Showing metabocard for N-Acetylserine (BMDB0002931)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:02:11 UTC
Update Date2020-05-11 20:40:16 UTC
BMDB IDBMDB0002931
Secondary Accession Numbers
  • BMDB02931
Metabolite Identification
Common NameN-Acetylserine
DescriptionN-Acetylserine belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetylserine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylserine exists in all living species, ranging from bacteria to humans. N-Acetylserine, with regard to humans, has been linked to the inborn metabolic disorder aminoacylase I deficiency.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AcetylserineHMDB
N-Acetyl-L-serineHMDB
(2S)-2-Acetamido-3-hydroxypropanoic acidHMDB
(2S)-2-Acetamido-3-hydroxypropionic acidHMDB
(S)-2-Acetamido-3-hydroxypropanoic acidHMDB
(S)-2-Acetamido-3-hydroxypropionic acidHMDB
N-AcetylserineMeSH
Chemical FormulaC5H9NO4
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
IUPAC Name(2S)-2-acetamido-3-hydroxypropanoic acid
Traditional Nameacetylserine
CAS Registry Number16354-58-8
SMILES
CC(=O)N[C@@H](CO)C(O)=O
InChI Identifier
InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10)/t4-/m0/s1
InChI KeyJJIHLJJYMXLCOY-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated 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 ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Serine or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point207.6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-1.8ChemAxon
logS-0.24ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.48 m³·mol⁻¹ChemAxon
Polarizability13.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002931
DrugBank IDDB02340
Phenol Explorer Compound IDNot Available
FooDB IDFDB000970
KNApSAcK IDNot Available
Chemspider ID58744
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Acetylserine
METLIN ID308
PubChem Compound65249
PDB IDNot Available
ChEBI ID45441
References
Synthesis ReferenceTsurumi, Kohti; Yamada, Sakae. L-Serine from D-glucosamine. Tohoku Journal of Experimental Medicine (1955), 62 329-31.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available