IMPPAT Phytochemical information: 
Robustin methyl ether

Robustin methyl ether
Summary

SMILES: COc1c(c2ccc3c(c2)OCO3)c(=O)oc2c1c(OC)c1c(c2)OC(C=C1)(C)C
InChI: InChI=1S/C23H20O7/c1-23(2)8-7-13-15(30-23)10-17-19(20(13)25-3)21(26-4)18(22(24)29-17)12-5-6-14-16(9-12)28-11-27-14/h5-10H,11H2,1-4H3
InChIKey: OJMVWQKOYQXIJO-UHFFFAOYSA-N
DeepSMILES: COcccccccc6)OCO5))))))))c=O)occ6cOC))ccc6)OCC=C6))C)C
Scaffold Graph/Node/Bond level: O=c1oc2cc3c(cc2cc1-c1ccc2c(c1)OCO2)C=CCO3
Scaffold Graph/Node level: OC1OC2CC3OCCCC3CC2CC1C1CCC2OCOC2C1
Scaffold Graph level: CC1CC2CC3CCCCC3CC2CC1C1CCC2CCCC2C1
Functional groups: c1cOCO1; c=O; cC=CC; cOC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflav-3-enes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Pyranocoumarins
Synonymous chemical names:
robustin methyl ether
External chemical identifiers:
CID:44260106; ZINC:ZINC000014687505
Chemical structure download


Robustin methyl ether
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 408.41
Log P RDKit 4.39
Topological polar surface area (Å2) RDKit 76.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5


Robustin methyl ether
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.595


Robustin methyl ether
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.99
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes