IMPPAT Phytochemical information: 
Limonin
Limonin
Summary

SMILES: O=C1OC[C@]23[C@H](C1)OC([C@@H]2CC(=O)[C@@]1([C@@H]3CC[C@@]2([C@]31O[C@@H]3C(=O)O[C@H]2c1cocc1)C)C)(C)C
InChI: InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1
InChIKey: KBDSLGBFQAGHBE-MSGMIQHVSA-N
DeepSMILES: O=COC[C@][C@H]C6)OC[C@@H]5CC=O)[C@@][C@@H]9CC[C@@][C@@]6O[C@@H]3C=O)O[C@H]7ccocc5)))))))))))C)))))C)))))C)C
Scaffold Graph/Node/Bond level: O=C1CC2OCC3CC(=O)C4C(CCC5C(c6ccoc6)OC(=O)C6OC654)C32CO1
Scaffold Graph/Node level: OC1CC2OCC3CC(O)C4C(CCC5C(C6CCOC6)OC(O)C6OC564)C32CO1
Scaffold Graph level: CC1CCC23C(CCC2CC(C)C2C3CCC3C(C4CCCC4)CC(C)C4CC432)C1
Functional groups: COC(=O)C; COC; CC(=O)C; C[C@]12CCOC(=O)[C@H]1O2; 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:
limonin, obaculactone, dictamnolactone, Limonin
External chemical identifiers:
CID:CID_179651; ChEMBL:CHEMBL517449; ChEBI:CHEBI:16226; ZINC:ZINC000004096134; FDASRS:L0F260866S; SureChEMBL:SCHEMBL320315; MolPort-001-742-490
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Limonin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 470.52
Log P RDKit 3.14
Topological polar surface area (Å2) RDKit 104.57
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 8
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 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Limonin
Drug-likeness
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.455458
Limonin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -7.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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
Limonin
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001647ENSG00000077498TYR7299ChEMBL, NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576BindingDB, ChEMBL, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS