IMPPAT Phytochemical information: 
Tinosporaside
Tinosporaside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2C=CC(=O)[C@@H]3[C@@]2(C)CC[C@@H]2[C@@]3(C)C[C@H](OC2=O)c2cocc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C25H32O10/c1-24-7-5-13-22(31)33-15(12-6-8-32-11-12)9-25(13,2)21(24)14(27)3-4-17(24)35-23-20(30)19(29)18(28)16(10-26)34-23/h3-4,6,8,11,13,15-21,23,26,28-30H,5,7,9-10H2,1-2H3/t13-,15-,16+,17+,18+,19-,20+,21+,23-,24-,25+/m0/s1
InChIKey: ZXHPKYMQXNHREV-LZLOTQJESA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]C=CC=O)[C@@H][C@@]6C)CC[C@@H][C@@]6C)C[C@H]OC6=O)))ccocc5))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)CC2C1CCC1C(OC3CCCCO3)C=CC(=O)C12
Scaffold Graph/Node level: OC1CCC(OC2CCCCO2)C2CCC3C(O)OC(C4CCOC4)CC3C12
Scaffold Graph level: CC1CC(C2CCCC2)CC2C1CCC1C(CC3CCCCC3)CCC(C)C12
Functional groups: CO; CO[C@@H](C)OC; CC=CC(=O)C; COC(=O)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
ClassyFire Subclass: Naphthopyranones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids|Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids|Limonoids
Synonymous chemical names:
tinosporaside
External chemical identifiers:
CID:CID_14194109; ZINC:ZINC000255288010
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tinosporaside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 492.52
Log P RDKit 0.63
Topological polar surface area (Å2) RDKit 155.89
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.44
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
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Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
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 0.439785
Tinosporaside
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 -9.13
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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