IMPPAT Phytochemical information: 
Picroside IV
Picroside IV
Summary

SMILES: OC[C@@]12O[C@H]2[C@H]([C@H]2[C@@H]1[C@@H](OC=C2)O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O)O
InChI: InChI=1S/C24H28O12/c25-10-24-16-13(17(28)21(24)36-24)7-8-32-22(16)35-23-20(31)19(30)18(29)14(34-23)9-33-15(27)6-3-11-1-4-12(26)5-2-11/h1-8,13-14,16-23,25-26,28-31H,9-10H2/b6-3+/t13-,14-,16-,17+,18-,19+,20-,21+,22+,23+,24-/m1/s1
InChIKey: AKYYFSOMEOHPPO-LQQBYVAQSA-N
DeepSMILES: OC[C@]O[C@H]3[C@H][C@H][C@@H]6[C@@H]OC=C6)))O[C@@H]O[C@H]COC=O)/C=C/cccccc6))O))))))))))[C@H][C@@H][C@H]6O))O))O)))))))))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1CCCC(OC2OC=CC3CC4OC4C32)O1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCCC(OC2OCCC3CC4OC4C32)O1
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCCC(CC2CCCC3CC4CC4C23)C1
Functional groups: CO; C[C@]1(C)O[C@H]1C; CO[C@@H](O[C@H]1CCC=CO1)C; c/C=C/C(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
picroside iv
External chemical identifiers:
CID:CID_23928135; ZINC:ZINC000038139738; MolPort-001-741-471
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Picroside IV
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 508.48
Log P RDKit -1.62
Topological polar surface area (Å2) RDKit 187.9
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
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
Picroside IV
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 2
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 0.140551
Picroside IV
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.44
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