IMPPAT Phytochemical information: 
Lygodinolide
Lygodinolide
Summary

SMILES: C=C1CC[C@H]2[C@@]([C@]31Oc1c(C3)c(=O)oc(c1C)C)(C)CC[C@@H]1[C@]2(C)CCC(=O)C1(C)C
InChI: InChI=1S/C27H36O4/c1-15-8-9-20-25(6)12-11-21(28)24(4,5)19(25)10-13-26(20,7)27(15)14-18-22(31-27)16(2)17(3)30-23(18)29/h19-20H,1,8-14H2,2-7H3/t19-,20+,25-,26+,27-/m0/s1
InChIKey: ABBZZTOIFXCLFD-YJHFSHLRSA-N
DeepSMILES: C=CCC[C@H][C@@][C@@]6OccC5)c=O)occ6C))C))))))))C)CC[C@@H][C@]6C)CCC=O)C6C)C
Scaffold Graph/Node/Bond level: C=C1CCC2C3CCC(=O)CC3CCC2C12Cc1c(ccoc1=O)O2
Scaffold Graph/Node level: CC1CCC2C3CCC(O)CC3CCC2C12CC1C(O)OCCC1O2
Scaffold Graph level: CC1CCC2C(CCC3C2CCC(C)C32CC3CCCC(C)C3C2)C1
Functional groups: C=C(C)C; cOC; c=O; coc; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Meroterpenoids|Diterpenoids
NP Classifier Class: Breviane diterpenoids|Spriromeroterpenoids|Triketide meroterpenoids
Synonymous chemical names:
Lygodinolide, lygodinolide
External chemical identifiers:
CID:CID_102059585; ZINC:ZINC000169669836
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lygodinolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 424.58
Log P RDKit 5.71
Topological polar surface area (Å2) RDKit 56.51
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
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 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Lygodinolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
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 0.5
Lygodinolide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.52
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 No