IMPPAT Phytochemical information: 
Cimigenoside
Cimigenoside
Summary

SMILES: O[C@H]1[C@H](O)CO[C@H]([C@@H]1O)O[C@H]1CC[C@]23[C@H](C1(C)C)CC[C@@H]1[C@@]3(C2)CC[C@]2([C@@]1(C)[C@@H](O)[C@@]13[C@@H]2[C@H](C)C[C@@H](O1)[C@H](O3)C(O)(C)C)C
InChI: InChI=1S/C35H56O9/c1-17-14-19-26(30(4,5)40)44-35(43-19)25(17)31(6)12-13-34-16-33(34)11-10-22(42-27-24(38)23(37)18(36)15-41-27)29(2,3)20(33)8-9-21(34)32(31,7)28(35)39/h17-28,36-40H,8-16H2,1-7H3/t17-,18-,19-,20+,21+,22+,23+,24-,25-,26+,27+,28-,31-,32-,33-,34+,35+/m1/s1
InChIKey: BTPYUWOBZFGKAI-XYGBCAHESA-N
DeepSMILES: O[C@H][C@H]O)CO[C@H][C@@H]6O))O[C@H]CC[C@@][C@H]C6C)C))CC[C@@H][C@@]6C7)CC[C@][C@@]6C)[C@@H]O)[C@@][C@@H]5[C@H]C)C[C@@H]O6)[C@H]O7)CO)C)C))))))))))C
Scaffold Graph/Node/Bond level: C1CCC(OC2CCC34CC35CCC3C(CC67OCC(CCC36)O7)C5CCC4C2)OC1
Scaffold Graph/Node level: C1CCC(OC2CCC34CC35CCC3C(CC67OCC(CCC36)O7)C5CCC4C2)OC1
Scaffold Graph level: C1CCC(CC2CCC34CC35CCC3C(CC67CCC(CCC36)C7)C5CCC4C2)CC1
Functional groups: CO; C[C@@]1(C)OCCO1; CO[C@@H](OC)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroidal glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cucurbitane triterpenoids|Cycloartane triterpenoids
Synonymous chemical names:
cimigenol-xyloside, cimigenol-3-o-beta-d-xylopyranoside, cimigenoside
External chemical identifiers:
CID:CID_16088242; ChEMBL:CHEMBL218613; ChEBI:CHEBI:70246; ZINC:ZINC000049942441; FDASRS:1CW26VCP4H; MolPort-039-052-391
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cimigenoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 620.82
Log P RDKit 3.12
Topological polar surface area (Å2) RDKit 138.07
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 17
Stereochemical complexity RDKit 0.49
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 35
Shape complexity RDKit 1
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Cimigenoside
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 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.301491
Cimigenoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -7.46
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