IMPPAT Phytochemical information: 
1,3-Benzodioxole-5-carboxylic acid, 6-(2-(dimethylamino)ethyl)-

1,3-Benzodioxole-5-carboxylic acid, 6-(2-(dimethylamino)ethyl)-
Summary

SMILES: CN(CCc1cc2OCOc2cc1C(=O)O)C
InChI: InChI=1S/C12H15NO4/c1-13(2)4-3-8-5-10-11(17-7-16-10)6-9(8)12(14)15/h5-6H,3-4,7H2,1-2H3,(H,14,15)
InChIKey: BOZYJTCKDCTZDN-UHFFFAOYSA-N
DeepSMILES: CNCCcccOCOc5cc9C=O)O)))))))))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)OCO2
Scaffold Graph/Node level: C1CCC2OCOC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CN(C)C; c1cOCO1; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzodioxoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
fumariflorine, Fumariflorine
External chemical identifiers:
CID:CID_156979; ZINC:ZINC000005957983
Chemical structure download


1,3-Benzodioxole-5-carboxylic acid, 6-(2-(dimethylamino)ethyl)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 237.26
Log P RDKit 1.22
Topological polar surface area (Å2) RDKit 59
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 5
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 7
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.42
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


1,3-Benzodioxole-5-carboxylic acid, 6-(2-(dimethylamino)ethyl)-
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 0.85


1,3-Benzodioxole-5-carboxylic acid, 6-(2-(dimethylamino)ethyl)-
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.26
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