1.0 2011-09-21 01:50:05 UTC 2017-04-03 04:56:44 UTC FDB029099 1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate The novel carbohydrate-derived b-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 ug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-b-carboline was also found in jams (up to 0.45 ug/g), and a relative high amount was present in tomato concentrate (6.5 ug/g) and sauce (up to 1.8 ug/g). This b-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of d-glucose and l-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this b-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-b-carboline.(PMID: 12137498) [HMDB] 1-(1,2,3,4,5-Pentahydroxypentyl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid 1-(1,2,3,4,5-Pentahydroxypentyl)-1,2,3,4-tetrahydrodemethylharmane-3-carboxylic acid anion PHPTCC C17H21N2O7 365.3578 365.134876036 1-(1,2,3,4,5-pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate 1-(1,2,3,4,5-pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate 7235-40-7 OCC(O)C(O)C(O)C(O)C1NC(CC2=C1NC1=C2C=CC=C1)C([O-])=O InChI=1S/C17H22N2O7/c20-6-11(21)14(22)16(24)15(23)13-12-8(5-10(19-13)17(25)26)7-3-1-2-4-9(7)18-12/h1-4,10-11,13-16,18-24H,5-6H2,(H,25,26)/p-1 LCHFAYIGHOVWSA-UHFFFAOYSA-M belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Acyl carnitines Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acid esters Aliphatic acyclic compounds Amines Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acid esters Carboxylic acid salts Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Secondary alcohols Tetraalkylammonium salts Acyl-carnitine Alcohol Aliphatic acyclic compound Amine Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Carboxylic acid salt Dicarboxylic acid or derivatives Hydrocarbon derivative Hydroxy acid Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organic zwitterion Organonitrogen compound Organooxygen compound Organopnictogen compound Quaternary ammonium salt Secondary alcohol Tetraalkylammonium salt Solid logp -0.48 ALOGPS logs -1.18 ALOGPS solubility 2.52e+01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 1.61 ChemAxon pka_strongest_basic 7.92 ChemAxon iupac 1-(1,2,3,4,5-pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate ChemAxon average_mass 365.3578 ChemAxon mono_mass 365.134876036 ChemAxon smiles OCC(O)C(O)C(O)C(O)C1NC(CC2=C1NC1=C2C=CC=C1)C([O-])=O ChemAxon formula C17H21N2O7 ChemAxon inchi InChI=1S/C17H22N2O7/c20-6-11(21)14(22)16(24)15(23)13-12-8(5-10(19-13)17(25)26)7-3-1-2-4-9(7)18-12/h1-4,10-11,13-16,18-24H,5-6H2,(H,25,26)/p-1 ChemAxon inchikey LCHFAYIGHOVWSA-UHFFFAOYSA-M ChemAxon polar_surface_area 169.1 ChemAxon refractivity 100.06 ChemAxon polarizability 36.85 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 8 ChemAxon donor_count 7 ChemAxon physiological_charge 0 ChemAxon formal_charge -1 ChemAxon Specdb::MsMs 337282 Specdb::MsMs 337283 Specdb::MsMs 337284 HMDB12492 #<Reference:0x00007f093c038f80>