IMPPAT Phytochemical information: 
Trifolione D

Trifolione D
Summary

SMILES: OCC1(CO)CC(=O)C[C@@]2([C@@H]1C[C@H](O)C1=C[C@](CC[C@@H]21)(C)C=C)C
InChI: InChI=1S/C20H30O4/c1-4-18(2)6-5-15-14(10-18)16(24)7-17-19(15,3)8-13(23)9-20(17,11-21)12-22/h4,10,15-17,21-22,24H,1,5-9,11-12H2,2-3H3/t15-,16+,17+,18-,19+/m1/s1
InChIKey: GUCMEFFLGFUFEJ-SPOLIRPYSA-N
DeepSMILES: OCCCO))CC=O)C[C@@][C@@H]6C[C@H]O)C=C[C@]CC[C@@H]%106)))C)C=C))))))))C
Scaffold Graph/Node/Bond level: O=C1CCC2CCC3=CCCCC3C2C1
Scaffold Graph/Node level: OC1CCC2CCC3CCCCC3C2C1
Scaffold Graph level: CC1CCC2CCC3CCCCC3C2C1
Functional groups: CO; CC(=O)C; CC=C(C)C; C=CC
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: Pimarane and Isopimarane diterpenoids
Synonymous chemical names:
trifolione d, Trifolione D
External chemical identifiers:
CID:CID_10568746; ZINC:ZINC000038784077
Chemical structure download


Trifolione D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 334.46
Log P RDKit 2.24
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3


Trifolione D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.69


Trifolione D
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.39
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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