IMPPAT Phytochemical information: 
Barringtogenol E
Barringtogenol E
Summary

SMILES: OC[C@]12[C@H](O)C[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CC[C@@H](C3(C)C)O)[C@@H]2CC([C@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)(C)C)C
InChI: InChI=1S/C44H58O7/c1-39(2)24-30-29-18-19-32-41(5)22-21-33(46)40(3,4)31(41)20-23-42(32,6)43(29,7)25-34(47)44(30,26-45)36(51-38(49)28-16-12-9-13-17-28)35(39)50-37(48)27-14-10-8-11-15-27/h8-18,30-36,45-47H,19-26H2,1-7H3/t30-,31-,32+,33-,34+,35-,36-,41-,42+,43+,44-/m0/s1
InChIKey: LIPKTXZLLQVEQO-HBSVFKPZSA-N
DeepSMILES: OC[C@@][C@H]O)C[C@@]C=CC[C@H][C@@]6C)CC[C@@H][C@]6C)CC[C@@H]C6C)C))O))))))))))))[C@@H]6CC[C@H][C@@H]%10OC=O)cccccc6)))))))))OC=O)cccccc6)))))))))C)C)))))C
Scaffold Graph/Node/Bond level: O=C(OC1CCC2C3=CCC4C5CCCCC5CCC4C3CCC2C1OC(=O)c1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(OC1CCC2C3CCC4C5CCCCC5CCC4C3CCC2C1OC(O)C1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CC1CCC2C(CCC3C4CCC5CCCCC5C4CCC23)C1CC(C)C1CCCCC1)C1CCCCC1
Functional groups: CO; cC(=O)OC; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Oleanane triterpenoids
Synonymous chemical names:
barringtogenol E, 3α,16α,28-trihydroxy-21β,22α-bis(benzoyloxy)-olean-12-en (barringtogenol e), barringtogenol e
External chemical identifiers:
CID:CID_102067269
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Barringtogenol E
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 698.94
Log P RDKit 7.78
Topological polar surface area (Å2) RDKit 113.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 51
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 28
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Barringtogenol E
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.22
Barringtogenol E
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.10
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 Yes
P-glycoprotein substrate SwissADME No