IMPPAT Phytochemical information: 
Macroxine

Macroxine
Summary

SMILES: C[C@@H](C[C@H]1C[C@H]2N3[C@@H]([C@H]1COC3)C[C@@]12c2ccccc2N(C1=O)C)O
InChI: InChI=1S/C20H26N2O3/c1-12(23)7-13-8-18-20(9-17-14(13)10-25-11-22(17)18)15-5-3-4-6-16(15)21(2)19(20)24/h3-6,12-14,17-18,23H,7-11H2,1-2H3/t12-,13-,14-,17+,18+,20-/m0/s1
InChIKey: IEZFIXTXFGQQGQ-SPNCAKCLSA-N
DeepSMILES: C[C@@H]C[C@H]C[C@H]N[C@@H][C@H]6COC6))))C[C@]5cccccc6NC9=O))C))))))))))))))))O
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CC1C3CCC2N1COC3
Scaffold Graph/Node level: OC1NC2CCCCC2C12CC1C3CCC2N1COC3
Scaffold Graph level: CC1CC2CCCCC2C12CC1C3CCCC1C2CC3
Functional groups: COCN(C)C; cN(C)C(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
Macroxine
Chemical structure download


Macroxine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 342.44
Log P RDKit 1.74
Topological polar surface area (Å2) RDKit 53.01
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
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 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Macroxine
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.889481


Macroxine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.26
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No