Compound: khellin
SMILES: O=c1c2c(oc(c1)C)c(OC)c3occc3c2OC
InChIKey: HSMPDPBYAYSOBC-UHFFFAOYSA-N
Synonyms: khellin, 82-02-0, Visammin, Viscardan, Khelloyd, Ammivin, Kellina, Khelline, Khellinum, Quelina, 4,9-Dimethoxy-7-methyl-5H-furo(3,2-g)(1)benzopyran-5-one, 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one, 4,9-Dimethoxy-7-methyl-5-oxofuro(3,2-g)-1,2-chromene, kelina, 5H-Furo[3,2-g][1]benzopyran-5-one, 4,9-dimethoxy-7-methyl-, CHEBI:6133, DTXSID9045267, NSC-25509, NSC-37744, 5G117T0TJZ, 4,9-dimethoxy-7-methylfuro[3,2-g]chromen-5-one, 5H-Furo(3,2-g)(1)benzopyran-5-one, 4,9-dimethoxy-7-methyl-, DTXCID7025267, 4,9-dimethoxy-7-methylfuro(3,2-g)chromen-5-one, RefChem:40691, 201-392-8, Methafrone, Amicardine, Amikellin, Ammipuran, Ammivisnagen, Benecardin, Corafurone, Gynokhellan, Medekellin, Kelamin, Kelourin, Rykellin, Interkhellin, Ammispasmin, Interkellin, Kalangin, Kelicorin, Kelincor, Khelangin, Khellamine, Khellanals, Khellinorm, Visammimix, Visnagalin, Norkel, Eskel, Kellosal, Khelfren, Khelisem, Lynamine, Mefurina, Simeskellina, Vasokellina, Visnagen, Amiptan, Chellin, Kelicor, Kellin, Cardio-khellin, Ammi-khellin, Bi-Kellina, Benekardin, Khelline I, 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one, Chellina, Ammicardine, 5,8-Dimethoxy-2-methyl-6,7-furanochromone, Viscardin, 5,8-Dimethoxy-2-methyl-4',5'-furo-6,7-chromone, IT-033, MFCD00005007, 5,8-Dimethoxy-2-methyl-4',5'-furano-6,7-chromone, 4,9-Dimethoxy-7-methyl-5-oxo-1,8-dioxabenz-(f)indene, 4,9-Dimethoxy-7-methyl-5-oxofuro(3,2-g)(1)benzopyran, NSC37744, Chorafurone, Vismagen, Khell, MLS000028448, 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]-[1]benzopyran-5-one, NSC8519, 5,7-furanochromone, CAS-82-02-0, NCGC00016327-01, SMR000058278, 4,2-g][1]benzopyran, 4,8-dioxabenz-[f]indene, 4,2-g]-1,2-chromene, 5,5'-furo-6,7-chromone, 5,5'-furano-6,7-chromone, Chellina [Italian], 4,9-Dimethoxy-7-methyl-furo[3,2-g]chromen-5-one, 5,9-dimethoxy-2-methylfurano[3,2-g]chromen-4-one, 4,2-g][1]benzopyran-5-one, Khellin [INN:DCF], Khelline [INN-French], Khellinum [INN-Latin], Quelina [INN-Spanish], 5H-Furo[3, 4,9-dimethoxy-7-methyl-, WLN: T C566 DO JV MOJ BO1 HO1 L1, SR-01000000072, EINECS 201-392-8, NSC 25509, NSC 37744, BRN 0263185, UNII-5G117T0TJZ, Gynokhellin, Intercellin, Hkelfren, AI3-52114, Visammin;, Kellin;, Prestwick_287, Spectrum_000079, Khellin, for microscopy, Opera_ID_372, KHELLIN [INN], KHELLIN [MI], KHELLIN [MART.], Prestwick0_000091, Prestwick1_000091, Prestwick2_000091, Prestwick3_000091, Spectrum2_000593, Spectrum3_000654, Spectrum4_001557, Spectrum5_000154, KHELLIN [WHO-DD], bmse000751, Epitope ID:613436, SCHEMBL9655, Khellin, analytical standard, BSPBio_000042, BSPBio_002287, KBioGR_002054, KBioSS_000479, SPECTRUM210866, 5-19-06-00320 (Beilstein Handbook Reference), MLS001076533, CHEMBL44746, DivK1c_000046, SPBio_000466, SPBio_001981, BPBio1_000048, MEGxp0_000331, orb1308645, orb3140201, SCHEMBL30839911, ACon0_000983, ACon1_000350, HMS500C08, HSMPDPBYAYSOBC-UHFFFAOYSA-, KBio1_000046, KBio2_000479, KBio2_003047, KBio2_005615, KBio3_001507, NINDS_000046, HMS1568C04, HMS1923M07, HMS2095C04, HMS2230B16, HMS3371C21, HMS3712C04, HMS5085L15, Pharmakon1600-00210866, ALBB-025052, HY-B1394, NSC-8519, NSC25509, Tox21_110374, BDBM50480260, CCG-36453, LMPK13110001, NSC755826, s5887, SBB072185, STL561007, AKOS002281934, Tox21_110374_1, EBC-380063, FK52456, NSC-755826, SDCCGMLS-0003040.P003, IDI1_000046, NCGC00016327-02, NCGC00016327-03, NCGC00016327-04, NCGC00016327-05, NCGC00016327-06, NCGC00016327-07, NCGC00016327-08, NCGC00016327-09, NCGC00016327-11, NCGC00023424-03, NCGC00023424-04, NCGC00169160-01, NCGC00169160-02, NCGC00169160-03, AS-35307, DA-54630, ST076676, SY051635, SBI-0051567.P002, CS-0013121, K0039, NS00005943, C09010, K-3400, AB00052134_16, AK-693/40760628, Q2079998, SR-01000000072-3, SR-01000000072-4, SR-01000000072-5, SR-01000000072-6, BRD-K80353807-001-05-5, BRD-K80353807-001-06-3, BRD-K80353807-001-16-2, BRD-K80353807-001-24-6, BRD-K80353807-001-25-3, 4,9-dimethoxy-7-methylpyrano[3,2-f][1]benzoxol-5-one, 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one #, 4,9-Dimethoxy-7-methyl-furo[3,2-g][1]benzopyran-5-one, InChI=1/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3
Theoretical properties:
molecular_formula: C14H12O5
molecular_weight: 260.24 g/mol
exact_mass: 260.06847348 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 19
topological_polar_surface_area: 57.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Khellin is a furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant Ammi visnaga it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator. It has a role as a bronchodilator agent, a cardiovascular drug, a vasodilator agent and an anti-asthmatic agent. It is a furanochromone, an organic heterotricyclic compound and an oxacycle. It is functionally related to a 5H-furo[3,2-g]chromen-5-one.
chebi: A furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant <em>Ammi visnaga</em> it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator.
chembl: KHELLIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Khellin has been used as an herbal folk medicine, with use in the Mediterranean dating back to Ancient Egypt, to treat a variety of maladies including: renal colic, kidney stones, coronary disease, bronchial asthma, vitiligo, and psoriasis. It is a major constituent of the plant Visnaga daucoides, also known as Ammi visnaga and as bishop's weed. Once purified, khellin exists as colorless, odorless, bitter-tasting needle-shaped crystals and is classified as a gamma-pyrone, a furanochromone derivative. In the early 20th century, researchers searched for khellin analogs with lower toxicity and better efficacy. A number of drugs were discovered through this research, such as amiodarone and cromolyn sodium, which are used in current medical practice. Efloxate is also mentioned as analog.