IMPPAT Phytochemical information: 
Acetonylchelerythrine
Acetonylchelerythrine
Summary

SMILES: COc1c(OC)ccc2-c3c(N([C@H](c12)CC(=O)C)C)c1cc2OCOc2cc1cc3
InChI: InChI=1S/C24H23NO5/c1-13(26)9-18-22-15(7-8-19(27-3)24(22)28-4)16-6-5-14-10-20-21(30-12-29-20)11-17(14)23(16)25(18)2/h5-8,10-11,18H,9,12H2,1-4H3/t18-/m0/s1
InChIKey: VGTQLFWIJIABSU-SFHVURJKSA-N
DeepSMILES: COccOC))ccc-ccN[C@H]c%106)CC=O)C))))C))cccOCOc5cc9cc%13
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CNc1c-2ccc2cc3c(cc12)OCO3
Scaffold Graph/Node level: C1CCC2C(C1)CNC1C3CC4OCOC4CC3CCC21
Scaffold Graph level: C1CC2CC3CCC4C5CCCCC5CCC4C3CC2C1
Functional groups: cOC; cN(C)C; CC(C)=O; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Benzophenanthridine alkaloids
ClassyFire Subclass: Dihydrobenzophenanthridine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
(+/-)-6-acetonyldihydrochelerythrine, +/--6-acetonyldihydrochelerythrine
External chemical identifiers:
CID:CID_185516; ChEMBL:CHEMBL250267; ZINC:ZINC000000900902
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Acetonylchelerythrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 405.45
Log P RDKit 4.72
Topological polar surface area (Å2) RDKit 57.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 4
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
Acetonylchelerythrine
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 0.63
Acetonylchelerythrine
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 -5.98
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes