IMPPAT Phytochemical information: 
(R)-3,4-Dihydro-8-hydroxy-3-tridecyl-1H-2-benzopyran-1-one

(R)-3,4-Dihydro-8-hydroxy-3-tridecyl-1H-2-benzopyran-1-one
Summary

SMILES: CCCCCCCCCCCCCC1OC(=O)c2c(C1)cccc2O
InChI: InChI=1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-15-19-17-18-14-13-16-20(23)21(18)22(24)25-19/h13-14,16,19,23H,2-12,15,17H2,1H3
InChIKey: GEFWCROCDVGECH-UHFFFAOYSA-N
DeepSMILES: CCCCCCCCCCCCCCOC=O)ccC6)cccc6O
Scaffold Graph/Node/Bond level: O=C1OCCc2ccccc21
Scaffold Graph/Node level: OC1OCCC2CCCCC21
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: cC(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 2-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Isocoumarins
Synonymous chemical names:
coumarin, iso,8-hydroxy-3-tridecyl-3,4-dihydro
External chemical identifiers:
CID:CID_71424251; SureChEMBL:SCHEMBL20741298
Chemical structure download


(R)-3,4-Dihydro-8-hydroxy-3-tridecyl-1H-2-benzopyran-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.51
Log P RDKit 6.17
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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


(R)-3,4-Dihydro-8-hydroxy-3-tridecyl-1H-2-benzopyran-1-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36


(R)-3,4-Dihydro-8-hydroxy-3-tridecyl-1H-2-benzopyran-1-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -2.21
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No