Compound: fumonisin b2
SMILES: O=C(O)[C@@H](CC(=O)O[C@@H]([C@@H](OC(=O)C[C@H](C(=O)O)CC(=O)O)C[C@H](CCCCCC[C@@H](O)C[C@H](O)[C@@H](N)C)C)[C@@H](CCCC)C)CC(=O)O
InChIKey: UXDPXZQHTDAXOZ-STOIETHLSA-N
Synonyms: fumonisin b2, 116355-84-1, fumonisin-B2, UX4WHT4MKB, CHEBI:38225, DTXSID80891857, (2R)-2-[2-[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid, 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-9,11-dihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl) ester, 1,2,3-Propanetricarboxylic acid, 1,1'-[(1S,2R)-1-[(2S,9R,11S,12S)-12-amino-9,11-dihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl] ester, (2R,2'R)-, (2R)-2-(2-((5R,6R,7S,9S,16R,18S,19S)-19-amino-6-((3R)-3,4-dicarboxybutanoyl)oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl)oxy-2-oxoethyl)butanedioic acid, RefChem:141698, DTXCID201031278, 1,2,3-Propanetricarboxylic acid, 1,1'-((1S,2R)-1-((2S,9R,11S,12S)-12-amino-9,11-dihydroxy-2-methyltridecyl)-2-((1R)-1-methylpentyl)-1,2-ethanediyl) ester, (2R,2'R)-, 2-(2-((19-amino-6-((3,4-dicarboxybutanoyl)oxy)-16,18-dihydroxy-5,9-dimethylicosan-7-yl)oxy)-2-oxoethyl)butanedioic acid, Fumonisin B2, Fusarium moniliforme, (2R,2'R)-2,2'-((((5R,6R,7S,9S,16R,18S,19S)-19-Amino-16,18-dihydroxy-5,9-dimethylicosane-6,7-diyl)bis(oxy))bis(2-oxoethane-2,1-diyl))disuccinic acid, (2R,2'R)-2,2'-{[(5R,6R,7S,9S,16R,18S,19S)-19-amino-16,18-dihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid, CCRIS 4434, UXDPXZQHTDAXOZ-STOIETHLSA-N, 1,2,3-Propanetricarboxylic acid, 1,1'-[1-(12-amino-9,11-dihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester, [2S-[1[1R*(S*),2S*(S*),2(S*)],2R*,9S*,11R*,12R*]]-; Fumonisin B2, UNII-UX4WHT4MKB, Epitope ID:874503, Fumonisin B2 (>90%), SCHEMBL622287, CHEMBL1700939, MSK7225, HY-N6723, LMSP01080023, MSK7225-100M, AKOS040741772, CCG-208209, NCGC00163557-01, BF162728, DA-53434, CS-0099766, Fumonisin B2 Solution in Methanol, 100ug/mL, C19242, G16932, SR-05000002349, Q5508613, SR-05000002349-2, (2R)-2-[2-[(1S,3S,10R,12S,13S)-13-amino-1-[(1R,2R)-1-[(3R)-3,4-dicarboxybutanoyl]oxy-2-methyl-hexyl]-10,12-dihydroxy-3-methyl-tetradecoxy]-2-oxo-ethyl]butanedioic acid, 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(2-amino-9,11-dihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl) ester, 1,2,3-Propanetricarboxylic acid, 1,1'-[1-(12-amino-9,11-dihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester, [2S-[1[1R*(S*),2S*(S*),2(S*)],2R*,9S*,11R*,12R*]]-
Theoretical properties:
molecular_formula: C34H59NO14
molecular_weight: 705.8 g/mol
exact_mass: 705.39355556 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 31
heavy_atom_count: 49
topological_polar_surface_area: 268 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Fumonisin B2 is a fumonisin that is (2S,3S,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,14,15-triol in which the hydroxy groups at positions 14 and 15 have each been esterified by condensation with the 1-carboxy group of 3-carboxyglutaric acid (giving a 3-carboxyglutarate ester group with R configuration in each case). It has a role as a carcinogenic agent and an Aspergillus metabolite. It is a diol, a fumonisin, a primary amino compound and a diester.
chebi: A fumonisin that is (2S,3S,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,14,15-triol in which the hydroxy groups at positions 14 and 15 have each been esterified by condensation with the 1-carboxy group of 3-carboxyglutaric acid (giving a 3-carboxyglutarate ester group with <i>R</i> configuration in each case).
chembl: FUMONISIN B2 is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Fumonisin B2 is a fumonisin mycotoxin produced by the fungi Fusarium verticillioides (formerly Fusarium moniliforme) and Aspergillus niger.
It is a structural analog of fumonisin B3, while it is lacking one hydroxy group compared to fumonisin B1.
Fumonisin B2 is more cytotoxic than fumonisin B1. Fumonisin B2 inhibits sphingosine acyltransferase.
Fumonisin B2 and other fumonisins frequently contaminate maize and other crops, while recently it has been shown using LC–MS/MS that FB2 can contaminate coffee beans as well.