IMPPAT Phytochemical information: 
Parsonsine

Parsonsine
Summary

SMILES: O=C1O[C@H](C)[C@@](O)(C(C)C)C(=O)OCC2=CCN3[C@H]2[C@H](OC(=O)[C@@](C1)(O)C(C)C)CC3
InChI: InChI=1S/C22H33NO8/c1-12(2)21(27)10-17(24)30-14(5)22(28,13(3)4)20(26)29-11-15-6-8-23-9-7-16(18(15)23)31-19(21)25/h6,12-14,16,18,27-28H,7-11H2,1-5H3/t14-,16-,18-,21+,22+/m1/s1
InChIKey: MPPSDVYCCOJJIB-QCNRXRGQSA-N
DeepSMILES: O=CO[C@H]C)[C@@]O)CC)C))C=O)OCC=CCN[C@H]5[C@H]OC=O)[C@@]C%17)O)CC)C)))))CC5
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: CC(=O)OC; CC=C(C)C; CN(C)C; CO; COC(C)=O
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:
parsonsine
External chemical identifiers:
CID:15060933; ChEBI:7937; ZINC:ZINC000056871323; FDASRS:249CZA0134
Chemical structure download


Parsonsine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 439.51
Log P RDKit 0.57
Topological polar surface area (Å2) RDKit 122.6
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.77
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


Parsonsine
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.361


Parsonsine
ADMET 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 High
Log Kp (Skin permeation, cm/s) SwissADME -8.31
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
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