IMPPAT Phytochemical information: 
Fumaridine

Fumaridine
Summary

SMILES: COc1c(OC)ccc2c1C(=O)N/C/2=C\c1cc2OCOc2cc1CCN(C)C
InChI: InChI=1S/C22H24N2O5/c1-24(2)8-7-13-10-18-19(29-12-28-18)11-14(13)9-16-15-5-6-17(26-3)21(27-4)20(15)22(25)23-16/h5-6,9-11H,7-8,12H2,1-4H3,(H,23,25)/b16-9-
InChIKey: ZMAHFZSTFDAVRW-SXGWCWSVSA-N
DeepSMILES: COccOC))cccc6C=O)N/C/5=C\cccOCOc5cc9CCNC)C
Scaffold Graph/Node/Bond level: O=C1NC(=Cc2ccc3c(c2)OCO3)c2ccccc21
Scaffold Graph/Node level: OC1NC(CC2CCC3OCOC3C2)C2CCCCC12
Scaffold Graph level: CC1CC(CC2CCC3CCCC3C2)C2CCCCC12
Functional groups: cOC; c/C=C1/ccC(=O)N1; c1cOCO1; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoindoles and derivatives
ClassyFire Subclass: Isoindolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids
Synonymous chemical names:
Fumaridine, fumaridine
External chemical identifiers:
CID:CID_6537302
Chemical structure download


Fumaridine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 396.44
Log P RDKit 2.78
Topological polar surface area (Å2) RDKit 69.26
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
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 15
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


Fumaridine
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 0.81


Fumaridine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.62
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes