IMPPAT Phytochemical information: 
3-(But-2-yn-1-yl)-8-hydroxy-1H-2-benzopyran-1-one

3-(But-2-yn-1-yl)-8-hydroxy-1H-2-benzopyran-1-one
Summary

SMILES: CC#CCc1cc2cccc(c2c(=O)o1)O
InChI: InChI=1S/C13H10O3/c1-2-3-6-10-8-9-5-4-7-11(14)12(9)13(15)16-10/h4-5,7-8,14H,6H2,1H3
InChIKey: GWACCTLVSACUOC-UHFFFAOYSA-N
DeepSMILES: CC#CCcccccccc6c=O)o%10)))O
Scaffold Graph/Node/Bond level: O=c1occc2ccccc12
Scaffold Graph/Node level: OC1OCCC2CCCCC21
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: CC#CC; c=O; coc; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isocoumarins and derivatives
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty acyls
NP Classifier Class: Hydrocarbons
Synonymous chemical names:
8-hydroxycapillarin, 8-oh-capillarin
External chemical identifiers:
CID:CID_44575587; ChEMBL:CHEMBL451484
Chemical structure download


3-(But-2-yn-1-yl)-8-hydroxy-1H-2-benzopyran-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 214.22
Log P RDKit 2.06
Topological polar surface area (Å2) RDKit 50.44
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 2
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


3-(But-2-yn-1-yl)-8-hydroxy-1H-2-benzopyran-1-one
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 0.739076


3-(But-2-yn-1-yl)-8-hydroxy-1H-2-benzopyran-1-one
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 -5.36
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No