Record Information
Version1.0
Creation date2011-09-21 00:05:17 UTC
Update date2015-10-09 22:29:56 UTC
Primary IDFDB021926
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Phosphoserine
DescriptionThe phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. This might be important in explaining some of the devastating consequences of diabetes. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. Serine, organic compound, one of the 20 amino acids commonly found in animal proteins. Only the L-stereoisomer appears in mammalian protein. It is not essential to the human diet, since it can be synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serine's structure was established in 1902. [HMDB]
CAS Number407-41-0
Structure
Thumb
Synonyms
SynonymSource
(+)-L-Serine dihydrogen phosphate (ester)ChEBI
(2S)-2-Amino-3-(phosphonooxy)propanoic acidChEBI
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphateChEBI
3-PhosphoserineChEBI
DexfosfoserineChEBI
L-O-PhosphoserineChEBI
O-PhosphoserineChEBI
3-Phospho-L-serineKegg
(+)-L-Serine dihydrogen phosphoric acid (ester)Generator
(2S)-2-Amino-3-(phosphonooxy)propanoateGenerator
(S)-2-Amino-3-hydroxypropanoate 3-phosphateGenerator
(S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acidGenerator
3-O-PhosphoserineHMDB
FosforinaHMDB
L-3-PhosphoserineHMDB
L-O-Serine phosphateHMDB
L-PhosphoserineHMDB
L-Serine dihydrogen phosphate (ester)HMDB
L-Serine phosphateHMDB
L-SerinephosphorateHMDB
L-Serinephosphoric acidHMDB
L-Seryl phosphateHMDB
PlasmenylserineHMDB
(+)-L-Serine dihydrogen ate (ester)ChEBI
(+)-L-Serine dihydrogen ic acid (ester)Generator
(2S)-2-amino-3-(Onooxy)propanoateGenerator
(2S)-2-amino-3-(Onooxy)propanoic acidChEBI
(S)-2-amino-3-Hydroxypropanoate 3-ateGenerator
(S)-2-amino-3-Hydroxypropanoic acid 3-ateChEBI
(S)-2-amino-3-Hydroxypropanoic acid 3-ic acidGenerator
3-O-OserineHMDB
3-OserineChEBI
Dexfosfoserine, INNdb_source
L-3-OserineHMDB
L-O-OserineChEBI
L-O-Serine ateHMDB
L-OserineHMDB
L-Serine ateHMDB
L-Serine dihydrogen ate (ester)HMDB
L-SerineorateHMDB
L-Serineoric acidHMDB
L-Seryl ateHMDB
O-O-L-SerineChEBI
O-OserineChEBI
OserineChEBI
S-Phosphoserinemanual
Predicted Properties
PropertyValueSource
Water Solubility19.9 g/LALOGPS
logP-2.3ALOGPS
logP-3.2ChemAxon
logS-0.97ALOGPS
pKa (Strongest Acidic)1.2ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.08 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.91 m³·mol⁻¹ChemAxon
Polarizability13.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H8NO6P
IUPAC name(2S)-2-amino-3-(phosphonooxy)propanoic acid
InChI IdentifierInChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1
InChI KeyBZQFBWGGLXLEPQ-REOHCLBHSA-N
Isomeric SMILESN[C@@H](COP(O)(O)=O)C(O)=O
Average Molecular Weight185.0725
Monoisotopic Molecular Weight185.008923505
Classification
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
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID62074
ChEMBL IDCHEMBL284377
KEGG Compound IDC01005
Pubchem Compound ID68841
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB04522
HMDB IDHMDB00272
CRC / DFC (Dictionary of Food Compounds) IDCJC00-O:CJC02-Q
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDSEP
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhosphoserine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phosphoserine aminotransferasePSAT1Q9Y617
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference