IMPPAT Phytochemical information: 
Paederosidic acid
Paederosidic acid
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2C(=C[C@@H]3O)COC(=O)SC)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C18H24O12S/c1-31-18(26)28-4-6-2-8(20)11-7(15(24)25)5-27-16(10(6)11)30-17-14(23)13(22)12(21)9(3-19)29-17/h2,5,8-14,16-17,19-23H,3-4H2,1H3,(H,24,25)/t8-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
InChIKey: ICTKKPLVSHVNDV-FCVLBCLDSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6C=C[C@@H]5O)))COC=O)SC))))))))C=O)O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC2C(C=COC2OC2CCCCO2)C1
Scaffold Graph/Node level: C1CCC(OC2OCCC3CCCC32)OC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCC32)CC1
Functional groups: CO; CO[C@@H](O[C@H]1CCC(C(=O)O)=CO1)C; CC(=CC)C; COC(=O)SC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
paederosidic acid
External chemical identifiers:
CID:CID_21592249; ZINC:ZINC000095914172; SureChEMBL:SCHEMBL424808; MolPort-039-141-290
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Paederosidic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 464.45
Log P RDKit -1.84
Topological polar surface area (Å2) RDKit 192.44
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
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
Paederosidic acid
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 1
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 0.19
Paederosidic acid
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 -10.74
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