IMPPAT Phytochemical information: 
(2S,3R,4S,5R)-2-[[(9S,12R,14S,17R)-2-hydroxy-3,8,8,17,19-pentamethyl-22-prop-1-en-2-yl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol
(2S,3R,4S,5R)-2-[[(9S,12R,14S,17R)-2-hydroxy-3,8,8,17,19-pentamethyl-22-prop-1-en-2-yl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol
Summary

SMILES: O[C@H]1[C@H](O)CO[C@H]([C@@H]1O)O[C@H]1CC[C@]23C(C1(C)C)CCC1[C@@]3(C2)CC[C@]2(C1(C)C(O)C13C2C(C)CC(O3)C(O1)C(=C)C)C
InChI: InChI=1S/C35H54O8/c1-17(2)26-20-14-18(3)27-31(6)12-13-34-16-33(34)11-10-23(41-28-25(38)24(37)19(36)15-40-28)30(4,5)21(33)8-9-22(34)32(31,7)29(39)35(27,42-20)43-26/h18-29,36-39H,1,8-16H2,2-7H3/t18?,19-,20?,21?,22?,23+,24+,25-,26?,27?,28+,29?,31-,32?,33-,34+,35?/m1/s1
InChIKey: CVBALRXHSITZGC-QHNYGKKLSA-N
DeepSMILES: O[C@H][C@H]O)CO[C@H][C@@H]6O))O[C@H]CC[C@@]CC6C)C))CCC[C@@]6C7)CC[C@]C6C)CO)CC5CC)CCO6)CO7)C=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; CC1(C)OCCO1; CO[C@@H](OC)C; C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Cycloartanols and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Cycloartane triterpenoids
Synonymous chemical names:
25-anhydrocimicigenol-3-o-β-d-xylopyranoside(cimiside e), cimiside e
External chemical identifiers:
CID:CID_6324929
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3R,4S,5R)-2-[[(9S,12R,14S,17R)-2-hydroxy-3,8,8,17,19-pentamethyl-22-prop-1-en-2-yl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 602.81
Log P RDKit 3.93
Topological polar surface area (Å2) RDKit 117.84
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 8
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 2
Number of sp3 hybridized carbon atoms RDKit 33
Shape complexity RDKit 0.94
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
(2S,3R,4S,5R)-2-[[(9S,12R,14S,17R)-2-hydroxy-3,8,8,17,19-pentamethyl-22-prop-1-en-2-yl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol
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 0.283743
(2S,3R,4S,5R)-2-[[(9S,12R,14S,17R)-2-hydroxy-3,8,8,17,19-pentamethyl-22-prop-1-en-2-yl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]oxane-3,4,5-triol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.43
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 Yes