IMPPAT Phytochemical information: 
Swazine

Swazine
Summary

SMILES: O=C1OC2CCN3C2C(=CC3)COC(=O)C(C2(C(C1=C)C)OC2)(C)O
InChI: InChI=1S/C18H23NO6/c1-10-11(2)18(9-24-18)17(3,22)16(21)23-8-12-4-6-19-7-5-13(14(12)19)25-15(10)20/h4,11,13-14,22H,1,5-9H2,2-3H3
InChIKey: WRPOYLQBTYIKSB-UHFFFAOYSA-N
DeepSMILES: O=COCCCNC5C=CC5))COC=O)CCCC%15=C))C))OC3)))C)O
Scaffold Graph/Node/Bond level: C=C1CC2(CO2)CC(=O)OCC2=CCN3CCC(OC1=O)C23
Scaffold Graph/Node level: CC1CC2(CO2)CC(O)OCC2CCN3CCC(OC1O)C23
Scaffold Graph level: CC1CCC2CCC3CCC(CC(C)C(C)CC4(CC4)C1)C23
Functional groups: C=C(C)C(=O)OC; CN(C)C; CC=C(C)C; COC(=O)C; CC1(C)CO1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
swazine, Swazine
External chemical identifiers:
CID:CID_279070; ChEMBL:CHEMBL1988972
Chemical structure download


Swazine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 349.38
Log P RDKit 0.18
Topological polar surface area (Å2) RDKit 88.6
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Swazine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.288817


Swazine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.50
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes