Hmdb loader

Showing metabocard for N-Acetyl-L-alanine (HMDB0000766)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:59 UTC
HMDB IDHMDB0000766
Secondary Accession Numbers
  • HMDB00766
Metabolite Identification
Common NameN-Acetyl-L-alanine
DescriptionN-Acetyl-L-alanine or N-Acetylalanine, 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-Acetyl-L-alanine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-alpha-Acetyl-L-alanine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-alanine. 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’s (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-Acetyl-L-alanine is a product of the enzyme known as ribosomal alanine N-acetyltransferase (EC 2.3.1.128) which catalyzes the transfer of the acetyl group of acetyl CoA to proteins bearing an N-terminal alanine. N-acetylated amino acids, such as N-acetylalanine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). Excessive amounts N-acetyl amino acids can be detected in the urine with individuals with aminoacylase I deficiency, a genetic disorder (PMID: 16465618 ). These include N-acetylalanine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylglycine, N-acetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine. 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-acetylalanine, are classified as uremic toxins (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 ). N-Acetyl-L-alanine has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1676999709
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000766 (N-Acetyl-L-alanine)

N-Acetyl-L-alanine.mol
  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  1  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000766 (N-Acetyl-L-alanine)

HMDB0000766
     RDKit          3D
N-Acetyl-L-alanine
 18 17  0  0  0  0  0  0  0  0999 V2000
    2.9569    0.0181   -0.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6523   -0.5081   -0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -1.6818    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152    0.3381   -0.1055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7674   -0.1708    0.3448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3896    0.7191    1.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -0.1398   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    0.2621   -1.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842   -0.5954   -0.6140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996   -0.7849   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344    0.4999    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.7789   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    1.3020   -0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669   -1.2014    0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569    1.1212    2.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    1.5735    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975    0.1247    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576   -0.5428   -1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  1
  6 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
Download

3D SDF for HMDB0000766 (N-Acetyl-L-alanine)

N-Acetyl-L-alanine.mol
  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  1  0  0  0
  1  5  2  0  0  0  0
  1  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000766

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](NC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1

> <INCHI_KEY>
KTHDTJVBEPMMGL-VKHMYHEASA-N

> <FORMULA>
C5H9NO3

> <MOLECULAR_WEIGHT>
131.1299

> <EXACT_MASS>
131.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.501187655687254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamidopropanoic acid

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-0.7598647116666665

> <ALOGPS_LOGS>
-0.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.629254426140378

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.889227666212694

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9647201220572619

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
29.941100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acetylalanine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000766 (N-Acetyl-L-alanine)

HMDB0000766
     RDKit          3D
N-Acetyl-L-alanine
 18 17  0  0  0  0  0  0  0  0999 V2000
    2.9569    0.0181   -0.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6523   -0.5081   -0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201   -1.6818    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5152    0.3381   -0.1055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7674   -0.1708    0.3448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3896    0.7191    1.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837   -0.1398   -0.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    0.2621   -1.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842   -0.5954   -0.6140 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5996   -0.7849   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5344    0.4999    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.7789   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941    1.3020   -0.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669   -1.2014    0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569    1.1212    2.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    1.5735    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975    0.1247    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6576   -0.5428   -1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  1
  6 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
Download

PDB for HMDB0000766 (N-Acetyl-L-alanine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: N-Acetyl-L-alanine.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.667   0.385   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -1.925   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.001   1.925   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -3.334  -0.385   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.001  -1.925   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.334   0.385   0.000  0.00  0.00           C+0
CONECT    1    3    5    6                                                  
CONECT    2    3    7                                                       
CONECT    3    2    1    4                                                  
CONECT    4    3                                                            
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    8    9    2                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
Download

3D PDB for HMDB0000766 (N-Acetyl-L-alanine)

COMPND    HMDB0000766
HETATM    1  C1  UNL     1       2.957   0.018  -0.490  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.652  -0.508  -0.029  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.620  -1.682   0.408  1.00  0.00           O  
HETATM    4  N1  UNL     1       0.515   0.338  -0.106  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.767  -0.171   0.345  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.390   0.719   1.393  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.684  -0.140  -0.840  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.327   0.262  -1.959  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.984  -0.595  -0.614  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.600  -0.785  -0.908  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.534   0.500   0.324  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.773   0.779  -1.261  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.594   1.302  -0.475  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.667  -1.201   0.702  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.657   1.121   2.113  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.915   1.574   0.894  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.198   0.125   1.876  1.00  0.00           H  
HETATM   18  H9  UNL     1      -3.658  -0.543  -1.373  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    4
CONECT    4    5   13
CONECT    5    6    7   14
CONECT    6   15   16   17
CONECT    7    8    8    9
CONECT    9   18
END
Download

SMILES for HMDB0000766 (N-Acetyl-L-alanine)

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

INCHI for HMDB0000766 (N-Acetyl-L-alanine)

InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-2-(Acetylamino)propanoic acidChEBI
2-Acetamidopropionic acidChEBI
Ac-ala-OHChEBI
AcetylalanineChEBI
L-N-AcetylalanineChEBI
N-Acetyl-L-alpha-alanineChEBI
N-Acetyl-S-alanineChEBI
N-AcetylalanineChEBI
(S)-2-(Acetylamino)propanoateGenerator
2-AcetamidopropionateGenerator
N-Acetyl-L-a-alanineGenerator
N-Acetyl-L-α-alanineGenerator
(S)-(-)-N-AcetylalanineHMDB
(S)-N-AcetylalanineHMDB
Acetyl-L-alanineHMDB
N-Acetyl-(S)-alanineHMDB
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name(2S)-2-acetamidopropanoic acid
Traditional NameN-acetylalanine
CAS Registry Number97-69-8
SMILES
C[C@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1
InChI KeyKTHDTJVBEPMMGL-VKHMYHEASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Alanine or derivatives
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility43.6 g/LALOGPS
logP-0.53ALOGPS
logP-0.76ChemAxon
logS-0.48ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.94 m³·mol⁻¹ChemAxon
Polarizability12.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.36731661259
DarkChem[M-H]-126.60831661259
AllCCS[M+H]+131.95632859911
AllCCS[M-H]-126.62232859911
DeepCCS[M+H]+124.47430932474
DeepCCS[M-H]-120.77430932474
DeepCCS[M-2H]-158.01630932474
DeepCCS[M+Na]+133.19530932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+135.732859911
AllCCS[M+Na]+136.832859911
AllCCS[M-H]-126.632859911
AllCCS[M+Na-2H]-129.432859911
AllCCS[M+HCOO]-132.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.1.84 minutes32390414
Predicted by Siyang on May 30, 20229.8042 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.14 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid180.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid995.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid336.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid63.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid193.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid58.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid252.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid299.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)265.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid629.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid137.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid824.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid201.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid200.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate646.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA277.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water270.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-alanineC[C@H](NC(C)=O)C(O)=O2051.9Standard polar33892256
N-Acetyl-L-alanineC[C@H](NC(C)=O)C(O)=O1166.3Standard non polar33892256
N-Acetyl-L-alanineC[C@H](NC(C)=O)C(O)=O1325.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl-L-alanine,1TMS,isomer #1CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C1245.3Semi standard non polar33892256
N-Acetyl-L-alanine,1TMS,isomer #2CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C1289.7Semi standard non polar33892256
N-Acetyl-L-alanine,2TMS,isomer #1CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1307.4Semi standard non polar33892256
N-Acetyl-L-alanine,2TMS,isomer #1CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1298.8Standard non polar33892256
N-Acetyl-L-alanine,2TMS,isomer #1CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1447.1Standard polar33892256
N-Acetyl-L-alanine,1TBDMS,isomer #1CC(=O)N[C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C1478.1Semi standard non polar33892256
N-Acetyl-L-alanine,1TBDMS,isomer #2CC(=O)N([C@@H](C)C(=O)O)[Si](C)(C)C(C)(C)C1536.9Semi standard non polar33892256
N-Acetyl-L-alanine,2TBDMS,isomer #1CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1768.2Semi standard non polar33892256
N-Acetyl-L-alanine,2TBDMS,isomer #1CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1760.6Standard non polar33892256
N-Acetyl-L-alanine,2TBDMS,isomer #1CC(=O)N([C@@H](C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1750.0Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified4.00 (1.75-8.27) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
  3. 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 ]
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDDB02518
Phenol Explorer Compound IDNot Available
FooDB IDFDB022231
KNApSAcK IDNot Available
Chemspider ID79449
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5733
PubChem Compound88064
PDB IDNot Available
ChEBI ID40992
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceVanzura, Jiri; Kasafirek, Evzen; Hrabalek, Alexandr; Vinsova, Jarmila; Krepelka, Jiri. Process for preparing highly pure N-acetyl-L- or -D-alanine. Czech. (1989), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]

Enzymes

Enzyme Details
1. Carbamoyl-phosphate synthase [ammonia], mitochondrial
General function:
Involved in catalytic activity
Specific function:
Involved in the urea cycle of ureotelic animals where the enzyme plays an important role in removing excess ammonia from the cell.
Gene Name:
CPS1
Uniprot ID:
P31327
Molecular weight:
165649.075
Enzyme Details
2. N-acetylglutamate synthase, mitochondrial
General function:
Involved in N-acetyltransferase activity
Specific function:
Plays a role in the regulation of ureagenesis by producing variable amounts of N-acetylglutamate (NAG), thus modulating carbamoylphosphate synthase I (CPSI) activity.
Gene Name:
NAGS
Uniprot ID:
Q8N159
Molecular weight:
58155.835