IMPPAT Phytochemical information: 
Tenacissoside I
Tenacissoside I
Summary

SMILES: CO[C@@H]1C[C@H](O[C@H]2CC[C@]3([C@H](C2)CC[C@@]24[C@@H]3[C@H](OC(=O)c3ccccc3)[C@@H](OC(=O)C)[C@]3([C@]4(O2)CC[C@H]3C(=O)C)C)C)O[C@@H]([C@H]1O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1O)OC)O)C
InChI: InChI=1S/C44H62O14/c1-22(45)29-16-19-44-42(29,6)38(54-25(4)46)36(56-39(49)26-12-10-9-11-13-26)37-41(5)17-15-28(20-27(41)14-18-43(37,44)58-44)55-31-21-30(50-7)34(24(3)52-31)57-40-33(48)35(51-8)32(47)23(2)53-40/h9-13,23-24,27-38,40,47-48H,14-21H2,1-8H3/t23-,24-,27+,28+,29+,30-,31+,32-,33-,34-,35-,36+,37-,38-,40+,41+,42+,43+,44-/m1/s1
InChIKey: HXIHLBDNTFYMIC-ROIFRVDESA-N
DeepSMILES: CO[C@@H]C[C@H]O[C@H]CC[C@][C@H]C6)CC[C@][C@@H]6[C@H]OC=O)cccccc6))))))))[C@@H]OC=O)C)))[C@][C@]6O7)CC[C@H]5C=O)C))))))C)))))))))C))))))O[C@@H][C@H]6O[C@@H]O[C@H]C)[C@H][C@H][C@H]6O))OC)))O)))))))C
Scaffold Graph/Node/Bond level: O=C(OC1CC2CCCC23OC32CCC3CC(OC4CCC(OC5CCCCO5)CO4)CCC3C12)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2CCCC23OC32CCC3CC(OC4CCC(OC5CCCCO5)CO4)CCC3C12)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCCC23CC32CCC3CC(CC4CCC(CC5CCCCC5)CC4)CCC3C12)C1CCCCC1
Functional groups: COC; C[C@H](OC)OC; C[C@]1(C)O[C@@]1(C)C; cC(=O)OC; CC(=O)OC; CC(C)=O; CO[C@@H](C)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid esters
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Pregnane steroids
Synonymous chemical names:
tenacissoside i
External chemical identifiers:
CID:CID_91973812; ZINC:ZINC000255218918; MolPort-039-338-298
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tenacissoside I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 814.97
Log P RDKit 4.29
Topological polar surface area (Å2) RDKit 178.04
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 58
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 19
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 35
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Tenacissoside I
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.194295
Tenacissoside I
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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