1.0 2011-09-21 00:37:03 UTC 2015-07-21 06:57:56 UTC FDB023935 10-Formyldihydrofolate 10-Formyldihydrofolate is a folate compound that has not been found as a component of intracellular folates in normal tissues but has been identified in the cytosol of methotrexate (MTX)-treated MCF-7 breast cancer cells and normal human myeloid precursor cells. The origin of 10-formyldihydrofolate remains an enigma. Its appearance only in the extracts from MTX-treated cells is not consistent with a simple oxidation of lO-formyl-H4folate during the extraction procedure. This, however, does not exclude the occurrence of spontaneous oxidation of 10-formyl-H4folate within the intact cells prior to the folate extraction. (PMID: 3366769) [HMDB] 10-Formyldihydrofolic acid 10-Formyldihydropteroylglutamate N-(10-Formyl-7,8-dihydropteroyl)-L-glutamate N-(10-Formyl-7,8-dihydropteroyl)-L-glutamic acid C20H21N7O7 471.4234 471.150246061 (2S)-2-[(4-{N-[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid 10-formyldihydrofolic acid 28459-40-7 NC1=NC2=C(N=C(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1 InChI=1S/C20H21N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,13H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t13-/m0/s1 UXFQDXABPXWSTK-ZDUSSCGKSA-N belongs to the class of organic compounds known as dihydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6-dihydropteroic acid/7,8-dihydropteroic acid skeleton conjugated with one or more L-glutamic acid units (or derivative thereof). Dihydrofolic acids and derivatives Organic compounds Organoheterocyclic compounds Pteridines and derivatives Pterins and derivatives Aromatic heteropolycyclic compounds Acylaminobenzoic acid and derivatives Amino acids Aminopyrimidines and derivatives Anilides Azacyclic compounds Benzoyl derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Glutamic acid and derivatives Heteroaromatic compounds Hippuric acids Hydrocarbon derivatives Ketimines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Primary amines Propargyl-type 1,3-dipolar organic compounds Pyrimidones Secondary alkylarylamines Secondary carboxylic acid amides Tertiary carboxylic acid amides Vinylogous amides Acylaminobenzoic acid or derivatives Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aminopyrimidine Anilide Aromatic heteropolycyclic compound Azacycle Benzamide Benzenoid Benzoic acid or derivatives Benzoyl Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Dihydrofolic acid or derivatives Glutamic acid or derivatives Heteroaromatic compound Hippuric acid Hippuric acid or derivatives Hydrocarbon derivative Imine Ketimine Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Propargyl-type 1,3-dipolar organic compound Pyrimidine Pyrimidone Secondary aliphatic/aromatic amine Secondary amine Secondary carboxylic acid amide Tertiary carboxylic acid amide Vinylogous amide dihydrofolic acids Solid logp -1.26 ALOGPS logs -3.66 ALOGPS solubility 1.04e-01 g/l ALOGPS logp -2.4 ChemAxon pka_strongest_acidic 2.96 ChemAxon pka_strongest_basic 3.51 ChemAxon iupac (2S)-2-[(4-{N-[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid ChemAxon average_mass 471.4234 ChemAxon mono_mass 471.150246061 ChemAxon smiles NC1=NC2=C(N=C(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1 ChemAxon formula C20H21N7O7 ChemAxon inchi InChI=1S/C20H21N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,13H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t13-/m0/s1 ChemAxon inchikey UXFQDXABPXWSTK-ZDUSSCGKSA-N ChemAxon polar_surface_area 215.88 ChemAxon refractivity 124.49 ChemAxon polarizability 44.82 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 11 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 25825 Specdb::CMs 39026 Specdb::CMs 134616 Specdb::CMs 142350 Specdb::NmrOneD 11022 Specdb::NmrOneD 11023 Specdb::NmrOneD 11024 Specdb::NmrOneD 11025 Specdb::NmrOneD 11026 Specdb::NmrOneD 11027 Specdb::NmrOneD 11028 Specdb::NmrOneD 11029 Specdb::NmrOneD 11030 Specdb::NmrOneD 11031 Specdb::NmrOneD 11032 Specdb::NmrOneD 11033 Specdb::NmrOneD 11034 Specdb::NmrOneD 11035 Specdb::NmrOneD 11036 Specdb::NmrOneD 11037 Specdb::NmrOneD 11038 Specdb::NmrOneD 11039 Specdb::NmrOneD 11040 Specdb::NmrOneD 11041 Specdb::MsMs 323248 Specdb::MsMs 323249 Specdb::MsMs 323250 Specdb::MsMs 371359 Specdb::MsMs 371360 Specdb::MsMs 371361 Specdb::MsMs 2450305 Specdb::MsMs 2450306 Specdb::MsMs 2450307 Specdb::MsMs 2488308 Specdb::MsMs 2488309 Specdb::MsMs 2488310 HMDB06485 #<Reference:0x000055ce3074e4e8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823