IMPPAT Phytochemical information: 
(4-Hexyl-2,5-dioxo-2,5-dihydro-3-furanyl)acetic acid
(4-Hexyl-2,5-dioxo-2,5-dihydro-3-furanyl)acetic acid
Summary

SMILES: CCCCCCC1=C(CC(=O)O)C(=O)OC1=O
InChI: InChI=1S/C12H16O5/c1-2-3-4-5-6-8-9(7-10(13)14)12(16)17-11(8)15/h2-7H2,1H3,(H,13,14)
InChIKey: UMHSTRUKUXAWBA-UHFFFAOYSA-N
DeepSMILES: CCCCCCC=CCC=O)O)))C=O)OC5=O
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)O1
Scaffold Graph/Node level: OC1CCC(O)O1
Scaffold Graph level: CC1CCC(C)C1
Functional groups: CC1=C(C)C(=O)OC1=O; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Polyketides
Synonymous chemical names:
4-hexyl-2,5-dihydro-2,5-dioxo-3-furanacetic acid
External chemical identifiers:
CID:CID_580944; ChEBI:CHEBI:87585; ZINC:ZINC000085550803
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(4-Hexyl-2,5-dioxo-2,5-dihydro-3-furanyl)acetic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 240.26
Log P RDKit 1.81
Topological polar surface area (Å2) RDKit 80.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 5
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 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1
(4-Hexyl-2,5-dioxo-2,5-dihydro-3-furanyl)acetic 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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.42
(4-Hexyl-2,5-dioxo-2,5-dihydro-3-furanyl)acetic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.12
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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