IMPPAT Phytochemical information: 
Clausenidinaric acid

Clausenidinaric acid
Summary

SMILES: C=CC(c1c(O)c(/C=C/C(=O)O)c2c(c1O)C(=O)CC(O2)(C)C)(C)C
InChI: InChI=1S/C19H22O6/c1-6-18(2,3)14-15(23)10(7-8-12(21)22)17-13(16(14)24)11(20)9-19(4,5)25-17/h6-8,23-24H,1,9H2,2-5H3,(H,21,22)/b8-7+
InChIKey: RCWHURATSALMKC-BQYQJAHWSA-N
DeepSMILES: C=CCccO)c/C=C/C=O)O))))ccc6O))C=O)CCO6)C)C)))))))))C)C
Scaffold Graph/Node/Bond level: O=C1CCOc2ccccc21
Scaffold Graph/Node level: OC1CCOC2CCCCC12
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: C=CC; cO; c/C=C/C(=O)O; cC(=O)C; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
Synonymous chemical names:
clausenidinaric acid
External chemical identifiers:
CID:CID_10043229; ChEMBL:CHEMBL453804; ZINC:ZINC000040836111
Chemical structure download


Clausenidinaric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.38
Log P RDKit 3.4
Topological polar surface area (Å2) RDKit 104.06
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
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 12
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.37
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 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


Clausenidinaric acid
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.570037


Clausenidinaric acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No