IMPPAT Phytochemical information: 
Erythraline

Erythraline
Summary

SMILES: CO[C@H]1C=CC2=CCN3[C@]2(C1)c1cc2OCOc2cc1CC3
InChI: InChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3/t14-,18-/m0/s1
InChIKey: TVOFUERNMZTYRM-KSSFIOAISA-N
DeepSMILES: CO[C@H]C=CC=CCN[C@]5C9)cccOCOc5cc9CC%13
Scaffold Graph/Node/Bond level: C1=CC2=CCN3CCc4cc5c(cc4C23CC1)OCO5
Scaffold Graph/Node level: C1CCC23C(C1)CCN2CCC1CC2OCOC2CC13
Scaffold Graph level: C1CC2CC3CCC4CCC5CCCCC54C3CC2C1
Functional groups: COC; CC=C(C)C=CC; CN(C)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Erythrina alkaloids
ClassyFire Subclass: Erythrinanes
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Indolizidine alkaloids
Synonymous chemical names:
(+)-erythraline, erythraline
External chemical identifiers:
CID:CID_5317205; ChEMBL:CHEMBL518262; FDASRS:J7P8WA50QO; SureChEMBL:SCHEMBL19584883
Chemical structure download


Erythraline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 297.35
Log P RDKit 2.38
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 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Erythraline
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7962


Erythraline
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.68
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No