IMPPAT Phytochemical information: 
(4aS)-5,6,8-trihydroxy-7-[(2R)-2-hydroxypropyl]-1,2,4a-trimethyl-4H-phenanthrene-3,9-dione
(4aS)-5,6,8-trihydroxy-7-[(2R)-2-hydroxypropyl]-1,2,4a-trimethyl-4H-phenanthrene-3,9-dione
Summary

SMILES: C[C@H](Cc1c(O)c(O)c2c(c1O)C(=O)C=C1[C@]2(C)CC(=O)C(=C1C)C)O
InChI: InChI=1S/C20H22O6/c1-8(21)5-11-17(24)15-13(22)6-12-9(2)10(3)14(23)7-20(12,4)16(15)19(26)18(11)25/h6,8,21,24-26H,5,7H2,1-4H3/t8-,20+/m1/s1
InChIKey: RHZKGSAKRGMZTK-SQFXPLBJSA-N
DeepSMILES: C[C@H]CccO)cO)ccc6O))C=O)C=C[C@]6C)CC=O)C=C6C))C))))))))))))))O
Scaffold Graph/Node/Bond level: O=C1C=CC2=CC(=O)c3ccccc3C2C1
Scaffold Graph/Node level: OC1CCC2CC(O)C3CCCCC3C2C1
Scaffold Graph level: CC1CCC2CC(C)C3CCCCC3C2C1
Functional groups: cO; cC(=O)C=C1CCC(=O)C(C)=C1C; 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:
16(r)-plectrinon-a
External chemical identifiers:
CID:CID_21768210; ZINC:ZINC000014659967
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(4aS)-5,6,8-trihydroxy-7-[(2R)-2-hydroxypropyl]-1,2,4a-trimethyl-4H-phenanthrene-3,9-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.39
Log P RDKit 2.42
Topological polar surface area (Å2) RDKit 115.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
(4aS)-5,6,8-trihydroxy-7-[(2R)-2-hydroxypropyl]-1,2,4a-trimethyl-4H-phenanthrene-3,9-dione
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47668
(4aS)-5,6,8-trihydroxy-7-[(2R)-2-hydroxypropyl]-1,2,4a-trimethyl-4H-phenanthrene-3,9-dione
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 -7.15
Number of PAINS structural alerts SwissADME 2
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