Showing Compound Card for DL-O-Phosphoserine (CDB005114)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:10:42 UTC
Updated at2020-11-18 16:39:23 UTC
CannabisDB IDCDB005114
Secondary Accession NumbersNot Available
Cannabis Compound 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). A serine derivative that is serine substituted at the oxygen atom by a phosphono group. DL-O-Phosphoserine is a very strong basic compound (based on its pKa). DL-O-Phosphoserine exists in all living species, ranging from bacteria to humans. DL-O-Phosphoserine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight185.07
Monoisotopic Molecular Weight185.0089
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

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDL-O-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9200000000-579f933727173ebf1101Spectrum
Predicted GC-MSDL-O-Phosphoserine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-6900000000-fbaee5e7f89c1dcb6669Spectrum
Predicted GC-MSDL-O-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-07c4d8f30a6ca83b8b552012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-c5a74679d970f7b6e2d52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-1d94e50890f1499da7f42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0002-9000000000-64c49953b5b27ea372c62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9300000000-2adf6419e88c778446e92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9200000000-04bb0aee57d7fffbcaa72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9100000000-2fb2869ecf3634b54a392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9000000000-2c6e3412bb661c65ec102021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9800000000-672ba3fb65a9cac250442016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-e63c25df326283cc3b7f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-dbc8b3072add030d17112016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9800000000-10234b7ff1b336489a5a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8a4c753dfa69ac6720e02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ebe13ec0e44d8c4f47712016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-5900000000-0165c58c1b2c713290ed2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-9300000000-8c803e99e72e9cb599132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9000000000-6ed59f8b5f83d923a8b42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9000000000-68e2a2413db514aab39e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Phosphoserine aminotransferasePSAT19q21.2Q9Y617 details
Phosphoserine phosphatasePSPH7p11.2P78330 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001721
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphoserine aminotransferase
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
Enzyme Details
2. Phosphoserine phosphatase
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