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Showing NP-Card for N-Acetylserine (NP0000867)

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Record Information
Version2.0
Created at2006-05-22 15:12:20 UTC
Updated at2024-09-03 04:22:28 UTC
NP-MRD IDNP0000867
Natural Product DOIhttps://doi.org/10.57994/2870
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetylserine
DescriptionN-acetyl-L-serine is an N-acetyl-L-amino acid in which the amino acid specified is L-serine. Metabolite observed in cancer metabolism. It has a role as a human metabolite. It is an acetyl-L-serine and a N-acetyl-L-amino acid. Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians,80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians, 80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. N-acetylated proteins are catabolized in the cytosol by the ATP-ubiquitin-dependent proteasomal pathway. Several types of aminoacylases can be distinguished on the basis of substrate specificity. Aminoacylase I (ACY1; EC 3.5.1.14), The most abundant type, is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. It is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that comprises 15 exons (OMIM 609924 ). Preferred substrates of ACY1 are aliphatic amino acids with a short-chain acyl moiety, especially N-acetyl-methionine. However, ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Functional aminoacylase I is crucial in the last step in this degradation as it catalyzes the hydrolysis of N-acetylated amino acids into acetate and the free amino acid. Although N-acetylation occurs in many metabolic pathways and N-acetylated metabolites are known to accumulate in several inborn errors, such as aminoacylase I deficiency. There are only a few reports on N-acetylated amino acids detected in urine. Identification of N-acetylated amino acids by routine GC-MS may be problematic for several reasons. The major problem is linked to the identification strategy itself. Identification of an unknown compound in mass spectrometry is usually based on comparison of its spectrum against a library of reference spectra (PMID: 16465618 , 16274666 , 17723438 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000867 (N-Acetylserine)


  Mrv1652304202019302D          

 10  9  0  0  0  0            999 V2000
 9984.3765 9984.8046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9984.3765 9983.9809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9985.0910 9983.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8065 9983.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.0910 9982.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6623 9985.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.9481 9984.8046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6623 9986.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.0910 9985.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8065 9984.8046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000867 (N-Acetylserine)

HMDB0002931
     RDKit          3D
N-Acetylserine
 19 18  0  0  0  0  0  0  0  0999 V2000
    2.9536   -0.7812   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -0.2990   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482   -0.0306   -1.9940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327   -0.1376    0.2604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871    0.3298   -0.0065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7557   -0.6713    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266   -0.9839    1.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    1.5844    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379    2.0695    1.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495    2.2191    0.6302 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3247   -0.3327    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509   -1.8801   -0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317   -0.4417   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207   -0.3639    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    0.5205   -1.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7678   -0.2872    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -1.6168   -0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462   -1.8236    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839    2.9262    1.2730 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
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  6
  6 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0000867 (N-Acetylserine)


  Mrv1652304202019302D          

 10  9  0  0  0  0            999 V2000
 9984.3765 9984.8046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9984.3765 9983.9809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9985.0910 9983.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8065 9983.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.0910 9982.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6623 9985.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.9481 9984.8046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6623 9986.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.0910 9985.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8065 9984.8046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@@H](CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1

> <INCHI_KEY>
JJIHLJJYMXLCOY-BYPYZUCNSA-N

> <FORMULA>
C5H9NO4

> <MOLECULAR_WEIGHT>
147.1293

> <EXACT_MASS>
147.053157781

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.426636456180455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamido-3-hydroxypropanoic acid

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-1.8067746783333332

> <ALOGPS_LOGS>
-0.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.997357799160714

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.611000903600003

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0355996977858735

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
31.4848

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylserine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000867 (N-Acetylserine)

HMDB0002931
     RDKit          3D
N-Acetylserine
 19 18  0  0  0  0  0  0  0  0999 V2000
    2.9536   -0.7812   -0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -0.2990   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482   -0.0306   -1.9940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327   -0.1376    0.2604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6871    0.3298   -0.0065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7557   -0.6713    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266   -0.9839    1.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    1.5844    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0379    2.0695    1.4649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495    2.2191    0.6302 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3247   -0.3327    0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509   -1.8801   -0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317   -0.4417   -1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207   -0.3639    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109    0.5205   -1.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7678   -0.2872    0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -1.6168   -0.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462   -1.8236    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839    2.9262    1.2730 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
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  5 15  1  6
  6 16  1  0
  6 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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PDB for NP0000867 (N-Acetylserine)

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8637.5038638.302   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8637.5038636.764   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8638.8378635.993   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8640.1728636.764   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8638.8378634.453   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8636.1708639.072   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8634.8368638.302   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8636.1708640.611   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8638.8378639.072   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8640.1728638.302   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000867 (N-Acetylserine)

COMPND    HMDB0002931
HETATM    1  C1  UNL     1       2.954  -0.781  -0.575  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.568  -0.299  -0.793  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.248  -0.031  -1.994  1.00  0.00           O  
HETATM    4  N1  UNL     1       0.633  -0.138   0.260  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.687   0.330  -0.007  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.756  -0.671   0.380  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.727  -0.984   1.723  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.922   1.584   0.743  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.038   2.070   1.465  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.150   2.219   0.630  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.325  -0.333   0.373  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.951  -1.880  -0.516  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.632  -0.442  -1.383  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.921  -0.364   1.229  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.811   0.520  -1.102  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.768  -0.287   0.141  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.643  -1.617  -0.192  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.246  -1.824   1.848  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.484   2.926   1.273  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14
CONECT    5    6    8   15
CONECT    6    7   16   17
CONECT    7   18
CONECT    8    9    9   10
CONECT   10   19
END
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SMILES for NP0000867 (N-Acetylserine)

CC(=O)N[C@@H](CO)C(O)=O
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INCHI for NP0000867 (N-Acetylserine)

InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1
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View in JSmol
Synonyms
ValueSource
AcetylserineHMDB
N-Acetyl-L-serineHMDB
(2S)-2-Acetamido-3-hydroxypropanoic acidHMDB
(2S)-2-Acetamido-3-hydroxypropionic acidHMDB
(S)-2-Acetamido-3-hydroxypropanoic acidHMDB
(S)-2-Acetamido-3-hydroxypropionic acidHMDB
N-AcetylserineMeSH
Chemical FormulaC5H9NO4
Average Mass147.1293 Da
Monoisotopic Mass147.05316 Da
IUPAC Name(2S)-2-acetamido-3-hydroxypropanoic acid
Traditional Nameacetylserine
CAS Registry Number16354-58-8
SMILES
CC(=O)N[C@@H](CO)C(O)=O
InChI Identifier
InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1
InChI KeyJJIHLJJYMXLCOY-BYPYZUCNSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, C2D6OS, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Asparagus officinalisLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Trypanosoma bruceiLOTUS 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
  • Serine or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen 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 Point207.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility84.6 g/LALOGPS
logP-1.4ALOGPS
logP-1.8ChemAxon
logS-0.24ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.48 m³·mol⁻¹ChemAxon
Polarizability13.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002931
DrugBank IDDB02340
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112180
KNApSAcK IDNot Available
Chemspider ID58744
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Acetylserine
METLIN ID308
PubChem Compound65249
PDB IDNot Available
ChEBI ID45441
Good Scents IDrw1811141
References
General References
  1. Sugahara K, Zhang J, Kodama H: Liquid chromatographic-mass spectrometric analysis of N-acetylamino acids in human urine. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):15-21. [PubMed:7952062 ]
  2. Boesgaard S, Aldershvile J, Poulsen HE, Christensen S, Dige-Petersen H, Giese J: N-acetylcysteine inhibits angiotensin converting enzyme in vivo. J Pharmacol Exp Ther. 1993 Jun;265(3):1239-44. [PubMed:8389858 ]
  3. Lynch AS, Tyrrell R, Smerdon SJ, Briggs GS, Wilkinson AJ: Characterization of the CysB protein of Klebsiella aerogenes: direct evidence that N-acetylserine rather than O-acetylserine serves as the inducer of the cysteine regulon. Biochem J. 1994 Apr 1;299 ( Pt 1):129-36. [PubMed:8166630 ]