1.0 2016-09-30 22:34:48 UTC 2020-05-11 20:37:34 UTC BMDB0000679 BMDB00679 Homocitrulline N(6)-(Aminocarbonyl)-L-lysine Homo-L-citrulline L-Homocitrulline N-e-Carbamyl-L-lysine N-epsilon-Carbamyl-L-lysine N6-Carbamoyl-L-lysine N6-Carbamoyl-lysine Ureidocaproic acid (S)-2-Amino-6-ureidohexanoic acid N-Ε-carbamyl-L-lysine N6-(Aminocarbonyl)-L-lysine Homocitrulline C7H15N3O3 189.2123 189.111341361 (2S)-2-amino-6-(carbamoylamino)hexanoic acid homocitrulline 1190-49-4 N[C@@H](CCCCNC(N)=O)C(O)=O InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1 XIGSAGMEBXLVJJ-YFKPBYRVSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues L-alpha-amino acids Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Ureas Aliphatic acyclic compound Amine Amino acid Amino fatty acid Carbonic acid derivative Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Medium-chain fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Urea Aliphatic acyclic compounds L-lysine derivative non-proteinogenic L-alpha-amino acid ureas Solid melting_point 211 - 212 °C water_solubility 600 mg/mL logp -3.13 ALOGPS logs -1.19 ALOGPS logp -3.5 ChemAxon pka_strongest_acidic 2.35 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac (2S)-2-amino-6-(carbamoylamino)hexanoic acid ChemAxon average_mass 189.2123 ChemAxon mono_mass 189.111341361 ChemAxon smiles N[C@@H](CCCCNC(N)=O)C(O)=O ChemAxon formula C7H15N3O3 ChemAxon inchi InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1 ChemAxon inchikey XIGSAGMEBXLVJJ-YFKPBYRVSA-N ChemAxon polar_surface_area 118.44 ChemAxon refractivity 45.93 ChemAxon polarizability 19.49 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsIr 22 Specdb::MsIr 37 Specdb::MsIr 49 Specdb::MsIr 733 Specdb::MsIr 734 Specdb::MsIr 735 Specdb::NmrTwoD 1420 Specdb::CMs 599 Specdb::CMs 22236 Specdb::CMs 30438 Specdb::CMs 37693 Specdb::CMs 137587 Specdb::CMs 145321 Specdb::CMs 1072404 Specdb::CMs 1072406 Specdb::CMs 1072408 Specdb::CMs 1072410 Specdb::CMs 1072412 Specdb::CMs 1072414 Specdb::CMs 1072416 Specdb::MsMs 942 Specdb::MsMs 943 Specdb::MsMs 944 Specdb::MsMs 315370 Specdb::MsMs 315371 Specdb::MsMs 315372 Specdb::MsMs 361327 Specdb::MsMs 361328 Specdb::MsMs 361329 Specdb::MsMs 2226235 Specdb::MsMs 2228487 Specdb::MsMs 2231637 Specdb::MsMs 2232538 Specdb::MsMs 2252281 Specdb::MsMs 2252824 Specdb::MsMs 2253663 Specdb::MsMs 2254192 Specdb::MsMs 2254396 Specdb::MsMs 2254844 Specdb::MsMs 2255714 Specdb::MsMs 2256193 Specdb::MsMs 2256320 Specdb::MsMs 2256801 Specdb::MsMs 2257802 Specdb::MsMs 2258246 Specdb::NmrOneD 2180 Specdb::NmrOneD 2869 Specdb::NmrOneD 316461 Specdb::NmrOneD 316462 Specdb::NmrOneD 316463 Specdb::NmrOneD 316464 Specdb::NmrOneD 316465 Specdb::NmrOneD 316466 Specdb::NmrOneD 316467 Specdb::NmrOneD 316468 Specdb::NmrOneD 316469 Specdb::NmrOneD 316470 Specdb::NmrOneD 316471 Specdb::NmrOneD 316472 Specdb::NmrOneD 316473 Specdb::NmrOneD 316474 Specdb::NmrOneD 316475 Specdb::NmrOneD 316476 Specdb::NmrOneD 316477 Specdb::NmrOneD 316478 Specdb::NmrOneD 316479 Specdb::NmrOneD 316480 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB022178 58582 C02427 65072 C00052314 17443 CPD-161 Homocitrulline 46 Stark, George R. Reactions of cyanate with functional groups of proteins. III. Reactions with amino and carboxyl groups. Biochemistry (1965), 4(6), 1030-6.