IMPPAT Phytochemical information: 
Leptosidin

Leptosidin
Summary

SMILES: COc1c(O)ccc2c1O/C(=C\c1ccc(c(c1)O)O)/C2=O
InChI: InChI=1S/C16H12O6/c1-21-16-11(18)5-3-9-14(20)13(22-15(9)16)7-8-2-4-10(17)12(19)6-8/h2-7,17-19H,1H3/b13-7-
InChIKey: PFRGTMTYWMVLMU-QPEQYQDCSA-N
DeepSMILES: COccO)cccc6O/C=C\cccccc6)O))O))))))/C5=O
Scaffold Graph/Node/Bond level: O=C1C(=Cc2ccccc2)Oc2ccccc21
Scaffold Graph/Node level: OC1C(CC2CCCCC2)OC2CCCCC21
Scaffold Graph level: CC1C(CC2CCCCC2)CC2CCCCC21
Functional groups: cOC; cO; c/C=C1\OccC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Aurone flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Aurones
Synonymous chemical names:
Leptosidin, leptosidin
External chemical identifiers:
CID:CID_5281257; ChEMBL:CHEMBL3799890; ChEBI:CHEBI:6412; ZINC:ZINC000004642934; SureChEMBL:SCHEMBL6804084
Chemical structure download


Leptosidin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 300.27
Log P RDKit 2.43
Topological polar surface area (Å2) RDKit 96.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 6
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 1
Shape complexity RDKit 0.06
Number of rotatable bonds RDKit 2
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 0
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


Leptosidin
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.582038


Leptosidin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.36
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No