IMPPAT Phytochemical information: 
Indicoside A
Indicoside A
Summary

SMILES: CO[C@@H]([C@@H]1O[C@H]([C@@H]([C@H]1O)O)OCC(C(C)C)(CC[C@H]([C@H]1C[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@@]2(O)[C@H](O)[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2)O)O)O)C)O)CO
InChI: InChI=1S/C35H62O12/c1-17(2)34(43,16-46-31-27(41)26(40)28(47-31)23(15-36)45-6)12-7-18(3)20-14-22(38)29-33(20,5)11-9-24-32(4)10-8-19(37)13-21(32)25(39)30(42)35(24,29)44/h17-31,36-44H,7-16H2,1-6H3/t18-,19+,20-,21-,22-,23-,24-,25-,26-,27-,28+,29-,30-,31-,32+,33-,34?,35+/m1/s1
InChIKey: XRSFADLIOJRIOB-UGMDJPENSA-N
DeepSMILES: CO[C@@H][C@@H]O[C@H][C@@H][C@H]5O))O))OCCCC)C))CC[C@H][C@H]C[C@H][C@@H][C@]5C)CC[C@H][C@@]6O)[C@H]O)[C@@H][C@@H][C@]6C)CC[C@@H]C6)O))))))O)))))))))O))))C))))O)))))))CO
Scaffold Graph/Node/Bond level: C(CCOC1CCCO1)CCC1CCC2C1CCC1C3CCCCC3CCC21
Scaffold Graph/Node level: C(CCOC1CCCO1)CCC1CCC2C1CCC1C3CCCCC3CCC21
Scaffold Graph level: C(CCCC1CCC2C1CCC1C3CCCCC3CCC21)CCC1CCCC1
Functional groups: COC; 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: Bile acids, alcohols and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Cholestane steroids|Ergostane steroids
Synonymous chemical names:
indicoside a
External chemical identifiers:
CID:CID_102058640
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Indicoside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 674.87
Log P RDKit 0.31
Topological polar surface area (Å2) RDKit 209.76
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 47
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 18
Stereochemical complexity RDKit 0.51
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 35
Shape complexity RDKit 1
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
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 5
Indicoside A
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 3
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 0.145074
Indicoside A
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 -10.09
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