IMPPAT Phytochemical information: 
[(1R,3R,4R,5R,6R,10S,12S,13S,16S,18S,21R)-4,6,12,17,17-pentamethyl-8-oxo-18-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-3-yl] acetate
[(1R,3R,4R,5R,6R,10S,12S,13S,16S,18S,21R)-4,6,12,17,17-pentamethyl-8-oxo-18-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-3-yl] acetate
Summary

SMILES: CC(=O)O[C@@H]1C[C@]23C[C@]43CC[C@@H](C([C@H]4CC[C@H]2[C@]2([C@@]1(C)[C@H]1[C@H](C)CC(=O)O[C@H]1C2)C)(C)C)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C33H50O9/c1-16-11-24(36)41-19-12-30(5)21-8-7-20-29(3,4)22(42-28-27(38)26(37)18(35)14-39-28)9-10-32(20)15-33(21,32)13-23(40-17(2)34)31(30,6)25(16)19/h16,18-23,25-28,35,37-38H,7-15H2,1-6H3/t16-,18+,19+,20-,21+,22+,23-,25+,26+,27-,28+,30+,31-,32-,33+/m1/s1
InChIKey: RKTWPXXLEHCPIO-ZCADTKORSA-N
DeepSMILES: CC=O)O[C@@H]C[C@@]C[C@@]3CC[C@@H]C[C@H]6CC[C@H]%11[C@][C@@]%15C)[C@H][C@H]C)CC=O)O[C@H]6C9))))))))C))))))C)C))O[C@@H]OC[C@@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CCC2C(CC3C2CCC24CC25CCC(OC2CCCCO2)CC5CCC34)O1
Scaffold Graph/Node level: OC1CCC2C(CC3C2CCC24CC25CCC(OC2CCCCO2)CC5CCC34)O1
Scaffold Graph level: CC1CCC2C(C1)CC1C2CCC23CC24CCC(CC2CCCCC2)CC4CCC13
Functional groups: CO[C@@H](OC)C; CC(=O)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cycloartane triterpenoids
Synonymous chemical names:
cimilactone a
External chemical identifiers:
CID:CID_637017
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1R,3R,4R,5R,6R,10S,12S,13S,16S,18S,21R)-4,6,12,17,17-pentamethyl-8-oxo-18-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-3-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 590.75
Log P RDKit 3.35
Topological polar surface area (Å2) RDKit 131.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 31
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
[(1R,3R,4R,5R,6R,10S,12S,13S,16S,18S,21R)-4,6,12,17,17-pentamethyl-8-oxo-18-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-3-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 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 0.334478
[(1R,3R,4R,5R,6R,10S,12S,13S,16S,18S,21R)-4,6,12,17,17-pentamethyl-8-oxo-18-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosan-3-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 -7.13
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