestwick1_000958
• Prestwick2_000958
• Prestwick3_000958
• 7A-Hydroxylithocholic acid
• D0G3SH
• URSODIOL [USP-RS]
• (3-alpha,5-beta,7-beta)-3,7-Dihydroxycholan-24-oic acid
• SCHEMBL27200
• BSPBio_000956
• 7bet.-Hydroxylithocholic acid
• cid_31401
• MLS001066373
• MLS002548885
• SPBio_003105
• 17-beta-(1-methyl-3-carboxypropyl)etiocholane-3-alpha,7beta-diol
• Ursodeoxycholic acid, >=99%
• URSODIOL [ORANGE BOOK]
• BPBio1_001052
• GTPL7104
• 7.beta.-Hydroxylithocholic acid
• Ursodiol (Ursodeoxycholic Acid)
• DTXSID6023731
• URSODIOL [USP MONOGRAPH]
• BDBM53721
• HMS1570P18
• HMS2097P18
• HMS2233L14
• HMS3259A13
• HMS3714P18
• Ursodeoxycholic acid (JP15/INN)
• Ursodeoxycholic acid (JP17/INN)
• URSODEOXYCHOLIC ACID [JAN]
• 3alpha,7beta-dihydroxycholanic acid
• 3a,7b-dihydroxy-5b-cholan-24-oate
• HB4645
• LMST04010033
• s1643
• URSODEOXYCHOLIC ACID [MART.]
• URSODEOXYCHOLIC ACID [WHO-DD]
• 5A-Cholan-24-oic acid-3A,7A-diol
• AKOS015955898
• CCG-220958
• CS-1932
• CS-O-30812
• DB01586
• KS-5243
• NC00487
• SMP2_000012
• 3.alpha.,7.beta.-Dihydroxycholanic acid
• 3A,7A-Dihydroxy-5A-holan-24-oic acid
• 3a,7b-dihydroxy-5b-cholan-24-oic acid
• NCGC00179363-01
• NCGC00179363-12
• AC-18919
• CAS#128-13-2
• CPD000058403
• HY-13771
• LS-53033
• NCI60_028904
• URSODEOXYCHOLIC ACID [EP IMPURITY]
• URSODEOXYCHOLIC ACID [EP MONOGRAPH]
• AB00513977
• (3a,5b,7b)-3,7-dihydroxy-cholan-24-oate
• 3alpha, 7beta-dihydroxy-5beta-cholanoic acid
• 5bet.-Cholan-24-oic acid-3alp.,7bet.-diol
• (3a,5b,7b)-3,7-dihydroxycholan-24-oic acid
• C07880
• D00734
• EN300-373707
• ((3a,5b,7b)-3,7-Dihydroxycholan-24-oic acid
• (3a,5b,7b)-3,7-dihydroxy-cholan-24-oic acid
• AB00513977-09
• AB00513977_10
• 3alp.,7bet.-Dihydroxy-5bet.-cholan-24-oic acid
• A905413
• Q241374
• 3.alpha.,7.beta.-Dihydroxy-5.beta.-cholanic acid
• J-005566
• J-650210
• SR-01000737091-3
• SR-01000737091-4
• BRD-K15697815-001-16-2
• 3.alpha.,7.beta.-Dihydroxy-5.beta.-cholan-24-oic acid
• Z2588039022
• 3.ALPHA.,7.BETA.-DIHYDROXY-5B-CHOLAN-24-OIC ACID
• 5.beta.-Cholan-24-oic acid, 3.alpha.,7.beta.-dihydroxy-
• Ursodiol, United States Pharmacopeia (USP) Reference Standard
• Ursodeoxycholic acid, British Pharmacopoeia (BP) Reference Standard
• Ursodeoxycholic acid, European Pharmacopoeia (EP) Reference Standard
• 17.beta.-(1-Methyl-3-carboxypropyl)etiocholane-3.alpha.,7.beta.-diol
• 3,7-Dihydroxycholan-24-oic acid-, (3.alpha.,5.beta.,7.beta.)- #
• Cholan-24-oic acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-beta)-(9CI)
• Ursodeoxycholic acid, 500 mug/mL in methanol, certified reference material
• Ursodiol, Pharmaceutical Secondary Standard; Certified Reference Material
• Ursodeoxycholic acid for system suitability, European Pharmacopoeia (EP) Reference Standard
• Ursodeoxycholic acid, UDCA, Ursosan, Ursofalk, Urso Forte, Udiliv, Ursodiol
• (4R)-4-[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
• (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,1.011,1]heptadecan-14-yl]pentanoic acid
• (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]pentanoic acid
• (4R)-4-[(3R,5S,7S,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]pentanoicacid
• (4R)-4-[(3R,5S,7S,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]valeric acid
• 108609-27-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9878	98.78%
Caco-2	-	0.6686	66.86%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7746	77.46%
OATP2B1 inhibitior	-	0.6352	63.52%
OATP1B1 inhibitior	-	0.3470	34.70%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8514	85.14%
P-glycoprotein inhibitior	+	0.8042	80.42%
P-glycoprotein substrate	-	0.6323	63.23%
CYP3A4 substrate	+	0.7851	78.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8413	84.13%
CYP3A4 inhibition	-	0.8405	84.05%
CYP2C9 inhibition	-	0.9456	94.56%
CYP2C19 inhibition	-	0.9707	97.07%
CYP2D6 inhibition	-	0.9781	97.81%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8745	87.45%
CYP inhibitory promiscuity	-	0.9563	95.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7446	74.46%
Eye corrosion	-	0.9960	99.60%
Eye irritation	-	0.9541	95.41%
Skin irritation	+	0.7839	78.39%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.7709	77.09%
Human Ether-a-go-go-Related Gene inhibition	-	0.6207	62.07%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.5300	53.00%
skin sensitisation	-	0.8126	81.26%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7911	79.11%
Acute Oral Toxicity (c)	III	0.7739	77.39%
Estrogen receptor binding	-	0.7138	71.38%
Androgen receptor binding	+	0.6716	67.16%
Thyroid receptor binding	+	0.6655	66.55%
Glucocorticoid receptor binding	+	0.8573	85.73%
Aromatase binding	+	0.6510	65.10%
PPAR gamma	+	0.5671	56.71%
Honey bee toxicity	-	0.8282	82.82%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9848	98.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5287	Q14973	Bile acid transporter	3600 nM	IC50	PMID: 10565843
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	36400 nM; 2390 nM	EC50; EC50	PMID: 18307294; PMID: 25735208

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.88%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.84%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.86%	97.25%
CHEMBL237	P41145	Kappa opioid receptor	92.55%	98.10%
CHEMBL220	P22303	Acetylcholinesterase	92.44%	94.45%
CHEMBL2179	P04062	Beta-glucocerebrosidase	92.11%	85.31%
CHEMBL2581	P07339	Cathepsin D	89.90%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.66%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.18%	95.89%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	88.30%	96.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.25%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.13%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	87.24%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.03%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.74%	90.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.35%	82.69%
CHEMBL238	Q01959	Dopamine transporter	85.30%	95.88%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.85%	89.05%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.83%	93.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.53%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.21%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.31%	100.00%
CHEMBL274	P51681	C-C chemokine receptor type 5	82.25%	98.77%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.60%	96.61%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	81.27%	97.86%
CHEMBL2514	O95665	Neurotensin receptor 2	80.23%	100.00%

Plants that contains it

• Chelidonium majus
• Hylomecon japonica
• Lamprocapnos spectabilis

Cross-Links

• PubChem: 31401
• NPASS: NPC171426
• ChEMBL: CHEMBL1551
• LOTUS: LTS0269802
• wikiData: Q241374