IMPPAT Phytochemical information: 
[(4S,5R,6R,11R,12R,15S,16R,17Z)-17-(2,2-dihydroxyethylidene)-5-hydroxy-3,7,7,11,15-pentamethyl-8,18-dioxo-19-oxapentacyclo[14.3.1.02,15.03,12.06,11]icosa-1,9-dien-4-yl] acetate
[(4S,5R,6R,11R,12R,15S,16R,17Z)-17-(2,2-dihydroxyethylidene)-5-hydroxy-3,7,7,11,15-pentamethyl-8,18-dioxo-19-oxapentacyclo[14.3.1.02,15.03,12.06,11]icosa-1,9-dien-4-yl] acetate
Summary

SMILES: CC(=O)O[C@@H]1[C@H](O)[C@@H]2[C@]([C@@H]3C1(C)C1=C4OC(=O)/C(=C\C(O)O)/[C@@H]([C@@]1(CC3)C)C4)(C)C=CC(=O)C2(C)C
InChI: InChI=1S/C28H36O8/c1-13(29)35-23-20(33)22-25(2,3)18(30)8-10-27(22,5)17-7-9-26(4)15-12-16(21(26)28(17,23)6)36-24(34)14(15)11-19(31)32/h8,10-11,15,17,19-20,22-23,31-33H,7,9,12H2,1-6H3/b14-11-/t15-,17+,20+,22-,23+,26-,27+,28?/m0/s1
InChIKey: DXWTUXKPOPZWFZ-ROVBDAAOSA-N
DeepSMILES: CC=O)O[C@@H][C@H]O)[C@@H][C@][C@@H]C6C)C=COC=O)/C=C\CO)O)))/[C@@H][C@@]7CC%11))C))C6)))))))))C)C=CC=O)C6C)C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2=C3C(CCC4C3CCC3CC(=O)C=CC34)C1C2
Scaffold Graph/Node level: CC1C(O)OC2CC1C1CCC3C4CCC(O)CC4CCC3C21
Scaffold Graph level: CC1CCC2C(CCC3C2CCC2C4CC(CC(C)C4C)C23)C1
Functional groups: CC(=O)C=CC; CC(=O)OC; CO; CC1=C2C[C@H](C1)/C(=C/C(O)O)C(=O)O2
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: Triterpenoids
NP Classifier Class: Apotirucallane triterpenoids
Synonymous chemical names:
nimocinolide
External chemical identifiers:
CID:CID_6442906
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(4S,5R,6R,11R,12R,15S,16R,17Z)-17-(2,2-dihydroxyethylidene)-5-hydroxy-3,7,7,11,15-pentamethyl-8,18-dioxo-19-oxapentacyclo[14.3.1.02,15.03,12.06,11]icosa-1,9-dien-4-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 500.59
Log P RDKit 2.57
Topological polar surface area (Å2) RDKit 130.36
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
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 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
[(4S,5R,6R,11R,12R,15S,16R,17Z)-17-(2,2-dihydroxyethylidene)-5-hydroxy-3,7,7,11,15-pentamethyl-8,18-dioxo-19-oxapentacyclo[14.3.1.02,15.03,12.06,11]icosa-1,9-dien-4-yl] acetate
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 Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.299654
[(4S,5R,6R,11R,12R,15S,16R,17Z)-17-(2,2-dihydroxyethylidene)-5-hydroxy-3,7,7,11,15-pentamethyl-8,18-dioxo-19-oxapentacyclo[14.3.1.02,15.03,12.06,11]icosa-1,9-dien-4-yl] acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.75
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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