IMPPAT Phytochemical information: 
Limbocidin
Limbocidin
Summary

SMILES: C/C=C(/C(=O)O[C@H]1C[C@@H](OC(=O)C)[C@]2([C@H]3[C@@]1(C)[C@H]1[C@H](O)[C@H](O)[C@]4([C@]5([C@]1(C)[C@@H]([C@H]3OC2)O)O[C@@H]5C(=O)[C@H]4C1=CC(=O)OC1=O)C)C)\C
InChI: InChI=1S/C33H40O13/c1-8-12(2)27(40)44-16-10-15(43-13(3)34)29(4)11-42-21-23(29)30(16,5)22-20(37)24(38)31(6)18(14-9-17(35)45-28(14)41)19(36)26-33(31,46-26)32(22,7)25(21)39/h8-9,15-16,18,20-26,37-39H,10-11H2,1-7H3/b12-8+/t15-,16+,18-,20+,21+,22-,23+,24+,25-,26-,29+,30-,31+,32+,33-/m1/s1
InChIKey: AXNCEELXJOSUOL-IETUTBKHSA-N
DeepSMILES: C/C=C/C=O)O[C@H]C[C@@H]OC=O)C)))[C@][C@H][C@@]6C)[C@H][C@H]O)[C@H]O)[C@][C@][C@]6C)[C@@H][C@H]%10OC%13)))O)))O[C@@H]3C=O)[C@H]6C=CC=O)OC5=O)))))))))))C)))))))C)))))))\C
Scaffold Graph/Node/Bond level: O=C1C=C(C2C(=O)C3OC34C2CCC2C3CCCC5COC(CC24)C53)C(=O)O1
Scaffold Graph/Node level: OC1CC(C2C(O)C3OC34C3CC5OCC6CCCC(C3CCC24)C65)C(O)O1
Scaffold Graph level: CC1CC(C)C(C2C(C)C3CC34C3CC5CCC6CCCC(C3CCC24)C65)C1
Functional groups: C/C=C(\C)C(=O)OC; CC(=O)OC; CO; C[C@]12CCC(=O)[C@H]1O2; COC; CC1=CC(=O)OC1=O
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:
limbocidin, Limbocidin
External chemical identifiers:
CID:CID_102588495
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Limbocidin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 644.67
Log P RDKit 0.31
Topological polar surface area (Å2) RDKit 195.49
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Limbocidin
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 3
Ghose rule RDKit Failed
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 0.12
Limbocidin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -9.71
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes