IMPPAT Phytochemical information: 
Bergapten
Bergapten
Summary

SMILES: COc1c2ccc(=O)oc2cc2c1cco2
InChI: InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
InChIKey: BGEBZHIAGXMEMV-UHFFFAOYSA-N
DeepSMILES: COccccc=O)oc6ccc%10cco5
Scaffold Graph/Node/Bond level: O=c1ccc2cc3ccoc3cc2o1
Scaffold Graph/Node level: OC1CCC2CC3CCOC3CC2O1
Scaffold Graph level: CC1CCC2CC3CCCC3CC2C1
Functional groups: coc; cOC; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Furanocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Furocoumarins|Simple coumarins
Synonymous chemical names:
bergapten, psoralen, 5-methoxy, 5-methoxypsoralen, bergaptene, Bergapten, 5-methoxy-psoralen, 5-methoxy psoralen, majudin (bergapten)
External chemical identifiers:
CID:CID_2355; ChEMBL:CHEMBL24171; ChEBI:CHEBI:18293; ZINC:ZINC000000057731; FDASRS:4FVK84C92X; SureChEMBL:SCHEMBL50066; MolPort-000-880-879
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bergapten
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 216.19
Log P RDKit 2.55
Topological polar surface area (Å2) RDKit 52.58
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
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 11
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.08
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3
Bergapten
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 0.586359
Bergapten
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -6.25
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Bergapten
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000306512IL8784
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.