Showing NP-Card for O-Acetylserine (NP0000254)

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Record Information
Version2.0
Created at2006-05-22 15:12:26 UTC
Updated at2024-09-17 15:41:24 UTC
NP-MRD IDNP0000254
Secondary Accession NumbersNone
Natural Product 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 NP0000254 (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
Download

3D MOL for NP0000254 (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
Download

3D SDF for NP0000254 (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>
NP0000254

> <DATABASE_NAME>
NP-MRD

> <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 NP0000254 (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
Download

PDB for NP0000254 (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 NP0000254 (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 NP0000254 (O-Acetylserine)

CC(=O)OC[C@H](N)C(O)=O
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INCHI for NP0000254 (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 Assignments
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 Mass147.1293 Da
Monoisotopic Mass147.05316 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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
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 Solubility174 g/LALOGPS
logP-2.8ALOGPS
logP-3.4ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.19 m³·mol⁻¹ChemAxon
Polarizability13.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003011
DrugBank IDDB01837
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004955
KNApSAcK IDC00007459
Chemspider ID89874
KEGG Compound IDC00979
BioCyc IDACETYLSERINE
BiGG IDNot Available
Wikipedia LinkO-Acetylserine
METLIN ID3270
PubChem Compound99478
PDB IDNot Available
ChEBI ID17981
Good Scents IDNot Available
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. Qiu J, Wang D, Ma Y, Jiang T, Xin Y: Identification and characterization of serine acetyltransferase encoded by the Mycobacterium tuberculosis Rv2335 gene. Int J Mol Med. 2013 May;31(5):1229-33. doi: 10.3892/ijmm.2013.1298. Epub 2013 Mar 12. [PubMed:23483228 ]
  3. Zhang Z, Wei J, Wang M, Zhang J, Wu B: Induced sulfur metabolism by sulfur dioxide maintains postharvest quality of 'Thompson Seedless' grape through increasing sulfite content. J Sci Food Agric. 2021 Aug 2. doi: 10.1002/jsfa.11454. [PubMed:34338316 ]
  4. Fernandez-Rodriguez C, Oyenarte I, Conter C, Gonzalez-Recio I, Nunez-Franco R, Gil-Pitarch C, Quintana I, Jimenez-Oses G, Dominici P, Martinez-Chantar ML, Astegno A, Martinez-Cruz LA: Structural insight into the unique conformation of cystathionine beta-synthase from Toxoplasma gondii. Comput Struct Biotechnol J. 2021 Jun 6;19:3542-3555. doi: 10.1016/j.csbj.2021.05.052. eCollection 2021. [PubMed:34194677 ]
  5. Kumar A, Kumar V, Dubey AK, Ansari MA, Narayan S, Meenakshi, Kumar S, Pandey V, Pande V, Sanyal I: Chickpea glutaredoxin (CaGrx) gene mitigates drought and salinity stress by modulating the physiological performance and antioxidant defense mechanisms. Physiol Mol Biol Plants. 2021 May;27(5):923-944. doi: 10.1007/s12298-021-00999-z. Epub 2021 May 6. [PubMed:34092945 ]