IMPPAT Phytochemical information: 
Acetyllithosenine
Acetyllithosenine
Summary

SMILES: O=C(CC(O)(C)C)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@](C(O)(C)C)([C@@H](OC(=O)C)C)O
InChI: InChI=1S/C22H35NO9/c1-13(31-14(2)24)22(29,21(5,6)28)19(26)30-12-15-7-9-23-10-8-16(18(15)23)32-17(25)11-20(3,4)27/h7,13,16,18,27-29H,8-12H2,1-6H3/t13-,16+,18+,22+/m0/s1
InChIKey: RWSVCNGLTCIUJD-RONDGGJASA-N
DeepSMILES: O=CCCO)C)C)))O[C@@H]CCN[C@@H]5C=CC5))COC=O)[C@@]CO)C)C))[C@@H]OC=O)C)))C))O
Scaffold Graph/Node/Bond level: C1=CC2CCCN2C1
Scaffold Graph/Node level: C1CC2CCCN2C1
Scaffold Graph level: C1CC2CCCC2C1
Functional groups: CC(=O)OC; CO; CN(C)C; CC=C(C)C; COC(C)=O
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:
acetyllithosenine
External chemical identifiers:
CID:CID_101674027; ZINC:ZINC000238777970
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Acetyllithosenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 457.52
Log P RDKit 0.07
Topological polar surface area (Å2) RDKit 142.83
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.18
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 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
Acetyllithosenine
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 Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25
Acetyllithosenine
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -9.10
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 Yes