1.0 2011-09-21 00:10:18 UTC 2015-10-09 22:28:48 UTC FDB022217 Homocarnosine Homocarnosine is a normal human metabolite, the brain-specific dipeptide of gamma-aminobutyric acid (GABA) and histidine. (PMID 1266573) Increased concentration of CSF homocarnosine has been found in familial spastic paraplegia. (PMID 842287) Homocarnosinosis (an inherited disorder, OMIM 236130) is characterized by an elevated level of the dipeptide homocarnosine (Hca) in the Cerebrospinal fluid (CSF) and the brain and by carnosinuria and serum carnosinase deficiency, and can co-exist with paraplegia, retinitis pigmentosa, and a progressive mental deficiency. (PMID 3736769) In glial tumors of human brain the content of homocarnosine has been found to be lower than in brain tissue (PMID 1032224), while an increase in content of homocarnosine was observed in brain tissue of animals under experimental trauma of cranium. (PMID 1025883) [HMDB] g-Aminobutyryl histidine g-Aminobutyryl-L-histidine g-Aminobutyrylhistidine gamma-Aminobutyryl histidine gamma-Aminobutyryl-L-histidine gamma-Aminobutyrylhistidine Homocarnosine L-Homocarnosine N-(4-amino-1-Oxobutyryl)histidine N-(4-aminobutyryl)-Histidine N-(4-aminobutyryl)-L-Histidine γ-aminobutyryl histidine C10H16N4O3 240.259 240.122240398 (2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid (2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid 3650-73-5 NCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1 CCLQKVKJOGVQLU-QMMMGPOBSA-N belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Hybrid peptides Organic compounds Organic acids and derivatives Peptidomimetics Hybrid peptides Aromatic heteromonocyclic compounds Amino acids Azacyclic compounds Carbonyl compounds Carboxylic acids Gamma amino acids and derivatives Heteroaromatic compounds Histidine and derivatives Hydrocarbon derivatives Imidazolyl carboxylic acids and derivatives Monoalkylamines Monocarboxylic acids and derivatives N-acyl amines N-acyl-L-alpha-amino acids Organic oxides Organopnictogen compounds Secondary carboxylic acid amides Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aromatic heteromonocyclic compound Azacycle Azole Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Fatty acyl Fatty amide Gamma amino acid or derivatives Heteroaromatic compound Histidine or derivatives Hybrid peptide Hydrocarbon derivative Imidazole Imidazolyl carboxylic acid derivative Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-acyl-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 Secondary carboxylic acid amide L-histidine derivative N-acyl-L-alpha-amino acid homocarnosine Solid logp -2.85 ALOGPS logs -1.51 ALOGPS solubility 7.37e+00 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 3.45 ChemAxon pka_strongest_basic 9.99 ChemAxon iupac (2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid ChemAxon average_mass 240.259 ChemAxon mono_mass 240.122240398 ChemAxon smiles NCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O ChemAxon formula C10H16N4O3 ChemAxon inchi InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1 ChemAxon inchikey CCLQKVKJOGVQLU-QMMMGPOBSA-N ChemAxon polar_surface_area 121.1 ChemAxon refractivity 59.75 ChemAxon polarizability 24.49 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1461 Specdb::CMs 635 Specdb::CMs 636 Specdb::CMs 637 Specdb::CMs 17203 Specdb::CMs 30205 Specdb::CMs 30311 Specdb::CMs 30884 Specdb::CMs 37737 Specdb::CMs 155367 Specdb::CMs 1074597 Specdb::CMs 1074599 Specdb::CMs 1074601 Specdb::CMs 1074603 Specdb::CMs 1074604 Specdb::CMs 1074606 Specdb::CMs 1074608 Specdb::NmrOneD 1515 Specdb::NmrOneD 145190 Specdb::NmrOneD 145191 Specdb::NmrOneD 145192 Specdb::NmrOneD 145193 Specdb::NmrOneD 145194 Specdb::NmrOneD 145195 Specdb::NmrOneD 145196 Specdb::NmrOneD 145197 Specdb::NmrOneD 145198 Specdb::NmrOneD 145199 Specdb::NmrOneD 145200 Specdb::NmrOneD 145201 Specdb::NmrOneD 145202 Specdb::NmrOneD 145203 Specdb::NmrOneD 145204 Specdb::NmrOneD 145205 Specdb::NmrOneD 145206 Specdb::NmrOneD 145207 Specdb::NmrOneD 145208 Specdb::NmrOneD 145209 Specdb::MsMs 1059 Specdb::MsMs 1060 Specdb::MsMs 1061 Specdb::MsMs 4599 Specdb::MsMs 4600 Specdb::MsMs 4601 Specdb::MsMs 4602 Specdb::MsMs 4603 Specdb::MsMs 4604 Specdb::MsMs 4605 Specdb::MsMs 4606 Specdb::MsMs 4607 Specdb::MsMs 4608 Specdb::MsMs 4609 Specdb::MsMs 4610 Specdb::MsMs 4611 Specdb::MsMs 4615 Specdb::MsMs 304051 Specdb::MsMs 304052 Specdb::MsMs 304053 Specdb::MsMs 347158 Specdb::MsMs 347159 Specdb::MsMs 347160 Specdb::MsMs 437786 Specdb::MsMs 437787 HMDB00745 #<Reference:0x000055ce31ddf950> #<Reference:0x000055ce31ddf798> #<Reference:0x000055ce31ddf5e0> #<Reference:0x000055ce31ddf428> #<Reference:0x000055ce31ddf270> #<Reference:0x000055ce31ddf0b8> #<Reference:0x000055ce31ddef00> #<Reference:0x000055ce31dded48> #<Reference:0x000055ce31ddeb90> #<Reference:0x000055ce31dde9d8> #<Reference:0x000055ce31dde820> #<Reference:0x000055ce31dde668> #<Reference:0x000055ce31dde4b0> #<Reference:0x000055ce31dde2f8> #<Reference:0x000055ce31dde140> #<Reference:0x000055ce31dddf60> 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