IMPPAT Phytochemical information: 
Julandine

Julandine
Summary

SMILES: COc1ccc(cc1)C1=C(C[C@@H]2N(C1)CCCC2)c1ccc(c(c1)OC)OC
InChI: InChI=1S/C24H29NO3/c1-26-20-10-7-17(8-11-20)22-16-25-13-5-4-6-19(25)15-21(22)18-9-12-23(27-2)24(14-18)28-3/h7-12,14,19H,4-6,13,15-16H2,1-3H3/t19-/m1/s1
InChIKey: GZQPRQAGPHGFNW-LJQANCHMSA-N
DeepSMILES: COcccccc6))C=CC[C@@H]NC6)CCCC6)))))))cccccc6)OC)))OC
Scaffold Graph/Node/Bond level: c1ccc(C2=C(c3ccccc3)CN3CCCCC3C2)cc1
Scaffold Graph/Node level: C1CCC(C2CC3CCCCN3CC2C2CCCCC2)CC1
Scaffold Graph level: C1CCC(C2CC3CCCCC3CC2C2CCCCC2)CC1
Functional groups: cOC; cC(=C(c)C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Indolizidine alkaloids
Synonymous chemical names:
Julandine, julandine
External chemical identifiers:
CID:CID_10407368; ZINC:ZINC000038795360
Chemical structure download


Julandine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 379.5
Log P RDKit 4.88
Topological polar surface area (Å2) RDKit 30.93
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Julandine
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74


Julandine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.68
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes