IMPPAT Phytochemical information: 
Marrubiin

Marrubiin
Summary

SMILES: C[C@@H]1C[C@H]2OC(=O)[C@@]3([C@H]2[C@]([C@@]1(O)CCc1cocc1)(C)CCC3)C
InChI: InChI=1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1
InChIKey: HQLLRHCTVDVUJB-OBHOOXMTSA-N
DeepSMILES: C[C@@H]C[C@H]OC=O)[C@@][C@H]5[C@][C@@]9O)CCccocc5))))))))C)CCC6)))))C
Scaffold Graph/Node/Bond level: O=C1OC2CCC(CCc3ccoc3)C3CCCC1C23
Scaffold Graph/Node level: OC1OC2CCC(CCC3CCOC3)C3CCCC1C23
Scaffold Graph level: CC1CC2CCC(CCC3CCCC3)C3CCCC1C23
Functional groups: COC(=O)C; CO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Lactones
ClassyFire Subclass: Gamma butyrolactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids
Synonymous chemical names:
Marrubiin, marrubiin
External chemical identifiers:
CID:CID_73401; ChEMBL:CHEMBL1999372; ChEBI:CHEBI:6696; ZINC:ZINC000003881918; FDASRS:AP086P88M4; SureChEMBL:SCHEMBL2784576; MolPort-003-804-189
Chemical structure download


Marrubiin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 332.44
Log P RDKit 3.72
Topological polar surface area (Å2) RDKit 59.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
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 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 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Marrubiin
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 0.86


Marrubiin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.68
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 No