IMPPAT Phytochemical information: 
(1S,2S,4S,6R,7S,9R,13R,17S)-15-methoxy-2,6,14,17-tetramethyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-14-ene-3,11,16-trione
(1S,2S,4S,6R,7S,9R,13R,17S)-15-methoxy-2,6,14,17-tetramethyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-14-ene-3,11,16-trione
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2C[C@@H](C)[C@H]3[C@@](C2=O)(C)[C@H]2C(=O)C(=C([C@H]4[C@@]2([C@@H](C3)OC(=O)C4)C)C)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H38O11/c1-10-6-14(36-25-20(32)19(31)18(30)15(9-28)37-25)24(34)27(4)12(10)7-16-26(3)13(8-17(29)38-16)11(2)22(35-5)21(33)23(26)27/h10,12-16,18-20,23,25,28,30-32H,6-9H2,1-5H3/t10-,12+,13+,14+,15-,16-,18-,19+,20-,23+,25-,26-,27+/m1/s1
InChIKey: WURBSTOWFYGBJO-YZUVTYPKSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]C[C@@H]C)[C@H][C@@]C6=O))C)[C@H]C=O)C=C[C@H][C@@]6[C@@H]C%10)OC=O)C6))))C)))C))OC)))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC2C=CC(=O)C3C4C(=O)C(OC5CCCCO5)CCC4CC(O1)C23
Scaffold Graph/Node level: OC1CC2CCC(O)C3C2C(CC2CCC(OC4CCCCO4)C(O)C23)O1
Scaffold Graph level: CC1CC2CCC(C)C3C2C(C1)CC1CCC(CC2CCCCC2)C(C)C13
Functional groups: CO; CO[C@@H](C)OC; CC(=O)C; COC(=C(C)C)C(=O)C; CC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Quassinoids
Synonymous chemical names:
picrasinoside a
External chemical identifiers:
CID:CID_101603254; ZINC:ZINC000085531534
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,2S,4S,6R,7S,9R,13R,17S)-15-methoxy-2,6,14,17-tetramethyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-14-ene-3,11,16-trione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 538.59
Log P RDKit -0.14
Topological polar surface area (Å2) RDKit 169.05
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 13
Stereochemical complexity RDKit 0.48
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.81
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
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 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(1S,2S,4S,6R,7S,9R,13R,17S)-15-methoxy-2,6,14,17-tetramethyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-14-ene-3,11,16-trione
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 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 0.277673
(1S,2S,4S,6R,7S,9R,13R,17S)-15-methoxy-2,6,14,17-tetramethyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-14-ene-3,11,16-trione
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 -9.57
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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