IMPPAT Phytochemical information: 
Pterygospermin

Pterygospermin
Summary

SMILES: S=C1OC2(N1Cc1ccccc1)C=CC1(C=C2)OC(=S)N1Cc1ccccc1
InChI: InChI=1S/C22H18N2O2S2/c27-19-23(15-17-7-3-1-4-8-17)21(25-19)11-13-22(14-12-21)24(20(28)26-22)16-18-9-5-2-6-10-18/h1-14H,15-16H2
InChIKey: OGWNPNIRZURLGD-UHFFFAOYSA-N
DeepSMILES: S=COCN4Ccccccc6))))))))C=CCC=C6))OC=S)N4Ccccccc6
Scaffold Graph/Node/Bond level: S=C1OC2(C=CC3(C=C2)OC(=S)N3Cc2ccccc2)N1Cc1ccccc1
Scaffold Graph/Node level: SC1OC2(CCC3(CC2)OC(S)N3CC2CCCCC2)N1CC1CCCCC1
Scaffold Graph level: CC1CC2(CCC3(CC2)CC(C)C3CC2CCCCC2)C1CC1CCCCC1
Functional groups: CN1C(=S)OC12C=CC1(C=C2)OC(=S)N1C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
pterygospermin
External chemical identifiers:
CID:CID_72201063; FDASRS:ZY5W9G83WU
Chemical structure download


Pterygospermin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 406.53
Log P RDKit 4.14
Topological polar surface area (Å2) RDKit 24.94
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 2
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 18
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Pterygospermin
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 0.56


Pterygospermin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.45
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No