IMPPAT Phytochemical information: 
Flexinine

Flexinine
Summary

SMILES: O[C@@H]1C[C@H]2N3CC[C@]2([C@@H]2[C@H]1O2)c1c(C3)cc2c(c1)OCO2
InChI: InChI=1S/C16H17NO4/c18-10-5-13-16(15-14(10)21-15)1-2-17(13)6-8-3-11-12(4-9(8)16)20-7-19-11/h3-4,10,13-15,18H,1-2,5-7H2/t10-,13-,14+,15+,16+/m1/s1
InChIKey: WWSZBGJLESQTHB-DMHMKPBJSA-N
DeepSMILES: O[C@@H]C[C@H]NCC[C@]5[C@@H][C@H]9O3)))ccC7)cccc6)OCO5
Scaffold Graph/Node/Bond level: c1c2c(cc3c1OCO3)C13CCN(C2)C1CCC1OC13
Scaffold Graph/Node level: C1OC2CC3CN4CCC5(C3CC2O1)C1OC1CCC45
Scaffold Graph level: C1CC2CC3CC4CCC5(C4CCC4CC45)C3CC2C1
Functional groups: CO; CN(C)C; C[C@@H]1O[C@@H]1C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Crinine- and Haemanthamine-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
flexinine
External chemical identifiers:
CID:CID_398936; ChEMBL:CHEMBL1997786; ZINC:ZINC000006018156
Chemical structure download


Flexinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 287.32
Log P RDKit 0.77
Topological polar surface area (Å2) RDKit 54.46
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
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 6
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Flexinine
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.71


Flexinine
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 -7.43
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 No
P-glycoprotein substrate SwissADME No