IMPPAT Phytochemical information: 
Marrubenol

Marrubenol
Summary

SMILES: OC[C@@]1(C)CCC[C@]2([C@H]1[C@H](O)C[C@H]([C@]2(O)CCc1cocc1)C)C
InChI: InChI=1S/C20H32O4/c1-14-11-16(22)17-18(2,13-21)7-4-8-19(17,3)20(14,23)9-5-15-6-10-24-12-15/h6,10,12,14,16-17,21-23H,4-5,7-9,11,13H2,1-3H3/t14-,16-,17+,18-,19+,20-/m1/s1
InChIKey: NZMHIKFTAXRIDL-FQFOHHTNSA-N
DeepSMILES: OC[C@@]C)CCC[C@][C@H]6[C@H]O)C[C@H][C@]6O)CCccocc5))))))))C)))))C
Scaffold Graph/Node/Bond level: c1cc(CCC2CCCC3CCCCC32)co1
Scaffold Graph/Node level: C1CCC2C(C1)CCCC2CCC1CCOC1
Scaffold Graph level: C1CCC(CCC2CCCC3CCCCC32)C1
Functional groups: CO; coc
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: Labdane diterpenoids
Synonymous chemical names:
marrubenol
External chemical identifiers:
CID:CID_10449689; ChEMBL:CHEMBL389065; ZINC:ZINC000028648780; SureChEMBL:SCHEMBL4450048
Chemical structure download


Marrubenol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 336.47
Log P RDKit 3.15
Topological polar surface area (Å2) RDKit 73.83
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 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
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


Marrubenol
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


Marrubenol
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 -6.21
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes