IMPPAT Phytochemical information: 
Lasiocarpin
Lasiocarpin
Summary

SMILES: CO[C@H]([C@@](C(O)(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)/C(=C/C)/C)O)C
InChI: InChI=1S/C21H33NO7/c1-7-13(2)18(23)29-16-9-11-22-10-8-15(17(16)22)12-28-19(24)21(26,14(3)27-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7+/t14-,16-,17+,21-/m0/s1
InChIKey: QHOZSLCIKHUPSU-QDYSVBJQSA-N
DeepSMILES: CO[C@H][C@@]CO)C)C))C=O)OCC=CCN[C@H]5[C@H]CC5))OC=O)/C=C/C))/C)))))))))))))O))C
Scaffold Graph/Node/Bond level: C1=CC2CCCN2C1
Scaffold Graph/Node level: C1CC2CCCN2C1
Scaffold Graph level: C1CC2CCCC2C1
Functional groups: COC; CO; COC(C)=O; CC=C(C)C; CN(C)C; C/C=C(\C)C(=O)OC
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:
Lasiocarpine, lasiocarpine, lasiocarpin, Lasiocarpin
External chemical identifiers:
CID:CID_12358997; ZINC:ZINC000016983010
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lasiocarpin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 411.5
Log P RDKit 0.96
Topological polar surface area (Å2) RDKit 105.53
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 10
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
Lasiocarpin
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.35
Lasiocarpin
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 High
Log Kp (Skin permeation, cm/s) SwissADME -7.90
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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