IMPPAT Phytochemical information: 
1-Cinnamoylmelianolone
1-Cinnamoylmelianolone
Summary

SMILES: OC[C@@]12[C@@H](OC(=O)/C=C/c3ccccc3)C[C@H]([C@@]3([C@@H]1[C@H](OC3)[C@H]([C@]([C@@H]2C(=O)C)(C)[C@@]12O[C@@]2(C)[C@@H]2C[C@@H]1O[C@@H]1[C@]2(O)C=CO1)O)C)O
InChI: InChI=1S/C35H42O11/c1-18(37)26-31(3,35-23-14-20(32(35,4)46-35)34(41)12-13-42-29(34)45-23)28(40)25-27-30(2,17-43-25)21(38)15-22(33(26,27)16-36)44-24(39)11-10-19-8-6-5-7-9-19/h5-13,20-23,25-29,36,38,40-41H,14-17H2,1-4H3/b11-10+/t20-,21+,22-,23-,25-,26-,27-,28+,29+,30+,31+,32-,33-,34-,35-/m0/s1
InChIKey: RCIYJWQVHDPQSQ-YVYVCLNRSA-N
DeepSMILES: OC[C@@][C@@H]OC=O)/C=C/cccccc6))))))))))C[C@H][C@@][C@@H]6[C@H]OC5))[C@H][C@][C@@H]%10C=O)C)))C)[C@]O[C@@]3C)[C@@H]C[C@@H]6O[C@@H][C@]6O)C=CO5)))))))))))))O))))C))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC2COC3CC(C45OC4C4CC5OC5OC=CC54)CC1C23
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC2COC3CC(C45OC4C4CC5OC5OCCC54)CC1C23
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC2CCC3CC(C45CC4C4CC5CC5CCCC54)CC1C23
Functional groups: CO; c/C=C/C(=O)OC; COC; CC(C)=O; C[C@@]1(C)O[C@]1(C)C; CO[C@@H]1CC=CO1
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: Limonoids
Synonymous chemical names:
1-cinnamoyl melianolone, 1-cinnamoylmelianolone
External chemical identifiers:
CID:CID_13819214
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1-Cinnamoylmelianolone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 638.71
Log P RDKit 1.51
Topological polar surface area (Å2) RDKit 164.51
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 0.66
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
1-Cinnamoylmelianolone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
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 0.202879
1-Cinnamoylmelianolone
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 -9.77
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