IMPPAT Phytochemical information: 
(4aS,10aR)-7-hydroxy-1,1,4a,6-tetramethyl-3,4,10,10a-tetrahydrophenanthrene-2,9-dione

(4aS,10aR)-7-hydroxy-1,1,4a,6-tetramethyl-3,4,10,10a-tetrahydrophenanthrene-2,9-dione
Summary

SMILES: O=C1CC[C@]2([C@H](C1(C)C)CC(=O)c1c2cc(C)c(c1)O)C
InChI: InChI=1S/C18H22O3/c1-10-7-12-11(8-13(10)19)14(20)9-15-17(2,3)16(21)5-6-18(12,15)4/h7-8,15,19H,5-6,9H2,1-4H3/t15-,18+/m0/s1
InChIKey: LADNAJMEYZHPOD-MAUKXSAKSA-N
DeepSMILES: O=CCC[C@][C@H]C6C)C))CC=O)cc6ccC)cc6)O)))))))))C
Scaffold Graph/Node/Bond level: O=C1CCC2c3ccccc3C(=O)CC2C1
Scaffold Graph/Node level: OC1CCC2C(C1)CC(O)C1CCCCC12
Scaffold Graph level: CC1CCC2C(C1)CC(C)C1CCCCC12
Functional groups: CC(=O)C; cC(=O)C; 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: Podocarpane diterpenoids
Synonymous chemical names:
Nimbione, nimbione
External chemical identifiers:
CID:CID_189404
Chemical structure download


(4aS,10aR)-7-hydroxy-1,1,4a,6-tetramethyl-3,4,10,10a-tetrahydrophenanthrene-2,9-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 286.37
Log P RDKit 3.55
Topological polar surface area (Å2) RDKit 54.37
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 0
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


(4aS,10aR)-7-hydroxy-1,1,4a,6-tetramethyl-3,4,10,10a-tetrahydrophenanthrene-2,9-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 0.79


(4aS,10aR)-7-hydroxy-1,1,4a,6-tetramethyl-3,4,10,10a-tetrahydrophenanthrene-2,9-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes