Natural Product (NP) Details

General Information of the NP (ID: NP5284)
Name
Ursodeoxycholic acid
Synonyms
ursodiol; URSODEOXYCHOLIC ACID; 128-13-2; Actigall; ursodeoxycholate; UDCA; Ursofalk; Ursolvan; Delursan; UrSO; Urso Forte; Ursodesoxycholic acid; Destolit; Ursochol; Cholit-ursan; Litursol; Solutrat; Ursobilin; Ursodamor; Arsacol; Deursil; Lyeton; Ursacol; Urso DS; UDCS; 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid; Ursosan; Ursodexycholic Acid; Urso 250; 7-beta-Hydroxylithocholic acid; 3-alpha,7-beta-Dioxycholanic acid; Ursocholic acid, deoxy-; 3-alpha,7-beta-Dihydroxycholanic acid; NSC 683769; (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid; 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid; Ursodeoxycholicacid; MFCD00003680; NSC 657950; UNII-724L30Y2QR; BRN 3219888; 3,7-Dihydroxycholan-24-oic acid; Peptarom; (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; CHEMBL1551; Ursodesoxycholic acid (UDCA); MLS000028461; CHEBI:9907; (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; 128-13-2 (free acid); 724L30Y2QR; Antigall; SMR000058403; Urosiol; Acido ursodeossicolico [Italian]; Acido ursodeoxicolico; Acido ursodeossicolico; Acido ursodeoxicolico [INN-Spanish]; Acidum ursodeoxycholicum [INN-Latin]; Acide ursodesoxycholique; Acide ursodesoxycholique [INN-French]; Acidum ursodeoxycholicum; Cholan-24-oic acid, 3,7-dihydroxy-, (3a,5b,7b)-; 7beta-Hydroxylithocholic acid; Actigall (TN); Ursodiol (USP); (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid; CCRIS 5502; Urso (TN); SR-01000737091; Ursodiol [USAN:USP]; EINECS 204-879-3; Ursodexycholate; Paptarom; Udiliv; Desol; Urdes; Urosdesoxycholate; 5beta-Cholan-24-oic acid-3alpha,7beta-diol; NSC-683769; 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol; Ursodeoxycholoc acid; Urosdesoxycholic acid; 5beta-Cholanic Acid-3alpha,7beta-diol; Ursodesoxy cholic acid; Cholan-24-oic acid, 3,7-dihydroxy-, (3alpha,5beta,7beta)-; 3alpha,7beta-Dihydroxy-5beta-cholanic acid; Ursodiol (Actigal Urso); Prestwick0_000958; Prestwick1_000958; Prestwick2_000958; Prestwick3_000958; U0030; 7A-Hydroxylithocholic acid; EC 204-879-3; U-9000; Ursodeoxycholic acid [INN]; Ursodeoxycholic acid, 99%; SCHEMBL27200; 5-beta-Cholan-24-oic acid; BSPBio_000956; 4-10-00-01604 (Beilstein Handbook Reference); 7bet.-Hydroxylithocholic acid; cid_31401; MLS001066373; MLS002548885; SPBio_003105; Ursodeoxycholic acid, >=99%; BPBio1_001052; GTPL7104; 7.beta.-Hydroxylithocholic acid; Ursodiol (Ursodeoxycholic Acid); 5-beta-Cholan-24-oic acid, 3-alpha,7-beta-dihydroxy-; DTXSID6023731; BDBM53721; AOB5075; (3alpha,5beta,7beta,8xi)-3,7-dihydroxycholan-24-oic acid; HMS1570P18; HMS2097P18; HMS2233L14; HMS3259A13; HMS3714P18; Ursodeoxycholic acid (JP17/INN); 3alpha,7beta-dihydroxycholanic acid; ACT02676; ZINC3914809; 3a,7b-dihydroxy-5b-cholan-24-oate; Cholan-24-oic acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.beta.)-; LMST04010033; s1643; 5A-Cholan-24-oic acid-3A,7A-diol; AKOS015955898; CCG-220958; CS-1932; DB01586; KS-5243; MCULE-4374611501; 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; NCI60_028904; 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; A-7799; C07880; D00734; J10139; (3a,5b,7b)-3,7-dihydroxy-cholan-24-oic acid; AB00513977-09; AB00513977_10; 3alp.,7bet.-Dihydroxy-5bet.-cholan-24-oic acid; 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; Z2786051717; 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; (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]valeric acid; 108609-27-4
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Autoimmune liver disease [ICD-11: DB96] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C24H40O4
PubChem CID
31401
Canonical SMILES
CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
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
InChIKey
RUDATBOHQWOJDD-UZVSRGJWSA-N
CAS Number
CAS 128-13-2
ChEBI ID
CHEBI:9907
Herb ID
HBIN047610
TTD Drug ID
D0G3SH
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Sorafenib      Renal cell carcinoma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation STAT3  Molecule Info 
Pathway MAP
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
Huh-BAT Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Sorafenib and ursodeoxycholic combination is efficacious in treating hepatocellular carcinoma by inhibiting cell proliferation and inducing apoptosis through reactive oxygen species dependent activation of ERK and dephosphorylation of STAT3.
          Bezafibrate      Hyper-lipoproteinaemia     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)		 Combination therapy of bezafibrate and UDCA improved biliary enzymes in non-cirrhotic Japanese patients with PBC refractory to UDCA.
          Amantadine + Biphenyl dimethyl dicarboxylate     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Activity STAT1  Molecule Info 
Pathway MAP
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The inhibition of viral gene replication was enhanced by the combination of triple combination of amantadine, ursodeoxycholic acidbip, and henyl dimethyl dicarboxylate.
Target and Pathway
Target(s) Biliverdin reductase A (BLVRA)  Molecule Info  [5]
Sodium-dependent vitamin C transporter 2 (SVCT2)  Molecule Info  [5]
BioCyc Heme degradation Click to Show/Hide
KEGG Pathway Porphyrin and chlorophyll metabolism Click to Show/Hide
Pathwhiz Pathway Porphyrin Metabolism Click to Show/Hide
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7104).
Reference 2 Synergistic effect of ursodeoxycholic acid on the antitumor activity of sorafenib in hepatocellular carcinoma cells via modulation of STAT3 and ERK. Int J Mol Med. 2018 Nov;42(5):2551-2559.
Reference 3 The efficacy of ursodeoxycholic acid and bezafibrate combination therapy for primary biliary cirrhosis: A prospective, multicenter study. Hepatol Res. 2008 Jun;38(6):557-64.
Reference 4 The potential anti-hBV effect of amantadine in combination with ursodeoxycholic acid and biphenyl dimethyl dicarboxylate in hepG2 2.2.15 cells. Arch Pharm Res. 2005 Apr;28(4):451-7.
Reference 5 Role of vitamin C transporters and biliverdin reductase in the dual pro-oxidant and anti-oxidant effect of biliary compounds on the placental-fetal... Toxicol Appl Pharmacol. 2008 Oct 15;232(2):327-36.
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