IMPPAT Phytochemical information: 
7-(Acetyloxy)-21-hydroxy-6-methoxy-4,4,8-trimethyl-3-oxocarda-1,14,20(22)-trienolide
7-(Acetyloxy)-21-hydroxy-6-methoxy-4,4,8-trimethyl-3-oxocarda-1,14,20(22)-trienolide
Summary

SMILES: COC1C(OC(=O)C)C2(C)C3=CCC(C3(C)CCC2C2(C1C(C)(C)C(=O)C=C2)C)C1=CC(=O)OC1O
InChI: InChI=1S/C29H38O7/c1-15(30)35-24-22(34-7)23-26(2,3)20(31)11-13-28(23,5)19-10-12-27(4)17(8-9-18(27)29(19,24)6)16-14-21(32)36-25(16)33/h9,11,13-14,17,19,22-25,33H,8,10,12H2,1-7H3
InChIKey: PKOYNOJAZZXAPP-UHFFFAOYSA-N
DeepSMILES: COCCOC=O)C)))CC)C=CCCC5C)CCC9CC%13CC)C)C=O)C=C6)))))C))))))C=CC=O)OC5O
Scaffold Graph/Node/Bond level: O=C1C=CC2C(CCC3C4=CCC(C5=CC(=O)OC5)C4CCC32)C1
Scaffold Graph/Node level: OC1CCC2C(CCC3C2CCC2C(C4COC(O)C4)CCC23)C1
Scaffold Graph level: CC1CCC2C(CCC3C2CCC2C(C4CCC(C)C4)CCC23)C1
Functional groups: CC1=CC(=O)OC1O; COC; COC(C)=O; CC=C(C)C; CC=CC(=O)C
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: Apotirucallane triterpenoids|Limonoids
Synonymous chemical names:
isonimolide, nimolide, iso
External chemical identifiers:
CID:CID_188754
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
7-(Acetyloxy)-21-hydroxy-6-methoxy-4,4,8-trimethyl-3-oxocarda-1,14,20(22)-trienolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 498.62
Log P RDKit 3.9
Topological polar surface area (Å2) RDKit 99.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.69
Number of rotatable bonds RDKit 4
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 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
7-(Acetyloxy)-21-hydroxy-6-methoxy-4,4,8-trimethyl-3-oxocarda-1,14,20(22)-trienolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 0.465306
7-(Acetyloxy)-21-hydroxy-6-methoxy-4,4,8-trimethyl-3-oxocarda-1,14,20(22)-trienolide
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 -6.85
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