IMPPAT Phytochemical information: 
5'-Acetyllasiocarpine
5'-Acetyllasiocarpine
Summary

SMILES: CO[C@H]([C@@](C(OC(=O)C)(C)C)(C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)/C(=C\C)/C)O)C
InChI: InChI=1S/C23H35NO8/c1-8-14(2)20(26)31-18-10-12-24-11-9-17(19(18)24)13-30-21(27)23(28,15(3)29-7)22(5,6)32-16(4)25/h8-9,15,18-19,28H,10-13H2,1-7H3/b14-8-/t15-,18-,19+,23-/m0/s1
InChIKey: XGLOPSNBSMBXSE-YELXYMKISA-N
DeepSMILES: CO[C@H][C@@]COC=O)C)))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; COC(C)=O; CC=C(C)C; CN(C)C; C/C=C(/C)C(=O)OC; 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:
5'-acetyllasiocarpine, acetyllasiocarpine
External chemical identifiers:
CID:CID_101915797; ZINC:ZINC000238759464
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5'-Acetyllasiocarpine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 453.53
Log P RDKit 1.53
Topological polar surface area (Å2) RDKit 111.6
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 12
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
5'-Acetyllasiocarpine
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 Bad
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 0.24
5'-Acetyllasiocarpine
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 -7.75
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No