Showing metabocard for O-Acetyl-L-serine (MMDBc0049875)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:45:20 UTC
Update Date2022-12-15 22:52:19 UTC
Metabolite IDMMDBc0049875
Metabolite Identification
Common NameO-Acetyl-L-serine
DescriptionO-Acetylserine is an α-amino acid with the chemical formula HO2CCH(NH2)CH2OC(O)CH3. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. O-Acetylserine is biosynthesized by acetylation of the serine by the enzyme serine transacetylase. The enzyme O-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releasing acetate. O-Acetylserine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. O-Acetylserine (OASS) is an acylated amino acid derivative. O-Acetylserine exists in all living species, ranging from bacteria to humans. Outside of the human body, O-Acetylserine has been detected, but not quantified in several different foods, such as okra, vaccinium (blueberry, cranberry, huckleberry), rapes, sparkleberries, and lingonberries. This could make O-acetylserine a potential biomarker for the consumption of these foods.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f5abd1cbcf8>

Untitled Document-1
  Mrv1652308122017342D          

 10  9  0  0  0  0            999 V2000
    0.7145   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f5abd1cbcf8>

HMDB0003011
     RDKit          3D
O-Acetylserine
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.0468   -1.0277   -0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -0.0958    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    0.6312    1.1214 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7647   -0.0191   -0.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    0.8431    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    0.6854   -0.2855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4372    1.6044    0.3874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -0.6902   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1124   -0.9467    0.4677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3472   -1.7583   -0.7107 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4902   -1.7773   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5605   -1.5565    0.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543   -0.4353   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2254    0.5833    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    1.8884    0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    0.9596   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    2.5562    0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    1.2729    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673   -2.7175   -0.4119 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  6
  7 17  1  0
  7 18  1  0
 10 19  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f5abd1cbcf8>

Untitled Document-1
  Mrv1652308122017342D          

 10  9  0  0  0  0            999 V2000
    0.7145   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049875

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1

> <INCHI_KEY>
VZXPDPZARILFQX-BYPYZUCNSA-N

> <FORMULA>
C5H9NO4

> <MOLECULAR_WEIGHT>
147.1293

> <EXACT_MASS>
147.053157781

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.444499866392562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-(acetyloxy)-2-aminopropanoic acid

> <ALOGPS_LOGP>
-2.85

> <JCHEM_LOGP>
-3.4461460799416375

> <ALOGPS_LOGS>
0.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8610845826775204

> <JCHEM_PKA_STRONGEST_BASIC>
8.603142088524868

> <JCHEM_POLAR_SURFACE_AREA>
89.62

> <JCHEM_REFRACTIVITY>
31.192500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-acetyl-L-serine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f5abd1cbcf8>

HMDB0003011
     RDKit          3D
O-Acetylserine
 19 18  0  0  0  0  0  0  0  0999 V2000
    3.0468   -1.0277   -0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0718   -0.0958    0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    0.6312    1.1214 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7647   -0.0191   -0.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1747    0.8431    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    0.6854   -0.2855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4372    1.6044    0.3874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -0.6902   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1124   -0.9467    0.4677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3472   -1.7583   -0.7107 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4902   -1.7773   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5605   -1.5565    0.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543   -0.4353   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2254    0.5833    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    1.8884    0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631    0.9596   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0068    2.5562    0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    1.2729    1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673   -2.7175   -0.4119 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  6 16  1  6
  7 17  1  0
  7 18  1  0
 10 19  1  0
M  END
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PDB for #<Metabolite:0x00007f5abd1cbcf8>

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-1                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  C   UNK     0       1.334  -0.385   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -1.925   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.000   0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -0.385   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667   0.385   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667   1.925   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.385   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.925   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -0.385   0.000  0.00  0.00           O+0
CONECT    1    2    3    8                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007f5abd1cbcf8>

COMPND    HMDB0003011
HETATM    1  C1  UNL     1       3.047  -1.028  -0.482  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.072  -0.096   0.182  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.457   0.631   1.121  1.00  0.00           O  
HETATM    4  O2  UNL     1       0.765  -0.019  -0.215  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.175   0.843   0.385  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.526   0.685  -0.285  1.00  0.00           C  
HETATM    7  N1  UNL     1      -2.437   1.604   0.387  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.047  -0.690  -0.147  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.112  -0.947   0.468  1.00  0.00           O  
HETATM   10  O4  UNL     1      -1.347  -1.758  -0.711  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.490  -1.777  -1.081  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.561  -1.556   0.342  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.754  -0.435  -1.072  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.225   0.583   1.463  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.175   1.888   0.312  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.463   0.960  -1.358  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.007   2.556   0.434  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.514   1.273   1.395  1.00  0.00           H  
HETATM   19  H9  UNL     1      -1.467  -2.717  -0.412  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   14   15
CONECT    6    7    8   16
CONECT    7   17   18
CONECT    8    9    9   10
CONECT   10   19
END
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SMILES for #<Metabolite:0x00007f5abd1cbcf8>

CC(=O)OC[C@H](N)C(O)=O
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INCHI for #<Metabolite:0x00007f5abd1cbcf8>

InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
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Synonyms
ValueSource
L-Serine, acetate (ester)ChEBI
O3-Acetyl-L-serineChEBI
L-Serine, acetic acid (ester)Generator
O-Acetyl-L-serineHMDB
O-Acetyl-serineHMDB
O-Acetylserine hydrobromide, (D)-isomerHMDB
O-Acetylserine, (L)-isomerHMDB
Serine acetate esterHMDB
O-AcetylserineMeSH
Molecular FormulaC5H9NO4
Average Mass147.1293
Monoisotopic Mass147.053157781
IUPAC Name(2S)-3-(acetyloxy)-2-aminopropanoic acid
Traditional NameO-acetyl-L-serine
CAS Registry Number66638-22-0
SMILES
CC(=O)OC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
InChI KeyVZXPDPZARILFQX-BYPYZUCNSA-N