IMPPAT Phytochemical information: 
Pseudosemiglabrin
Pseudosemiglabrin
Summary

SMILES: CC(=O)O[C@H]1[C@@H]2[C@H](OC1(C)C)Oc1c2c2oc(cc(=O)c2cc1)c1ccccc1
InChI: InChI=1S/C23H20O6/c1-12(24)26-21-19-18-16(28-22(19)29-23(21,2)3)10-9-14-15(25)11-17(27-20(14)18)13-7-5-4-6-8-13/h4-11,19,21-22H,1-3H3/t19-,21+,22+/m1/s1
InChIKey: XTIQPKJOGKMOSY-HJNYFJLDSA-N
DeepSMILES: CC=O)O[C@H][C@@H][C@H]OC5C)C)))Occ5coccc=O)c6cc%10)))))cccccc6
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2c3c(ccc12)OC1OCCC31
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2C1CCC1OC3OCCC3C12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2C1CCC1CC3CCCC3C12
Functional groups: CC(=O)OC; cO[C@H](C)OC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
(-)-pseudosemiglabrin, pseudo semiglabrin
External chemical identifiers:
CID:CID_10408186; ChEMBL:CHEMBL517326; ZINC:ZINC000014695520
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Pseudosemiglabrin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 392.41
Log P RDKit 4
Topological polar surface area (Å2) RDKit 74.97
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.3
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Pseudosemiglabrin
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61
Pseudosemiglabrin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.32
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No