Home > Compound List > Compound details
56-86-0 molecular structure
click picture or here to close

(2S)-2-aminopentanedioic acid

ChemBase ID: 28
Molecular Formular: C5H9NO4
Molecular Mass: 147.12926
Monoisotopic Mass: 147.05315777
SMILES and InChIs

SMILES:
OC(=O)[C@@H](N)CCC(=O)O
Canonical SMILES:
OC(=O)CC[C@@H](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

Cite this record

CBID:28 http://www.chembase.cn/molecule-28.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-aminopentanedioic acid
IUPAC Traditional name
L-glutamic acid
Brand Name
Aciglut
Glusate
Glutacid
Glutamicol
Glutamidex
Glutaminol
Glutaton
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-Glutamic acid
a-Aminoglutaric acid
L-(+)-Glutamic acid
L-a-Aminoglutaric acid
L-Glutamate
L-Glutaminic acid
Glutaminic acid
Glutamic acid
L-Glutamic Acid
L-(+)-Glutamic acid
L-2-Aminopentanedioic acid
L-Glutamic acid
Glu
L-GLUTAMIC ACID FREE ACID
(S)-2-Amino-1,5-pentanedioic Acid
Glusate
Glutacid
Glutamicol
Glutamidex
Glutaminol
Glutaton
Acidum glutamicum
L-2-Aminoglutaric acid
2-AMinopentanedioic acid
L-α-Aminoglutaric Acid
α-Glutamic Acid
(S)-2-AMinopentanedioic acid
H-Glu-OH
(S)-2-氨基戊二酸
L-谷氨酸
谷氨酸
CAS Number
56-86-0
617-65-2
EC Number
200-293-7
MDL Number
MFCD00002634
Beilstein Number
1723801
Merck Index
144469
PubChem SID
24895223
24895340
46505816
160963491
24846358
24895052
24901609
24872908
PubChem CID
33032
FEMA ID
3285
E Number
E620

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.8777773  H Acceptors
H Donor LogD (pH = 5.5) -4.4458017 
LogD (pH = 7.4) -6.180975  Log P -3.241447 
Molar Refractivity 31.2877 cm3 Polarizability 12.69048 Å3
Polar Surface Area 100.62 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -3.54  LOG S -0.26 
Solubility (Water) 8.06e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble1 M at 20 °C, clear, colorless expand Show data source
1 M HCl: soluble100 mg/mL expand Show data source
8.57 mg/mL at 25 oC [BULL,HB et al. (1978)] expand Show data source
Water expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
189-192°C dec. expand Show data source
199-201°C expand Show data source
205 °C (dec.)(lit.) expand Show data source
224-225°C expand Show data source
Density
1.525 expand Show data source
1.538 g/ml @ 20°C expand Show data source
Optical Rotation
[α]20/D +31.5±1.0°, c = 5% in 5 M HCl expand Show data source
[α]20/D +31.5°, c = 2 in 5 M HCl expand Show data source
[α]20/D +32°, c = 10 in 2 M HCl expand Show data source
+31 (c=5 in 5N HCl) expand Show data source
Absorption Wavelength
λ: 260 nm Amax: 0.1 expand Show data source
λ: 280 nm Amax: 0.1 expand Show data source
Hydrophobicity(logP)
-3.3 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
LZ9700000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
20-25°C expand Show data source
Regulation Compliance
FCC expand Show data source
FDA 21 CFR (172.320) expand Show data source
FDA 21 CFR (182.1045) expand Show data source
Gene Information
human ... CCR2(1231), GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK5(2901), GRIN2B(2904), GRM2(2912), SLC1A1(6505), SLC1A2(6506)rat ... Gria1(50592), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grm1(24414), Grm2(24415), Grm3(24416), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672), Slc1a2(29482) expand Show data source
human ... CCR2(1231), GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK2(2898), GRIK3(2899), GRIK5(2901), GRIN2B(2904), GRM2(2912), SLC1A1(6505), SLC1A2(6506)rat ... Gria1(50592), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grm1(24414), Grm2(24415), Grm3(24416), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672), Slc1a2(29482) expand Show data source
Purity
≥98.5% expand Show data source
≥99% (TLC) expand Show data source
≥99.0% expand Show data source
≥99.0% (NT) expand Show data source
≥99.5% (NT) expand Show data source
97% expand Show data source
98% expand Show data source
98.5-100.5% expand Show data source
99% expand Show data source
99+% expand Show data source
99-100% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
JIS special grade expand Show data source
Kosher expand Show data source
NI expand Show data source
Ph Eur expand Show data source
PharmaGrade expand Show data source
ReagentPlus® expand Show data source
TraceCERT® expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets EP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.05% (as SO4) expand Show data source
≤0.1% (as SO4) expand Show data source
Impurities
≤0.5% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤200 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤200 mg/kg expand Show data source
NH4+: ≤100 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤150 mg/kg expand Show data source
sulfate (SO42-): ≤200 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.05% loss on drying, 20 °C (HV) expand Show data source
≤0.1% loss on drying, 110 °C expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
λ
1 M in 1 M HCl expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Product Line
BioUltra expand Show data source
Linear Formula
HO2CCH2CH2CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals TRC TRC
DrugBank - DB00142 external link
Item Information
Drug Groups approved; nutraceutical
Description A peptide that is a homopolymer of glutamic acid. [PubChem]
Indication Considered to be nature's "Brain food" by improving mental capacities; helps speed the healing of ulcers; gives a "lift" from fatigue; helps control alcoholism, schizophrenia and the craving for sugar.
Pharmacology In addition to being one of the building blocks in protein synthesis, it is the most widespread neurotransmitter in brain function, as an excitatory neurotransmitter and as a precursor for the synthesis of GABA in GABAergic neurons.
Toxicity Glutamate causes neuronal damage and eventual cell death, particularly when NMDA receptors are activated, High dosages of glutamic acid may include symptoms such as headaches and neurological problems.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Absorbed from the lumen of the small intestine into the enterocytes.Absorption is efficient and occurs by an active transport mechanism.
References
Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. [Pubmed]
Okumoto S, Looger LL, Micheva KD, Reimer RJ, Smith SJ, Frommer WB: Detection of glutamate release from neurons by genetically encoded surface-displayed FRET nanosensors. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8740-5. Epub 2005 Jun 6. [Pubmed]
Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. [Pubmed]
Corrie JE, DeSantis A, Katayama Y, Khodakhah K, Messenger JB, Ogden DC, Trentham DR: Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a 'caged' L-glutamate. J Physiol. 1993 Jun;465:1-8. [Pubmed]
Augustin H, Grosjean Y, Chen K, Sheng Q, Featherstone DE: Nonvesicular release of glutamate by glial xCT transporters suppresses glutamate receptor clustering in vivo. J Neurosci. 2007 Jan 3;27(1):111-23. [Pubmed]
External Links
Wikipedia
Sigma Aldrich - G8415 external link
Biochem/physiol Actions
Glutamic acid, or glutamate, the salt form of glutamic acid, functions as a neurotransmitter. Glutamic acid also plays a key role in many metabolic pathways. It is converted to α-ketoglutarate, a key component of the TCA cycle, and a precursor for the biosynthesis of nucleic acids and certain amino acids. In cells, glutamine is converted to glutamate by the enzyme glutaminase.
一种兴奋性氨基酸神经递质,为谷氨酸盐受体所有亚型(代谢型红藻氨酸、NMDA 和 AMPA)的激动剂。
包装
10 mg in autosmp vl
Sigma Aldrich - G1251 external link
Biochem/physiol Actions
一种兴奋性氨基酸神经递质,为谷氨酸盐受体所有亚型(代谢型红藻氨酸、NMDA 和 AMPA)的激动剂。
包装
1 kg in poly bottle
100, 500 g in poly bottle
5 kg in poly drum
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC
Sigma Aldrich - 128430 external link
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Packaging
1 kg in poly bottle
100 g in poly bottle
Sigma Aldrich - 49449 external link
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Other Notes
Lesion-sparing agent, has excitotoxic properties1; May function as precipitating agent in protein crystallization2; Growth requirement of various microorganisms3
Sigma Aldrich - 49450 external link
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Sigma Aldrich - G5667 external link
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - 09581 external link
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Sigma Aldrich - 12-0880 external link
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Sigma Aldrich - 95436 external link
Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - W328502 external link
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10, 25 kg in fiber drum
MP Biomedicals - 02101793 external link
Free Acid
Purity: 99-100%
Crystalline
MP Biomedicals - 02194676 external link
Free Acid
Cell Culture Reagent
Purity: 99-100%
Crystalline
Toronto Research Chemicals - G596960 external link
A non-essential amino acid. Its salt form (glutamate) is an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory. It is also a key molecule in cellular metabolism.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • For use as a chiral building-block in the synthesis of the (S)-isomer of -butyrolactone-4-carboxylic acid, see: Org. Synth. Coll., 7, 99 (1990):
  • • For the differential protection of the ɑ-carboxyl group of N-protected glutamic acid by reaction with formaldehyde to form the cyclic 5-oxazolidinone, see: Synthesis, 542 (1989).
  • • McEntee, W., et al.: Psychopharmacology, 111, 391 (1993)
  • • Manev, H., et al.: Mol. Pharmacol., 36, 106 (1993)
  • • Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. Pubmed
  • • Okumoto S, Looger LL, Micheva KD, Reimer RJ, Smith SJ, Frommer WB: Detection of glutamate release from neurons by genetically encoded surface-displayed FRET nanosensors. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8740-5. Epub 2005 Jun 6. Pubmed
  • • Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. Pubmed
  • • Corrie JE, DeSantis A, Katayama Y, Khodakhah K, Messenger JB, Ogden DC, Trentham DR: Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a 'caged' L-glutamate. J Physiol. 1993 Jun;465:1-8. Pubmed
  • • Augustin H, Grosjean Y, Chen K, Sheng Q, Featherstone DE: Nonvesicular release of glutamate by glial xCT transporters suppresses glutamate receptor clustering in vivo. J Neurosci. 2007 Jan 3;27(1):111-23. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle