IMPPAT Phytochemical information: 
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione
Summary

SMILES: C[C@H]([C@@]1(O)C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3)O
InChI: InChI=1S/C18H27NO7/c1-10-8-18(24,11(2)20)16(22)26-13-5-7-19-6-4-12(14(13)19)9-25-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1
InChIKey: FMWJEBGSMAOQNN-YLFNNMARSA-N
DeepSMILES: C[C@H][C@@]O)C[C@@H]C)[C@@]C)O)C=O)OCC=CCN[C@H]5[C@H]OC%15=O)))CC5)))))))))))))))O
Scaffold Graph/Node/Bond level: O=C1CCCCC(=O)OC2CCN3CC=C(CO1)C23
Scaffold Graph/Node level: OC1CCCCC(O)OC2CCN3CCC(CO1)C23
Scaffold Graph level: CC1CCCCC(C)CC2CCC3CCC(CC1)C32
Functional groups: CO; COC(=O)C; CC=C(C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
Jacoline, jacoline
External chemical identifiers:
CID:CID_78358487; ChEBI:CHEBI:136452; ZINC:ZINC000169420762; MolPort-044-754-047
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 369.41
Log P RDKit -0.64
Topological polar surface area (Å2) RDKit 116.53
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 1
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
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione
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 1
Ghose filter RDKit Failed
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 0.412773
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione
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 -8.66
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