IMPPAT Phytochemical information: 
Omacetaxine mepesuccinate

Omacetaxine mepesuccinate
Summary

SMILES: COC(=O)C[C@@](C(=O)O[C@@H]1C(=C[C@]23[C@@H]1c1cc4OCOc4cc1CCN3CCC2)OC)(CCCC(O)(C)C)O
InChI: InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1
InChIKey: HYFHYPWGAURHIV-JFIAXGOJSA-N
DeepSMILES: COC=O)C[C@@]C=O)O[C@@H]C=C[C@@][C@@H]5cccOCOc5cc9CCN%14CCC%17))))))))))))))))))OC))))))CCCCO)C)C)))))O
Scaffold Graph/Node/Bond level: C1=CC23CCCN2CCc2cc4c(cc2C3C1)OCO4
Scaffold Graph/Node level: C1CC2C3CC4OCOC4CC3CCN3CCCC23C1
Scaffold Graph level: C1CC2CC3CCC4CCCC45CCCC5C3CC2C1
Functional groups: CN(C)C; CO; COC(C)=CC; COC(C)=O; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Cephalotaxus alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Cephalotaxus alkaloids
Synonymous chemical names:
homoharringtonine
External chemical identifiers:
CID:285033; ChEMBL:CHEMBL46286; ChEBI:71019; ZINC:ZINC000026011099; FDASRS:6FG8041S5B; SureChEMBL:SCHEMBL12745687; MolPort-003-983-592
Chemical structure download


Omacetaxine mepesuccinate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 545.63
Log P RDKit 2.58
Topological polar surface area (Å2) RDKit 123.99
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.66
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Omacetaxine mepesuccinate
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 Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4476


Omacetaxine mepesuccinate
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.05
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No