IMPPAT Phytochemical information: 
Robustic acid methyl ether

Robustic acid methyl ether
Summary

SMILES: COc1c(c2ccc(cc2)OC)c(=O)oc2c1c(OC)c1c(c2)OC(C=C1)(C)C
InChI: InChI=1S/C23H22O6/c1-23(2)11-10-15-16(29-23)12-17-19(20(15)26-4)21(27-5)18(22(24)28-17)13-6-8-14(25-3)9-7-13/h6-12H,1-5H3
InChIKey: UPHWJAWTGRBPAJ-UHFFFAOYSA-N
DeepSMILES: COcccccccc6))OC))))))c=O)occ6cOC))ccc6)OCC=C6))C)C
Scaffold Graph/Node/Bond level: O=c1oc2cc3c(cc2cc1-c1ccccc1)C=CCO3
Scaffold Graph/Node level: OC1OC2CC3OCCCC3CC2CC1C1CCCCC1
Scaffold Graph level: CC1CC2CC3CCCCC3CC2CC1C1CCCCC1
Functional groups: cOC; c=O; coc; cC=CC
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:
robustic acid me ether
External chemical identifiers:
CID:CID_4262362; ChEMBL:CHEMBL3039033; ZINC:ZINC000003978531; SureChEMBL:SCHEMBL12062097
Chemical structure download


Robustic acid methyl ether
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 394.42
Log P RDKit 4.67
Topological polar surface area (Å2) RDKit 67.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
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 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


Robustic acid methyl ether
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6


Robustic acid methyl ether
ADME 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.79
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No