IMPPAT Phytochemical information: 
Picrasidine S

Picrasidine S
Summary

SMILES: COc1c[n+]2C(CCCc2c2c1c1cccc(c1[nH]2)OC)c1ncc(c2c1[nH]c1c2cccc1OC)OC
InChI: InChI=1S/C30H28N4O4/c1-35-20-12-6-9-17-25-23(38-4)15-34-18(28(25)32-26(17)20)10-7-11-19(34)29-30-24(22(37-3)14-31-29)16-8-5-13-21(36-2)27(16)33-30/h5-6,8-9,12-15,19H,7,10-11H2,1-4H3,(H,31,33)/p+1
InChIKey: ZHIAAGUQJJWYBK-UHFFFAOYSA-O
DeepSMILES: COcc[n+]CCCCc6cc%10cccccc6[nH]9))OC)))))))))))))cncccc6[nH]cc5cccc6OC)))))))))))OC
Scaffold Graph/Node/Bond level: c1ccc2c(c1)[nH]c1c(C3CCCc4c5[nH]c6ccccc6c5cc[n+]43)nccc12
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCNC1C1CCCC2C3NC4CCCCC4C3CCN21
Scaffold Graph level: C1CCC2C(C1)CC1C2CCCC1C1CCCC2C3CC4CCCCC4C3CCC21
Functional groups: cOC; c[n+](c)C; c[nH]c; cnc
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 s
External chemical identifiers:
CID:5318873; MolPort-035-705-724
Chemical structure download


Picrasidine S
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 509.59
Log P RDKit 5.6
Topological polar surface area (Å2) RDKit 85.27
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.03
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 22
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.27
Number of rotatable bonds RDKit 5
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 4
Number of aromatic rings RDKit 6
Total number of rings RDKit 7
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 7


Picrasidine S
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
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 0.2957


Picrasidine S
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.73
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes