IMPPAT Phytochemical information: 
[(2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
[(2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@]23C[C@@H]4[C@@]3(COC(=O)c3ccccc3)C3O[C@@]2(C)C[C@]4(O3)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C23H28O11/c1-20-9-22(29)13-7-23(20,32-18-16(27)15(26)14(25)12(8-24)31-18)21(13,19(33-20)34-22)10-30-17(28)11-5-3-2-4-6-11/h2-6,12-16,18-19,24-27,29H,7-10H2,1H3/t12-,13-,14-,15+,16-,18+,19?,20+,21+,22-,23+/m1/s1
InChIKey: YKRGDOXKVOZESV-XUKLQFQFSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@]C[C@@H][C@@]4COC=O)cccccc6)))))))))CO[C@@]7C)C[C@]7O6)O)))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OCC12C3OC4CC(O3)C1(OC1CCCCO1)CC42)c1ccccc1
Scaffold Graph/Node level: OC(OCC12C3OC4CC(O3)C1(OC1CCCCO1)CC42)C1CCCCC1
Scaffold Graph level: CC(CCC12C3CC4CC(C3)C1(CC1CCCCC1)CC42)C1CCCCC1
Functional groups: CO; CO[C@@H](C)OC; cC(=O)OC; O[C@@]12CCOC(CC1)O2
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Pinane monoterpenoids
Synonymous chemical names:
paeoniflorin
External chemical identifiers:
CID:CID_102004404; MolPort-039-052-268
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 480.47
Log P RDKit -1.36
Topological polar surface area (Å2) RDKit 164.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.48
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 4
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 3
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
[(2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
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 0.31
[(2S,3R,5R,6R,8S)-6-hydroxy-8-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl benzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -9.96
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