IMPPAT Phytochemical information: 
methyl (1S,4aS,5S,6R,7R,7aR)-6-benzoyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
methyl (1S,4aS,5S,6R,7R,7aR)-6-benzoyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@H](C)[C@H]([C@H]3O)OC(=O)c2ccccc2)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H30O12/c1-10-14-15(17(27)20(10)35-21(30)11-6-4-3-5-7-11)12(22(31)32-2)9-33-23(14)36-24-19(29)18(28)16(26)13(8-25)34-24/h3-7,9-10,13-20,23-29H,8H2,1-2H3/t10-,13-,14-,15-,16-,17+,18+,19-,20-,23+,24+/m1/s1
InChIKey: CKHOFHNVFXPKRY-BTFZNIMDSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@@H]C)[C@H][C@H]5O))OC=O)cccccc6))))))))))))C=O)OC))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OC1CC2C=COC(OC3CCCCO3)C2C1)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2CCOC(OC3CCCCO3)C2C1)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCCC(CC3CCCCC3)C2C1)C1CCCCC1
Functional groups: CO; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1; cC(=O)OC
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: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
arborside c
External chemical identifiers:
CID:CID_15747848; ZINC:ZINC000140900893
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (1S,4aS,5S,6R,7R,7aR)-6-benzoyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 510.49
Log P RDKit -1.32
Topological polar surface area (Å2) RDKit 181.44
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
methyl (1S,4aS,5S,6R,7R,7aR)-6-benzoyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-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 0.285378
methyl (1S,4aS,5S,6R,7R,7aR)-6-benzoyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -9.51
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 No