IMPPAT Phytochemical information: 
methyl 7-methyl-6-oxo-1-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
methyl 7-methyl-6-oxo-1-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Summary

SMILES: OC[C@H]1O[C@@H](OC2OC=C(C3C2C(C)C(=O)C3)C(=O)OC)[C@@H]([C@@H]([C@@H]1O)O)O
InChI: InChI=1S/C17H24O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,10-14,16-18,20-22H,3-4H2,1-2H3/t6?,7?,10-,11?,12-,13-,14-,16?,17+/m1/s1
InChIKey: LPOVXLVQNSEZGE-WNVPRDAPSA-N
DeepSMILES: OC[C@H]O[C@@H]OCOC=CCC6CC)C=O)C5)))))C=O)OC))))))))[C@@H][C@@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC2C=COC(OC3CCCCO3)C2C1
Scaffold Graph/Node level: OC1CC2CCOC(OC3CCCCO3)C2C1
Scaffold Graph level: CC1CC2CCCC(CC3CCCCC3)C2C1
Functional groups: CO; COC(=O)C1=COC(O[C@@H](C)OC)CC1; CC(=O)C
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:
dehydrologanin
External chemical identifiers:
CID:CID_21550278
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl 7-methyl-6-oxo-1-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 388.37
Log P RDKit -1.94
Topological polar surface area (Å2) RDKit 151.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.53
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3
methyl 7-methyl-6-oxo-1-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.400161
methyl 7-methyl-6-oxo-1-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -9.85
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