IMPPAT Phytochemical information: 
8-O-Cinnamoylmussaenosidic Acid
8-O-Cinnamoylmussaenosidic Acid
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@](C)(CC3)OC(=O)/C=C/c2ccccc2)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C25H30O11/c1-25(36-17(27)8-7-13-5-3-2-4-6-13)10-9-14-15(22(31)32)12-33-23(18(14)25)35-24-21(30)20(29)19(28)16(11-26)34-24/h2-8,12,14,16,18-21,23-24,26,28-30H,9-11H2,1H3,(H,31,32)/b8-7+/t14-,16-,18-,19-,20+,21-,23+,24+,25+/m1/s1
InChIKey: SKMCYGKNAPIRGG-GKBUEBNRSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@]C)CC5))OC=O)/C=C/cccccc6)))))))))))))C=O)O)))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC2C=COC(OC3CCCCO3)C21
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC2CCOC(OC3CCCCO3)C21
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC2CCCC(CC3CCCCC3)C21
Functional groups: CO; CO[C@@H](O[C@H]1CCC(C(=O)O)=CO1)C; c/C=C/C(=O)OC
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:
8-o-cinnamoylmussaenosidic acid
External chemical identifiers:
CID:CID_10744170; ChEMBL:CHEMBL1782503; ChEBI:CHEBI:67352; ZINC:ZINC000071281725
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
8-O-Cinnamoylmussaenosidic Acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 506.5
Log P RDKit 0.17
Topological polar surface area (Å2) RDKit 172.21
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.52
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 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
8-O-Cinnamoylmussaenosidic Acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.252041
8-O-Cinnamoylmussaenosidic Acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -8.90
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