Drug Information

General Information
Drug ID
DR00005
Drug Name
L-glutamic acid
Synonyms
(2S)-2-Aminopentanedioic acid; (S)-(+)-Glutamic acid; (S)-2-Aminopentanedioic acid; (S)-Glutamic acid; 1-Aminopropane-1,3-dicarboxylic acid; 2-Aminoglutaric acid; 2-aminopentanedioic acid; A-Aminoglutaric acid; A-Glutamic acid; Acide glutamique; Acide glutamique [INN-French]; Acido glutamico; Acido glutamico [INN-Spanish]; Acidum glutamicum; Acidum glutamicum [INN-Latin]; Acidum glutaminicum; Aciglut; Alpha-Aminoglutaric acid (VAN); Alpha-Glutamic acid; Alpha-L-Glutamic acid polymer; Alpha-aminoglutaric acid; D-Glutamiensuur; E 620; GLUTAMIC ACID; Glu; Glusate; Glut; Glutacid; Glutamate; Glutamic Acid (L-glutamic acid); Glutamic Acid [USAN:INN]; Glutamic acid (H-3); Glutamic acid (VAN); Glutamic acid polymer; Glutamic acid, L-(7CI,8CI); Glutamic acid, L-, peptides; Glutamicol; Glutamidex; Glutaminic acid; Glutaminic acid (VAN); Glutaminol; Glutaton; Gulutamine; Gulutamine (USP); H-Glu-OH; L-(+)-glutamic acid; L-2-Aminoglutaric acid; L-Glutamic acid (9CI); L-Glutamic acid (JAN); L-Glutamic acid hydrochloride; L-Glutamic acid, homopolymer; L-Glutamic acid, homopolymer (9CI); L-Glutaminic acid; L-Glutaminsaeure; L-a-Aminoglutaric acid; L-alpha-Aminoglutaric acid; L-glu; L-glutamate; POLYGLUTAMIC ACID; Poly(alpha-L-glutamic acid); Poly-L-glutamate; Sodium Glutamate (L-glutamic Acid)
Drug Type
Small molecular drug
Indication Indigestion [ICD11:DD90] Approved [1]
Schizophrenia [ICD11:6A20] Approved [1]
Therapeutic Class
Dietary supplement
Structure
3D MOL 2D MOL
Formula
C5H9NO4
Canonical SMILES
C(CC(=O)O)C(C(=O)O)N
InChI
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
InChIKey
WHUUTDBJXJRKMK-VKHMYHEASA-N
CAS Number
CAS 56-86-0
Pharmaceutical Properties Molecular Weight 147.13 Topological Polar Surface Area 101
Heavy Atom Count 10 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
XLogP
-3.7
PubChem CID
33032
PubChem SID
10527679 ,11110117 ,11110137 ,11113412 ,11528393 ,11538992 ,14710662 ,14716143 ,14719817 ,14719819 ,15297417 ,16918839 ,17404216 ,17422134 ,17422293 ,24846358 ,24872908 ,24895052 ,24895223 ,24895340 ,24901609 ,24902257 ,26746616 ,26751652 ,3327 ,34674977 ,46391925 ,627126 ,7847075 ,7887923 ,7979423 ,8023666 ,8026291 ,8026293 ,8143737 ,8172949 ,820094 ,820617 ,822192 ,822517 ,822724 ,822932 ,823119 ,825074 ,826975 ,828108 ,841758 ,854467 ,854468 ,854502
ChEBI ID
ChEBI:16015
TTD Drug ID
D00ENY
DT(s) Transporting This Drug AGT1 Transporter Info Sodium-independent aspartate/glutamate transporter 1 Substrate [2]
ARALAR1 Transporter Info Calcium-binding mitochondrial carrier protein Aralar1 Substrate [3]
ARALAR2 Transporter Info Calcium-binding mitochondrial carrier protein Aralar2 Substrate [4]
EAAT1 Transporter Info Excitatory amino acid transporter 1 Substrate [5]
EAAT2 Transporter Info Excitatory amino acid transporter 2 Substrate [6]
EAAT3 Transporter Info Excitatory amino acid transporter 3 Substrate [7]
EAAT4 Transporter Info Excitatory amino acid transporter 4 Substrate [5]
EAAT5 Transporter Info Excitatory amino acid transporter 5 Substrate [5]
GC1 Transporter Info Mitochondrial glutamate carrier 1 Substrate [8]
GC2 Transporter Info Mitochondrial glutamate carrier 2 Substrate [9]
OAT4 Transporter Info Organic anion transporter 4 Substrate [10]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [11]
OCTL3 Transporter Info Organic cation transporter-like 3 Substrate [12]
SLC38A10 Transporter Info Putative sodium-coupled neutral amino acid transporter 10 Substrate [13]
SLC38A8 Transporter Info Putative sodium-coupled neutral amino acid transporter 8 Substrate [14]
SLC7A11 Transporter Info Cystine/glutamate transporter Substrate [15]
VGLUT1 Transporter Info Vesicular glutamate transporter 1 Substrate [16]
VGLUT2 Transporter Info Vesicular glutamate transporter 2 Substrate [16]
VGLUT3 Transporter Info Vesicular glutamate transporter 3 Substrate [16]
Drug-Transporter Activity Data
Drug-Transporter Activity Data EAAT2 Transporter Info Km =21 microM Human embryonic kidney cells (HEK293)-EAAT2 [17]
EAAT2 Transporter Info Km =21 microM Human embryonic kidney cells (HEK293)-EAAT2 [18]
EAAT3 Transporter Info Km =9.9 microM Human embryonic kidney cells (HEK293)-EAAT3 [18]
EAAT3 Transporter Info Km =25 microM Human embryonic kidney cells (HEK293)-EAAT3 [17]
References
1 L-glutamic acid was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Novel cystine transporter in renal proximal tubule identified as a missing partner of cystinuria-related plasma membrane protein rBAT/SLC3A1. Proc Natl Acad Sci U S A. 2016 Jan 19;113(3):775-80.
3 Mitochondrial Aspartate/Glutamate Carrier SLC25A12 and Autism Spectrum Disorder: a Meta-Analysis. Mol Neurobiol. 2016 Apr;53(3):1579-1588.
4 Epigenetic upregulation and functional role of the mitochondrial aspartate/glutamate carrier isoform 1 in hepatocellular carcinoma. Biochim Biophys Acta Mol Basis Dis. 2019 Jan;1865(1):38-47.
5 The SLC1 high-affinity glutamate and neutral amino acid transporter family. Mol Aspects Med. 2013 Apr-Jun;34(2-3):108-20.
6 EAAT2 (GLT-1; slc1a2) glutamate transporters reconstituted in liposomes argues against heteroexchange being substantially faster than net uptake. J Neurosci. 2014 Oct 1;34(40):13472-85.
7 Loss-of-function mutations in the glutamate transporter SLC1A1 cause human dicarboxylic aminoaciduria. J Clin Invest. 2011 Jan;121(1):446-53.
8 Impaired mitochondrial glutamate transport in autosomal recessive neonatal myoclonic epilepsy. Am J Hum Genet. 2005 Feb;76(2):334-9.
9 The ABCs of membrane transporters in health and disease (SLC series): Introduction. Molecular Aspects of Medicine, 2013, 34(2-3):95-107. (GeneName=SLC25A18)
10 The role of the intracellular glutamate gradient in driving organic anion transporter function.
11 The Transporter Classification Database (TCDB): recent advances. Nucleic Acids Res. 2016 Jan 4;44(D1):D372-9. (ID: 2.A.60.1.20)
12 SLC22A13 catalyses unidirectional efflux of aspartate and glutamate at the basolateral membrane of type A intercalated cells in the renal collecting duct. Biochem J. 2014 Jan 15;457(2):243-51.
13 The neuronal and astrocytic protein SLC38A10 transports glutamine, glutamate, and aspartate, suggesting a role in neurotransmission. FEBS Open Bio. 2017 Apr 26;7(6):730-746.
14 Structural modeling of a novel SLC38A8 mutation that causes foveal hypoplasia. Mol Genet Genomic Med. 2017 Feb 26;5(3):202-209.
15 The glutamate/cystine antiporter SLC7A11/xCT enhances cancer cell dependency on glucose by exporting glutamate. J Biol Chem. 2017 Aug 25;292(34):14240-14249.
16 Molecular pharmacology of glutamate transporters, EAATs and VGLUTs. Brain Res Brain Res Rev. 2004 Jul;45(3):250-65.
17 Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3. J Med Chem. 2005 Dec 15;48(25):7980-92.
18 Stereoselective chemoenzymatic synthesis of the four stereoisomers of l-2-(2-carboxycyclobutyl)glycine and pharmacological characterization at human excitatory amino acid transporter subtypes 1, 2, and 3. J Med Chem. 2006 Nov 2;49(22):6532-8.

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