Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2006-05-22 15:12:26 UTC
Updated at2021-06-29 00:47:39 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
Thumb
Synonyms
ValueSource
L-Serine, acetate (ester)ChEBI
O3-Acetyl-L-serineChEBI
L-Serine, acetic acid (ester)Generator
O-Acetylserine hydrobromide, (D)-isomerMeSH
O-Acetylserine, (L)-isomerMeSH
Serine acetate esterMeSH
O-Acetyl-L-serineHMDB
O-Acetyl-serineHMDB
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaKNApSAcK Database
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
External Links
HMDB IDHMDB0003011
DrugBank IDDB01837
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  3. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
  4. 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 ]
  5. 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 ]