L-threo-3-phenylserine (PAMDB120228)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120228
Identification
Name: L-threo-3-phenylserine
Description:Zwitterionic form of L-threo-3-phenylserine arising from transfer of a proton from the carboxy to the α-amino group; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S,3S)-2-ammonio-3-hydroxy-3-phenylpropanoate
  • L-threo-3-phenylserine
Chemical Formula: C9H11NO3
Average Molecular Weight: 181.191
Monoisotopic Molecular Weight: 182.08171
InChI Key: VHVGNTVUSQUXPS-YUMQZZPRSA-N
InChI: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
CAS number: 6254-48-4
IUPAC Name:(2S,3S)-2-azaniumyl-3-hydroxy-3-phenylpropanoate
Traditional IUPAC Name: 3-phenyl-L-serine
SMILES:C([O-])(=O)C(C(C1(C=CC=CC=1))O)[N+]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as phenylalanine and derivatives. These 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Phenylalanine 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 Framework Aromatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.32 m3·mol-1ChemAxon
Polarizability17.77 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
L-threo-3-phenylserine → benzaldehyde + Glycine
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • 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. [13566053 ]
    Synthesis Reference: Bruns, 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)
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC57901
    HMDBHMDB02184
    CHEBI57901
    PUBCHEM6919633
    LIGAND-CPDC03290