IMPPAT Phytochemical information: 
methyl (6S,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,6,9,10,10a-hexahydrobenzo[f]isochromene-7-carboxylate
methyl (6S,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,6,9,10,10a-hexahydrobenzo[f]isochromene-7-carboxylate
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2C=C3C(=O)OC(C[C@]3([C@H]3[C@]2(C)C(=CCC3)C(=O)OC)C)c2cocc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H34O11/c1-26-10-16(13-7-8-35-12-13)36-24(33)15(26)9-19(27(2)14(23(32)34-3)5-4-6-18(26)27)38-25-22(31)21(30)20(29)17(11-28)37-25/h5,7-9,12,16-22,25,28-31H,4,6,10-11H2,1-3H3/t16?,17-,18+,19+,20-,21+,22-,25+,26-,27+/m1/s1
InChIKey: UQBSOXXWYBLSSJ-DZIODUNCSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]C=CC=O)OCC[C@]6[C@H][C@]%10C)C=CCC6)))C=O)OC))))))C)))ccocc5))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)CC2C1=CC(OC1CCCCO1)C1C=CCCC21
Scaffold Graph/Node level: OC1OC(C2CCOC2)CC2C1CC(OC1CCCCO1)C1CCCCC12
Scaffold Graph level: CC1CC(C2CCCC2)CC2C1CC(CC1CCCCC1)C1CCCCC12
Functional groups: CO; CO[C@@H](C)OC; COC(=O)C(=CC)C; CC=C(C(=O)OC)C; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
borapetoside f
External chemical identifiers:
CID:CID_101696498
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (6S,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,6,9,10,10a-hexahydrobenzo[f]isochromene-7-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 534.56
Log P RDKit 0.91
Topological polar surface area (Å2) RDKit 165.12
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.63
Number of rotatable bonds RDKit 6
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 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
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 5
methyl (6S,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,6,9,10,10a-hexahydrobenzo[f]isochromene-7-carboxylate
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 2
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 0.39692
methyl (6S,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,6,9,10,10a-hexahydrobenzo[f]isochromene-7-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.73
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 No
P-glycoprotein substrate SwissADME Yes