IMPPAT Phytochemical information: 
Flaccidine

Flaccidine
Summary

SMILES: C/C=C(\C(=O)Oc1c(oc2c(c1=O)c(O)cc(c2OC)O)c1ccc(c(c1)OC)OC)/C
InChI: InChI=1S/C23H22O9/c1-6-11(2)23(27)32-22-18(26)17-13(24)10-14(25)20(30-5)21(17)31-19(22)12-7-8-15(28-3)16(9-12)29-4/h6-10,24-25H,1-5H3/b11-6-
InChIKey: NSTVGBOIHUUJLX-WDZFZDKYSA-N
DeepSMILES: C/C=C\C=O)Occoccc6=O))cO)ccc6OC)))O)))))))cccccc6)OC)))OC))))))))))/C
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2ccccc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCCC12
Functional groups: cOC(=O)/C(C)=C\C; coc; c=O; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: O-methylated flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavonols
Synonymous chemical names:
flaccidine, Flaccidine
External chemical identifiers:
CID:CID_44260021; ZINC:ZINC000014437074
Chemical structure download


Flaccidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 442.42
Log P RDKit 3.77
Topological polar surface area (Å2) RDKit 124.66
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 9
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 18
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.22
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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


Flaccidine
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.433406


Flaccidine
ADME 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 High
Log Kp (Skin permeation, cm/s) SwissADME -6.09
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 No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No