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: CO; CO[C@@H](C)OC; CC1=CC(=O)C(=C(C)C)C1; COC(=O)C
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: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 0.427296
(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
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -9.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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