IMPPAT Phytochemical information: 
Sinococuline

Sinococuline
Summary

SMILES: COC1=C2[C@H]3NCC[C@]2(C[C@@H]([C@@H]1O)O)c1c(C3)ccc(c1O)OC
InChI: InChI=1S/C18H23NO5/c1-23-12-4-3-9-7-10-14-17(24-2)15(21)11(20)8-18(14,5-6-19-10)13(9)16(12)22/h3-4,10-11,15,19-22H,5-8H2,1-2H3/t10-,11-,15-,18-/m0/s1
InChIKey: MFKPWBJXKCSPGK-KNORBDTNSA-N
DeepSMILES: COC=C[C@H]NCC[C@]6C[C@@H][C@@H]%10O))O)))ccC8)cccc6O))OC
Scaffold Graph/Node/Bond level: C1=C2C3Cc4ccccc4C2(CCC1)CCN3
Scaffold Graph/Node level: C1CCC2C(C1)CC1NCCC23CCCCC13
Scaffold Graph level: C1CCC2C(C1)CC1CCCC23CCCCC13
Functional groups: COC(=C(C)C)C; CNC; CO; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Morphinan alkaloids
Synonymous chemical names:
sinococuline
External chemical identifiers:
CID:CID_5489400; ChEMBL:CHEMBL524026; SureChEMBL:SCHEMBL166476
Chemical structure download


Sinococuline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 333.38
Log P RDKit 0.58
Topological polar surface area (Å2) RDKit 91.18
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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


Sinococuline
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 0.63


Sinococuline
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 -8.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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