IMPPAT Phytochemical information: 
Osmanthuside A
Osmanthuside A
Summary

SMILES: OC[C@H]1O[C@@H](OCCc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(cc1)O)O)O
InChI: InChI=1S/C23H26O9/c24-13-18-22(32-19(27)10-5-14-1-6-16(25)7-2-14)20(28)21(29)23(31-18)30-12-11-15-3-8-17(26)9-4-15/h1-10,18,20-26,28-29H,11-13H2/b10-5+/t18-,20-,21-,22-,23-/m1/s1
InChIKey: TXIKDCCKEBXQGU-WYSYKVOOSA-N
DeepSMILES: OC[C@H]O[C@@H]OCCcccccc6))O))))))))[C@@H][C@H][C@@H]6OC=O)/C=C/cccccc6))O))))))))))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC(OCCc2ccccc2)OC1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC(OCCC2CCCCC2)OC1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC(CCCC2CCCCC2)CC1
Functional groups: CO; CO[C@@H](C)OC; cO; c/C=C/C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylethanoids (C6-C2)|Phenylpropanoids (C6-C3)
NP Classifier Class: Cinnamic acids and derivatives|Phenylethanoids
Synonymous chemical names:
osmanthuside a
External chemical identifiers:
CID:CID_101629458
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Osmanthuside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 446.45
Log P RDKit 0.72
Topological polar surface area (Å2) RDKit 145.91
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 32
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 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
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
Osmanthuside 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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.292388
Osmanthuside A
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 -8.10
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