IMPPAT Phytochemical information: 
Apiumoside
Apiumoside
Summary

SMILES: O=C(OCC1OC(OC(C2Cc3c(O2)c(O)c2c(c3)ccc(=O)o2)(C)C)C(C(C1O)O)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C29H30O12/c1-29(2,19-12-16-11-15-6-10-21(32)40-26(15)25(36)27(16)39-19)41-28-24(35)23(34)22(33)18(38-28)13-37-20(31)9-5-14-3-7-17(30)8-4-14/h3-11,18-19,22-24,28,30,33-36H,12-13H2,1-2H3/b9-5+
InChIKey: PUPQENMYBCRTJC-WEVVVXLNSA-N
DeepSMILES: O=COCCOCOCCCccO5)cO)ccc6)ccc=O)o6)))))))))))C)C)))CCC6O))O))O)))))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1CCCC(OCC2Cc3cc4ccc(=O)oc4cc3O2)O1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCCC(OCC2CC3CC4CCC(O)OC4CC3O2)O1
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCCC(CCC2CC3CC4CCC(C)CC4CC3C2)C1
Functional groups: c/C=C/C(=O)OC; COC(OC)C; cO; cOC; c=O; coc; CO
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
Synonymous chemical names:
apiumoside
External chemical identifiers:
CID:CID_131752524; ChEBI:CHEBI:172744
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Apiumoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 570.55
Log P RDKit 1.37
Topological polar surface area (Å2) RDKit 185.35
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5
Apiumoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.16
Apiumoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.56
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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