IMPPAT Phytochemical information: 
Limocinin
Limocinin
Summary

SMILES: COC1OCC(C1)(O)[C@H]1CC=C2[C@@]1(C)CC[C@H]1[C@@]2(C)[C@@H](C[C@@H]2[C@]1(C)C=CC(=O)C2(C)C)OC(=O)c1ccccc1
InChI: InChI=1S/C34H44O6/c1-30(2)25-18-27(40-29(36)21-10-8-7-9-11-21)33(5)22-12-13-24(34(37)19-28(38-6)39-20-34)31(22,3)16-14-23(33)32(25,4)17-15-26(30)35/h7-12,15,17,23-25,27-28,37H,13-14,16,18-20H2,1-6H3/t23-,24+,25+,27-,28?,31-,32-,33+,34?/m1/s1
InChIKey: BWKWJBPOVKXAOA-HZWVKPFWSA-N
DeepSMILES: COCOCCC5)O)[C@H]CC=C[C@@]5C)CC[C@H][C@@]6C)[C@@H]C[C@@H][C@]6C)C=CC=O)C6C)C))))))))OC=O)cccccc6
Scaffold Graph/Node/Bond level: O=C1C=CC2C(C1)CC(OC(=O)c1ccccc1)C1C3=CCC(C4CCOC4)C3CCC21
Scaffold Graph/Node level: OC1CCC2C(C1)CC(OC(O)C1CCCCC1)C1C2CCC2C(C3CCOC3)CCC21
Scaffold Graph level: CC1CCC2C(C1)CC(CC(C)C1CCCCC1)C1C2CCC2C(C3CCCC3)CCC21
Functional groups: cC(=O)OC; COC(C)OC; CO; CC=C(C)C; CC(=O)C=CC
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: Apotirucallane triterpenoids
Synonymous chemical names:
limocinin
External chemical identifiers:
CID:CID_14845550
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Limocinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 548.72
Log P RDKit 5.9
Topological polar surface area (Å2) RDKit 82.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Limocinin
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 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.37
Limocinin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.37
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