IMPPAT Phytochemical information: 
5,8-Dihydroxy-7-(2-hydroxypropyl)-1,2,4a-trimethyl-4,4a-dihydrophenanthrene-3,6-dione
5,8-Dihydroxy-7-(2-hydroxypropyl)-1,2,4a-trimethyl-4,4a-dihydrophenanthrene-3,6-dione
Summary

SMILES: CC(CC1=C(O)C2=CC=C3C(C2=C(C1=O)O)(C)CC(=O)C(=C3C)C)O
InChI: InChI=1S/C20H22O5/c1-9(21)7-13-17(23)12-5-6-14-10(2)11(3)15(22)8-20(14,4)16(12)19(25)18(13)24/h5-6,9,21,23,25H,7-8H2,1-4H3
InChIKey: ZPXWCKGSWWRWCO-UHFFFAOYSA-N
DeepSMILES: CCCC=CO)C=CC=CCC6=CC%10=O))O)))C)CC=O)C=C6C))C))))))))))))O
Scaffold Graph/Node/Bond level: O=C1C=CC2=CC=C3C=CC(=O)CC3C2=C1
Scaffold Graph/Node level: OC1CCC2CCC3CCC(O)CC3C2C1
Scaffold Graph level: CC1CCC2CCC3CCC(C)CC3C2C1
Functional groups: CC1=C(C)C2=CC=C3C(O)=C(C)C(=O)C(O)=C3C2CC1=O; 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: Abeoabietane diterpenoids
Synonymous chemical names:
coleon e, coleon E
External chemical identifiers:
CID:CID_5182088
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5,8-Dihydroxy-7-(2-hydroxypropyl)-1,2,4a-trimethyl-4,4a-dihydrophenanthrene-3,6-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 342.39
Log P RDKit 3.15
Topological polar surface area (Å2) RDKit 94.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 2
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 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
5,8-Dihydroxy-7-(2-hydroxypropyl)-1,2,4a-trimethyl-4,4a-dihydrophenanthrene-3,6-dione
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.72
5,8-Dihydroxy-7-(2-hydroxypropyl)-1,2,4a-trimethyl-4,4a-dihydrophenanthrene-3,6-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -7.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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