IMPPAT Phytochemical information: 
9-Ethyl-4,5,9-trihydroxy-8-methyl-4-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
9-Ethyl-4,5,9-trihydroxy-8-methyl-4-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
Summary

SMILES: CCC1(O)C(=O)OCC2=CCN3C2C(CC3)OC(=O)C(C(C(=O)OC1C)O)(O)C(C)C
InChI: InChI=1S/C21H31NO9/c1-5-20(27)12(4)30-17(24)16(23)21(28,11(2)3)19(26)31-14-7-9-22-8-6-13(15(14)22)10-29-18(20)25/h6,11-12,14-16,23,27-28H,5,7-10H2,1-4H3
InChIKey: SAPQZIXQNLIRLW-UHFFFAOYSA-N
DeepSMILES: CCCO)C=O)OCC=CCNC5CCC5))OC=O)CCC=O)OC%17C))))O))O)CC)C
Scaffold Graph/Node/Bond level: O=C1CCC(=O)OC2CCN3CC=C(COC(=O)CCO1)C23
Scaffold Graph/Node level: OC1CCC(O)OC2CCN3CCC(COC(O)CCO1)C23
Scaffold Graph level: CC1CCCC(C)CCC2CCC3CCC(CC(C)CC1)C23
Functional groups: CO; COC(=O)C; CC=C(C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
parsonsianine
External chemical identifiers:
CID:CID_14680171
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
9-Ethyl-4,5,9-trihydroxy-8-methyl-4-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 441.48
Log P RDKit -0.71
Topological polar surface area (Å2) RDKit 142.83
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3
9-Ethyl-4,5,9-trihydroxy-8-methyl-4-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
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 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.29
9-Ethyl-4,5,9-trihydroxy-8-methyl-4-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.02
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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