IMPPAT Phytochemical information: 
Macusine A

Macusine A
Summary

SMILES: C/C=C\1/C[N@@+]2(C)[C@H]3C[C@@H]1[C@@]([C@@H]2Cc1c3[nH]c2c1cccc2)(CO)C(=O)OC
InChI: InChI=1S/C22H27N2O3/c1-4-13-11-24(2)18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23-20(15)18/h4-8,16,18-19,23,25H,9-12H2,1-3H3/q+1/b13-4-/t16-,18-,19-,22+,24-/m0/s1
InChIKey: HOIYLJHQHXMJGO-ILWGPPALSA-N
DeepSMILES: C/C=C/C[N@@+]C)[C@H]C[C@@H]/6[C@@][C@@H]6Ccc8[nH]cc5cccc6)))))))))))CO))C=O)OC
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; COC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
Synonymous chemical names:
Macusine A, macusine a
External chemical identifiers:
CID:CID_91617759; FDASRS:PXX2QL95LV
Chemical structure download


Macusine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 367.47
Log P RDKit 2.71
Topological polar surface area (Å2) RDKit 62.32
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 3
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


Macusine A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49


Macusine A
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 -7.46
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes