IMPPAT Phytochemical information: 
Ligularidine
Ligularidine
Summary

SMILES: C/C=C/1\C[C@@H](C)[C@](C)(OC(=O)C)C(=O)OCC2=CCN(CC[C@@H](OC1=O)C2=O)C
InChI: InChI=1S/C21H29NO7/c1-6-15-11-13(2)21(4,29-14(3)23)20(26)27-12-16-7-9-22(5)10-8-17(18(16)24)28-19(15)25/h6-7,13,17H,8-12H2,1-5H3/b15-6+,16-7-/t13-,17-,21+/m1/s1
InChIKey: ZOIAVVNLMDKOIV-BPYQQJMWSA-N
DeepSMILES: C/C=C\C[C@@H]C)[C@]C)OC=O)C)))C=O)OCC=CCNCC[C@@H]OC\%16=O)))C8=O)))))C
Scaffold Graph/Node/Bond level: C=C1CCCC(=O)OCC2=CCNCCC(OC1=O)C2=O
Scaffold Graph/Node level: CC1CCCC(O)OCC2CCNCCC(OC1O)C2O
Scaffold Graph level: CC1CCCC(C)C(C)CC2CCCCCC(CC1)C2C
Functional groups: C/C=C(\C)C(=O)OC; CC(=O)OC; COC(=O)C; CC=C(C)C(=O)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
o-acetylcrotaverrine
External chemical identifiers:
CID:CID_6440207
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ligularidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 407.46
Log P RDKit 1.58
Topological polar surface area (Å2) RDKit 99.21
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
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 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 2
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
Ligularidine
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 0.37
Ligularidine
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 -7.37
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 No