2.0 2012-05-31 14:23:09 -0600 2015-06-03 17:19:08 -0600 ECMDB20018 M2MDB000867 (S)(+)-Allantoin Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin, glyoxyldiureide, and 5-ureidohydantoin. It is a product of oxidation of uric acid. It is a diureide of glyoxylic acid. (Wikipedia) In E. coli K-12, the enzyme allantoinase (EC 3.5.2.5) catalyzes the conversion of (S)(+)-Allantoin to Allantoate (KEGG). (+/-)-allantoin (2,5-dioxo-4-imidazolidinyl)-Urea (2,5-Dioxo-4-imidazolidinyl)urea (S)-allantoin 1-(2,5-Dioxoimidazolidin-4-yl)urea 2,5-Dioxo-4-imidazolidinyl-urea 4-Ureido-2,5-Imidazolidinedione 5-Ureido-2,4-imidazolidindion 5-Ureido-Hydantoin 5-Ureidohydantoin 5-Ureidohydrantoin Alantan Allantoin Allantoin (8CI) Allantoin (jan/usp) Allantoin [usan:ban] Allantol Alloxantin Avc/dienestrolcream Cordianine Cutemol emollient DL-allantoin Fancol toin Glyoxyldiureid Glyoxyldiureide Glyoxylic diureide Glyoxylic(acid) diureide Hemocane N-(2,5-Dioxo-4-imidazolidinyl)urea N-(2,5-Dioxoimidazolidin-4-yl)urea N-[2,5-Dioxoimidazolidin-4-yl]urea Paxyl Prestwick_11 Psoralon Sebical Septalan Uniderm a Urea, (2,5-dioxo-4-imidazolidinyl)- (9CI) Ureidohydantoin C4H6N4O3 158.1154 158.043990078 N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid 97-59-6 [H][C@]1(NC(O)=N)N=C(O)N=C1O InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)/t1-/m0/s1 POJWUDADGALRAB-SFOWXEAESA-N Solid Cytoplasm Periplasm logp -1.53 ALOGPS logs -2.17 ALOGPS solubility 1.07e+00 g/l ALOGPS melting_point 239 oC logp -1.7 ChemAxon pka_strongest_acidic 2.76 ChemAxon pka_strongest_basic 5.49 ChemAxon iupac N-[(4S)-2,5-dihydroxy-4H-imidazol-4-yl]carbamimidic acid ChemAxon average_mass 158.1154 ChemAxon mono_mass 158.043990078 ChemAxon smiles [H][C@]1(NC(O)=N)N=C(O)N=C1O ChemAxon formula C4H6N4O3 ChemAxon inchi InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)/t1-/m0/s1 ChemAxon inchikey POJWUDADGALRAB-SFOWXEAESA-N ChemAxon polar_surface_area 121.29 ChemAxon refractivity 44 ChemAxon polarizability 13.07 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Specdb::CMs 1083528 Specdb::NmrOneD 262608 Specdb::NmrOneD 262609 Specdb::NmrOneD 262610 Specdb::NmrOneD 262611 Specdb::NmrOneD 262612 Specdb::NmrOneD 262613 Specdb::NmrOneD 262614 Specdb::NmrOneD 262615 Specdb::NmrOneD 262616 Specdb::NmrOneD 262617 Specdb::NmrOneD 262618 Specdb::NmrOneD 262619 Specdb::NmrOneD 262620 Specdb::NmrOneD 262621 Specdb::NmrOneD 262622 Specdb::NmrOneD 262623 Specdb::NmrOneD 262624 Specdb::NmrOneD 262625 Specdb::NmrOneD 262626 Specdb::NmrOneD 262627 Specdb::MsMs 28031 Specdb::MsMs 28032 Specdb::MsMs 28033 Specdb::MsMs 34589 Specdb::MsMs 34590 Specdb::MsMs 34591 204 388780 C02350 15678 ALLANTOIN 3AL Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Allantoinase P77671 ALLB_ECOLI allB http://ecmdb.ca/proteins/P77671.xml (S)(+)-Allantoin + Water <> Allantoic acid R02425 (S)(+)-Allantoin + Water > Allantoic acid