1.0 2011-09-21 00:37:49 UTC 2015-07-21 06:57:57 UTC FDB023974 Hexaglutamyl folate Hexaglutamyl folate is a naturally occurring form of folic acid. The bioavailability of dietary folate may be hampered by the need of the glutamate moieties to be deconjugated before absorption. Folate deficiency in humans leads to anemia, neural tube defects and, possibly, chronic diseases such as cardiovascular disease, colon cancer, and neurocognitive dysfunction. Folate status is ascertained not only by the intake of folate but also by its bioavailability. Bioavailability is defined as the proportion of ingested folate that is absorbed and available for metabolic processes and storage. In humans, the bioavailability of folate from the diet is assumed to be {approx}50%, whereas the bioavailability of synthetic folic acid used in supplements and as a food fortificant is estimated to range from 76% to 97%. (PMID: 17093166) Patients with pernicious anemia in relapse and postgastrectomy macrocytic anemia cannot readily utilize for hematopoiesis a naturally occurring conjugate of pteroylglutamic acid although they respond promptly to administration of the free vitamin. This effect varies in different patients. Inability to utilize the conjugated vitamin appears to depend at least in part upon a conjugase-inhibiting substance present in natural sources of conjugate. (PMID: 1082804) [HMDB] Hexaglutamate folate N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-g-glutamyl-L-g-glutamyl-L-g-glutamyl-L-g-glutamyl-L-g-glutamyl-L-Glutamic acid N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-gamma-glutamyl-L-gamma-glutamyl-L-gamma-glutamyl-L-Glutamic acid N-[N-[N-[N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-g-glutamyl]-L-g-glutamyl]-L-g-glutamyl]-L-g-glutamyl]-L-g-glutamyl]-L-Glutamic acid N-[N-[N-[N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-gamma-glutamyl]-L-Glutamic acid Pteglu6 Pteroyl-g-hexaglutamate Pteroyl-gamma-hexaglutamate Pteroylhexaglutamic acid C44H54N12O21 1086.9674 1086.35264685 (2S,7R,11S)-2,11-diamino-6-[(4S)-4-amino-4-carboxybutanoyl]-7-{N-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-(carboxymethyl)-5,8-dioxododecanedioic acid (2S,7R,11S)-2,11-diamino-6-[(4S)-4-amino-4-carboxybutanoyl]-7-{N-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-1H-pteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-(carboxymethyl)-5,8-dioxododecanedioic acid 35409-55-3 N[C@@H](CCC(=O)OC(=O)[C@](N(C(=O)CC[C@H](N)C(O)=O)C(=O)C1=CC=C(NCC2=CN=C3NC(N)=NC(=O)C3=N2)C=C1)(C(=O)CC[C@H](N)C(O)=O)C(CC(O)=O)(C(=O)CC[C@H](N)C(O)=O)C(=O)CC[C@H](N)C(O)=O)C(O)=O InChI=1S/C44H54N12O21/c45-21(36(66)67)5-10-26(57)43(15-30(61)62,27(58)11-6-22(46)37(68)69)44(28(59)12-7-23(47)38(70)71,41(76)77-31(63)14-9-25(49)40(74)75)56(29(60)13-8-24(48)39(72)73)35(65)18-1-3-19(4-2-18)51-16-20-17-52-33-32(53-20)34(64)55-42(50)54-33/h1-4,17,21-25,51H,5-16,45-49H2,(H,61,62)(H,66,67)(H,68,69)(H,70,71)(H,72,73)(H,74,75)(H3,50,52,54,55,64)/t21-,22-,23-,24-,25-,44+/m0/s1 FWAQAOUHULVCBP-HCVVFSGQSA-N belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Glutamine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic heteropolycyclic compounds Amino acids Amino fatty acids Aminobenzamides Aminopyrimidines and derivatives Aniline and substituted anilines Azacyclic compounds Benzoyl derivatives Beta-keto acids and derivatives Carboxylic acid anhydrides Carboxylic acids Dicarboximides Gamma-amino ketones Gamma-keto acids and derivatives Glutamic acid and derivatives Heteroaromatic compounds Hippuric acids and derivatives Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines N-acyl amines N-substituted carboxylic acid imides Organic oxides Organopnictogen compounds Phenylalkylamines Pterins and derivatives Pyrazines Pyrimidones Secondary alkylarylamines Vinylogous amides Alpha-amino acid Amine Amino acid Amino fatty acid Aminobenzamide Aminobenzoic acid or derivatives Aminopyrimidine Aniline or substituted anilines Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Benzoic acid or derivatives Benzoyl Beta-keto acid Carbonyl group Carboxylic acid Carboxylic acid anhydride Carboxylic acid imide Carboxylic acid imide, n-substituted Dicarboximide Fatty acyl Gamma-aminoketone Gamma-keto acid Glutamic acid or derivatives Glutamine or derivatives Heteroaromatic compound Hippuric acid or derivatives Hydrocarbon derivative Keto acid Ketone L-alpha-amino acid Monocyclic benzene moiety N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalkylamine Primary aliphatic amine Primary amine Pteridine Pterin Pyrazine Pyrimidine Pyrimidone Secondary aliphatic/aromatic amine Secondary amine Vinylogous amide Solid logp -2.58 ALOGPS logs -3.44 ALOGPS solubility 3.93e-01 g/l ALOGPS logp -8.8 ChemAxon pka_strongest_acidic 1.1 ChemAxon pka_strongest_basic 9.01 ChemAxon iupac (2S,7R,11S)-2,11-diamino-6-[(4S)-4-amino-4-carboxybutanoyl]-7-{N-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-6-(carboxymethyl)-5,8-dioxododecanedioic acid ChemAxon average_mass 1086.9674 ChemAxon mono_mass 1086.35264685 ChemAxon smiles N[C@@H](CCC(=O)OC(=O)[C@](N(C(=O)CC[C@H](N)C(O)=O)C(=O)C1=CC=C(NCC2=CN=C3NC(N)=NC(=O)C3=N2)C=C1)(C(=O)CC[C@H](N)C(O)=O)C(CC(O)=O)(C(=O)CC[C@H](N)C(O)=O)C(=O)CC[C@H](N)C(O)=O)C(O)=O ChemAxon formula C44H54N12O21 ChemAxon inchi InChI=1S/C44H54N12O21/c45-21(36(66)67)5-10-26(57)43(15-30(61)62,27(58)11-6-22(46)37(68)69)44(28(59)12-7-23(47)38(70)71,41(76)77-31(63)14-9-25(49)40(74)75)56(29(60)13-8-24(48)39(72)73)35(65)18-1-3-19(4-2-18)51-16-20-17-52-33-32(53-20)34(64)55-42(50)54-33/h1-4,17,21-25,51H,5-16,45-49H2,(H,61,62)(H,66,67)(H,68,69)(H,70,71)(H,72,73)(H,74,75)(H3,50,52,54,55,64)/t21-,22-,23-,24-,25-,44+/m0/s1 ChemAxon inchikey FWAQAOUHULVCBP-HCVVFSGQSA-N ChemAxon polar_surface_area 591.15 ChemAxon refractivity 252.39 ChemAxon polarizability 102.78 ChemAxon rotatable_bond_count 34 ChemAxon acceptor_count 31 ChemAxon donor_count 14 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 292711 Specdb::MsMs 292712 Specdb::MsMs 292713 Specdb::MsMs 332986 Specdb::MsMs 332987 Specdb::MsMs 332988 Specdb::MsMs 2396178 Specdb::MsMs 2396179 Specdb::MsMs 2396180 Specdb::MsMs 2539853 Specdb::MsMs 2539854 Specdb::MsMs 2539855 Specdb::NmrOneD 80852 Specdb::NmrOneD 80853 Specdb::NmrOneD 80854 Specdb::NmrOneD 80855 Specdb::NmrOneD 80856 Specdb::NmrOneD 80857 Specdb::NmrOneD 80858 Specdb::NmrOneD 80859 Specdb::NmrOneD 80860 Specdb::NmrOneD 80861 Specdb::NmrOneD 80862 Specdb::NmrOneD 80863 Specdb::NmrOneD 80864 Specdb::NmrOneD 80865 Specdb::NmrOneD 80866 Specdb::NmrOneD 80867 Specdb::NmrOneD 80868 Specdb::NmrOneD 80869 Specdb::NmrOneD 80870 Specdb::NmrOneD 80871 HMDB06563 #<Reference:0x000055ce32799c20> #<Reference:0x000055ce32799a40> 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