IMPPAT Phytochemical information: 
Cascaroside D
Cascaroside D
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cccc3c2C(=O)c2c([C@@H]3[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H32O13/c1-9-5-11-16(26-24(36)22(34)19(31)14(7-28)38-26)10-3-2-4-13(18(10)21(33)17(11)12(30)6-9)39-27-25(37)23(35)20(32)15(8-29)40-27/h2-6,14-16,19-20,22-32,34-37H,7-8H2,1H3/t14-,15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
InChIKey: GQPFUOPPYJYZHE-OPEXUXIQSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6C=O)cc[C@@H]6[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O))))))cccc6O)))C)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(C2CCCCO2)c2cccc(OC3CCCCO3)c21
Scaffold Graph/Node level: OC1C2CCCCC2C(C2CCCCO2)C2CCCC(OC3CCCCO3)C12
Scaffold Graph level: CC1C2CCCCC2C(C2CCCCC2)C2CCCC(CC3CCCCC3)C12
Functional groups: CO; cO; cO[C@@H](C)OC; cC(=O)c; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
cascaroside d
External chemical identifiers:
CID:CID_46173831; ChEBI:CHEBI:80737; ZINC:ZINC000095628105; FDASRS:H1745HQ16C
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cascaroside D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 564.54
Log P RDKit -2.6
Topological polar surface area (Å2) RDKit 226.83
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Cascaroside D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.181737
Cascaroside D
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -10.23
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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