IMPPAT Phytochemical information: 
Valoneic acid dilactone

Valoneic acid dilactone
Summary

SMILES: OC(=O)c1cc(O)c(c(c1Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O)O)O
InChI: InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29)
InChIKey: BPAOAXAAABIQKR-UHFFFAOYSA-N
DeepSMILES: OC=O)cccO)ccc6Occcc=O)occc6cc%10O))oc=O)c6ccc%10O))O)))))))))))))))))O))O
Scaffold Graph/Node/Bond level: O=c1oc2cc(Oc3ccccc3)cc3c(=O)oc4cccc1c4c23
Scaffold Graph/Node level: OC1OC2CC(OC3CCCCC3)CC3C(O)OC4CCCC1C4C23
Scaffold Graph level: CC1CC2CC(CC3CCCCC3)CC3C(C)CC4CCCC1C4C23
Functional groups: cC(=O)O; cO; cOc; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenolic acids (C6-C1)
NP Classifier Class: Gallotannins
Synonymous chemical names:
valoneic acid dilactone
External chemical identifiers:
CID:CID_10151874; ZINC:ZINC000014827345
Chemical structure download


Valoneic acid dilactone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 470.3
Log P RDKit 2.21
Topological polar surface area (Å2) RDKit 228.33
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 13
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 21
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 5
Total number of rings RDKit 5
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 5


Valoneic acid dilactone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.11


Valoneic acid dilactone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.14
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No