IMPPAT Phytochemical information: 
Picrasidine O
Picrasidine O
Summary

SMILES: COc1c2-c3c(ccn2C)c2c(n3c(=O)c1=O)cccc2
InChI: InChI=1S/C16H12N2O3/c1-17-8-7-10-9-5-3-4-6-11(9)18-12(10)13(17)15(21-2)14(19)16(18)20/h3-8H,1-2H3
InChIKey: HPAUUBGCMSMJQK-UHFFFAOYSA-N
DeepSMILES: COcc-ccccn6C))))ccn5c=O)c9=O))))cccc6
Scaffold Graph/Node/Bond level: O=c1cc2[nH]ccc3c-2n(c1=O)c1ccccc31
Scaffold Graph/Node level: OC1CC2NCCC3C4CCCCC4N(C1O)C23
Scaffold Graph level: CC1CC2CCCC3C4CCCCC4C(C1C)C23
Functional groups: cOC; cn(C)c; cn(c)c; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Indolonaphthyridine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Quinoline alkaloids
Synonymous chemical names:
Picrasidine O, picrasidine o
External chemical identifiers:
CID:CID_5320558; ChEMBL:CHEMBL1700463
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Picrasidine O
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 280.28
Log P RDKit 1.7
Topological polar surface area (Å2) RDKit 52.71
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
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 14
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.12
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Picrasidine O
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.5
Picrasidine O
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.45
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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