IMPPAT Phytochemical information: 
methyl (5E)-5-ethylidene-4-propyl-6-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
methyl (5E)-5-ethylidene-4-propyl-6-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Summary

SMILES: CCCC1/C(=C\C)/C(OC=C1C(=O)OC)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O
InChI: InChI=1S/C18H28O9/c1-4-6-10-9(5-2)17(25-8-11(10)16(23)24-3)27-18-15(22)14(21)13(20)12(7-19)26-18/h5,8,10,12-15,17-22H,4,6-7H2,1-3H3/b9-5+/t10?,12-,13+,14+,15+,17?,18+/m1/s1
InChIKey: SDKGJLREAMABGO-BSXPSEOHSA-N
DeepSMILES: CCCC/C=C\C))/COC=C6C=O)OC))))))O[C@@H]O[C@H]CO))[C@@H][C@@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C=C1CC=COC1OC1CCCCO1
Scaffold Graph/Node level: CC1CCCOC1OC1CCCCO1
Scaffold Graph level: CC1CCCCC1CC1CCCCC1
Functional groups: C/C=C1\CC(C(=O)OC)=COC1O[C@@H](C)OC; 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: Secoiridoid monoterpenoids
Synonymous chemical names:
nuezhengalaside
External chemical identifiers:
CID:CID_11968803
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
methyl (5E)-5-ethylidene-4-propyl-6-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 388.41
Log P RDKit -0.42
Topological polar surface area (Å2) RDKit 134.91
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.72
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
methyl (5E)-5-ethylidene-4-propyl-6-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
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 Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.35
methyl (5E)-5-ethylidene-4-propyl-6-[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
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 -8.60
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