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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:40 UTC
Update Date2021-09-14 15:39:04 UTC
HMDB IDHMDB0002184
Secondary Accession Numbers
  • HMDB02184
Metabolite Identification
Common NameL-Threo-3-Phenylserine
DescriptionL-Threo-3-Phenylserine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Threo-3-Phenylserine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make L-threo-3-phenylserine a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on L-Threo-3-Phenylserine.
Structure
Data?1582752234
Synonyms
ValueSource
L-threo-b-PhenylserineHMDB
L-threo-beta-PhenylserineHMDB
threo-b-Hydroxy-L-phenylalanineHMDB
threo-beta-Hydroxy-L-phenylalanineHMDB
beta-PhenylserineMeSH, HMDB
threo-beta-PhenylserineMeSH, HMDB
beta-Hydroxyphenylalanine, erythro-(DL)-isomerMeSH, HMDB
beta-Hydroxyphenylalanine, threo-(DL)-isomerMeSH, HMDB
beta-HydroxyphenylalanineMeSH, HMDB
beta-Hydroxyphenylalanine, threo-(L)-isomerMeSH, HMDB
(2Rs,3Sr)-2-amino-3-Hydroxy-3-phenylpropanoic acidMeSH, HMDB
beta-Hydroxyphenylalanine, (DL)-isomerMeSH, HMDB
(2S)-2-Amino-3-hydroxy-3-phenylpropanoateGenerator, HMDB
3-PhenylserineMeSH, HMDB
PhenylserineMeSH, HMDB
Threo-DL-phenyl-serineMeSH, HMDB
DL-3-PhenylserineMeSH, HMDB
Chemical FormulaC9H11NO3
Average Molecular Weight181.1885
Monoisotopic Molecular Weight181.073893223
IUPAC Name(2S)-2-amino-3-hydroxy-3-phenylpropanoic acid
Traditional Name3-phenyl-L-serine
CAS Registry Number6254-48-4
SMILES
N[C@@H](C(O)C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C9H11NO3/c10-7(9(12)13)8(11)6-4-2-1-3-5-6/h1-5,7-8,11H,10H2,(H,12,13)/t7-,8?/m0/s1
InChI KeyVHVGNTVUSQUXPS-JAMMHHFISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • L-alpha-amino acid
  • Beta-hydroxy acid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Aromatic alcohol
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.1 g/LALOGPS
logP-1.8ALOGPS
logP-2.1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.16ChemAxon
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.32 m³·mol⁻¹ChemAxon
Polarizability17.77 ųChemAxon
Number of Rings1ChemAxon
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]+141.98831661259
DarkChem[M-H]-138.66831661259
DeepCCS[M+H]+136.79230932474
DeepCCS[M-H]-134.39630932474
DeepCCS[M-2H]-169.63830932474
DeepCCS[M+Na]+144.09730932474
AllCCS[M+H]+141.232859911
AllCCS[M+H-H2O]+137.032859911
AllCCS[M+NH4]+145.232859911
AllCCS[M+Na]+146.332859911
AllCCS[M-H]-137.632859911
AllCCS[M+Na-2H]-138.532859911
AllCCS[M+HCOO]-139.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-Threo-3-PhenylserineN[C@@H](C(O)C1=CC=CC=C1)C(O)=O2879.9Standard polar33892256
L-Threo-3-PhenylserineN[C@@H](C(O)C1=CC=CC=C1)C(O)=O1650.2Standard non polar33892256
L-Threo-3-PhenylserineN[C@@H](C(O)C1=CC=CC=C1)C(O)=O2032.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Threo-3-Phenylserine,1TMS,isomer #1C[Si](C)(C)OC(C1=CC=CC=C1)[C@H](N)C(=O)O1668.2Semi standard non polar33892256
L-Threo-3-Phenylserine,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)C(O)C1=CC=CC=C11654.9Semi standard non polar33892256
L-Threo-3-Phenylserine,1TMS,isomer #3C[Si](C)(C)N[C@H](C(=O)O)C(O)C1=CC=CC=C11744.2Semi standard non polar33892256
L-Threo-3-Phenylserine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)C(O[Si](C)(C)C)C1=CC=CC=C11668.5Semi standard non polar33892256
L-Threo-3-Phenylserine,2TMS,isomer #2C[Si](C)(C)N[C@H](C(=O)O)C(O[Si](C)(C)C)C1=CC=CC=C11729.4Semi standard non polar33892256
L-Threo-3-Phenylserine,2TMS,isomer #3C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O)C1=CC=CC=C11731.8Semi standard non polar33892256
L-Threo-3-Phenylserine,2TMS,isomer #4C[Si](C)(C)N([C@H](C(=O)O)C(O)C1=CC=CC=C1)[Si](C)(C)C1893.6Semi standard non polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #1C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C11723.4Semi standard non polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #1C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C11811.7Standard non polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #1C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CC=CC=C12041.3Standard polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #2C[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1916.9Semi standard non polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #2C[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1858.6Standard non polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #2C[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2145.4Standard polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1917.7Semi standard non polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1881.4Standard non polar33892256
L-Threo-3-Phenylserine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C2171.7Standard polar33892256
L-Threo-3-Phenylserine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1973.6Semi standard non polar33892256
L-Threo-3-Phenylserine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C1948.7Standard non polar33892256
L-Threo-3-Phenylserine,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C2028.6Standard polar33892256
L-Threo-3-Phenylserine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@H](N)C(=O)O1930.0Semi standard non polar33892256
L-Threo-3-Phenylserine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C(O)C1=CC=CC=C11911.2Semi standard non polar33892256
L-Threo-3-Phenylserine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@H](C(=O)O)C(O)C1=CC=CC=C11979.8Semi standard non polar33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12160.2Semi standard non polar33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@H](C(=O)O)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12183.2Semi standard non polar33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O)C1=CC=CC=C12185.7Semi standard non polar33892256
L-Threo-3-Phenylserine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@H](C(=O)O)C(O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2336.1Semi standard non polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12370.7Semi standard non polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12390.4Standard non polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C12445.1Standard polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2575.4Semi standard non polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2435.8Standard non polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2478.5Standard polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2568.0Semi standard non polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2466.5Standard non polar33892256
L-Threo-3-Phenylserine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2493.9Standard polar33892256
L-Threo-3-Phenylserine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2797.9Semi standard non polar33892256
L-Threo-3-Phenylserine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2681.5Standard non polar33892256
L-Threo-3-Phenylserine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](C(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2464.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-ac17c8cf04308cfbf46e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5920000000-af65a901a0e2ee257a0f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Threo-3-Phenylserine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Positive-QTOFsplash10-01qi-0900000000-23514fbcf274c89d0cb72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Positive-QTOFsplash10-00kr-0900000000-f372732e79c55b239dd92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Positive-QTOFsplash10-05r0-9300000000-ba241a9d0d7acb3fad1f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Negative-QTOFsplash10-001i-0900000000-efa96cba215699148b922017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Negative-QTOFsplash10-0aei-4900000000-d1f163f6dba4af36de4e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Negative-QTOFsplash10-00di-9000000000-b1e85af153ad7acb90ff2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Negative-QTOFsplash10-03e9-1900000000-6a8534e62614caf028262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Negative-QTOFsplash10-062a-9700000000-111064f1b9bd7957351e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Negative-QTOFsplash10-016r-9800000000-097aee8d9061f5e463d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 10V, Positive-QTOFsplash10-02mi-0900000000-61f6d72660986df761642021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 20V, Positive-QTOFsplash10-00xr-0900000000-60667427da53fcb174392021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Threo-3-Phenylserine 40V, Positive-QTOFsplash10-004i-9000000000-3052f2cb9b8f0395cd332021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022892
KNApSAcK IDNot Available
Chemspider ID13628311
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6532
PubChem Compound12314153
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBruns, Friedrich H.; Fiedler, Liselore. Enzymic cleavage and synthesis of L-threo-b-phenylserine and L-erythro-b-phenylserine. Biochemische Zeitschrift (1958), 330 324-41.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. BRUNS FH, FIEDLER L: Enzymatic cleavage and synthesis of L-threo-beta-phenylserine and L-erythro-beta-Phenyldrine. Nature. 1958 May 31;181(4622):1533-4. [PubMed:13566053 ]