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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-03-17 15:16:48 UTC

Update Date

2023-07-07 20:53:58 UTC

HMDB ID

HMDB0011756

Secondary Accession Numbers

HMDB11756

Metabolite Identification

Common Name

N-Acetyl-Leu

Description

N-Acetyl-L-leucine or N-Acetylleucine, 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-Acetylleucine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylleucine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-lecuine. 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-acetylleucine 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 leucine can also occur. In particular, N-Acetylleucine can be biosynthesized from L-leucine and acetyl-CoA by the enzyme leucine N-acetyltransferase (EC 2.3.1.66). Excessive amounts N-acetyl amino acids including N-acetylleucine (as well as N-acetylglycine, N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, N-acetylmethionine and smaller amounts of N-acetylthreonine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylleucine 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      26.620 -17.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.080 -17.566   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.310 -18.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.310 -16.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.770 -16.232   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.000 -17.566   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      22.770 -18.899   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      20.460 -17.566   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      22.000 -14.898   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      22.770 -13.565   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.000 -12.232   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      24.310 -13.565   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0011756
HETATM    1  C1  UNL     1       3.178  -1.062   1.865  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.405  -1.007   0.593  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.787  -1.835  -0.304  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.322  -0.111   0.368  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.657  -0.147  -0.884  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.752  -0.610  -0.912  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.756   0.137  -0.132  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.537   0.205   1.345  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.100  -0.583  -0.328  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.782   1.217  -1.510  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.400   2.117  -0.895  1.00  0.00           O  
HETATM   12  O3  UNL     1       0.202   1.406  -2.745  1.00  0.00           O  
HETATM   13  H1  UNL     1       4.174  -0.623   1.676  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.669  -0.533   2.687  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.317  -2.111   2.133  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.100   0.526   1.165  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.220  -0.884  -1.546  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.806  -1.711  -0.664  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.061  -0.591  -2.000  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.862   1.178  -0.528  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.890  -0.639   1.706  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.119   1.168   1.685  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.507   0.113   1.918  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.638  -0.168  -1.203  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.717  -0.525   0.588  1.00  0.00           H  
HETATM   26  H14 UNL     1      -2.894  -1.660  -0.505  1.00  0.00           H  
HETATM   27  H15 UNL     1       0.425   0.856  -3.572  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3    4
CONECT    4    5   16
CONECT    5    6   10   17
CONECT    6    7   18   19
CONECT    7    8    9   20
CONECT    8   21   22   23
CONECT    9   24   25   26
CONECT   10   11   11   12
CONECT   12   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acetylleucine	ChEBI
N-Acetyl-leu	ChEBI
Lasdol	MeSH
Tanganil	MeSH
Acetyl-DL-leucine	MeSH
Acetyl-L-leucine	HMDB
N-Acetyl-L-leucin	HMDB
N-Acetyl-L-leucine	HMDB
N-Acetylleucine	ChEBI

Chemical Formula

C₈H₁₅NO₃

Average Molecular Weight

173.2096

Monoisotopic Molecular Weight

173.105193351

IUPAC Name

(2S)-2-acetamido-4-methylpentanoic acid

Traditional Name

N-acetyl-leu

CAS Registry Number

1188-21-2

SMILES

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

InChI Identifier

InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t7-/m0/s1

InChI Key

WXNXCEHXYPACJF-ZETCQYMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine 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

Leucine and derivatives

Alternative Parents

Substituents

Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Branched fatty acid
Methyl-branched fatty acid
Fatty acid
Fatty acyl
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acetyl-L-amino acid (CHEBI:17786 )
L-leucine derivative (CHEBI:17786 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Source

Endogenous

Endogenous (HMDB: HMDB0011756)

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	8.1 mg/mL at 25 °C	Not Available
LogP	0.79	MEYLAN,WM & HOWARD,PH (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	140.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002071

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.9 g/L	ALOGPS
logP	0.78	ALOGPS
logP	0.49	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.61 m³·mol⁻¹	ChemAxon
Polarizability	18.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	142.357	31661259
DarkChem	[M-H]-	139.913	31661259
DeepCCS	[M+H]+	139.082	30932474
DeepCCS	[M-H]-	135.255	30932474
DeepCCS	[M-2H]-	172.728	30932474
DeepCCS	[M+Na]+	148.266	30932474
AllCCS	[M+H]+	140.7	32859911
AllCCS	[M+H-H2O]+	136.9	32859911
AllCCS	[M+NH4]+	144.2	32859911
AllCCS	[M+Na]+	145.2	32859911
AllCCS	[M-H]-	138.6	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	142.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylleucine	CC(C)C[C@H](NC(C)=O)C(O)=O	2353.8	Standard polar	33892256
N-Acetylleucine	CC(C)C[C@H](NC(C)=O)C(O)=O	1396.3	Standard non polar	33892256
N-Acetylleucine	CC(C)C[C@H](NC(C)=O)C(O)=O	1458.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylleucine,1TMS,isomer #1	CC(=O)N[C@@H](CC(C)C)C(=O)O[Si](C)(C)C	1425.4	Semi standard non polar	33892256
N-Acetylleucine,1TMS,isomer #2	CC(=O)N([C@@H](CC(C)C)C(=O)O)[Si](C)(C)C	1439.3	Semi standard non polar	33892256
N-Acetylleucine,2TMS,isomer #1	CC(=O)N([C@@H](CC(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1465.5	Semi standard non polar	33892256
N-Acetylleucine,2TMS,isomer #1	CC(=O)N([C@@H](CC(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1480.6	Standard non polar	33892256
N-Acetylleucine,2TMS,isomer #1	CC(=O)N([C@@H](CC(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1599.6	Standard polar	33892256
N-Acetylleucine,1TBDMS,isomer #1	CC(=O)N[C@@H](CC(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1657.4	Semi standard non polar	33892256
N-Acetylleucine,1TBDMS,isomer #2	CC(=O)N([C@@H](CC(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	1669.7	Semi standard non polar	33892256
N-Acetylleucine,2TBDMS,isomer #1	CC(=O)N([C@@H](CC(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1917.3	Semi standard non polar	33892256
N-Acetylleucine,2TBDMS,isomer #1	CC(=O)N([C@@H](CC(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1918.0	Standard non polar	33892256
N-Acetylleucine,2TBDMS,isomer #1	CC(=O)N([C@@H](CC(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1917.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu EI-B (Non-derivatized)	splash10-000i-6910000000-4832dfe7d6d4267d6e52	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu GC-EI-TOF (Non-derivatized)	splash10-002r-6910000000-84a47055ce5d856cbf9e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu GC-EI-TOF (Non-derivatized)	splash10-000i-7900000000-a0b6f75cf19418bded48	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu GC-EI-TOF (Non-derivatized)	splash10-0udi-0930000000-f27350f13ea712c9ca5c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu EI-B (Non-derivatized)	splash10-000i-6910000000-4832dfe7d6d4267d6e52	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu GC-EI-TOF (Non-derivatized)	splash10-002r-6910000000-84a47055ce5d856cbf9e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu GC-EI-TOF (Non-derivatized)	splash10-000i-7900000000-a0b6f75cf19418bded48	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - N-Acetyl-Leu GC-EI-TOF (Non-derivatized)	splash10-0udi-0930000000-f27350f13ea712c9ca5c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-Leu GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-ad6cdad728e4ab043e38	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-Leu GC-MS (1 TMS) - 70eV, Positive	splash10-010c-9300000000-ce0116c32d01ba5b766c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-Leu GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-Leu 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-Acetyl-Leu LC-ESI-QQ , negative-QTOF	splash10-00di-0900000000-467d952fc32fb0bb8af3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , negative-QTOF	splash10-001i-0900000000-fdb9099645f68121fb32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , negative-QTOF	splash10-001i-0900000000-a148fb266810cd2b9b3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , negative-QTOF	splash10-001i-5900000000-7b9d62f34c7b6fc2ae4e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-e5aaef8422c96f086069	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu , negative-QTOF	splash10-001i-0900000000-18d02e7d5844662f8a29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , positive-QTOF	splash10-0adi-0900000000-cedccfd459609718718d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , positive-QTOF	splash10-000i-9600000000-065fa320d009e309b319	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , positive-QTOF	splash10-000i-9100000000-ba88448ef117528982de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , positive-QTOF	splash10-000f-9000000000-20376a815d3377cfbd83	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-dcb83ed9d2b4eb878bc0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 30V, Negative-QTOF	splash10-001i-7900000000-884cd757a0bb6c943f1e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 10V, Positive-QTOF	splash10-000i-9300000000-996f7e233ed61eb9f1db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 30V, Positive-QTOF	splash10-0006-9000000000-c02e8a0ef249a980c557	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 20V, Negative-QTOF	splash10-001i-1900000000-7a33d6856c0373f3c0cc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 30V, Positive-QTOF	splash10-0006-9000000000-277408d6cc88e96641c7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 0V, Positive-QTOF	splash10-00dr-2900000000-57e7bf1dcfd4157f8a83	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 40V, Negative-QTOF	splash10-05mo-9000000000-1f318b754db7ea1fa9ef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Acetyl-Leu 0V, Positive-QTOF	splash10-00gr-2900000000-da6f6595c0d7eaa983e3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-Leu 10V, Positive-QTOF	splash10-00e9-1900000000-a7e7f933b2155a59555c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-Leu 20V, Positive-QTOF	splash10-001r-9800000000-f0cf22f10972ee728fe4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-Leu 40V, Positive-QTOF	splash10-0a4i-9100000000-598d0e4c77dbf9794ee1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-Leu 10V, Negative-QTOF	splash10-00di-1900000000-15626e7c74e213c4fb23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-Leu 20V, Negative-QTOF	splash10-05ai-4900000000-5a450ad57fd8bd9d9f69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetyl-Leu 40V, Negative-QTOF	splash10-052f-9200000000-f0db45895855a83c4418	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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
Saliva
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	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	0.54 (0.34-1.12) 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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	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

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028426

KNApSAcK ID

Not Available

Chemspider ID

64075

KEGG Compound ID

C02710

BioCyc ID

CPD-433

BiGG ID

Not Available

Wikipedia Link

Acetylleucine

METLIN ID

Not Available

PubChem Compound

70912

PDB ID

Not Available

ChEBI ID

17786

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)

Download (PDF)

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 ]
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
Tsutsui H, Maeda T, Min JZ, Inagaki S, Higashi T, Kagawa Y, Toyo'oka T: Biomarker discovery in biological specimens (plasma, hair, liver and kidney) of diabetic mice based upon metabolite profiling using ultra-performance liquid chromatography with electrospray ionization time-of-flight mass spectrometry. Clin Chim Acta. 2011 May 12;412(11-12):861-72. doi: 10.1016/j.cca.2010.12.023. Epub 2010 Dec 24. [PubMed:21185819 ]
Jellum E, Horn L, Thoresen O, Kvittingen EA, Stokke O: Urinary excretion of N-acetyl amino acids in patients with some inborn errors of amino acid metabolism. Scand J Clin Lab Invest Suppl. 1986;184:21-6. [PubMed:3473611 ]
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-Acetyl-Leu (HMDB0011756)

MOL for HMDB0011756 (N-Acetyl-Leu)

3D MOL for HMDB0011756 (N-Acetyl-Leu)

3D SDF for HMDB0011756 (N-Acetyl-Leu)

3D-SDF for HMDB0011756 (N-Acetyl-Leu)

PDB for HMDB0011756 (N-Acetyl-Leu)

3D PDB for HMDB0011756 (N-Acetyl-Leu)

SMILES for HMDB0011756 (N-Acetyl-Leu)

INCHI for HMDB0011756 (N-Acetyl-Leu)

Structure for HMDB0011756 (N-Acetyl-Leu)

3D Structure for HMDB0011756 (N-Acetyl-Leu)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra