IMPPAT Phytochemical information: 
Pentanoic acid, 2-hydroxy-2-(1-hydroxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester
Pentanoic acid, 2-hydroxy-2-(1-hydroxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester
Summary

SMILES: CCC(C(C(=O)OCC1=CCN2C1CCC2)(C(O)C)O)C
InChI: InChI=1S/C16H27NO4/c1-4-11(2)16(20,12(3)18)15(19)21-10-13-7-9-17-8-5-6-14(13)17/h7,11-12,14,18,20H,4-6,8-10H2,1-3H3
InChIKey: WNDKUMUAOQFAGL-UHFFFAOYSA-N
DeepSMILES: CCCCC=O)OCC=CCNC5CCC5)))))))))))CO)C))O))C
Scaffold Graph/Node/Bond level: C1=CC2CCCN2C1
Scaffold Graph/Node level: C1CC2CCCN2C1
Scaffold Graph level: C1CC2CCCC2C1
Functional groups: COC(C)=O; CC=C(C)C; CN(C)C; 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:
curassavinine, Curassavinine
External chemical identifiers:
CID:CID_158633
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Pentanoic acid, 2-hydroxy-2-(1-hydroxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 297.4
Log P RDKit 1.09
Topological polar surface area (Å2) RDKit 70
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.81
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Pentanoic acid, 2-hydroxy-2-(1-hydroxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.57
Pentanoic acid, 2-hydroxy-2-(1-hydroxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl ester
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 -7.48
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No