IMPPAT Phytochemical information: 
Clausarin

Clausarin
Summary

SMILES: C=CC(c1c2OC(C)(C)C=Cc2c(c2c1oc(=O)c(c2)C(C=C)(C)C)O)(C)C
InChI: InChI=1S/C24H28O4/c1-9-22(3,4)16-13-15-18(25)14-11-12-24(7,8)28-20(14)17(23(5,6)10-2)19(15)27-21(16)26/h9-13,25H,1-2H2,3-8H3
InChIKey: LMEKIDFKWUPZGE-UHFFFAOYSA-N
DeepSMILES: C=CCccOCC)C)C=Cc6ccc%10oc=O)cc6)CC=C))C)C)))))))O)))))))))C)C
Scaffold Graph/Node/Bond level: O=c1ccc2cc3c(cc2o1)OCC=C3
Scaffold Graph/Node level: OC1CCC2CC3CCCOC3CC2O1
Scaffold Graph level: CC1CCC2CC3CCCCC3CC2C1
Functional groups: C=CC; cOC; cC=CC; coc; c=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Pyranocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Pyranocoumarins|Simple coumarins
Synonymous chemical names:
clausarin
External chemical identifiers:
CID:CID_5315945; ChEMBL:CHEMBL158198; ZINC:ZINC000014927453; SureChEMBL:SCHEMBL3366447; MolPort-005-944-760
Chemical structure download


Clausarin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 380.48
Log P RDKit 5.61
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 24
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 4
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 15
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.38
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 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Clausarin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
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 0.553122


Clausarin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly 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 -4.09
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No