1.0 2011-09-21 00:18:36 UTC 2015-07-21 06:57:20 UTC FDB022730 Pteroyltriglutamic acid A crystalline conjugate of folic acid containing three molecules of glutamic acid instead of one and having the general properties of a polypeptide. (http://medical-dictionary.thefreedictionary.com/pteropterin) As a measure of enterocyte function, the deconjugation of Pteroylpolyglutamic acid (pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid) to folic acid and subsequent active absorption was measured in 19 patients with progressive systemic sclerosis and compared with 14 controls. The absorption step of folic acid was identical in the two groups, while deconjugation of pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid was significantly decreased in the patients with progressive systemic sclerosis. This observation suggests a primary epithelial defect of the small intestine in patients with progressive systemic sclerosis. (PMID 3583071) Glutamyl hydrolase cleaves the poly-g-glutamate chain folate and antifolate poly-g-glutamates. Its cellular location is lysosomal with large amts. of the enzyme constitutively secreted. The highest levels of glutamyl hydrolase mRNA in humans is found in the liver and kidney. (PMID: 10598552) [HMDB] Folic acid diglutamate N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-Glutamic acid N-[N-(N-pteroyl-L-gamma-glutamyl)-L-gamma-glutamyl]-Glutamic acid N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-.gamma.-glutamyl]-L-.gamma.-glutamyl]- L-Glutamic acid Pteropterin Pteroyl-gamma-triglutamic acid Pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid Pteroyltri-gamma-L-glutamic acid Pteroyltriglutamic acid C29H33N9O12 699.6254 699.224867565 2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid 2-(4-{4-[(4-{[(2-amino-4-oxo-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid 89-38-3 NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1 InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44) WOLQREOUPKZMEX-UHFFFAOYSA-N belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Oligopeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic heteropolycyclic compounds Amino acids Aminobenzamides Aminopyrimidines and derivatives Aniline and substituted anilines Azacyclic compounds Benzoyl derivatives Carbonyl compounds Carboxylic acids Gamma-glutamyl amino acids Glutamic acid and derivatives Glutamine and derivatives Heteroaromatic compounds Hippuric acids Hydrocarbon derivatives N-acyl amines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Phenylalkylamines Primary amines Pterins and derivatives Pyrazines Pyrimidones Secondary alkylarylamines Secondary carboxylic acid amides Tetracarboxylic acids and derivatives Vinylogous amides Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Aminobenzamide Aminobenzoic acid or derivatives Aminopyrimidine Aniline or substituted anilines Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzamide Benzenoid Benzoic acid or derivatives Benzoyl Carbonyl group Carboxamide group Carboxylic acid Fatty acyl Fatty amide Gamma-glutamyl alpha-amino acid Glutamic acid or derivatives Glutamine or derivatives Heteroaromatic compound Hippuric acid Hippuric acid or derivatives Hydrocarbon derivative Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalkylamine Primary amine Pteridine Pterin Pyrazine Pyrimidine Pyrimidone Secondary aliphatic/aromatic amine Secondary amine Secondary carboxylic acid amide Tetracarboxylic acid or derivatives Vinylogous amide Solid logp -0.55 ALOGPS logs -3.91 ALOGPS solubility 8.63e-02 g/l ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 2.98 ChemAxon pka_strongest_basic 2.08 ChemAxon iupac 2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid ChemAxon average_mass 699.6254 ChemAxon mono_mass 699.224867565 ChemAxon smiles NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1 ChemAxon formula C29H33N9O12 ChemAxon inchi InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44) ChemAxon inchikey WOLQREOUPKZMEX-UHFFFAOYSA-N ChemAxon polar_surface_area 341.79 ChemAxon refractivity 167.19 ChemAxon polarizability 67.38 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 18 ChemAxon donor_count 10 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1732 Specdb::MsMs 293608 Specdb::MsMs 293609 Specdb::MsMs 293610 Specdb::MsMs 334114 Specdb::MsMs 334115 Specdb::MsMs 334116 Specdb::MsMs 2780128 Specdb::MsMs 2780129 Specdb::MsMs 2780130 Specdb::MsMs 2925352 Specdb::MsMs 2925353 Specdb::MsMs 2925354 Specdb::NmrOneD 1792 Specdb::NmrOneD 148560 Specdb::NmrOneD 148561 Specdb::NmrOneD 148562 Specdb::NmrOneD 148563 Specdb::NmrOneD 148564 Specdb::NmrOneD 148565 Specdb::NmrOneD 148566 Specdb::NmrOneD 148567 Specdb::NmrOneD 148568 Specdb::NmrOneD 148569 Specdb::NmrOneD 148570 Specdb::NmrOneD 148571 Specdb::NmrOneD 148572 Specdb::NmrOneD 148573 Specdb::NmrOneD 148574 Specdb::NmrOneD 148575 Specdb::NmrOneD 148576 Specdb::NmrOneD 148577 Specdb::NmrOneD 148578 Specdb::NmrOneD 148579 Specdb::CMs 12542 Specdb::CMs 748711 Specdb::CMs 748712 Specdb::CMs 748713 Specdb::CMs 748714 Specdb::CMs 748715 Specdb::CMs 748716 Specdb::CMs 748717 Specdb::CMs 748718 Specdb::CMs 748719 Specdb::CMs 748720 Specdb::CMs 748721 Specdb::CMs 748722 Specdb::CMs 748723 Specdb::CMs 748724 Specdb::CMs 748725 Specdb::CMs 748726 Specdb::CMs 748727 Specdb::CMs 748728 Specdb::CMs 748729 Specdb::CMs 748730 Specdb::CMs 748731 Specdb::CMs 748732 Specdb::CMs 748733 Specdb::CMs 748734 HMDB01902 #<Reference:0x000055ce31ec81c8> #<Reference:0x000055ce31ec8010> 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