Compound: Bergapten
SMILES: O=c1oc2c(c(OC)c3ccoc3c2)cc1
InChIKey: BGEBZHIAGXMEMV-UHFFFAOYSA-N
Synonyms: Bergapten, 5-Methoxypsoralen, 484-20-8, bergaptene, Heraclin, Majudin, BERGAPTAN, 5-Mop, Psoraderm, O-Methylbergaptol, 5-Methoxy psoralen, 5-Methoxy-6,7-furanocoumarin, 5-Methoxyfuranocoumarin, 4-methoxyfuro[3,2-g]chromen-7-one, Geralen, 4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one, 7H-Furo[3,2-g][1]benzopyran-7-one, 4-methoxy-, 5 methoxypsoralen, DTXSID1025560, 4-methoxy-7H-furo[3,2-g][1]benzopyran-7-one, NSC-95437, 6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, gamma-lactone, 4FVK84C92X, 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-methoxy-, DTXCID305560, CHEBI:18293, 5-methoxy-2H-furo[3,2-g]chromen-2-one, 5 Methoxy Psoralen, 5-methoxy-2H-furo(3,2-g)chromen-2-one, 4-METHOXYFURO(3,2-G)CHROMEN-7-ONE, RefChem:29910, 207-604-5, 4-Methoxy-7H-furo[3,2-g]chromen-7-one, Pentaderm, 5-methoxypsoralene, 4-Methoxyfuro[3,2-g]benzopyran-7-one, MFCD00010272, NSC 95437, Bergaptene (DCF), 4-Methoxyfuro[3,2-g]benzopyrane-7-one, 5-Methoxypsoralen with ultraviolet A therapy, NSC95437, 4-Methoxy-furo[3,2-g]chromen-7-one, CHEMBL24171, 5-methoxyfurano[3,2-g]chromen-2-one, 4-Methoxy-7H-furo[3,2-g]benzopyran-7-one, 5-Methoxypsoralen; Bergapten, CAS-484-20-8, SMR000112435, CCRIS 4348, HSDB 3466, SR-05000002173, EINECS 207-604-5, BRN 0019560, UNII-4FVK84C92X, alpha-bergapten, 5-Methoxypsoralen (Bergapten), Heraclin;, Pentaderm (TN), 5-methoxy-psoralen, Bergapten (Standard), Spectrum_000794, BERGAPTEN [MI], Spectrum2_000534, Spectrum3_000663, Spectrum4_001478, Spectrum5_000155, 5-Methoxypsoralen, 99%, bmse000758, 5-Methoxypsoralen (obsol.), 7H-Furo[3, 4-methoxy-, Oprea1_562364, SCHEMBL50066, BSPBio_002325, KBioGR_002055, KBioSS_001274, SPECTRUM300546, 5-19-06-00004 (Beilstein Handbook Reference), MLS002207272, MLS002454380, Bergapten, analytical standard, DivK1c_000529, SPBio_000547, MEGxp0_000990, orb1306366, orb3025861, SCHEMBL29529284, ACon0_000984, ACon1_001979, GTPL12431, HMS501K11, HY-N0370R, KBio1_000529, KBio2_001274, KBio2_003842, KBio2_006410, KBio3_001545, 5-METHOXYPSORALEN [IARC], NINDS_000529, HMS1923G13, HMS2268M24, HMS3652F19, HMS5082N16, Pharmakon1600-00300546, 5-METHOXYPSORALEN [MART.], 5-METHOXYPSORALEN [WHO-DD], HY-N0370, TNP00299, Tox21_202357, Tox21_303255, BDBM50067880, CCG-39946, MSK000532, NSC755877, s4239, STK333038, AKOS000276715, DB12216, DS-2970, EBC-457062, FM05395, NSC-755877, SDCCGMLS-0066492.P001, IDI1_000529, 4-Methoxyfuro[3,2-?]benzopyrane-7-one, NCGC00017357-01, NCGC00017357-02, NCGC00017357-03, NCGC00017357-04, NCGC00017357-05, NCGC00017357-06, NCGC00017357-07, NCGC00017357-08, NCGC00091582-01, NCGC00091582-02, NCGC00091582-03, NCGC00091582-04, NCGC00178705-01, NCGC00178705-02, NCGC00256998-01, NCGC00259906-01, AC-20189, AC-34208, NCI60_042121, ST057259, SY051831, SBI-0051583.P002, DB-051552, NS00015832, SW220008-1, 4-Methoxy-7H-furo[3,2-g]chromen-7-one #, C01557, D07521, AB00052148_06, AB00052148_07, F328941, Q414779, Q-100536, SR-05000002173-2, SR-05000002173-3, SR-05000002173-5, BRD-K12968785-001-02-6, BRD-K12968785-001-03-4, BRD-K12968785-001-06-7, BRD-K12968785-001-11-7, BRD-K12968785-001-12-5, BRD-K12968785-001-13-3, 6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, .gamma.-lactone, InChI=1/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H
Theoretical properties:
molecular_formula: C12H8O4
molecular_weight: 216.19 g/mol
exact_mass: 216.04225873 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 16
topological_polar_surface_area: 48.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Needles from alcohol
color: Needles from alcohol
melting_point: 370 °F (sublimes) (NTP, 1992)
solubility: less than 1 mg/mL at 66 °F (NTP, 1992)
Descriptions:
pubchem: 5-Methoxypsoralen with ultraviolet A therapy can cause cancer according to an independent committee of scientific and health experts.
chebi: A 5-methoxyfurocoumarin that is psoralen substituted by a methoxy group at position 5.
chembl: BERGAPTEN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Bergapten (5-methoxypsoralen) is a naturally occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.
Bergapten belongs to a class of chemical compounds known as the furanocoumarins. In 1834, Kalbrunner isolated 5-methoxypsoralen from bergamot essential oil, hence the common name "bergapten". It was the first furanocoumarin to be isolated and identified.