IMPPAT Phytochemical information: 
[(2S,4S,7R,9R,13S,14R,15S,17S)-4-acetyloxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecan-16-yl] 1,3-benzodioxole-5-carboxylate
[(2S,4S,7R,9R,13S,14R,15S,17S)-4-acetyloxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecan-16-yl] 1,3-benzodioxole-5-carboxylate
Summary

SMILES: CO[C@H]1[C@H](C)[C@@H]2CC(=O)O[C@H]3[C@@]2(C(C1OC(=O)c1ccc2c(c1)OCO2)[C@]1(C)[C@@H](C3)CC[C@@H](C1=O)OC(=O)C)C
InChI: InChI=1S/C30H36O10/c1-14-18-12-23(32)39-22-11-17-7-9-20(38-15(2)31)27(33)29(17,3)26(30(18,22)4)25(24(14)35-5)40-28(34)16-6-8-19-21(10-16)37-13-36-19/h6,8,10,14,17-18,20,22,24-26H,7,9,11-13H2,1-5H3/t14-,17-,18+,20+,22-,24+,25?,26?,29+,30-/m1/s1
InChIKey: YCZNVLDLPPSWPK-OCAQMLFFSA-N
DeepSMILES: CO[C@H][C@H]C)[C@@H]CC=O)O[C@H][C@@]6CC%10OC=O)cccccc6)OCO5)))))))))))[C@]C)[C@@H]C6)CC[C@@H]C6=O))OC=O)C)))))))))C
Scaffold Graph/Node/Bond level: O=C1CC2CCC(OC(=O)c3ccc4c(c3)OCO4)C3C4C(=O)CCCC4CC(O1)C23
Scaffold Graph/Node level: OC1CC2CCC(OC(O)C3CCC4OCOC4C3)C3C4C(O)CCCC4CC(O1)C23
Scaffold Graph level: CC1CC2CCC(CC(C)C3CCC4CCCC4C3)C3C4C(C)CCCC4CC(C1)C23
Functional groups: COC; CC(=O)C; CC(=O)OC; cC(=O)OC; c1cOCO1
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:
javanicin n
External chemical identifiers:
CID:CID_132472136
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2S,4S,7R,9R,13S,14R,15S,17S)-4-acetyloxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecan-16-yl] 1,3-benzodioxole-5-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 556.61
Log P RDKit 3.48
Topological polar surface area (Å2) RDKit 123.66
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
[(2S,4S,7R,9R,13S,14R,15S,17S)-4-acetyloxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecan-16-yl] 1,3-benzodioxole-5-carboxylate
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 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.402178
[(2S,4S,7R,9R,13S,14R,15S,17S)-4-acetyloxy-15-methoxy-2,14,17-trimethyl-3,11-dioxo-10-oxatetracyclo[7.7.1.02,7.013,17]heptadecan-16-yl] 1,3-benzodioxole-5-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.90
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