IMPPAT Phytochemical information: 
4-Hydroxy-2-(1-methylethenyl)-2,3-dihydrobenzofuran-5-carboxylic acid

4-Hydroxy-2-(1-methylethenyl)-2,3-dihydrobenzofuran-5-carboxylic acid
Summary

SMILES: CC(=C)C1Oc2c(C1)c(O)c(cc2)C(=O)O
InChI: InChI=1S/C12H12O4/c1-6(2)10-5-8-9(16-10)4-3-7(11(8)13)12(14)15/h3-4,10,13H,1,5H2,2H3,(H,14,15)
InChIKey: CMXGHLJKXLIMAQ-UHFFFAOYSA-N
DeepSMILES: CC=C)COccC5)cO)ccc6))C=O)O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCO2
Scaffold Graph/Node level: C1CCC2OCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: C=C(C)C; cOC; cO; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids|Terpenoids
Synonymous chemical names:
Tubaic acid, tubaic acid
External chemical identifiers:
CID:CID_3919910; ChEMBL:CHEMBL1479987; ChEBI:CHEBI:91480; SureChEMBL:SCHEMBL4279694
Chemical structure download


4-Hydroxy-2-(1-methylethenyl)-2,3-dihydrobenzofuran-5-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 220.22
Log P RDKit 1.97
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 2
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


4-Hydroxy-2-(1-methylethenyl)-2,3-dihydrobenzofuran-5-carboxylic acid
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


4-Hydroxy-2-(1-methylethenyl)-2,3-dihydrobenzofuran-5-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -5.55
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