IMPPAT Phytochemical information: 
(3S,3aS,9aS,9bS)-3,6-dimethyl-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
(3S,3aS,9aS,9bS)-3,6-dimethyl-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Summary

SMILES: OC[C@H]1O[C@@H](OCC2=CC(=O)C3=C(C)CC[C@@H]4[C@@H]([C@@H]23)OC(=O)[C@H]4C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H28O9/c1-8-3-4-11-9(2)20(27)30-19(11)15-10(5-12(23)14(8)15)7-28-21-18(26)17(25)16(24)13(6-22)29-21/h5,9,11,13,15-19,21-22,24-26H,3-4,6-7H2,1-2H3/t9-,11-,13+,15-,16+,17-,18+,19-,21+/m0/s1
InChIKey: BUHZTPLXMFRPCK-CKCUUXPSSA-N
DeepSMILES: OC[C@H]O[C@@H]OCC=CC=O)C=CC)CC[C@@H][C@@H][C@@H]%107)OC=O)[C@H]5C)))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC2CCC=C3C(=O)C=C(COC4CCCCO4)C3C2O1
Scaffold Graph/Node level: OC1CC2CCCC3C(O)CC(COC4CCCCO4)C3C2O1
Scaffold Graph level: CC1CC2CCCC3C(C)CC(CCC4CCCCC4)C3C2C1
Functional groups: CC1=CC(=O)C(=C(C)C)C1; CO; COC(C)=O; CO[C@@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Guaiane sesquiterpenoids
Synonymous chemical names:
crepidiaside b
External chemical identifiers:
CID:101683332; ZINC:ZINC000096014906
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(3S,3aS,9aS,9bS)-3,6-dimethyl-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 424.45
Log P RDKit -0.78
Topological polar surface area (Å2) RDKit 142.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(3S,3aS,9aS,9bS)-3,6-dimethyl-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
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 0.4273
(3S,3aS,9aS,9bS)-3,6-dimethyl-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
ADMET 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 Low
Log Kp (Skin permeation, cm/s) SwissADME -9.76
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
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