IMPPAT Phytochemical information: 
Heleurine N-oxide

Heleurine N-oxide
Summary

SMILES: CO[C@@H]([C@@](C(=O)OCC1=CC[N+]2([C@H]1CCC2)[O-])(C(C)C)O)C
InChI: InChI=1S/C16H27NO5/c1-11(2)16(19,12(3)21-4)15(18)22-10-13-7-9-17(20)8-5-6-14(13)17/h7,11-12,14,19H,5-6,8-10H2,1-4H3/t12-,14+,16-,17?/m1/s1
InChIKey: JOPJYQKWCBEYGN-NOCHINKJSA-N
DeepSMILES: CO[C@@H][C@@]C=O)OCC=CC[N+][C@H]5CCC5))))[O-]))))))))CC)C))O))C
Scaffold Graph/Node/Bond level: C1=CC2CCC[NH+]2C1
Scaffold Graph/Node level: C1CC2CCCN2C1
Scaffold Graph level: C1CC2CCCC2C1
Functional groups: COC; COC(C)=O; CC=C(C)C; C[N+]([O-])(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
Synonymous chemical names:
heleurine-n-oxide
External chemical identifiers:
CID:CID_102122200; ZINC:ZINC000136855063
Chemical structure download


Heleurine N-oxide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 313.39
Log P RDKit 1.37
Topological polar surface area (Å2) RDKit 78.82
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.81
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2


Heleurine N-oxide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.346664


Heleurine N-oxide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.79
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 No