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Showing metabocard for O-Acetylserine (HMDB0003011)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:26 UTC
Update Date2023-02-21 17:16:30 UTC
HMDB IDHMDB0003011
Secondary Accession Numbers
  • HMDB03011
Metabolite Identification
Common NameO-Acetylserine
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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003011 (O-Acetylserine)

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 HMDB0003011 (O-Acetylserine)

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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3D SDF for HMDB0003011 (O-Acetylserine)

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>
HMDB0003011

> <DATABASE_NAME>
hmdb

> <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 HMDB0003011 (O-Acetylserine)

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 HMDB0003011 (O-Acetylserine)

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 HMDB0003011 (O-Acetylserine)

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 HMDB0003011 (O-Acetylserine)

CC(=O)OC[C@H](N)C(O)=O
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INCHI for HMDB0003011 (O-Acetylserine)

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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View in JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC5H9NO4
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
IUPAC Name(2S)-3-(acetyloxy)-2-aminopropanoic acid
Traditional NameO-acetyl-L-serine
CAS Registry Number5147-00-2
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
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available130.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002164
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified24.7 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01837
Phenol Explorer Compound IDNot Available
FooDB IDFDB031064
KNApSAcK IDC00007459
Chemspider ID89874
KEGG Compound IDC00979
BioCyc IDACETYLSERINE
BiGG IDNot Available
Wikipedia LinkO-Acetylserine
METLIN ID3270
PubChem Compound99478
PDB IDNot Available
ChEBI ID17981
Food Biomarker OntologyNot Available
VMH IDACSER
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  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 ]
  2. 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 ]