IMPPAT Phytochemical information: 
5-Oxoleurosine
5-Oxoleurosine
Summary

SMILES: COc1cc2N(C)C3C4(c2cc1[C@]1(CC2CN(CCc5c1[nH]c1c5cccc1)C(=O)[C@]1([C@@H]2O1)CC)C(=O)OC)CCN1C4[C@@]([C@H](C3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
InChI: InChI=1S/C46H54N4O10/c1-8-42-16-12-18-49-20-17-43(36(42)49)29-21-30(33(56-5)22-32(29)48(4)37(43)46(55,41(54)58-7)38(42)59-25(3)51)44(40(53)57-6)23-26-24-50(39(52)45(9-2)35(26)60-45)19-15-28-27-13-10-11-14-31(27)47-34(28)44/h10-14,16,21-22,26,35-38,47,55H,8-9,15,17-20,23-24H2,1-7H3/t26?,35-,36?,37?,38-,42-,43?,44+,45-,46?/m1/s1
InChIKey: IXEWHIPHOXLHJV-YBLQZKTJSA-N
DeepSMILES: COcccNC)CCc5cc9[C@]CCCNCCcc9[nH]cc5cccc6)))))))))))C=O)[C@][C@@H]6O3))CC))))))))C=O)OC)))))))CCNC5[C@@][C@H]C9O)C=O)OC))))OC=O)C))))CC))C=CC6
Scaffold Graph/Node/Bond level: O=C1C2OC2C2CC(c3ccc4c(c3)C35CCN6CC=CC(CCC3N4)C65)c3[nH]c4ccccc4c3CCN1C2
Scaffold Graph/Node level: OC1C2OC2C2CC(C3CCC4NC5CCC6CCCN7CCC5(C4C3)C67)C3NC4CCCCC4C3CCN1C2
Scaffold Graph level: CC1C2CCC3C4CCCCC4CC3C(C3CCC4CC5CCC6CCCC7CCC5(C4C3)C67)CC(C2)C2CC12
Functional groups: cOC; cN(C)C; CN1CC[C@H]2O[C@@]2(C)C1=O; c[nH]c; COC(C)=O; CN(C)C; CO; CC(=O)OC; CC=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Vinca alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type|Aspidosperma-Iboga hybrid type (Vinca alkaloids)
Synonymous chemical names:
5'-oxoeurosine, 21'-oxoleurosine
External chemical identifiers:
CID:CID_124201479
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5-Oxoleurosine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 822.96
Log P RDKit 3.53
Topological polar surface area (Å2) RDKit 163.47
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 46
Number of heavy atoms RDKit 60
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
5-Oxoleurosine
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.154647
5-Oxoleurosine
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 -8.93
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 Yes
P-glycoprotein substrate SwissADME Yes