IMPPAT Phytochemical information: 
(1S,4aR,7S)-4a-hydroxy-7-methyl-1-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
(1S,4aR,7S)-4a-hydroxy-7-methyl-1-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
Summary

SMILES: O=CC1=COC(C2[C@]1(O)CC[C@@H]2C)OC1OC(C)C(C(C1O)O)O
InChI: InChI=1S/C16H24O8/c1-7-3-4-16(21)9(5-17)6-22-14(10(7)16)24-15-13(20)12(19)11(18)8(2)23-15/h5-8,10-15,18-21H,3-4H2,1-2H3/t7-,8?,10?,11?,12?,13?,14?,15?,16-/m0/s1
InChIKey: QEPMZEDPTMKURV-SCROJHFDSA-N
DeepSMILES: O=CC=COCC[C@]6O)CC[C@@H]5C))))))OCOCC)CCC6O))O))O
Scaffold Graph/Node/Bond level: C1=CC2CCCC2C(OC2CCCCO2)O1
Scaffold Graph/Node level: C1CCC(OC2OCCC3CCCC32)OC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCC32)CC1
Functional groups: COC(OC1CCC(C=O)=CO1)C; CO
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:
5-deoxystansioside
External chemical identifiers:
CID:CID_50990244
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,4aR,7S)-4a-hydroxy-7-methyl-1-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 344.36
Log P RDKit -0.95
Topological polar surface area (Å2) RDKit 125.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.81
Number of rotatable bonds RDKit 3
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
(1S,4aR,7S)-4a-hydroxy-7-methyl-1-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.48
(1S,4aR,7S)-4a-hydroxy-7-methyl-1-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.99
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