IMPPAT Phytochemical information: 
Mikanolide
Mikanolide
Summary

SMILES: O=C1O[C@@H]2C=C1[C@H]1O[C@H]1[C@@H]1O[C@]1(C[C@H]1[C@H]2C(=C)C(=O)O1)C
InChI: InChI=1S/C15H14O6/c1-5-9-7-3-6(14(17)18-7)10-11(20-10)12-15(2,21-12)4-8(9)19-13(5)16/h3,7-12H,1,4H2,2H3/t7-,8+,9+,10-,11-,12+,15+/m1/s1
InChIKey: JRZGAAFGODYEEA-ATNXOXLHSA-N
DeepSMILES: O=CO[C@@H]C=C5[C@H]O[C@H]3[C@@H]O[C@]3C[C@H][C@H]%12C=C)C=O)O5))))))C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2CC3OC3C3OC3C3=CC(OC3=O)C12
Scaffold Graph/Node level: CC1C(O)OC2CC3OC3C3OC3C3CC(OC3O)C21
Scaffold Graph level: CC1CC2CC3CC3C3CC3C3CC(CC3C)C2C1C
Functional groups: C[C@@]1(C)O[C@H]1[C@@H]1O[C@@H]1C1=CCOC1=O; C=C1CCOC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Lactones
ClassyFire Subclass: Gamma butyrolactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Germacrane sesquiterpenoids
Synonymous chemical names:
Mikanolide, mikanolide
External chemical identifiers:
CID:CID_442282; ChEBI:CHEBI:6936; ZINC:ZINC000004098155
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Mikanolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 290.27
Log P RDKit 0.26
Topological polar surface area (Å2) RDKit 77.66
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.47
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Mikanolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36
Mikanolide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.89
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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