IMPPAT Phytochemical information: 
(3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-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]phenanthrene-10-carbaldehyde
(3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-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]phenanthrene-10-carbaldehyde
Summary

SMILES: O=C[C@@]12CC[C@@H](C[C@@]2(O)CCC2C1C(O)C[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@H]1OC(C)[C@H](C(C1O)O)O
InChI: InChI=1S/C29H42O11/c1-14-22(33)23(34)24(35)25(39-14)40-16-3-6-27(13-30)21-18(4-7-28(27,36)10-16)29(37)8-5-17(15-9-20(32)38-12-15)26(29,2)11-19(21)31/h9,13-14,16-19,21-25,31,33-37H,3-8,10-12H2,1-2H3/t14?,16-,17+,18?,19?,21?,22+,23?,24?,25+,26+,27-,28-,29-/m0/s1
InChIKey: AZOXLPPOBHVORY-RQTNDROZSA-N
DeepSMILES: O=C[C@]CC[C@@H]C[C@@]6O)CCCC%10CO)C[C@][C@]6O)CC[C@@H]5C=CC=O)OC5)))))))))C))))))))))O[C@H]OCC)[C@H]CC6O))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: CC=O; CO; CC1=CC(=O)OC1; CO[C@H](OC)C
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:
tholloside
External chemical identifiers:
CID:CID_23312
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-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]phenanthrene-10-carbaldehyde
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 566.64
Log P RDKit -0.28
Topological polar surface area (Å2) RDKit 183.21
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.48
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.86
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
(3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-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]phenanthrene-10-carbaldehyde
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
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 0.15
(3S,5S,10S,11R,13R,14S,17R)-5,11,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2S,5S)-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]phenanthrene-10-carbaldehyde
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 -10.92
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 No