IMPPAT Phytochemical information: 
4H-3,1-Benzoxazin-4-one, 2-(4-(4-hydroxyphenyl)-1,3-butadienyl)-

4H-3,1-Benzoxazin-4-one, 2-(4-(4-hydroxyphenyl)-1,3-butadienyl)-
Summary

SMILES: Oc1ccc(cc1)/C=C/C=C/c1nc2ccccc2c(=O)o1
InChI: InChI=1S/C18H13NO3/c20-14-11-9-13(10-12-14)5-1-4-8-17-19-16-7-3-2-6-15(16)18(21)22-17/h1-12,20H/b5-1+,8-4+
InChIKey: ASJBOIQMTVOWBG-LZSLGQGWSA-N
DeepSMILES: Occcccc6))/C=C/C=C/cncccccc6c=O)o%10
Scaffold Graph/Node/Bond level: O=c1oc(C=CC=Cc2ccccc2)nc2ccccc12
Scaffold Graph/Node level: OC1OC(CCCCC2CCCCC2)NC2CCCCC21
Scaffold Graph level: CC1CC(CCCCC2CCCCC2)CC2CCCCC12
Functional groups: cO; c/C=C/C=C/c; cnc; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzoxazines
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
Synonymous chemical names:
avenalumin iii
External chemical identifiers:
CID:CID_135764904; ChEBI:CHEBI:168448
Chemical structure download


4H-3,1-Benzoxazin-4-one, 2-(4-(4-hydroxyphenyl)-1,3-butadienyl)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 291.31
Log P RDKit 3.62
Topological polar surface area (Å2) RDKit 63.33
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
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 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3


4H-3,1-Benzoxazin-4-one, 2-(4-(4-hydroxyphenyl)-1,3-butadienyl)-
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 0.75


4H-3,1-Benzoxazin-4-one, 2-(4-(4-hydroxyphenyl)-1,3-butadienyl)-
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 -5.49
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No