IMPPAT Phytochemical information: 
Celereoside
Celereoside
Summary

SMILES: OCC1OC(OC(C2Oc3c(C2)c(O)c2c(c3)oc(=O)cc2)(C)C)C(C(C1O)O)O
InChI: InChI=1S/C20H24O10/c1-20(2,30-19-18(26)17(25)16(24)12(7-21)29-19)13-5-9-11(27-13)6-10-8(15(9)23)3-4-14(22)28-10/h3-4,6,12-13,16-19,21,23-26H,5,7H2,1-2H3
InChIKey: JMWIRXQFQXREAB-UHFFFAOYSA-N
DeepSMILES: OCCOCOCCOccC5)cO)ccc6)oc=O)cc6)))))))))))C)C)))CCC6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccc2cc3c(cc2o1)OC(COC1CCCCO1)C3
Scaffold Graph/Node level: OC1CCC2CC3CC(COC4CCCCO4)OC3CC2O1
Scaffold Graph level: CC1CCC2CC3CC(CCC4CCCCC4)CC3CC2C1
Functional groups: CO; COC(OC)C; cOC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Furanocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins|Simple coumarins
Synonymous chemical names:
celeroside, celereoside
External chemical identifiers:
CID:CID_73989751; ChEBI:CHEBI:176056
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Celereoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 424.4
Log P RDKit -0.6
Topological polar surface area (Å2) RDKit 159.05
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
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 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Celereoside
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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.401095
Celereoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.91
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