IMPPAT Phytochemical information: 
Cnidioside A

Cnidioside A
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc3occc3cc2CCC(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C17H20O9/c18-7-12-14(21)15(22)16(23)17(26-12)25-11-6-10-9(3-4-24-10)5-8(11)1-2-13(19)20/h3-6,12,14-18,21-23H,1-2,7H2,(H,19,20)/t12-,14-,15+,16-,17-/m1/s1
InChIKey: OHMWGMHIZWOKHV-USACIQFYSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcoccc5cc9CCC=O)O))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1cc2ccc(OC3CCCCO3)cc2o1
Scaffold Graph/Node level: C1CCC(OC2CCC3CCOC3C2)OC1
Scaffold Graph level: C1CCC(CC2CCC3CCCC3C2)CC1
Functional groups: CO; cO[C@@H](C)OC; coc; 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: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
cnidioside a
External chemical identifiers:
CID:CID_21592256; ZINC:ZINC000031158287; SureChEMBL:SCHEMBL15397923; MolPort-001-741-095
Chemical structure download


Cnidioside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.34
Log P RDKit -0.37
Topological polar surface area (Å2) RDKit 149.82
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 6
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


Cnidioside A
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 0
Ghose filter RDKit Passed
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 0.45996


Cnidioside A
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.60
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