IMPPAT Phytochemical information: 
Eseramine

Eseramine
Summary

SMILES: CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C(=O)NC
InChI: InChI=1S/C16H22N4O3/c1-16-7-8-20(14(21)17-2)13(16)19(4)12-6-5-10(9-11(12)16)23-15(22)18-3/h5-6,9,13H,7-8H2,1-4H3,(H,17,21)(H,18,22)/t13-,16-/m0/s1
InChIKey: PYEMNABYODPRPP-BBRMVZONSA-N
DeepSMILES: CNC=O)Occcccc6)[C@]C)CCN[C@@H]5N8C)))C=O)NC
Scaffold Graph/Node/Bond level: c1ccc2c(c1)NC1NCCC21
Scaffold Graph/Node level: C1CCC2C(C1)NC1NCCC12
Scaffold Graph level: C1CCC2C(C1)CC1CCCC12
Functional groups: cOC(=O)NC; cN(C)[C@H](C)N(C(=O)NC)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyrroloindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Pyrroloindole alkaloids
Synonymous chemical names:
eseranine, eseramine
External chemical identifiers:
CID:CID_442077; ChEBI:CHEBI:4854; FDASRS:PE4VD738WT; SureChEMBL:SCHEMBL2685980
Chemical structure download


Eseramine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 318.38
Log P RDKit 1.48
Topological polar surface area (Å2) RDKit 73.91
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3


Eseramine
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 0.82


Eseramine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.62
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes