IMPPAT Phytochemical information: 
methyl (1R,2S,3R,6R,13R,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate
methyl (1R,2S,3R,6R,13R,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate
Summary

SMILES: COC(=O)[C@@]12OC[C@]34[C@H]2[C@@H](OC(=O)/C=C(/C(OC(=O)C)(C)C)\C)C(=O)O[C@@H]4CC2=C(C(=O)C=C[C@@]2([C@H]3[C@H]([C@@H]1O)O)C)C
InChI: InChI=1S/C30H36O12/c1-13(27(4,5)42-15(3)31)10-19(33)41-21-23-29-12-39-30(23,26(37)38-7)24(35)20(34)22(29)28(6)9-8-17(32)14(2)16(28)11-18(29)40-25(21)36/h8-10,18,20-24,34-35H,11-12H2,1-7H3/b13-10+/t18-,20-,21-,22-,23-,24+,28+,29-,30+/m1/s1
InChIKey: WLJSEHYSSBQUMT-HEPJHHOPSA-N
DeepSMILES: COC=O)[C@]OC[C@@][C@H]5[C@@H]OC=O)/C=C/COC=O)C)))C)C))\C)))))C=O)O[C@@H]6CC=CC=O)C=C[C@@]6[C@H]%14[C@H][C@@H]%19O))O)))C)))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2C(=C1)CC1OC(=O)CC3C4CCC2C13CO4
Scaffold Graph/Node level: OC1CCC2C(C1)CC1OC(O)CC3C4CCC2C13CO4
Scaffold Graph level: CC1CCC2C(C1)CC1CC(C)CC3C4CCC2C13CC4
Functional groups: COC(C)=O; COC; C/C(C)=C/C(=O)OC; COC(=O)C; CC1=C(C)C(=O)C=CC1; CO
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:
dehydrobruceantinol
External chemical identifiers:
CID:CID_101659156
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1R,2S,3R,6R,13R,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 588.61
Log P RDKit 0.87
Topological polar surface area (Å2) RDKit 171.96
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.63
Number of rotatable bonds RDKit 8
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
methyl (1R,2S,3R,6R,13R,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate
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 3
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 0.264162
methyl (1R,2S,3R,6R,13R,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate
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 -8.78
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 Yes