L-histidine   

GtoPdb Ligand ID: 3310

Abbreviated name: L-His
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 92
Molecular weight 155.07
XLogP -3.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES NC(C(=O)O)Cc1c[nH]cn1
Isomeric SMILES N[C@H](C(=O)O)Cc1c[nH]cn1
InChI InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
InChI Key HNDVDQJCIGZPNO-YFKPBYRVSA-N
References
1. Albers A, Bröer A, Wagner CA, Setiawan I, Lang PA, Kranz EU, Lang F, Bröer S. (2001)
Na+ transport by the neural glutamine transporter ATA1.
Pflugers Arch., 443 (1): 92-101. [PMID:11692272]
2. Bhardwaj RK, Herrera-Ruiz D, Eltoukhy N, Saad M, Knipp GT. (2006)
The functional evaluation of human peptide/histidine transporter 1 (hPHT1) in transiently transfected COS-7 cells.
Eur J Pharm Sci, 27 (5): 533-42. [PMID:16289537]
3. Conigrave AD, Quinn SJ, Brown EM. (2000)
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
Proc. Natl. Acad. Sci. U.S.A., 97 (9): 4814-9. [PMID:10781086]
4. Fei YJ, Sugawara M, Nakanishi T, Huang W, Wang H, Prasad PD, Leibach FH, Ganapathy V. (2000)
Primary structure, genomic organization, and functional and electrogenic characteristics of human system N 1, a Na+- and H+-coupled glutamine transporter.
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5. Fiermonte G, Dolce V, David L, Santorelli FM, Dionisi-Vici C, Palmieri F, Walker JE. (2003)
The mitochondrial ornithine transporter. Bacterial expression, reconstitution, functional characterization, and tissue distribution of two human isoforms.
J. Biol. Chem., 278 (35): 32778-83. [PMID:12807890]
6. Hatanaka T, Huang W, Ling R, Prasad PD, Sugawara M, Leibach FH, Ganapathy V. (2001)
Evidence for the transport of neutral as well as cationic amino acids by ATA3, a novel and liver-specific subtype of amino acid transport system A.
Biochim. Biophys. Acta, 1510 (1-2): 10-7. [PMID:11342143]
7. Hägglund MG, Sreedharan S, Nilsson VC, Shaik JH, Almkvist IM, Bäcklin S, Wrange O, Fredriksson R. (2011)
Identification of SLC38A7 (SNAT7) protein as a glutamine transporter expressed in neurons.
J. Biol. Chem., 286 (23): 20500-11. [PMID:21511949]
8. Kobayashi T, Shimabukuro-Demoto S, Yoshida-Sugitani R, Furuyama-Tanaka K, Karyu H, Sugiura Y, Shimizu Y, Hosaka T, Goto M, Kato N et al.. (2014)
The histidine transporter SLC15A4 coordinates mTOR-dependent inflammatory responses and pathogenic antibody production.
Immunity, 41 (3): 375-88. [PMID:25238095]
9. Mandal A, Pal D, Mitra AK. (2016)
Circumvention of P-gp and MRP2 mediated efflux of lopinavir by a histidine based dipeptide prodrug.
Int J Pharm, 512 (1): 49-60. [PMID:27543355]
10. Nakanishi T, Sugawara M, Huang W, Martindale RG, Leibach FH, Ganapathy ME, Prasad PD, Ganapathy V. (2001)
Structure, function, and tissue expression pattern of human SN2, a subtype of the amino acid transport system N.
Biochem. Biophys. Res. Commun., 281 (5): 1343-8. [PMID:11243884]
11. Sakata K, Yamashita T, Maeda M, Moriyama Y, Shimada S, Tohyama M. (2001)
Cloning of a lymphatic peptide/histidine transporter.
Biochem. J., 356 (Pt 1): 53-60. [PMID:11336635]
12. Temperini C, Scozzafava A, Vullo D, Supuran CT. (2006)
Carbonic anhydrase activators. Activation of isozymes I, II, IV, VA, VII, and XIV with l- and d-histidine and crystallographic analysis of their adducts with isoform II: engineering proton-transfer processes within the active site of an enzyme.
Chemistry, 12 (27): 7057-66. [PMID:16807956]
13. Vanslambrouck JM, Bröer A, Thavyogarajah T, Holst J, Bailey CG, Bröer S, Rasko JE. (2010)
Renal imino acid and glycine transport system ontogeny and involvement in developmental iminoglycinuria.
Biochem. J., 428 (3): 397-407. [PMID:20377526]
14. Wang XX, Hu Y, Keep RF, Toyama-Sorimachi N, Smith DE. (2017)
A novel role for PHT1 in the disposition of l-histidine in brain: In vitro slice and in vivo pharmacokinetic studies in wildtype and Pht1 null mice.
Biochem. Pharmacol., 124: 94-102. [PMID:27845049]
15. Yamashita T, Shimada S, Guo W, Sato K, Kohmura E, Hayakawa T, Takagi T, Tohyama M. (1997)
Cloning and functional expression of a brain peptide/histidine transporter.
J. Biol. Chem., 272 (15): 10205-11. [PMID:9092568]
16. Zaia KA, Reimer RJ. (2009)
Synaptic Vesicle Protein NTT4/XT1 (SLC6A17) Catalyzes Na+-coupled Neutral Amino Acid Transport.
J. Biol. Chem., 284 (13): 8439-48. [PMID:19147495]