IMPPAT Phytochemical information: 
Zeanoside B

Zeanoside B
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cccc3c2[nH]c(=O)cc3C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C16H17NO9/c18-5-9-12(20)13(21)14(22)16(26-9)25-8-3-1-2-6-7(15(23)24)4-10(19)17-11(6)8/h1-4,9,12-14,16,18,20-22H,5H2,(H,17,19)(H,23,24)/t9-,12-,13+,14-,16-/m1/s1
InChIKey: GRKTWUMXBYWXNZ-JCILWVLBSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6[nH]c=O)cc6C=O)O)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccc2cccc(OC3CCCCO3)c2[nH]1
Scaffold Graph/Node level: OC1CCC2CCCC(OC3CCCCO3)C2N1
Scaffold Graph level: CC1CCC2CCCC(CC3CCCCC3)C2C1
Functional groups: CO; cO[C@@H](C)OC; c[nH]c; c=O; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
zeanoside a
External chemical identifiers:
CID:CID_13988327
Chemical structure download


Zeanoside B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 367.31
Log P RDKit -1.6
Topological polar surface area (Å2) RDKit 169.54
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Zeanoside B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
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 0.37


Zeanoside B
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 -9.66
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 No