IMPPAT Phytochemical information: 
Ingenol 3,20-dibenzoate
Ingenol 3,20-dibenzoate
Summary

SMILES: O=C(c1ccccc1)OCC1=C[C@H]2[C@H]3[C@H](C3(C)C)C[C@H]([C@]3([C@@]([C@@H]1O)(O)[C@@H](OC(=O)c1ccccc1)C(=C3)C)C2=O)C
InChI: InChI=1S/C34H36O7/c1-19-17-33-20(2)15-25-26(32(25,3)4)24(28(33)36)16-23(18-40-30(37)21-11-7-5-8-12-21)27(35)34(33,39)29(19)41-31(38)22-13-9-6-10-14-22/h5-14,16-17,20,24-27,29,35,39H,15,18H2,1-4H3/t20-,24+,25-,26+,27-,29+,33?,34+/m1/s1
InChIKey: GIMKEHNOTHXONN-HNIMUKOUSA-N
DeepSMILES: O=Ccccccc6))))))OCC=C[C@H][C@H][C@H]C3C)C))C[C@H][C@][C@@][C@@H]%10O))O)[C@@H]OC=O)cccccc6))))))))C=C5)C))))C7=O)))C
Scaffold Graph/Node/Bond level: O=C(OCC1=CC2C(=O)C3(C=CC(OC(=O)c4ccccc4)C3C1)CCC1CC12)c1ccccc1
Scaffold Graph/Node level: OC(OCC1CC2C3CC3CCC3(CCC(OC(O)C4CCCCC4)C3C1)C2O)C1CCCCC1
Scaffold Graph level: CC(CCC1CC2C3CC3CCC3(CCC(CC(C)C4CCCCC4)C3C1)C2C)C1CCCCC1
Functional groups: cC(=O)OC; CC(=CC)C; CC(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Ingenane diterpenoids|Tetracyclic diterpenoids
Synonymous chemical names:
ingenol-3,20-dibenzoate
External chemical identifiers:
CID:CID_442043; ChEMBL:CHEMBL2165713; ChEBI:CHEBI:5923; ZINC:ZINC000100901395; SureChEMBL:SCHEMBL18873016
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ingenol 3,20-dibenzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 556.66
Log P RDKit 4.54
Topological polar surface area (Å2) RDKit 110.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Ingenol 3,20-dibenzoate
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 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41
Ingenol 3,20-dibenzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.77
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes