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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2014-04-16 18:03:49 UTC

Update Date

2023-05-30 20:55:51 UTC

HMDB ID

HMDB0061684

Secondary Accession Numbers

HMDB61684

Metabolite Identification

Common Name

N-Acetylisoleucine

Description

N-Acetyl-L-isoleucine or N-Acetylisoleucine, 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-Acetylisoleucine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylisoleucine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-isolecuine. 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-acetylisoleucine 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 isoleucine can also occur. In particular, N-Acetylisoleucine can be biosynthesized from L-isoleucine and acetyl-CoA by the enzyme leucine/isoleucine N-acetyltransferase (EC 2.3.1.66). Excessive amounts N-acetyl amino acids including N-acetylisoleucine (as well as N-acetylglycine, N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, N-acetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, 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-acetylisoleucine 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                                 08-MAR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-19         0                                  
HETATM    1  C   UNK     0    8667.3338665.899   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.0008665.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.6678665.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.3338665.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8666.0008663.587   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8667.3338667.436   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8668.6688668.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.0008667.436   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8668.6688669.746   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8668.6688665.127   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8670.0008665.899   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8668.6688663.587   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0061684
HETATM    1  C1  UNL     1      -3.233   0.054   0.451  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.006  -0.797   0.144  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.814   0.102  -0.041  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.004   1.077  -1.175  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.467  -0.657  -0.139  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.532   0.321  -0.314  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.556   0.498   0.651  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.605   1.511   0.405  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.592  -0.186   1.710  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.495  -1.695  -1.180  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.366  -1.682  -2.095  1.00  0.00           O  
HETATM   12  O3  UNL     1      -0.421  -2.734  -1.212  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.108  -0.247  -0.161  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.479  -0.087   1.537  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.046   1.129   0.308  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.253  -1.355  -0.798  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.799  -1.485   0.983  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.746   0.716   0.906  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.739   2.111  -0.923  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.350   0.750  -2.021  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.082   0.992  -1.484  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.650  -1.168   0.837  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.506   0.888  -1.187  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.660   1.725  -0.680  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.620   1.147   0.699  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.387   2.477   0.920  1.00  0.00           H  
HETATM   27  H15 UNL     1      -0.355  -3.408  -0.439  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4    5   18
CONECT    4   19   20   21
CONECT    5    6   10   22
CONECT    6    7   23
CONECT    7    8    9    9
CONECT    8   24   25   26
CONECT   10   11   11   12
CONECT   12   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Acetyl-L-isoleucine	HMDB
N-Acetylisoleucine	HMDB

Chemical Formula

C₈H₁₅NO₃

Average Molecular Weight

173.212

Monoisotopic Molecular Weight

173.105193347

IUPAC Name

(2S,3S)-2-acetamido-3-methylpentanoic acid

Traditional Name

(2S,3S)-2-acetamido-3-methylpentanoic acid

CAS Registry Number

3077-46-1

SMILES

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

InChI Identifier

InChI=1S/C8H15NO3/c1-4-5(2)7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)/t5-,7-/m0/s1

InChI Key

JDTWZSUNGHMMJM-FSPLSTOPSA-N

Chemical Taxonomy

Description

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

Isoleucine and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

L-isoleucine derivative (CHEBI:21555 )
N-acetyl-L-amino acid (CHEBI:21555 )
N-acetylisoleucine (CHEBI:21555 )

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: 27275383)

Source

Exogenous

Exogenous (HMDB: HMDB0061684)

Process

Not Available

Role

Biological role

Waste product (PMID: 35448883)

Physical Properties

State

Not Available

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	25.2 g/L	ALOGPS
logP	0.77	ALOGPS
logP	0.57	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-1.6	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	43.54 m³·mol⁻¹	ChemAxon
Polarizability	18.24 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
DeepCCS	[M+H]+	139.288	30932474
DeepCCS	[M-H]-	136.911	30932474
DeepCCS	[M-2H]-	171.712	30932474
DeepCCS	[M+Na]+	146.749	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.06 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7902 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.36 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1417.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	299.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	100.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	341.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	423.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	757.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	336.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1105.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	263.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	375.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	223.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	101.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylisoleucine	CC[C@H](C)[C@H](NC(C)=O)C(O)=O	2253.2	Standard polar	33892256
N-Acetylisoleucine	CC[C@H](C)[C@H](NC(C)=O)C(O)=O	1459.3	Standard non polar	33892256
N-Acetylisoleucine	CC[C@H](C)[C@H](NC(C)=O)C(O)=O	1466.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylisoleucine,1TMS,isomer #1	CC[C@H](C)[C@H](NC(C)=O)C(=O)O[Si](C)(C)C	1435.7	Semi standard non polar	33892256
N-Acetylisoleucine,1TMS,isomer #2	CC[C@H](C)[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C	1450.6	Semi standard non polar	33892256
N-Acetylisoleucine,2TMS,isomer #1	CC[C@H](C)[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	1467.1	Semi standard non polar	33892256
N-Acetylisoleucine,2TMS,isomer #1	CC[C@H](C)[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	1474.6	Standard non polar	33892256
N-Acetylisoleucine,2TMS,isomer #1	CC[C@H](C)[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	1620.7	Standard polar	33892256
N-Acetylisoleucine,1TBDMS,isomer #1	CC[C@H](C)[C@H](NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C	1668.7	Semi standard non polar	33892256
N-Acetylisoleucine,1TBDMS,isomer #2	CC[C@H](C)[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C	1668.2	Semi standard non polar	33892256
N-Acetylisoleucine,2TBDMS,isomer #1	CC[C@H](C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	1923.7	Semi standard non polar	33892256
N-Acetylisoleucine,2TBDMS,isomer #1	CC[C@H](C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	1904.4	Standard non polar	33892256
N-Acetylisoleucine,2TBDMS,isomer #1	CC[C@H](C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	1926.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylisoleucine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylisoleucine 10V, Negative-QTOF	splash10-001i-0900000000-609e437cf2ac060af44f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylisoleucine 20V, Negative-QTOF	splash10-001i-3900000000-9b51475a5da15f8eaf25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylisoleucine 40V, Negative-QTOF	splash10-0006-9000000000-c26bfff8c0984b37883d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylisoleucine 10V, Positive-QTOF	splash10-004i-2900000000-d5828facfca52464b957	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylisoleucine 20V, Positive-QTOF	splash10-08gi-7900000000-c80b9454ed64aa64141c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylisoleucine 40V, Positive-QTOF	splash10-0006-9000000000-5bfdf3e204a666e2e1c9	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart 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	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
Urine	Detected and Quantified	0.47 (0.32-0.74) 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	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 ]
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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5397969

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7036275

PDB ID

Not Available

ChEBI ID

21555

Food Biomarker Ontology

Not Available

VMH ID

ACILE_L

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 ]
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-Acetylisoleucine (HMDB0061684)

MOL for HMDB0061684 (N-Acetylisoleucine)

3D MOL for HMDB0061684 (N-Acetylisoleucine)

3D SDF for HMDB0061684 (N-Acetylisoleucine)

3D-SDF for HMDB0061684 (N-Acetylisoleucine)

PDB for HMDB0061684 (N-Acetylisoleucine)

3D PDB for HMDB0061684 (N-Acetylisoleucine)

SMILES for HMDB0061684 (N-Acetylisoleucine)

INCHI for HMDB0061684 (N-Acetylisoleucine)

Structure for HMDB0061684 (N-Acetylisoleucine)

3D Structure for HMDB0061684 (N-Acetylisoleucine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra