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: COC(=O)C; CN(C)C; CC=C(C)C; CO
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, monocrotaline
External chemical identifiers:
CID:CID_9415; ChEMBL:CHEMBL521035; ChEBI: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 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 Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.46
Monocrotaline
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 High
Log Kp (Skin permeation, cm/s) SwissADME -8.80
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
Monocrotaline
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.