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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 20:36:33 UTC

Update Date

2023-05-30 20:55:57 UTC

HMDB ID

HMDB0006028

Secondary Accession Numbers

HMDB06028

Metabolite Identification

Common Name

N-Acetylasparagine

Description

N-Acetyl-L-asparagine or N-Acetylasparagine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylasparagine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylasparagine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-asparagine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT‚Äôs (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylasparagine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free asparagine can also occur. In particular, N-Acetylasparagine can be biosynthesized from L-asparagine and acetyl-CoA by the enzyme NAT1 or the arylamine acetyltransferase I (https://doi.org/10.1096/fasebj.31.1_supplement.821.8). Many N-acetylamino acids are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      25.814 -30.244   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.274 -30.244   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      23.504 -28.910   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      23.504 -31.577   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      24.274 -32.911   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.504 -34.245   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.964 -34.245   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      21.194 -35.578   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      21.194 -32.911   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      25.814 -32.911   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      26.584 -31.577   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.584 -34.245   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Acetyl-L-asparagine	MeSH
N-Acetylasparagine, (14)C-labeled	MeSH
N-Acetylasparagine, (D)-isomer	MeSH
N-Acetylasparagine, (D,L)-isomer	MeSH
AcAsn	HMDB
N2-Acetyl-L-asparagine	HMDB
(2S)-3-(C-Hydroxycarbonimidoyl)-2-[(1-hydroxyethylidene)amino]propanoate	Generator, HMDB
N-Acetylasparagine	MeSH

Chemical Formula

C₆H₁₀N₂O₄

Average Molecular Weight

174.1546

Monoisotopic Molecular Weight

174.064056818

IUPAC Name

(2S)-3-carbamoyl-2-acetamidopropanoic acid

Traditional Name

L-asparagine, N -acetyl-

CAS Registry Number

4033-40-3

SMILES

CC(=O)N[C@@H](CC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C6H10N2O4/c1-3(9)8-4(6(11)12)2-5(7)10/h4H,2H2,1H3,(H2,7,10)(H,8,9)(H,11,12)/t4-/m0/s1

InChI Key

HXFOXFJUNFFYMO-BYPYZUCNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Asparagine and derivatives

Alternative Parents

Substituents

Asparagine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Fatty amide
Fatty acyl
Fatty acid
Acetamide
Carboxamide group
Primary carboxylic acid amide
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Feces (PMID: 29808030)

Source

Endogenous

Endogenous (HMDB: HMDB0006028)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Biological role

Waste product (PMID: 35448883)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-2.60	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	137.87	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001753

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.8 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.2	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	37.8 m³·mol⁻¹	ChemAxon
Polarizability	15.8 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.071	31661259
DarkChem	[M-H]-	132.83	31661259
DeepCCS	[M+H]+	132.117	30932474
DeepCCS	[M-H]-	129.308	30932474
DeepCCS	[M-2H]-	165.551	30932474
DeepCCS	[M+Na]+	141.013	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	136.2	32859911
AllCCS	[M+NH4]+	143.5	32859911
AllCCS	[M+Na]+	144.5	32859911
AllCCS	[M-H]-	133.4	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	136.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylasparagine	CC(=O)N[C@@H](CC(N)=O)C(O)=O	2487.4	Standard polar	33892256
N-Acetylasparagine	CC(=O)N[C@@H](CC(N)=O)C(O)=O	1615.3	Standard non polar	33892256
N-Acetylasparagine	CC(=O)N[C@@H](CC(N)=O)C(O)=O	1944.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylasparagine,1TMS,isomer #1	CC(=O)N[C@@H](CC(N)=O)C(=O)O[Si](C)(C)C	1674.2	Semi standard non polar	33892256
N-Acetylasparagine,1TMS,isomer #2	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C)C(=O)O	1716.6	Semi standard non polar	33892256
N-Acetylasparagine,1TMS,isomer #3	CC(=O)N([C@@H](CC(N)=O)C(=O)O)[Si](C)(C)C	1745.3	Semi standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #1	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1799.0	Semi standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #1	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	1833.0	Standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #1	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C	2538.0	Standard polar	33892256
N-Acetylasparagine,2TMS,isomer #2	CC(=O)N([C@@H](CC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1759.3	Semi standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #2	CC(=O)N([C@@H](CC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1759.5	Standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #2	CC(=O)N([C@@H](CC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2716.8	Standard polar	33892256
N-Acetylasparagine,2TMS,isomer #3	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1806.1	Semi standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #3	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1893.7	Standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #3	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2456.8	Standard polar	33892256
N-Acetylasparagine,2TMS,isomer #4	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1884.0	Semi standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #4	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	1873.3	Standard non polar	33892256
N-Acetylasparagine,2TMS,isomer #4	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2823.5	Standard polar	33892256
N-Acetylasparagine,3TMS,isomer #1	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1825.3	Semi standard non polar	33892256
N-Acetylasparagine,3TMS,isomer #1	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1869.2	Standard non polar	33892256
N-Acetylasparagine,3TMS,isomer #1	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2125.8	Standard polar	33892256
N-Acetylasparagine,3TMS,isomer #2	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1927.2	Semi standard non polar	33892256
N-Acetylasparagine,3TMS,isomer #2	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	1884.0	Standard non polar	33892256
N-Acetylasparagine,3TMS,isomer #2	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2266.5	Standard polar	33892256
N-Acetylasparagine,3TMS,isomer #3	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1881.6	Semi standard non polar	33892256
N-Acetylasparagine,3TMS,isomer #3	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1932.9	Standard non polar	33892256
N-Acetylasparagine,3TMS,isomer #3	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2260.2	Standard polar	33892256
N-Acetylasparagine,4TMS,isomer #1	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1911.3	Semi standard non polar	33892256
N-Acetylasparagine,4TMS,isomer #1	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1954.8	Standard non polar	33892256
N-Acetylasparagine,4TMS,isomer #1	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2006.7	Standard polar	33892256
N-Acetylasparagine,1TBDMS,isomer #1	CC(=O)N[C@@H](CC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C	1933.0	Semi standard non polar	33892256
N-Acetylasparagine,1TBDMS,isomer #2	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O	1990.9	Semi standard non polar	33892256
N-Acetylasparagine,1TBDMS,isomer #3	CC(=O)N([C@@H](CC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C	1982.4	Semi standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #1	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2252.7	Semi standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #1	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2196.4	Standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #1	CC(=O)N[C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2543.3	Standard polar	33892256
N-Acetylasparagine,2TBDMS,isomer #2	CC(=O)N([C@@H](CC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2203.1	Semi standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #2	CC(=O)N([C@@H](CC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2170.7	Standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #2	CC(=O)N([C@@H](CC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2718.7	Standard polar	33892256
N-Acetylasparagine,2TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2271.1	Semi standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2234.3	Standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2512.8	Standard polar	33892256
N-Acetylasparagine,2TBDMS,isomer #4	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2348.0	Semi standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #4	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2251.6	Standard non polar	33892256
N-Acetylasparagine,2TBDMS,isomer #4	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	2676.4	Standard polar	33892256
N-Acetylasparagine,3TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2481.4	Semi standard non polar	33892256
N-Acetylasparagine,3TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2442.6	Standard non polar	33892256
N-Acetylasparagine,3TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2463.8	Standard polar	33892256
N-Acetylasparagine,3TBDMS,isomer #2	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2564.8	Semi standard non polar	33892256
N-Acetylasparagine,3TBDMS,isomer #2	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2473.3	Standard non polar	33892256
N-Acetylasparagine,3TBDMS,isomer #2	CC(=O)N[C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2506.7	Standard polar	33892256
N-Acetylasparagine,3TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2560.4	Semi standard non polar	33892256
N-Acetylasparagine,3TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2509.8	Standard non polar	33892256
N-Acetylasparagine,3TBDMS,isomer #3	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2515.4	Standard polar	33892256
N-Acetylasparagine,4TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2767.9	Semi standard non polar	33892256
N-Acetylasparagine,4TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2710.0	Standard non polar	33892256
N-Acetylasparagine,4TBDMS,isomer #1	CC(=O)N([C@@H](CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2461.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylasparagine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-b13eeaca2c25cbc9f456	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylasparagine GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-9420000000-604cb710b20d05a3f618	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylasparagine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine , positive-QTOF	splash10-053i-5900000000-fb6ca749095a56c9fa37	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 20V, Negative-QTOF	splash10-0a4i-9100000000-ef6824e63e48346ecf8e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 40V, Positive-QTOF	splash10-0006-9000000000-3dbf3137475280540961	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 20V, Positive-QTOF	splash10-0079-9100000000-a4dad880a6e4b4d6ac75	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 40V, Negative-QTOF	splash10-002f-9200000000-d35b92f28a03db1fd982	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 40V, Negative-QTOF	splash10-052f-9000000000-a5eac1a53960cd1ad60f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 10V, Negative-QTOF	splash10-0a4i-5900000000-77b89c142f9423474561	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 30V, Negative-QTOF	splash10-052o-9200000000-7e4f917fad36828834b2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 20V, Negative-QTOF	splash10-0a4l-9300000000-646c48424a1ee9c66039	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 35V, Negative-QTOF	splash10-0a4i-4900000000-650cda900598467adb02	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 10V, Negative-QTOF	splash10-0a4i-8900000000-c31a1a62d30990efa330	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 30V, Positive-QTOF	splash10-006x-9000000000-b6d08a6edb5bb0eaf145	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 10V, Positive-QTOF	splash10-0019-9600000000-0d65a0348f56236d70a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 30V, Positive-QTOF	splash10-0006-9000000000-d233e6273ffebdf206e4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 0V, Positive-QTOF	splash10-054k-0900000000-a2758ee224d2782967f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 10V, Positive-QTOF	splash10-01q3-9300000000-c18cfead66066718c9e0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 0V, Positive-QTOF	splash10-056s-0900000000-18425d848f34e94f4523	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 10V, Positive-QTOF	splash10-0019-9500000000-5ba169884f12213ef686	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetylasparagine 20V, Positive-QTOF	splash10-007c-9000000000-bf8a80be7a8d980ac568	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylasparagine 10V, Positive-QTOF	splash10-0a6r-0900000000-8c813627aa0389206361	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylasparagine 20V, Positive-QTOF	splash10-0cg0-3900000000-47d73a3d4010aae93586	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylasparagine 40V, Positive-QTOF	splash10-0079-9100000000-d7309e40e7520eb65fff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylasparagine 10V, Negative-QTOF	splash10-00di-0900000000-ef08da45f088072696bd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylasparagine 20V, Negative-QTOF	splash10-06rx-6900000000-202909feace18174ddf3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylasparagine 40V, Negative-QTOF	splash10-0006-9000000000-4f702074e5ce12c24940	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	2.69 (2.05-4.40) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023807

KNApSAcK ID

Not Available

Chemspider ID

90090

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99715

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]

Showing metabocard for N-Acetylasparagine (HMDB0006028)

MOL for HMDB0006028 (N-Acetylasparagine)

3D MOL for HMDB0006028 (N-Acetylasparagine)

3D SDF for HMDB0006028 (N-Acetylasparagine)

3D-SDF for HMDB0006028 (N-Acetylasparagine)

PDB for HMDB0006028 (N-Acetylasparagine)

3D PDB for HMDB0006028 (N-Acetylasparagine)

SMILES for HMDB0006028 (N-Acetylasparagine)

INCHI for HMDB0006028 (N-Acetylasparagine)

Structure for HMDB0006028 (N-Acetylasparagine)

3D Structure for HMDB0006028 (N-Acetylasparagine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra