IMPPAT Phytochemical information: 
Oxyavicine

Oxyavicine
Summary

SMILES: Cn1c(=O)c2cc3OCOc3cc2c2c1c1cc3OCOc3cc1cc2
InChI: InChI=1S/C20H13NO5/c1-21-19-11(3-2-10-4-15-16(5-12(10)19)24-8-23-15)13-6-17-18(26-9-25-17)7-14(13)20(21)22/h2-7H,8-9H2,1H3
InChIKey: NAFSMPFYCYCHSJ-UHFFFAOYSA-N
DeepSMILES: Cnc=O)cccOCOc5cc9cc%13cccOCOc5cc9cc%13
Scaffold Graph/Node/Bond level: O=c1[nH]c2c3cc4c(cc3ccc2c2cc3c(cc12)OCO3)OCO4
Scaffold Graph/Node level: OC1NC2C3CC4OCOC4CC3CCC2C2CC3OCOC3CC12
Scaffold Graph level: CC1CC2C3CC4CCCC4CC3CCC2C2CC3CCCC3CC12
Functional groups: cn(C)c; c=O; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
Oxyavicine, oxyavicine
External chemical identifiers:
CID:CID_12313849; ZINC:ZINC000013458939
Chemical structure download


Oxyavicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 347.33
Log P RDKit 3.3
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.15
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6


Oxyavicine
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 0.456908


Oxyavicine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.92
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No