Np mrd loader

Showing NP-Card for N-Acetyl-L-alanine (NP0000354)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:27 UTC
NP-MRD IDNP0000354
Secondary Accession NumbersNone
Natural Product 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000354 (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 NP0000354 (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 NP0000354 (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>
NP0000354

> <DATABASE_NAME>
NP-MRD

> <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 NP0000354 (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 NP0000354 (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 NP0000354 (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 NP0000354 (N-Acetyl-L-alanine)

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

INCHI for NP0000354 (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 JSmol
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 Mass131.1299 Da
Monoisotopic Mass131.05824 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-07-29View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vitis viniferaLOTUS Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0000766
DrugBank IDDB02518
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. Bruyneel C, Chandra AK, Uchimaru T, Zeegers-Huyskens T: Theoretical and experimental study of the vibrational spectrum of N-acetyl-L-alanine. Spectrochim Acta A Mol Biomol Spectrosc. 2000 Feb 15;56(3):591-602. doi: 10.1016/s1386-1425(99)00258-9. [PubMed:10794474 ]
  2. Yamaguchi H, Hirano T, Kiminami H, Taura D, Harada A: Asymmetric hydrogenation with antibody-achiral rhodium complex. Org Biomol Chem. 2006 Oct 7;4(19):3571-3. doi: 10.1039/b609242j. Epub 2006 Aug 25. [PubMed:16990931 ]
  3. Karakawa WW, Kane JA: Immunochemical analysis of a Smith-like antigen isolated from two human strains of Staphylococcus aureus. J Immunol. 1975 Aug;115(2):564-8. [PubMed:50368 ]