IMPPAT Phytochemical information: 
Macrophyllicin
Macrophyllicin
Summary

SMILES: OC[C@H]1O[C@H](O[C@H]2O[C@H](C(=O)OC3CC[C@]4(C(C3(C)C)[C@@H](O)C[C@@]3(C4CC=C4[C@@]3(C)C[C@@H]([C@@]3([C@@H]4CC(C)(C)CC3)CO)O)C)C)[C@H]([C@@H]([C@H]2O[C@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)[C@@H]([C@H]([C@H]1O)O)O
InChI: InChI=1S/C54H88O24/c1-21-30(60)33(63)36(66)45(71-21)75-40-39(69)41(76-48(78-47-38(68)35(65)32(62)26(19-56)73-47)42(40)77-46-37(67)34(64)31(61)25(18-55)72-46)44(70)74-29-11-12-51(6)27-10-9-22-23-15-49(2,3)13-14-54(23,20-57)28(59)17-52(22,7)53(27,8)16-24(58)43(51)50(29,4)5/h9,21,23-43,45-48,55-69H,10-20H2,1-8H3/t21-,23+,24-,25+,26+,27?,28-,29?,30-,31+,32-,33+,34-,35-,36+,37+,38+,39-,40-,41-,42+,43?,45-,46+,47+,48+,51+,52+,53+,54+/m0/s1
InChIKey: CDYAORBMMPRWHL-XOJINRSKSA-N
DeepSMILES: OC[C@H]O[C@H]O[C@H]O[C@H]C=O)OCCC[C@]CC6C)C))[C@@H]O)C[C@@]C6CC=C[C@@]6C)C[C@@H][C@@][C@@H]6CCC)C)CC6)))))CO)))O))))))))C)))))C)))))))[C@H][C@@H][C@H]6O[C@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O)))))))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O)))))))O))))))[C@@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OC1CCC2C(CCC3C4CCC5CCCCC5C4=CCC23)C1)C1CC(OC2CCCCO2)C(OC2CCCCO2)C(OC2CCCCO2)O1
Scaffold Graph/Node level: OC(OC1CCC2C(CCC3C2CCC2C4CCCCC4CCC23)C1)C1CC(OC2CCCCO2)C(OC2CCCCO2)C(OC2CCCCO2)O1
Scaffold Graph level: CC(CC1CCC2C(CCC3C2CCC2C4CCCCC4CCC23)C1)C1CC(CC2CCCCC2)C(CC2CCCCC2)C(CC2CCCCC2)C1
Functional groups: CC=C(C)C; CO; COC(C)=O; CO[C@@H](C)OC; CO[C@@H](C)O[C@H](C)OC; CO[C@H](C)OC
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:
macrophyllicin
External chemical identifiers:
CID:44150651
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Macrophyllicin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1121.27
Log P RDKit -3.07
Topological polar surface area (Å2) RDKit 394.36
Number of hydrogen bond acceptors RDKit 24
Number of hydrogen bond donors RDKit 15
Number of carbon atoms RDKit 54
Number of heavy atoms RDKit 78
Number of heteroatoms RDKit 24
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 30
Stereochemical complexity RDKit 0.56
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 51
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 9
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
Macrophyllicin
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 0.0721