Details of the Drug

General Information of Drug (ID: DM7JT24)

Drug Name
Acocantherin
Synonyms
Ouabain; Ouabagenin L-Rhamnoside; Ouabagenin L-rhamnoside; Acocantherin; Acocantherine; Acolongifloroside K; Astrobain; G-Strophanthin; G-Strophanthin (JAN); G-Strophicor; Gratibain; Gratus strophanthin; Kombetin; O 3125; OBN; Ouabagenin-L-rhamnosid; Ouabagenin-L-rhamnosid [German]; Ouabain (anhydrous); Ouabain anhydrous; Ouabain octahydrate; Ouabain, Octahydrate; Ouabaine; Oubain; Purostrophan; Quabain; Rectobaina; Solufantina; Strodival; Strophalen; Strophanthin G; Strophanthin-G; Strophoperm; Strophosan; Uabaina; Uabanin
Indication
Disease Entry ICD 11 Status REF
Atrial fibrillation BC81.3 Approved [1]
Heart failure BD10-BD13 Approved [1]
Middle East Respiratory Syndrome (MERS) 1D64 Investigative [2]
Therapeutic Class
Cardiotonic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 584.7
Logarithm of the Partition Coefficient (xlogp) -1.7
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 12
Chemical Identifiers
Formula
C29H44O12
IUPAC Name
3-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Canonical SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O
InChI
InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
InChIKey
LPMXVESGRSUGHW-HBYQJFLCSA-N
Cross-matching ID
PubChem CID
439501
ChEBI ID
CHEBI:472805
CAS Number
630-60-4
DrugBank ID
DB01092
TTD ID
D0AR3J
VARIDT ID
DR00155
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sodium pump subunit alpha-1 (ATP1A1) TTWK8D0 AT1A1_HUMAN Binder [3]
HUMAN sodium pump subunit alpha-1 (ATP1A1) TTWNK8B AT1A1_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporting polypeptide 4C1 (SLCO4C1) DTY0QMU SO4C1_HUMAN Substrate [4]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [5]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [6]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 (PLCG1) OTSBQR6D PLCG1_HUMAN Gene/Protein Processing [8]
3-ketoacyl-CoA thiolase, mitochondrial (ACAA2) OTGLVWOP THIM_HUMAN Gene/Protein Processing [9]
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [9]
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [8]
Acid ceramidase (ASAH1) OT1DNGXL ASAH1_HUMAN Gene/Protein Processing [9]
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [9]
Actin-related protein 2/3 complex subunit 5 (ARPC5) OTFNMMDL ARPC5_HUMAN Gene/Protein Processing [9]
Alcohol dehydrogenase 1C (ADH1C) OTO1DV7F ADH1G_HUMAN Gene/Protein Processing [9]
Alpha-2-macroglobulin (A2M) OTFTX90K A2MG_HUMAN Gene/Protein Processing [9]
Annexin A1 (ANXA1) OT5OFDJC ANXA1_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Atrial fibrillation
ICD Disease Classification BC81.3
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Sodium pump subunit alpha-1 (ATP1A1) DTT ATP1A1 4.66E-01 1.00E-02 0.06
Sodium pump subunit alpha-1 (ATP1A1) DTT ATP1A1 3.31E-01 -0.03 -0.19
Organic anion transporting polypeptide 4C1 (SLCO4C1) DTP OATP4C1 4.06E-01 2.99E-02 7.03E-02
Organic anion transporting polypeptide 4C1 (SLCO4C1) DTP OATP4C1 1.84E-07 -3.88E-01 -1.02E+00
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTP OATP1A2 1.26E-02 1.81E-01 6.48E-01
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTP OATP1A2 8.14E-02 2.55E-02 2.32E-01
Organic anion transporting polypeptide 1B3 (SLCO1B3) DTP OATP1B3 3.20E-01 2.15E-02 1.15E-01
Organic anion transporting polypeptide 1B3 (SLCO1B3) DTP OATP1B3 1.40E-02 -4.58E-02 -1.12E-01
Organic anion transporting polypeptide 1B1 (SLCO1B1) DTP OATP1B1 2.41E-01 -2.63E-02 -8.50E-02
Organic anion transporting polypeptide 1B1 (SLCO1B1) DTP OATP1B1 5.54E-01 -1.65E-02 -1.24E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

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: 4826).
2 Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
3 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
4 Isolation and characterization of a digoxin transporter and its rat homologue expressed in the kidney. Proc Natl Acad Sci U S A. 2004 Mar 9;101(10):3569-74.
5 Molecular cloning and functional characterization of the mouse organic-anion-transporting polypeptide 1 (Oatp1) and mapping of the gene to chromosome X. Biochem J. 2000 Jan 1;345 Pt 1:115-20.
6 Regulation of Organic Anion Transporting Polypeptides (OATP) 1B1- and OATP1B3-Mediated Transport: An Updated Review in the Context of OATP-Mediated Drug-Drug Interactions. Int J Mol Sci. 2018 Mar 14;19(3). pii: E855.
7 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
8 Ouabain impairs cell migration, and invasion and alters gene expression of human osteosarcoma U-2 OS cells. Environ Toxicol. 2017 Nov;32(11):2400-2413. doi: 10.1002/tox.22453. Epub 2017 Aug 10.
9 Proteomics analysis of the proliferative effect of low-dose ouabain on human endothelial cells. Biol Pharm Bull. 2007 Feb;30(2):247-53. doi: 10.1248/bpb.30.247.