IMPPAT Phytochemical information: 
Zeanoside C
Zeanoside C
Summary

SMILES: OCC1OC(Oc2cccc3c2NC(=O)C3(O)CC(=O)O)C(C(C1O)O)O
InChI: InChI=1S/C16H19NO10/c18-5-8-11(21)12(22)13(23)14(27-8)26-7-3-1-2-6-10(7)17-15(24)16(6,25)4-9(19)20/h1-3,8,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)
InChIKey: VNIXZLMYLWKZLU-UHFFFAOYSA-N
DeepSMILES: OCCOCOcccccc6NC=O)C5O)CC=O)O)))))))))))))CCC6O))O))O
Scaffold Graph/Node/Bond level: O=C1Cc2cccc(OC3CCCCO3)c2N1
Scaffold Graph/Node level: OC1CC2CCCC(OC3CCCCO3)C2N1
Scaffold Graph level: CC1CC2CCCC(CC3CCCCC3)C2C1
Functional groups: CO; cOC(C)OC; cNC(=O)C; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple oxindole alkaloids
Synonymous chemical names:
zeanoside c
External chemical identifiers:
CID:CID_13988324
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Zeanoside C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 385.33
Log P RDKit -2.52
Topological polar surface area (Å2) RDKit 186.01
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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 C
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 0.29
Zeanoside C
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 -10.12
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