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56-86-0 分子结构
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(2S)-2-aminopentanedioic acid

ChemBase编号:28
分子式:C5H9NO4
平均质量:147.12926
单一同位素质量:147.05315777
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-2-aminopentanedioic acid
IUPAC传统名
L-glutamic acid
商标名
Aciglut
Glusate
Glutacid
Glutamicol
Glutamidex
Glutaminol
Glutaton
别名
(S)-2-氨基戊二酸
L-谷氨酸
谷氨酸
(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-2-Aminopentanedioic acid
L-(+)-Glutamic acid
L-Glutamic acid
Glu
L-GLUTAMIC ACID FREE ACID
Acidum glutamicum
(S)-2-Amino-1,5-pentanedioic Acid
Glusate
Glutacid
Glutamicol
Glutamidex
Glutaminol
Glutaton
L-α-Aminoglutaric Acid
α-Glutamic Acid
L-2-Aminoglutaric acid
H-Glu-OH
2-AMinopentanedioic acid
(S)-2-AMinopentanedioic acid
CAS号
56-86-0
617-65-2
EC号
200-293-7
MDL号
MFCD00002634
Beilstein号
1723801
默克索引号
144469
PubChem SID
24872908
24895340
46505816
24901609
24895223
160963491
24846358
24895052
PubChem CID
33032
FEMA编号
3285
E编码
E620

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 1.8777773  质子受体
质子供体 LogD (pH = 5.5) -4.4458017 
LogD (pH = 7.4) -6.180975  Log P -3.241447 
摩尔折射率 31.2877 cm3 极化性 12.69048 Å3
极化表面积 100.62 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -3.54  LOG S -0.26 
溶解度 8.06e+01 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
1 M HCl: soluble1 M at 20 °C, clear, colorless expand 查看数据来源
1 M HCl: soluble100 mg/mL expand 查看数据来源
8.57 mg/mL at 25 oC [BULL,HB et al. (1978)] expand 查看数据来源
Water expand 查看数据来源
外观
powder expand 查看数据来源
White Solid expand 查看数据来源
熔点
189-192°C dec. expand 查看数据来源
199-201°C expand 查看数据来源
205 °C (dec.)(lit.) expand 查看数据来源
224-225°C expand 查看数据来源
密度
1.525 expand 查看数据来源
1.538 g/ml @ 20°C expand 查看数据来源
比旋光度
[α]20/D +31.5±1.0°, c = 5% in 5 M HCl expand 查看数据来源
[α]20/D +31.5°, c = 2 in 5 M HCl expand 查看数据来源
[α]20/D +32°, c = 10 in 2 M HCl expand 查看数据来源
+31 (c=5 in 5N HCl) expand 查看数据来源
紫外吸收波长
λ: 260 nm Amax: 0.1 expand 查看数据来源
λ: 280 nm Amax: 0.1 expand 查看数据来源
疏水性(logP)
-3.3 expand 查看数据来源
保存条件
Refrigerator expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
LZ9700000 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
1 expand 查看数据来源
TSCA收录
expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
20-25°C expand 查看数据来源
Regulation Compliance
FCC expand 查看数据来源
FDA 21 CFR (172.320) expand 查看数据来源
FDA 21 CFR (182.1045) expand 查看数据来源
相关基因信息
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 查看数据来源
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 查看数据来源
纯度
≥98.5% expand 查看数据来源
≥99% (TLC) expand 查看数据来源
≥99.0% expand 查看数据来源
≥99.0% (NT) expand 查看数据来源
≥99.5% (NT) expand 查看数据来源
97% expand 查看数据来源
98% expand 查看数据来源
98.5-100.5% expand 查看数据来源
99% expand 查看数据来源
99+% expand 查看数据来源
99-100% expand 查看数据来源
级别
certified reference material expand 查看数据来源
EP expand 查看数据来源
JIS special grade expand 查看数据来源
Kosher expand 查看数据来源
NI expand 查看数据来源
Ph Eur expand 查看数据来源
PharmaGrade expand 查看数据来源
ReagentPlus® expand 查看数据来源
TraceCERT® expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
适用性
meets EP testing specifications expand 查看数据来源
suitable for cell culture expand 查看数据来源
suitable for manufacturing use expand 查看数据来源
燃烧残渣
≤0.05% (as SO4) expand 查看数据来源
≤0.1% (as SO4) expand 查看数据来源
杂质
≤0.5% foreign amino acids expand 查看数据来源
endotoxin, tested expand 查看数据来源
insoluble matter, passes filter test expand 查看数据来源
痕量阳离子
Al: ≤5 mg/kg expand 查看数据来源
Ba: ≤5 mg/kg expand 查看数据来源
Bi: ≤5 mg/kg expand 查看数据来源
Ca: ≤200 mg/kg expand 查看数据来源
Cd: ≤5 mg/kg expand 查看数据来源
Co: ≤5 mg/kg expand 查看数据来源
Cr: ≤5 mg/kg expand 查看数据来源
Cu: ≤5 mg/kg expand 查看数据来源
Fe: ≤5 mg/kg expand 查看数据来源
K: ≤50 mg/kg expand 查看数据来源
Li: ≤5 mg/kg expand 查看数据来源
Mg: ≤5 mg/kg expand 查看数据来源
Mn: ≤5 mg/kg expand 查看数据来源
Mo: ≤5 mg/kg expand 查看数据来源
Na: ≤200 mg/kg expand 查看数据来源
NH4+: ≤100 mg/kg expand 查看数据来源
Ni: ≤5 mg/kg expand 查看数据来源
Pb: ≤5 mg/kg expand 查看数据来源
Sr: ≤5 mg/kg expand 查看数据来源
Zn: ≤5 mg/kg expand 查看数据来源
痕量阴离子
chloride (Cl-): ≤100 mg/kg expand 查看数据来源
sulfate (SO42-): ≤150 mg/kg expand 查看数据来源
sulfate (SO42-): ≤200 mg/kg expand 查看数据来源
生物来源
from non-animal source expand 查看数据来源
干燥失重
≤0.05% loss on drying, 20 °C (HV) expand 查看数据来源
≤0.1% loss on drying, 110 °C expand 查看数据来源
产品质量级别
GMP-COMPENDIA expand 查看数据来源
λ
1 M in 1 M HCl expand 查看数据来源
药典
testing & handling conforms to Pharmacopeia expand 查看数据来源
产品线
BioUltra expand 查看数据来源
线性分子式
HO2CCH2CH2CH(NH2)CO2H expand 查看数据来源

详细说明

详细说明

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 -  128430 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 g in poly bottle
Sigma Aldrich -  G5667 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
根据 cGMP 制造和包装
Sigma Aldrich -  49450 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。
Sigma Aldrich -  09581 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。
Sigma Aldrich -  12-0880 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。
Sigma Aldrich -  W328502 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
1 sample in glass bottle
5, 10, 25 kg in fiber drum
Sigma Aldrich -  49449 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。
Other Notes
Lesion-sparing agent, has excitotoxic properties1; May function as precipitating agent in protein crystallization2; Growth requirement of various microorganisms3
Sigma Aldrich -  95436 external link
Analysis Note
该有证标准物质 (CRM) 根据 ISO/IEC 17025 和 ISO 指南 34 生产和认证。该有证标准物质可溯源到 NIST 标准参考物质。
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。
General description
证书上给出了含不确定度的认证含量(定量 NMR 法测定)和有效期。 证书下载:http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC
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
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.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • 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
  • McEntee, W., et al.: Psychopharmacology, 111, 391 (1993)
  • Manev, H., et al.: Mol. Pharmacol., 36, 106 (1993)
  • 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).
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专利

专利

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