IMPPAT Phytochemical information: 
Picrasidine A

Picrasidine A
Summary

SMILES: COc1cccc2c1[nH]c1c2c(OC)cnc1CCC(=O)c1nccc2c1[nH]c1c2cccc1
InChI: InChI=1S/C27H22N4O3/c1-33-21-9-5-7-17-23-22(34-2)14-29-19(26(23)31-24(17)21)10-11-20(32)27-25-16(12-13-28-27)15-6-3-4-8-18(15)30-25/h3-9,12-14,30-31H,10-11H2,1-2H3
InChIKey: MSRXRROCBIUJCG-UHFFFAOYSA-N
DeepSMILES: COcccccc6[nH]cc5cOC))cnc6CCC=O)cncccc6[nH]cc5cccc6
Scaffold Graph/Node/Bond level: O=C(CCc1nccc2c1[nH]c1ccccc12)c1nccc2c1[nH]c1ccccc12
Scaffold Graph/Node level: OC(CCC1NCCC2C3CCCCC3NC12)C1NCCC2C3CCCCC3NC21
Scaffold Graph level: CC(CCC1CCCC2C3CCCCC3CC12)C1CCCC2C3CCCCC3CC12
Functional groups: cOC; c[nH]c; cnc; cC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Harmala alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
picrasidine a
External chemical identifiers:
CID:CID_5315686; ChEMBL:CHEMBL2229722; ZINC:ZINC000014655498
Chemical structure download


Picrasidine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 450.5
Log P RDKit 5.58
Topological polar surface area (Å2) RDKit 92.89
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 4
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 23
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 6
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 4
Number of aromatic rings RDKit 6
Total number of rings RDKit 6
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 6


Picrasidine A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
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 0.323318


Picrasidine A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.78
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