IMPPAT Phytochemical information: 
Hercynine

Hercynine
Summary

SMILES: [O-]C(=O)[C@@H]([N+](C)(C)C)Cc1[nH]cnc1
InChI: InChI=1S/C9H15N3O2/c1-12(2,3)8(9(13)14)4-7-5-10-6-11-7/h5-6,8H,4H2,1-3H3,(H-,10,11,13,14)/t8-/m0/s1
InChIKey: GPPYTCRVKHULJH-QMMMGPOBSA-N
DeepSMILES: [O-]C=O)[C@@H][N+]C)C)C))Cc[nH]cnc5
Scaffold Graph/Node/Bond level: c1c[nH]cn1
Scaffold Graph/Node level: C1CNCN1
Scaffold Graph level: C1CCCC1
Functional groups: CC(=O)[O-]; C[N+](C)(C)C; c[nH]c; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
Synonymous chemical names:
hercynine
External chemical identifiers:
CID:CID_5459798; ChEBI:CHEBI:15781; FDASRS:M8MWM6K25V; SureChEMBL:SCHEMBL1331027
Chemical structure download


Hercynine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 197.24
Log P RDKit -1.22
Topological polar surface area (Å2) RDKit 68.81
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


Hercynine
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 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61


Hercynine
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 -7.47
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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