L-α-Aminoadipic acid - ≥98% , CAS No.1118-90-7

CAS: 1118-90-7 Cat. No.: A100535 Molecular Weight: 161.16 Beilstein Registry Number: 1724348 EC Number: 601-134-8

GRADE & PURITY ≥98%

Synonyms

L-2-Aminoadipic Acid | (S)-2-Aminohexanedioic Acid | L-Homoglutamic acid

Storage

Room temperature

Shipped In

Normal

Overview

L-α-Aminoadipic acid, a gliotoxic analogue of glutamate, has been shown to competitively inhibit the transport protein of D-[3H]-aspartate. Experiments have reported that this compound also causes a reduction in ischemic glutamate release in murine hippocampal slices in vitro. Additional research suggests that L-α-Aminoadipic acid inhibits astrocyte culture Kynurenic acid synthesis which demonstrates the ability to modulate neuronal degeneration. L-α-Aminoadipic acid is a inhibitor of GluR and Gl Syn.
An inhibitor of ischemic glutamate release

Specifications

Synonyms

L-2-Aminoadipic Acid | (S)-2-Aminohexanedioic Acid | L-Homoglutamic acid

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488186685
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186685
• Canonical Smiles: C(CC(C(=O)O)N)CC(=O)O
• IUPAC Name: (2S)-2-aminohexanedioic acid
• InChIKey: OYIFNHCXNCRBQI-BYPYZUCNSA-N
• INCHI: 1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1
• Isomeric SMILES: C(C[C@@H](C(=O)O)N)CC(=O)O
• WGK Germany: 3
• Molecular Weight: 161.16
• Beilstein: 1724348
• Reaxy-Rn: 1724349
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1724349&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 L-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: L-alpha-amino acids
• Alternative Parents: Medium-chain fatty acids Amino fatty acids Dicarboxylic acids and derivatives Amino acids Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: L-alpha-amino acid - Medium-chain fatty acid - Amino fatty acid - Dicarboxylic acid or derivatives - Fatty acid - Fatty acyl - Amino acid - Carboxylic acid - Organopnictogen compound - Organic nitrogen compound - Amine - Organic oxygen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
• External Descriptors: 2-aminoadipic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM4 Tchem Metabotropic glutamate receptor 4 (2320 Activities)

Discover Target: GRM4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM6 Tchem Metabotropic glutamate receptor 6 (361 Activities)

Discover Target: GRM6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM1 Tchem Metabotropic glutamate receptor 1 (2309 Activities)

Discover Target: GRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRM5 Tchem Metabotropic glutamate receptor 5 (5733 Activities)

Discover Target: GRM5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

THP-1 (11052 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BLM Tchem Bloom syndrome protein (4248 Activities)

Discover Target: BLM

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Associated Targets(non-human)

Cruzipain (33337 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grm2 Metabotropic glutamate receptor 2 (1326 Activities)

Discover Target: Grm2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pfk 6-phospho-1-fructokinase (7870 Activities)

Discover Target: pfk

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in 1N HCl (50 mg/ml), and water (slightly).
• Specific Rotation[α]: 25 ° (C=5, 6mol/L HCl)
• Melt Point(°C): 203-205°C
• Molecular Weight: 161.160 g/mol
• XLogP3: -3.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 161.069 Da
• Monoisotopic Mass: 161.069 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 157.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Li Wendi, Li Shanshan, Cao Zhenju, Sun Yi, Qiu Wei, Jia Mei, Su Ming.  (2022)  Exploration of the amino acid metabolic signature in anthracycline-induced cardiotoxicity using an optimized targeted metabolomics approach based on UPLC-MS/MS.  NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY,  395  (10): (1209-1224).  [PMID:35879430] [10.1007/s00210-022-02271-x]

2. Lili Zhang, Wen Duan, Yan Huang, Yuyu Zhang, Baoguo Sun, Dandan Pu, Yizhuang Tang, Chao Liu.  (2020)  Sensory taste properties of chicken (Hy-Line brown) soup as prepared with five different parts of the chicken.  INTERNATIONAL JOURNAL OF FOOD PROPERTIES,      [PMID:] [10.1080/10942912.2020.1828455]

3. YuLing Yang, JiaNi Zhang, SiWen Wu, Yu Deng, ShiHan Wang, Li Xie, XiaoPeng Li, Li Yang.  (2024)  Exosome/antimicrobial peptide laden hydrogel wound dressings promote scarless wound healing through miR-21-5p-mediated multiple functions.  BIOMATERIALS,      [PMID:38581764] [10.1016/j.biomaterials.2024.122558]

4. Shan Huang, Wenqian Zhang, Bo Li, Guixin Li, Wei Ni, Yi Fang, Fuxiang Wei, Qi Xiao.  (2025)  Mn-doped carbon dots-based fluorescent-colorimetric dual-mode probes for selective and sensitive detection of Cr(VI) ions and l-ascorbic acid via smartphone-integrated analytical platform.  ANALYTICA CHIMICA ACTA,      [PMID:40915727] [10.1016/j.aca.2025.344493]