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: c1cOCO1; c=O; cn(c)C
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
External chemical identifiers:
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 0.4569


Oxyavicine
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 1.0
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