IMPPAT Phytochemical information: 
Fumariline
Fumariline
Summary

SMILES: CN1CCc2c([C@@]31Cc1c(C3=O)c3OCOc3cc1)cc1c(c2)OCO1
InChI: InChI=1S/C20H17NO5/c1-21-5-4-11-6-15-16(25-9-24-15)7-13(11)20(21)8-12-2-3-14-18(26-10-23-14)17(12)19(20)22/h2-3,6-7H,4-5,8-10H2,1H3/t20-/m0/s1
InChIKey: GGQGUBWFVKJOER-FQEVSTJZSA-N
DeepSMILES: CNCCcc[C@]6CccC5=O))cOCOc5cc9)))))))))))cccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1c2c(ccc3c2OCO3)CC12NCCc1cc3c(cc12)OCO3
Scaffold Graph/Node level: OC1C2C(CCC3OCOC32)CC12NCCC1CC3OCOC3CC12
Scaffold Graph level: CC1C2C(CCC3CCCC32)CC12CCCC1CC3CCCC3CC12
Functional groups: CN(C)C; cC(=O)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Indanes
ClassyFire Subclass: Indanones
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Protopine alkaloids
Synonymous chemical names:
(+)-fumariline, fumariline, Fumariline
External chemical identifiers:
CID:CID_159888
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Fumariline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 351.36
Log P RDKit 2.27
Topological polar surface area (Å2) RDKit 57.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Fumariline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.725753
Fumariline
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 -6.33
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No