IMPPAT Phytochemical information: 
Cleomiscosin A

Cleomiscosin A
Summary

SMILES: OC[C@H]1Oc2c(O[C@@H]1c1ccc(c(c1)OC)O)c(OC)cc1c2oc(=O)cc1
InChI: InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-20-18-11(4-6-16(23)27-18)8-14(25-2)19(20)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17-/m1/s1
InChIKey: OCBGWPJNUZMLCA-NVXWUHKLSA-N
DeepSMILES: OC[C@H]OccO[C@@H]6cccccc6)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; cOC; cO; coc; c=O
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 a
External chemical identifiers:
CID:CID_442510; ChEMBL:CHEMBL510091; ChEBI:CHEBI:3740; ZINC:ZINC000001580260; SureChEMBL:SCHEMBL2727534; MolPort-028-599-889
Chemical structure download


Cleomiscosin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 386.36
Log P RDKit 2.39
Topological polar surface area (Å2) RDKit 107.59
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 8
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 5
Shape complexity RDKit 0.25
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


Cleomiscosin A
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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.66


Cleomiscosin A
ADME 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 -7.15
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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