IMPPAT Phytochemical information: 
1-Cinnamoyl-3-acetyl-11-hydroxymeliacarpin
1-Cinnamoyl-3-acetyl-11-hydroxymeliacarpin
Summary

SMILES: COC(=O)[C@@]1(O)OC[C@]23[C@@H]1[C@@](C)([C@H](O)[C@H]1[C@H]3[C@]([C@@H](C[C@@H]2OC(=O)/C=C/c2ccccc2)OC(=O)C)(C)CO1)[C@@]12O[C@@]2(C)[C@H]2C[C@@H]1O[C@H]1[C@]2(O)C=CO1
InChI: InChI=1S/C38H44O14/c1-19(39)49-22-16-23(50-25(40)12-11-20-9-7-6-8-10-20)35-18-48-37(44,30(42)45-5)29(35)33(3,28(41)26-27(35)32(22,2)17-47-26)38-24-15-21(34(38,4)52-38)36(43)13-14-46-31(36)51-24/h6-14,21-24,26-29,31,41,43-44H,15-18H2,1-5H3/b12-11+/t21-,22-,23+,24+,26-,27+,28-,29+,31+,32-,33-,34+,35+,36+,37+,38+/m1/s1
InChIKey: KNVLLSFFGRMTCL-WBTUQHCOSA-N
DeepSMILES: COC=O)[C@@]O)OC[C@@][C@@H]5[C@@]C)[C@H]O)[C@H][C@H]6[C@][C@@H]C[C@@H]%10OC=O)/C=C/cccccc6))))))))))))OC=O)C))))C)CO5))))))[C@]O[C@@]3C)[C@H]C[C@@H]6O[C@H][C@]6O)C=CO5
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCC2COC3CC(C45OC4C4CC5OC5OC=CC54)C4COCC14C23
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCC2COC3CC(C45OC4C4CC5OC5OCCC54)C4COCC14C23
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC2CCC3CC(C45CC4C4CC5CC5CCCC54)C4CCCC14C23
Functional groups: COC(=O)[C@](O)(C)OC; CO; c/C=C/C(=O)OC; CC(=O)OC; COC; 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-3-acetyl-11-hydroxymeliacarpin
External chemical identifiers:
CID:CID_10818659
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1-Cinnamoyl-3-acetyl-11-hydroxymeliacarpin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 724.76
Log P RDKit 1.39
Topological polar surface area (Å2) RDKit 189.04
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 52
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.42
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.66
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
1-Cinnamoyl-3-acetyl-11-hydroxymeliacarpin
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 0.165263
1-Cinnamoyl-3-acetyl-11-hydroxymeliacarpin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -8.63
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
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