IMPPAT Phytochemical information: 
Ouabain
Ouabain
Summary

SMILES: OC[C@@]12[C@H](O)C[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1[C@H](O)C[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)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
DeepSMILES: OC[C@][C@H]O)C[C@@H]C[C@@]6O)CC[C@@H][C@@H]%10[C@H]O)C[C@][C@]6O)CC[C@@H]5C=CC=O)OC5)))))))))C))))))))))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C=C(C2CCC3C2CCC2C4CCC(OC5CCCCO5)CC4CCC23)CO1
Scaffold Graph/Node level: OC1CC(C2CCC3C2CCC2C4CCC(OC5CCCCO5)CC4CCC23)CO1
Scaffold Graph level: CC1CCC(C2CCC3C2CCC2C4CCC(CC5CCCCC5)CC4CCC23)C1
Functional groups: CO; CO[C@@H](C)OC; CC1=CC(=O)OC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Cardenolides
Synonymous chemical names:
ouabain g-strophanthin, ouabain, Ouabain
External chemical identifiers:
CID:CID_439501; ChEMBL:CHEMBL222863; ChEBI:CHEBI:472805; ZINC:ZINC000008143614; FDASRS:5ACL011P69; SureChEMBL:SCHEMBL15433
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ouabain
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 584.66
Log P RDKit -1.52
Topological polar surface area (Å2) RDKit 206.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.52
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Ouabain
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.140164
Ouabain
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.07
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Ouabain
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000354490ATP1A2868
ENSP00000353483MAPK8800
ENSP00000321106TAC1859
ENSP00000332931SLC8A1950
ENSP00000333363DNAH8969
ENSP00000334216ATP4B736
ENSP00000338018HIF1A700
ENSP00000348762LSS759
ENSP00000317985ROCK2750
ENSP00000350941SRC903
ENSP00000412237IL10800
ENSP00000385269ELAVL1800
ENSP00000382697ROCK1750
ENSP00000359635FGF13800
ENSP00000356789ATP1B1874
ENSP00000355759PARP1700
ENSP00000414303BDNF816
ENSP00000311032CASP3726
ENSP00000357060ATP1A4862
ENSP00000302397ATP1A3937
ENSP00000218548ATP12A948
ENSP00000262186KCNH2725
ENSP00000262623ATP4A937
ENSP00000264498FGF2814
ENSP00000265724ABCB1841
ENSP00000270202AKT1818
ENSP00000272190REN991
ENSP00000304236CD14786
ENSP00000295598ATP1A1982
ENSP00000292476CPSF4800
ENSP00000292079FXYD2829
ENSP00000287647FANCD2824
ENSP00000283558ATP11A899
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.