IMPPAT Phytochemical information: 
Jacobine
Jacobine
Summary

SMILES: O=C1OCC2=CCN3[C@H]2[C@@H](CC3)OC(=O)[C@@]2(C[C@H]([C@@]1(C)O)C)O[C@H]2C
InChI: InChI=1S/C18H25NO6/c1-10-8-18(11(2)25-18)16(21)24-13-5-7-19-6-4-12(14(13)19)9-23-15(20)17(10,3)22/h4,10-11,13-14,22H,5-9H2,1-3H3/t10-,11+,13-,14-,17-,18+/m1/s1
InChIKey: IAPHXJRHXBQDQJ-WKMWQDDRSA-N
DeepSMILES: O=COCC=CCN[C@H]5[C@@H]CC5))OC=O)[C@@]C[C@H][C@@]%15C)O))C)))O[C@H]3C
Scaffold Graph/Node/Bond level: O=C1CCCC2(CO2)C(=O)OC2CCN3CC=C(CO1)C23
Scaffold Graph/Node level: OC1CCCC2(CO2)C(O)OC2CCN3CCC(CO1)C23
Scaffold Graph level: CC1CCCC2(CC2)C(C)CC2CCC3CCC(CC1)C32
Functional groups: COC(=O)C; CC=C(C)C; CN(C)C; C[C@@H]1O[C@]1(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:
jacobine, Jacobine
External chemical identifiers:
CID:CID_442741; ChEBI:CHEBI:6080; FDASRS:GM32U80H1R
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Jacobine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 351.4
Log P RDKit 0.4
Topological polar surface area (Å2) RDKit 88.6
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 7
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 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Jacobine
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 0.38
Jacobine
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 -8.23
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 Yes