IMPPAT Phytochemical information: 
[(2S,3R,6R,8S,11R,12R,18R)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.02,11.03,8.06,8.017,21]henicosa-1(21),13-dien-12-yl] acetate
[(2S,3R,6R,8S,11R,12R,18R)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.02,11.03,8.06,8.017,21]henicosa-1(21),13-dien-12-yl] acetate
Summary

SMILES: CC(=O)O[C@@H]1C2=CCCC3(C2=C([C@@]2([C@@]1(O)C(=O)C(C)(C)[C@]14[C@]2(C)OC(=O)[C@@H]4O1)O)C(=O)O[C@H]3c1ccoc1)C
InChI: InChI=1S/C28H28O11/c1-12(29)36-18-14-7-6-9-24(4)15(14)16(20(30)37-17(24)13-8-10-35-11-13)27(34)25(5)28(19(38-28)21(31)39-25)23(2,3)22(32)26(18,27)33/h7-8,10-11,17-19,33-34H,6,9H2,1-5H3/t17-,18+,19-,24?,25+,26-,27+,28+/m0/s1
InChIKey: HOJFTRARYIFTJU-KGARTDGWSA-N
DeepSMILES: CC=O)O[C@@H]C=CCCCC6=C[C@@][C@@]%10O)C=O)CC)C)[C@@][C@]6C)OC=O)[C@@H]5O6)))))))))O))C=O)O[C@H]6cccoc5))))))))))C
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)C2CCC=C3CC4C(=O)CC56OC5C(=O)OC6C4C1=C32
Scaffold Graph/Node level: OC1CC23OC2C(O)OC3C2C1CC1CCCC3C(C4CCOC4)OC(O)C2C13
Scaffold Graph level: CC1CC23CC2C(C)CC3C2C1CC1CCCC3C(C4CCCC4)CC(C)C2C13
Functional groups: CC(=O)OC; CC=C(C)C1=C(C)C(=O)OCC1; CO; CC(=O)C; C[C@@]12COC(=O)[C@@H]1O2; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Limonoids
Synonymous chemical names:
dukunolide c
External chemical identifiers:
CID:CID_101419918
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2S,3R,6R,8S,11R,12R,18R)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.02,11.03,8.06,8.017,21]henicosa-1(21),13-dien-12-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 540.52
Log P RDKit 1.37
Topological polar surface area (Å2) RDKit 162.1
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 3
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 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
[(2S,3R,6R,8S,11R,12R,18R)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.02,11.03,8.06,8.017,21]henicosa-1(21),13-dien-12-yl] acetate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.316485
[(2S,3R,6R,8S,11R,12R,18R)-18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-5,10,20-trioxo-4,7,19-trioxahexacyclo[11.7.1.02,11.03,8.06,8.017,21]henicosa-1(21),13-dien-12-yl] acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.94
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 Yes