IMPPAT Phytochemical information: 
Monocrotaline
Monocrotaline
Summary

SMILES: O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]([C@H]1C)(C)O)(C)O
InChI: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1
InChIKey: QVCMHGGNRFRMAD-XFGHUUIASA-N
DeepSMILES: O=CO[C@@H]CCN[C@@H]5C=CC5))COC=O)[C@][C@][C@H]%14C))C)O))C)O
Scaffold Graph/Node/Bond level: O=C1CCCC(=O)OC2CCN3CC=C(CO1)C23
Scaffold Graph/Node level: OC1CCCC(O)OC2CCN3CCC(CO1)C23
Scaffold Graph level: CC1CCCC(C)CC2CCC3CCC(CC1)C32
Functional groups: CC=C(C)C; CN(C)C; CO; COC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Pyrrolizines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
crotaline, monocrotaline, pyrrolizidine alkaloid
External chemical identifiers:
CID:9415; ChEMBL:CHEMBL521035; ChEBI:6980; ZINC:ZINC000053195720; FDASRS:73077K8HYV; SureChEMBL:SCHEMBL164486; MolPort-001-742-605
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Monocrotaline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 325.36
Log P RDKit -0.39
Topological polar surface area (Å2) RDKit 96.3
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Monocrotaline
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 0.4623
Monocrotaline
ADMET 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 High
Log Kp (Skin permeation, cm/s) SwissADME -8.8
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
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
Monocrotaline
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000225831CCL2818
ENSP00000258743IL6829
ENSP00000337915CYP3A4700
ENSP00000355930SLC22A1700
ENSP00000360372CYP2C19700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.