IMPPAT Phytochemical information: 
Cleomiscosin C

Cleomiscosin C
Summary

SMILES: OC[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O)c(OC)cc1c2oc(=O)cc1
InChI: InChI=1S/C21H20O9/c1-25-12-7-11(8-13(26-2)17(12)24)18-15(9-22)28-21-19-10(4-5-16(23)29-19)6-14(27-3)20(21)30-18/h4-8,15,18,22,24H,9H2,1-3H3/t15-,18-/m1/s1
InChIKey: GZXPCBAETDEQAX-CRAIPNDOSA-N
DeepSMILES: OC[C@H]OccO[C@@H]6cccOC))ccc6)OC)))O)))))))cOC))ccc6oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2ccc3c(c2o1)OCC(c1ccccc1)O3
Scaffold Graph/Node level: OC1CCC2CCC3OC(C4CCCCC4)COC3C2O1
Scaffold Graph level: CC1CCC2CCC3CC(C4CCCCC4)CCC3C2C1
Functional groups: CO; c=O; cO; cOC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Coumarinolignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins|Lignans
NP Classifier Class: Coumarinolignans
Synonymous chemical names:
cleomiscosin c
External chemical identifiers:
CID:11464176; ChEMBL:CHEMBL465491; ZINC:ZINC000013400299; SureChEMBL:SCHEMBL4545353; MolPort-035-706-073
Chemical structure download


Cleomiscosin C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 416.38
Log P RDKit 2.4
Topological polar surface area (Å2) RDKit 116.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 5
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


Cleomiscosin C
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6047


Cleomiscosin C
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.35
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes