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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-20 22:13:21 UTC
Update Date2021-09-14 15:20:03 UTC
HMDB IDHMDB0001721
Secondary Accession Numbers
  • HMDB01721
Metabolite Identification
Common NameDL-O-Phosphoserine
DescriptionDL-O-Phosphoserine, also known as DL-O-phosphorylserine or DL-O-serine phosphate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Serine proteases are a common type of protease. DL-O-Phosphoserine exists in all living species, ranging from bacteria to humans. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes.
Structure
Data?1582752211
Synonyms
ValueSource
2-Amino-3-(phosphonooxy)propanoic acidChEBI
DL-Serine dihydrogen phosphateChEBI
DL-Serine, dihydrogen phosphate (ester)ChEBI
PhosphoserineChEBI
2-Amino-3-(phosphonooxy)propanoateGenerator
DL-Serine dihydrogen phosphoric acidGenerator
DL-Serine, dihydrogen phosphoric acid (ester)Generator
3-Phospho-1-serineHMDB
3-Phospho-serineHMDB
3-PhosphoserineHMDB
DL-O-PhosphorylserineHMDB
DL-O-Serine phosphateHMDB
DL-Serine monophosphorateHMDB
DL-Serine monophosphoric acidHMDB
EnergoserinaHMDB
O-Phospho-DL-serineHMDB
O-Phospho-L-serineHMDB
O-PhosphonoserineHMDB
p-SerineHMDB
PhosphorylserineHMDB
Serine phosphateHMDB
Serine-3-phosphateHMDB
SerophenHMDB
Phosphate, serylHMDB
Seryl phosphateHMDB
Phosphate, serineHMDB
Chemical FormulaC3H8NO6P
Average Molecular Weight185.0725
Monoisotopic Molecular Weight185.008923505
IUPAC Name2-amino-3-(phosphonooxy)propanoic acid
Traditional NameP-serine
CAS Registry Number17885-08-4
SMILES
NC(COP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)
InChI KeyBZQFBWGGLXLEPQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability14.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.13831661259
DarkChem[M-H]-131.77131661259
AllCCS[M+H]+140.55632859911
AllCCS[M-H]-130.5932859911
DeepCCS[M+H]+126.54930932474
DeepCCS[M-H]-122.86930932474
DeepCCS[M-2H]-160.23930932474
DeepCCS[M+Na]+135.27130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DL-O-PhosphoserineNC(COP(O)(O)=O)C(O)=O2388.5Standard polar33892256
DL-O-PhosphoserineNC(COP(O)(O)=O)C(O)=O1542.9Standard non polar33892256
DL-O-PhosphoserineNC(COP(O)(O)=O)C(O)=O1982.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
DL-O-Phosphoserine,1TMS,isomer #1C[Si](C)(C)OC(=O)C(N)COP(=O)(O)O1737.8Semi standard non polar33892256
DL-O-Phosphoserine,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)OCC(N)C(=O)O1763.9Semi standard non polar33892256
DL-O-Phosphoserine,1TMS,isomer #3C[Si](C)(C)NC(COP(=O)(O)O)C(=O)O1822.1Semi standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)COP(=O)(O)O[Si](C)(C)C1744.1Semi standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)COP(=O)(O)O[Si](C)(C)C1757.4Standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)COP(=O)(O)O[Si](C)(C)C2659.8Standard polar33892256
DL-O-Phosphoserine,2TMS,isomer #2C[Si](C)(C)NC(COP(=O)(O)O)C(=O)O[Si](C)(C)C1807.1Semi standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #2C[Si](C)(C)NC(COP(=O)(O)O)C(=O)O[Si](C)(C)C1821.0Standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #2C[Si](C)(C)NC(COP(=O)(O)O)C(=O)O[Si](C)(C)C2780.3Standard polar33892256
DL-O-Phosphoserine,2TMS,isomer #3C[Si](C)(C)OP(=O)(OCC(N)C(=O)O)O[Si](C)(C)C1792.4Semi standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #3C[Si](C)(C)OP(=O)(OCC(N)C(=O)O)O[Si](C)(C)C1759.5Standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #3C[Si](C)(C)OP(=O)(OCC(N)C(=O)O)O[Si](C)(C)C2731.8Standard polar33892256
DL-O-Phosphoserine,2TMS,isomer #4C[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C)C(=O)O1848.2Semi standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #4C[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C)C(=O)O1796.1Standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #4C[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C)C(=O)O2576.8Standard polar33892256
DL-O-Phosphoserine,2TMS,isomer #5C[Si](C)(C)N(C(COP(=O)(O)O)C(=O)O)[Si](C)(C)C1949.3Semi standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #5C[Si](C)(C)N(C(COP(=O)(O)O)C(=O)O)[Si](C)(C)C1919.2Standard non polar33892256
DL-O-Phosphoserine,2TMS,isomer #5C[Si](C)(C)N(C(COP(=O)(O)O)C(=O)O)[Si](C)(C)C2922.0Standard polar33892256
DL-O-Phosphoserine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1784.1Semi standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1828.1Standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #1C[Si](C)(C)OC(=O)C(N)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2364.7Standard polar33892256
DL-O-Phosphoserine,3TMS,isomer #2C[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1854.8Semi standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #2C[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1865.3Standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #2C[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2307.2Standard polar33892256
DL-O-Phosphoserine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C1943.2Semi standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C1969.4Standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #3C[Si](C)(C)OC(=O)C(COP(=O)(O)O)N([Si](C)(C)C)[Si](C)(C)C2599.2Standard polar33892256
DL-O-Phosphoserine,3TMS,isomer #4C[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1889.9Semi standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #4C[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O1870.9Standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #4C[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O2204.5Standard polar33892256
DL-O-Phosphoserine,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1982.1Semi standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1926.8Standard non polar33892256
DL-O-Phosphoserine,3TMS,isomer #5C[Si](C)(C)OP(=O)(O)OCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2419.3Standard polar33892256
DL-O-Phosphoserine,4TMS,isomer #1C[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1893.1Semi standard non polar33892256
DL-O-Phosphoserine,4TMS,isomer #1C[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1927.6Standard non polar33892256
DL-O-Phosphoserine,4TMS,isomer #1C[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C2031.5Standard polar33892256
DL-O-Phosphoserine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1971.7Semi standard non polar33892256
DL-O-Phosphoserine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1988.0Standard non polar33892256
DL-O-Phosphoserine,4TMS,isomer #2C[Si](C)(C)OC(=O)C(COP(=O)(O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2235.2Standard polar33892256
DL-O-Phosphoserine,4TMS,isomer #3C[Si](C)(C)OP(=O)(OCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2007.8Semi standard non polar33892256
DL-O-Phosphoserine,4TMS,isomer #3C[Si](C)(C)OP(=O)(OCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1990.1Standard non polar33892256
DL-O-Phosphoserine,4TMS,isomer #3C[Si](C)(C)OP(=O)(OCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C2139.4Standard polar33892256
DL-O-Phosphoserine,5TMS,isomer #1C[Si](C)(C)OC(=O)C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2029.5Semi standard non polar33892256
DL-O-Phosphoserine,5TMS,isomer #1C[Si](C)(C)OC(=O)C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2030.6Standard non polar33892256
DL-O-Phosphoserine,5TMS,isomer #1C[Si](C)(C)OC(=O)C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2034.5Standard polar33892256
DL-O-Phosphoserine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)COP(=O)(O)O1969.4Semi standard non polar33892256
DL-O-Phosphoserine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(N)C(=O)O2004.2Semi standard non polar33892256
DL-O-Phosphoserine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O)C(=O)O2024.9Semi standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)COP(=O)(O)O[Si](C)(C)C(C)(C)C2166.1Semi standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)COP(=O)(O)O[Si](C)(C)C(C)(C)C2205.9Standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)COP(=O)(O)O[Si](C)(C)C(C)(C)C2788.4Standard polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C2203.1Semi standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C2265.5Standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O)C(=O)O[Si](C)(C)C(C)(C)C2886.9Standard polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC(N)C(=O)O)O[Si](C)(C)C(C)(C)C2219.4Semi standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC(N)C(=O)O)O[Si](C)(C)C(C)(C)C2202.6Standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC(N)C(=O)O)O[Si](C)(C)C(C)(C)C2800.9Standard polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2237.2Semi standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2224.1Standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O2717.9Standard polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(COP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C2372.1Semi standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(COP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C2332.2Standard non polar33892256
DL-O-Phosphoserine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N(C(COP(=O)(O)O)C(=O)O)[Si](C)(C)C(C)(C)C2951.2Standard polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2398.2Semi standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2401.8Standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2574.9Standard polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2448.7Semi standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2460.0Standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2587.1Standard polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2565.1Semi standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2575.9Standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2793.1Standard polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2484.0Semi standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2436.7Standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O2514.6Standard polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2601.5Semi standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2508.7Standard non polar33892256
DL-O-Phosphoserine,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2654.1Standard polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2682.9Semi standard non polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2606.2Standard non polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2464.5Standard polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2807.0Semi standard non polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2724.8Standard non polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2576.1Standard polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2836.6Semi standard non polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2663.2Standard non polar33892256
DL-O-Phosphoserine,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2507.9Standard polar33892256
DL-O-Phosphoserine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3022.8Semi standard non polar33892256
DL-O-Phosphoserine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2845.4Standard non polar33892256
DL-O-Phosphoserine,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2516.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - DL-O-Phosphoserine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-579f933727173ebf11012016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-O-Phosphoserine GC-MS (1 TMS) - 70eV, Positivesplash10-0006-6900000000-fbaee5e7f89c1dcb66692017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-O-Phosphoserine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b552012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine , negative-QTOFsplash10-0002-9000000000-64c49953b5b27ea372c62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine , positive-QTOFsplash10-000i-9300000000-2adf6419e88c778446e92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine , positive-QTOFsplash10-000i-9200000000-04bb0aee57d7fffbcaa72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine 35V, Positive-QTOFsplash10-000i-9100000000-2fb2869ecf3634b54a392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-O-Phosphoserine 35V, Positive-QTOFsplash10-000i-9000000000-2c6e3412bb661c65ec102021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 10V, Positive-QTOFsplash10-000l-9800000000-672ba3fb65a9cac250442016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 20V, Positive-QTOFsplash10-0006-9300000000-e63c25df326283cc3b7f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 40V, Positive-QTOFsplash10-0006-9000000000-dbc8b3072add030d17112016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 10V, Negative-QTOFsplash10-003r-9800000000-10234b7ff1b336489a5a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 20V, Negative-QTOFsplash10-004i-9100000000-8a4c753dfa69ac6720e02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 40V, Negative-QTOFsplash10-004i-9000000000-ebe13ec0e44d8c4f47712016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 10V, Positive-QTOFsplash10-0007-5900000000-0165c58c1b2c713290ed2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 20V, Positive-QTOFsplash10-0005-9300000000-8c803e99e72e9cb599132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 40V, Positive-QTOFsplash10-000x-9000000000-6ed59f8b5f83d923a8b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 10V, Negative-QTOFsplash10-002b-9000000000-68e2a2413db514aab39e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 20V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-O-Phosphoserine 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Epidermis
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified1.05 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.33 +/- 0.001 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022700
KNApSAcK IDNot Available
Chemspider ID104
KEGG Compound IDC01005
BioCyc IDNot Available
BiGG ID36594
Wikipedia LinkPhosphoserine
METLIN ID6338
PubChem Compound106
PDB IDNot Available
ChEBI ID37712
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLacombe J M; Andriamanampisoa F; Pavia A A Solid-phase synthesis of peptides containing phosphoserine using phosphate tert.-butyl protecting group. International journal of peptide and protein research (1990), 36(3), 275-80.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Glaus M, Schneider W: Iron release from transferrin induced by mixed ligand complexes of copper(II). Biol Met. 1989;2(3):185-90. [PubMed:2490073 ]
  2. Driscoll J, Zuo Y, Xu T, Choi JR, Troxler RF, Oppenheim FG: Functional comparison of native and recombinant human salivary histatin 1. J Dent Res. 1995 Dec;74(12):1837-44. [PubMed:8600179 ]
  3. Kataoka H, Nakai K, Katagiri Y, Makita M: Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection. Biomed Chromatogr. 1993 Jul-Aug;7(4):184-8. [PubMed:7693088 ]
  4. Wishart MJ, Denu JM, Williams JA, Dixon JE: A single mutation converts a novel phosphotyrosine binding domain into a dual-specificity phosphatase. J Biol Chem. 1995 Nov 10;270(45):26782-5. [PubMed:7592916 ]
  5. Patten BM, Harati Y, Acosta L, Jung SS, Felmus MT: Free amino acid levels in amyotrophic lateral sclerosis. Ann Neurol. 1978 Apr;3(4):305-9. [PubMed:666270 ]
  6. Etheredge RE, Han S, Fossel E, Tanzer ML, Glimcher MJ: Identification and quantitation of O-phosphoserine in human plasma fibronectin. FEBS Lett. 1985 Jul 8;186(2):259-62. [PubMed:3924662 ]
  7. Pond CD, Leachman SA, Warters RL: Accumulation, activation and interindividual variation of the epidermal TP53 protein in response to ionizing radiation in organ cultured human skin. Radiat Res. 2004 Jun;161(6):739-45. [PubMed:15161345 ]
  8. Partsch G, Schwarzer C, Eberl R: Influence of anticoagulant substances on phosphoserine and taurine of human blood. Arzneimittelforschung. 1979;29(5):820-2. [PubMed:115479 ]
  9. Millan JL, Whyte MP, Avioli LV, Fishman WH: Hypophosphatasia (adult form): quantitation of serum alkaline phosphatase isoenzyme activity in a large kindred. Clin Chem. 1980 Jun;26(7):840-5. [PubMed:7379306 ]
  10. Kataoka H, Nakai K, Makita M: Identification of O-phosphoamino acids in urine hydrolysate by gas chromatography-mass spectrometry. J Chromatogr. 1993 May 19;615(1):136-41. [PubMed:7688003 ]

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
General function:
Involved in catalytic activity
Specific function:
Catalyzes the last step in the biosynthesis of serine from carbohydrates. The reaction mechanism proceeds via the formation of a phosphoryl-enzyme intermediates.
Gene Name:
PSPH
Uniprot ID:
P78330
Molecular weight:
25007.49