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
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000265ENSG00000255974CYP2A61548BindingDB, ChEMBL, NPASS
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000264ENSG00000138061CYP1B11545ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000262ENSG00000140465CYP1A11543ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000270ENSG00000197408CYP2B61555ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000790ENSG00000177301KCNA23737BindingDB, ChEMBL, NPASS
TAR_EXP_000791ENSG00000177272KCNA33738BindingDB, NPASS
TAR_EXP_000792ENSG00000130037KCNA53741ChEMBL, NPASS
TAR_EXP_000793ENSG00000151079KCNA63742BindingDB, NPASS
TAR_EXP_000795ENSG00000129159KCNC13746BindingDB, NPASS
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000789ENSG00000111262KCNA13736ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_000773ENSG00000169083AR367ChEMBL, NPASS
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, ChEMBL, NPASS
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000614ENSG00000087460GNAS2778NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL