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
Molecular FormulaC5H9NO4
Average Mass147.12930
Monoisotopic Mass147.05316
IUPAC Name(2S)-3-(acetyloxy)-2-aminopropanoic acid
Traditional NameO-acetyl-l-serine
CAS Registry Number5147-00-2
SMILESCC(=O)OC[C@H]([NH3+])C(=O)[O-]
InChI IdentifierInChI=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
CHEBI IDCHEBI:58340
HMDB IDHMDB0003011
StateSolid
Water Solubility1.74e+02 g/l
logP-2.85
logS0.07
pKa (Strongest Acidic)1.86
pKa (Strongest Basic)8.60
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area89.62 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity31.19 m³·mol⁻¹
Polarizability13.44

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