IMPPAT Phytochemical information: 
[1-(5,8-Dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbutanoate
[1-(5,8-Dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbutanoate
Summary

SMILES: CC(CC(=O)OC(C1=CC(=O)c2c(C1=O)c(O)ccc2O)CC=C(C)C)C
InChI: InChI=1S/C21H24O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,10,12,17,22-23H,8-9H2,1-4H3
InChIKey: UTOUNDHZJFIVPK-UHFFFAOYSA-N
DeepSMILES: CCCC=O)OCC=CC=O)ccC6=O))cO)ccc6O))))))))))CC=CC)C))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2ccccc21
Scaffold Graph/Node level: OC1CCC(O)C2CCCCC12
Scaffold Graph level: CC1CCC(C)C2CCCCC12
Functional groups: COC(C)=O; CC1=CC(=O)ccC1=O; cO; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
Synonymous chemical names:
alkannin isovalerate
External chemical identifiers:
CID:CID_335426; SureChEMBL:SCHEMBL13389448
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[1-(5,8-Dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbutanoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 372.42
Log P RDKit 3.72
Topological polar surface area (Å2) RDKit 100.9
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
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 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
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
[1-(5,8-Dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbutanoate
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 0.448339
[1-(5,8-Dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbutanoate
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.16
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No