| Common Name |
N-Alpha-acetyllysine
| Description |
N-Alpha-acetyllysine is a N-acetylated amino acid. It is a normal constituent of human urine with concentrations in normal samples too small to allow its routine detection; however, it has been found at increased levels in the urine of a patient with aminoacylase I deficiency. (PMID 16274666 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
6-amino-L-2-AcetamidohexanoateHMDB
6-amino-L-2-Acetamidohexanoic acidHMDB
AcetyllysineHMDB
N-a-Acetyl-L-lysineHMDB
N-a-AcetyllysineHMDB
N-Acetyl poly-L-lysineHMDB
N-Acetyl-L-lysineHMDB
N-alpha-Acetyl-L-lysineHMDB
N2-Acetyl-L-lysineHMDB
N2-AcetyllysineHMDB
N-Acetyl polylysineMeSH
| Chemical Formlia |
C8H16N2O3
| Average Molecliar Weight |
188.2242
| Monoisotopic Molecliar Weight |
188.116092388
| IUPAC Name |
6-amino-2-acetamidohexanoic acid
| Traditional Name |
6-amino-2-acetamidohexanoic acid
| CAS Registry Number |
1946-82-3
| SMILES |
CC(=O)NC(CCCCN)C(O)=O
| InChI Identifier |
InChI=1S/C8H16N2O3/c1-6(11)10-7(8(12)13)4-2-3-5-9/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)
| InChI Key |
VEYYWZRYIYDQJM-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
N-acyl-alpha amino acids
| Alternative Parents |
Medium-chain fatty acids
Amino fatty acids
Acetamides
Secondary carboxylic acid amides
Amino acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organopnictogen compounds
Organic oxides
Monoalkylamines
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
N-acyl-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Detected but not Quantified
| Origin |
Endogenous
| Biofunction |
Protein synthesis, amino acid biosynthesis
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point256 – 258 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility16.1 mg/mLALOGPS
logP-2.5ALOGPS
logP-3.2ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity47.25 m3·mol-1ChemAxon
Polarizability19.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted GC-MS |
Predicted GC-MS Spectrum – GC-MSNot Available
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-003i-1900000000-1bb977fd5835c87c7d01View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9200000000-08d9b5954a220181ea5fView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-9404d66c59d266164c23View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| 1D NMR |
1H NMR SpectrumNot Available
| 1D NMR |
13C NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Feces
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
FecesDetected but not Quantified Not SpecifiedBoth
Normal
25486321
details
FecesDetected but not Quantified Adlit (>18 years old)FemaleNormal
26709303
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022051
| KNApSAcK ID |
Not Available
| Chemspider ID |
167134
| KEGG Compound ID |
C12989
| BioCyc ID |
N-ACETYL-L-LYSINE
| BiGG ID |
Not Available
| Wikipedia Link |
Acetyllysine
| NuGOwiki Link |
HMDB00446
| Metagene Link |
HMDB00446
| METLIN ID |
5435
| PubChem Compound |
192590
| PDB ID |
Not Available
| ChEBI ID |
35704
Product: Oleanolic acid derivative 2
References |
| Synthesis Reference |
Akagi, Aru; Soejima, Yasuhiro; Izumiya, Nobuo. Facile syntheses of e-acyl-L-lysines and abnormal optical rotations of a-acyl-L-lysines. Kyushu Sangyo Daigaku Kogakubu Kenkyu Hokoku (1992), 29 119-24. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Van Coster RN, Gerlo EA, Giardina TG, Engelke UF, Smet JE, De Praeter CM, Meersschaut VA, De Meirleir LJ, Seneca SH, Devreese B, Leroy JG, Herga S, Perrier JP, Wevers RA, Lissens W: Aminoacylase I deficiency: a novel inborn error of metabolism. Biochem Biophys Res Commun. 2005 Dec 23;338(3):1322-6. Epub 2005 Nov 2. [PubMed:16274666 ]
|
PMID: 22420341