IMPPAT Phytochemical information: 
cinchonain Ib

cinchonain Ib
Summary

SMILES: O=C1Oc2cc(O)c3c(c2[C@H](C1)c1ccc(c(c1)O)O)O[C@@H]([C@@H](C3)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C24H20O9/c25-14-3-1-10(5-17(14)28)12-8-21(31)32-20-9-16(27)13-7-19(30)23(33-24(13)22(12)20)11-2-4-15(26)18(29)6-11/h1-6,9,12,19,23,25-30H,7-8H2/t12-,19-,23-/m1/s1
InChIKey: LKCOZWLUAKSRQM-UMAWSMADSA-N
DeepSMILES: O=COcccO)ccc6[C@H]C%10)cccccc6)O))O)))))))O[C@@H][C@@H]C6)O))cccccc6)O))O
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)c2c(ccc3c2OC(c2ccccc2)CC3)O1
Scaffold Graph/Node level: OC1CC(C2CCCCC2)C2C(CCC3CCC(C4CCCCC4)OC32)O1
Scaffold Graph level: CC1CC2CCC3CCC(C4CCCCC4)CC3C2C(C2CCCCC2)C1
Functional groups: CO; cO; cOC; cOC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavan-3-ols
Synonymous chemical names:
cinchonain ib
External chemical identifiers:
CID:442675; ChEMBL:CHEMBL251476; ChEBI:3702; SureChEMBL:SCHEMBL1769333
Chemical structure download


cinchonain Ib
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 452.42
Log P RDKit 2.69
Topological polar surface area (Å2) RDKit 156.91
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5


cinchonain Ib
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 0
Ghose filter RDKit Passed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.1954


cinchonain Ib
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.47
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No