L-phenylalanine   Click here for help

GtoPdb Ligand ID: 3313

Abbreviated name: L-Phe
PDB Ligand
Compound class: Metabolite
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 63.32
Molecular weight 165.08
XLogP -1.38
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NC(C(=O)O)Cc1ccccc1
Isomeric SMILES N[C@H](C(=O)O)Cc1ccccc1
InChI InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1
InChI Key COLNVLDHVKWLRT-QMMMGPOBSA-N
References
1. Babu E, Kanai Y, Chairoungdua A, Kim DK, Iribe Y, Tangtrongsup S, Jutabha P, Li Y, Ahmed N, Sakamoto S et al.. (2003)
Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters.
J Biol Chem, 278 (44): 43838-45. [PMID:12930836]
2. Bröer S. (2006)
The SLC6 orphans are forming a family of amino acid transporters.
Neurochem Int, 48 (6-7): 559-67. [PMID:16540203]
3. Conigrave AD, Quinn SJ, Brown EM. (2000)
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
Proc Natl Acad Sci USA, 97 (9): 4814-9. [PMID:10781086]
4. 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]
5. Hatanaka T, Huang W, Wang H, Sugawara M, Prasad PD, Leibach FH, Ganapathy V. (2000)
Primary structure, functional characteristics and tissue expression pattern of human ATA2, a subtype of amino acid transport system A.
Biochim Biophys Acta, 1467 (1): 1-6. [PMID:10930503]
6. Isberg V, Andersen KB, Bisig C, Dietz GP, Bräuner-Osborne H, Gloriam DE. (2014)
Computer-aided discovery of aromatic l-α-amino acids as agonists of the orphan G protein-coupled receptor GPR139.
J Chem Inf Model, 54 (6): 1553-7. [PMID:24826842]
7. Liu C, Bonaventure P, Lee G, Nepomuceno D, Kuei C, Wu J, Li Q, Joseph V, Sutton SW, Eckert W et al.. (2015)
GPR139, an Orphan Receptor Highly Enriched in the Habenula and Septum, Is Activated by the Essential Amino Acids L-Tryptophan and L-Phenylalanine.
Mol Pharmacol, 88 (5): 911-25. [PMID:26349500]
8. Sloan JL, Mager S. (1999)
Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+).
J Biol Chem, 274 (34): 23740-5. [PMID:10446133]
9. 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]