IMPPAT Phytochemical information: 
Limonoic acid
Limonoic acid
Summary

SMILES: OC[C@]12[C@H](CC(=O)O)OC([C@@H]1CC(=O)[C@@]1([C@@H]2CC[C@@]([C@]21O[C@@H]2C(=O)O)(C)[C@H](c1cocc1)O)C)(C)C
InChI: InChI=1S/C26H34O10/c1-22(2)15-9-16(28)24(4)14(25(15,12-27)17(35-22)10-18(29)30)5-7-23(3,19(31)13-6-8-34-11-13)26(24)20(36-26)21(32)33/h6,8,11,14-15,17,19-20,27,31H,5,7,9-10,12H2,1-4H3,(H,29,30)(H,32,33)/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1
InChIKey: WOJQWDNWUNSRTA-MSGMIQHVSA-N
DeepSMILES: OC[C@][C@H]CC=O)O)))OC[C@@H]5CC=O)[C@@][C@@H]9CC[C@@][C@@]6O[C@@H]3C=O)O)))))C)[C@H]ccocc5)))))O))))))C)))))C)C
Scaffold Graph/Node/Bond level: O=C1CC2COCC2C2CCC(Cc3ccoc3)C3(CO3)C12
Scaffold Graph/Node level: OC1CC2COCC2C2CCC(CC3CCOC3)C3(CO3)C12
Scaffold Graph level: CC1CC2CCCC2C2CCC(CC3CCCC3)C3(CC3)C12
Functional groups: CO; CC(=O)O; COC; CC(=O)C; C[C@@]1(C)O[C@@H]1C(=O)O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
limonoic acid
External chemical identifiers:
CID:CID_439529; ChEBI:CHEBI:16419; ZINC:ZINC000004095675
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Limonoic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 506.55
Log P RDKit 2.18
Topological polar surface area (Å2) RDKit 167.03
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Limonoic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.419854
Limonoic acid
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 -9.25
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes