1.0 2011-09-21 01:38:19 UTC 2015-07-21 06:59:23 UTC FDB028346 2-(3-Carboxy-3-aminopropyl)-L-histidine 2-(3-Carboxy-3-aminopropyl)-L-histidine is an unusual amino acid that results from the post-translational modification of histidine in certain proteins. In particular, it is a post-translational derivative of histidine that exists in protein synthesis elongation factor 2 (EF2) at the site of diphtheria toxin-catalyzed ADP-ribosylation of elongation factor 2. It is a precursor for diphthamide. This compound is a substrate for the enzyme diphthine synthase (EC 2.1.1.98). This enzyme catalyzes the chemical reaction: S-adenosyl-L-methionine + 2-(3-carboxy-3-aminopropyl)-L-histidine = S-adenosyl-L-homocysteine + 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine. [HMDB] 2-(3-amino-3-carboxypropyl)-L-histidine 2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoate 2-amino-4-[[4-(2-amino-2-carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acid C10H16N4O4 256.2584 256.11715502 2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid 2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid NC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1 CJCSNWWKPUXVRD-MLWJPKLSSA-N belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Histidine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic heteromonocyclic compounds Amino acids Aralkylamines Azacyclic compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Heteroaromatic compounds Hydrocarbon derivatives Imidazolyl carboxylic acids and derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Alpha-amino acid Amine Amino acid Aralkylamine Aromatic heteromonocyclic compound Azacycle Azole Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Heteroaromatic compound Histidine or derivatives Hydrocarbon derivative Imidazole Imidazolyl carboxylic acid derivative L-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine L-histidine derivative non-proteinogenic L-alpha-amino acid Solid logp -4.08 ALOGPS logs -1.47 ALOGPS solubility 8.71e+00 g/l ALOGPS logp -6.5 ChemAxon pka_strongest_acidic 1.63 ChemAxon pka_strongest_basic 9.78 ChemAxon iupac 2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid ChemAxon average_mass 256.2584 ChemAxon mono_mass 256.11715502 ChemAxon smiles NC(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O ChemAxon formula C10H16N4O4 ChemAxon inchi InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1 ChemAxon inchikey CJCSNWWKPUXVRD-MLWJPKLSSA-N ChemAxon polar_surface_area 155.32 ChemAxon refractivity 61.14 ChemAxon polarizability 25.54 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 2383 Specdb::CMs 39746 Specdb::CMs 150829 Specdb::NmrOneD 93852 Specdb::NmrOneD 93853 Specdb::NmrOneD 93854 Specdb::NmrOneD 93855 Specdb::NmrOneD 93856 Specdb::NmrOneD 93857 Specdb::NmrOneD 93858 Specdb::NmrOneD 93859 Specdb::NmrOneD 93860 Specdb::NmrOneD 93861 Specdb::NmrOneD 93862 Specdb::NmrOneD 93863 Specdb::NmrOneD 93864 Specdb::NmrOneD 93865 Specdb::NmrOneD 93866 Specdb::NmrOneD 93867 Specdb::NmrOneD 93868 Specdb::NmrOneD 93869 Specdb::NmrOneD 93870 Specdb::NmrOneD 93871 Specdb::MsMs 178053 Specdb::MsMs 178054 Specdb::MsMs 178055 Specdb::MsMs 180366 Specdb::MsMs 180367 Specdb::MsMs 180368 Specdb::MsMs 2449966 Specdb::MsMs 2449967 Specdb::MsMs 2449968 Specdb::MsMs 2486316 Specdb::MsMs 2486317 Specdb::MsMs 2486318 HMDB11655 17144 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