IMPPAT Phytochemical information: 
Alkaloid A
Alkaloid A
Summary

SMILES: C/C=C(\C(=O)OC1CCN2C1C(=CC2)COC(=O)/C(=C/C)/CO)/C
InChI: InChI=1S/C18H25NO5/c1-4-12(3)17(21)24-15-7-9-19-8-6-14(16(15)19)11-23-18(22)13(5-2)10-20/h4-6,15-16,20H,7-11H2,1-3H3/b12-4-,13-5+
InChIKey: GOENJWUGVSLZDQ-JBWWEBJPSA-N
DeepSMILES: C/C=C\C=O)OCCCNC5C=CC5))COC=O)/C=C/C))/CO))))))))))))))/C
Scaffold Graph/Node/Bond level: C1=CC2CCCN2C1
Scaffold Graph/Node level: C1CC2CCCN2C1
Scaffold Graph level: C1CC2CCCC2C1
Functional groups: C/C=C(/C)C(=O)OC; CN(C)C; CC=C(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:
alkaloid a
External chemical identifiers:
CID:CID_5372257
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Alkaloid A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 335.4
Log P RDKit 1.36
Topological polar surface area (Å2) RDKit 76.07
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 8
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
Alkaloid A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.448682
Alkaloid A
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 -7.07
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 No