Basic information
- CAS
1118-90-7- Standard SMILES
N[C@@H](CCCC(=O)O)C(=O)O- InChIKey
OYIFNHCXNCRBQI-BYPYZUCNSA-N- Molecular formula
- C6H11NO4
- Average molar mass
- 161.16 g/mol
- Monoisotopic mass
- 161.06880783
Overview
L-2-aminoadipic acid is the L-enantiomer of 2-aminoadipic acid. It has a role as an Escherichia coli metabolite and a human metabolite. It is functionally related to an adipic acid. It is a conjugate acid of a L-2-aminoadipate(2-) and a L-2-aminoadipate(1-). It is an enantiomer of a D-2-aminoadipic acid.
Names & identifiers
- Preferred name
- L-2-Aminoadipic Acid
- IUPAC
- (2S)-2-aminohexanedioic acid
- English name
- L-2-Aminoadipic acid
- Molecular formula
- C6H11NO4
- Molecular weight
- 161.16
Names & synonyms
L-2-Aminoadipic acid(S)-2-aminohexanedioic acid(2S)-2-aminohexanedioic acidhexanedioic acid, 2-amino-, (2S)-2-Aminoadipic acid, L-88ZH74L7SRALHA-AMINOADIPATECHEBI:37023HEXANEDIOIC ACID, 2-AMINO-, L-RefChem:794410601-134-81118-90-7
Show more names
AADL-α-Aminoadipic AcidHOMOGLUTAMIC ACIDL-Aad-OHα-Aminoadipic acidH-2-AAD-OH(S)-2-Amin
(S)-2-Aminoadipic acidL-alpha-Aminoadipic acidL-alpha-AminoadipateL-2-Aminoadipateh-aad-ohL-Homoglutamic acidMFCD00002636Aminoadipate
Database identifiers
- CAS
1118-90-7- PubChem CID
- 92136
- DTXSID
DTXSID801017096- ChEMBL
CHEMBL88804- ChEBI
CHEBI:37023- UNII
- 88ZH74L7SR
Properties
Computed structural properties
- XLogP
- -3.1
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 157
Experimental & physicochemical properties
Solubility2.2 mg/mL
Melting Point196 - 198 °C
Physical DescriptionSolid
Collision Cross Section
142.23 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
130.8 Ų [M-H]-
Physicochemical properties
- Melting point
- 203 · 203-205 °C (dec.)(lit.)
- alpha
- 22 · 22 º (c=2, 5 N HCl 25 ºC)
- Boiling point
- 287.44 °C · 287.44°C (rough estimate)
- Density
- 1.3482 · 1.3482 (rough estimate)
- refractive index
- 1.423 · 1.4230 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- 1 N · 1N HCl: 10 mg/ml; PBS (pH 7.2): 0.5 mg/ml
- form
- Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Health EffectsChronically high levels of aminoadipic acid are associated with at least 2 inborn errors of metabolism including: : 2-aminoadipic and 2-oxoadipic aciduria.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29224999
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications
UsesAn inhibitor of ischemic glutamate release
UsesL-2-Aminoadipic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.
General DescriptionL-2-Aminoadipic acid/α-aminoadipate is a gliotoxin and is a structural analog of glutamine. It is generated by the catabolism of lysine saccharopine (SAC)/pipecolic acid (PIP) pathways.
Upstream & downstream products
Upstream raw materials
Related reactions
4 records
Compound notes
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