IMPPAT Phytochemical information: 
Cardenolide 2
Cardenolide 2
Summary

SMILES: O=C[C@@]12CC[C@@H](C[C@@]2(O)C=C[C@@H]2[C@@H]1CC[C@]1([C@]2(O)CC[C@H]1C1=CC(=O)OC1)C)OC1CC(O)C(C(O1)C)O
InChI: InChI=1S/C29H40O9/c1-16-25(33)22(31)12-24(37-16)38-18-3-8-27(15-30)20-4-7-26(2)19(17-11-23(32)36-14-17)6-10-29(26,35)21(20)5-9-28(27,34)13-18/h5,9,11,15-16,18-22,24-25,31,33-35H,3-4,6-8,10,12-14H2,1-2H3/t16?,18-,19-,20-,21+,22?,24?,25?,26+,27-,28-,29-/m0/s1
InChIKey: YRCCUUYOXFAUMW-NYCXNGLCSA-N
DeepSMILES: O=C[C@]CC[C@@H]C[C@@]6O)C=C[C@@H][C@@H]%10CC[C@][C@]6O)CC[C@H]5C=CC=O)OC5)))))))))C))))))))))OCCCO)CCO6)C))O
Scaffold Graph/Node/Bond level: O=C1C=C(C2CCC3C4C=CC5CC(OC6CCCCO6)CCC5C4CCC23)CO1
Scaffold Graph/Node level: OC1CC(C2CCC3C2CCC2C4CCC(OC5CCCCO5)CC4CCC23)CO1
Scaffold Graph level: CC1CCC(C2CCC3C2CCC2C4CCC(CC5CCCCC5)CC4CCC23)C1
Functional groups: CC=O; CO; COC(OC)C; CC=CC; 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: Steroidal glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Cardenolides
Synonymous chemical names:
cardeonlides
External chemical identifiers:
CID:CID_388098; ChEMBL:CHEMBL2004236
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cardenolide 2
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 532.63
Log P RDKit 1.56
Topological polar surface area (Å2) RDKit 142.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 0.79
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 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Cardenolide 2
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.24
Cardenolide 2
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -9.05
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes