IMPPAT Phytochemical information: 
Hernandonine

Hernandonine
Summary

SMILES: O=C1c2ccc3c(c2-c2c4c1nccc4cc1c2OCO1)OCO3
InChI: InChI=1S/C18H9NO5/c20-16-9-1-2-10-17(23-6-21-10)13(9)14-12-8(3-4-19-15(12)16)5-11-18(14)24-7-22-11/h1-5H,6-7H2
InChIKey: QHFWZNALDDSHFJ-UHFFFAOYSA-N
DeepSMILES: O=Ccccccc6-ccc%10nccc6ccc%10OCO5))))))))))))))OCO5
Scaffold Graph/Node/Bond level: O=C1c2ccc3c(c2-c2c4c(cc5ccnc1c25)OCO4)OCO3
Scaffold Graph/Node level: OC1C2CCC3OCOC3C2C2C3OCOC3CC3CCNC1C32
Scaffold Graph level: CC1C2CCCC3CC4CCCC4C(C32)C2C3CCCC3CCC12
Functional groups: cC(=O)c; cnc; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids|Isoquinoline alkaloids
Synonymous chemical names:
hernandonine
External chemical identifiers:
CID:CID_500428; ChEBI:CHEBI:66011
Chemical structure download


Hernandonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 319.27
Log P RDKit 2.9
Topological polar surface area (Å2) RDKit 66.88
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
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 6


Hernandonine
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 0.5


Hernandonine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.98
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No