IMPPAT Phytochemical information: 
Unii-E695J9A64A

Unii-E695J9A64A
Summary

SMILES: C/C=C\1/C[N@+]2(C)[C@@H]3[C@@H]([C@H]1C[C@H]2c1c(C3)c2c([nH]1)cccc2)CO
InChI: InChI=1S/C20H25N2O/c1-3-12-10-22(2)18-9-15-13-6-4-5-7-17(13)21-20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,21,23H,8-11H2,1-2H3/q+1/b12-3-/t14-,16+,18-,19-,22+/m0/s1
InChIKey: KRTATNOTKFNEFT-GXFHUVTISA-N
DeepSMILES: C/C=C/C[N@+]C)[C@@H][C@@H][C@H]/6C[C@H]6ccC8)cc[nH]5)cccc6)))))))))))CO
Scaffold Graph/Node/Bond level: C=C1C[NH+]2C3Cc4c([nH]c5ccccc45)C2CC1C3
Scaffold Graph/Node level: CC1CN2C3CC1CC2C1NC2CCCCC2C1C3
Scaffold Graph level: CC1CC2C3CC1CC2C1CC2CCCCC2C1C3
Functional groups: C/C=C(/C)C; C[N@+](C)(C)C; c[nH]c; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
Synonymous chemical names:
macusine b, Macusine B
External chemical identifiers:
CID:CID_91617603; ZINC:ZINC000255223802; FDASRS:E695J9A64A
Chemical structure download


Unii-E695J9A64A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.43
Log P RDKit 3.17
Topological polar surface area (Å2) RDKit 36.02
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
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 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6


Unii-E695J9A64A
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 0.615902


Unii-E695J9A64A
ADME 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.70
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes