IMPPAT Phytochemical information: 
(1S,3R,4R,7S,8S,11S,12R,15R,16S,17R)-7-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-4,7,16,17-tetrahydroxy-8,12-dimethyl-18-oxapentacyclo[13.2.1.03,11.04,8.012,17]octadecan-13-one
(1S,3R,4R,7S,8S,11S,12R,15R,16S,17R)-7-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-4,7,16,17-tetrahydroxy-8,12-dimethyl-18-oxapentacyclo[13.2.1.03,11.04,8.012,17]octadecan-13-one
Summary

SMILES: CC1=C(C)C(=O)O[C@H](C1)[C@@]([C@]1(O)CC[C@@]2([C@]1(C)CC[C@H]1[C@H]2C[C@H]2[C@]3([C@]1(C)C(=O)C[C@@H](O2)[C@@H]3O)O)O)(O)C
InChI: InChI=1S/C28H40O9/c1-13-10-19(37-22(31)14(13)2)25(5,32)27(34)9-8-26(33)16-11-20-28(35)21(30)17(36-20)12-18(29)24(28,4)15(16)6-7-23(26,27)3/h15-17,19-21,30,32-35H,6-12H2,1-5H3/t15-,16+,17+,19+,20-,21-,23-,24-,25-,26+,27-,28-/m0/s1
InChIKey: DMAZCUJZFYKTRY-AURYBRBTSA-N
DeepSMILES: CC=CC)C=O)O[C@H]C6)[C@@][C@]O)CC[C@@][C@]5C)CC[C@H][C@H]6C[C@H][C@][C@]6C)C=O)C[C@@H]O7)[C@@H]6O))))))O)))))))))O)))))O)C
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CCC3C2CCC2C3CC3OC4CC(=O)C2C3C4)O1
Scaffold Graph/Node level: OC1CCCC(CC2CCC3C2CCC2C3CC3OC4CC(O)C2C3C4)O1
Scaffold Graph level: CC1CCCC(CC2CCC3C2CCC2C3CC3CC4CC(C)C2C3C4)C1
Functional groups: CO; CC1=C(C)C(=O)OCC1; CC(=O)C; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ergostane steroids
Synonymous chemical names:
withaperuvin d, Withaperuvin D
External chemical identifiers:
CID:CID_101293639
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,3R,4R,7S,8S,11S,12R,15R,16S,17R)-7-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-4,7,16,17-tetrahydroxy-8,12-dimethyl-18-oxapentacyclo[13.2.1.03,11.04,8.012,17]octadecan-13-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 520.62
Log P RDKit 0.92
Topological polar surface area (Å2) RDKit 153.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.86
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
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 6
(1S,3R,4R,7S,8S,11S,12R,15R,16S,17R)-7-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-4,7,16,17-tetrahydroxy-8,12-dimethyl-18-oxapentacyclo[13.2.1.03,11.04,8.012,17]octadecan-13-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
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 0.334506
(1S,3R,4R,7S,8S,11S,12R,15R,16S,17R)-7-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-4,7,16,17-tetrahydroxy-8,12-dimethyl-18-oxapentacyclo[13.2.1.03,11.04,8.012,17]octadecan-13-one
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 -9.72
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