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(3S)-3-hydroxy-L-aspartic acid (YMDB00166)

Identification
YMDB IDYMDB00166
Name(3S)-3-hydroxy-L-aspartic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Hydroxyaspartate is not found in normal proteins, it is found in cinnamycin, a 19-amino acid peptide with anti-tumor and anti-microbial activities that is produced by Streptomyces strains. (3S)-3-Hydroxy-L-aspartic acid (threo-3-hydroxyaspartate) is converted to oxaloacetate and ammonia by a 3-hydroxyaspartate dehydratase (SRY1p) in yeast. The role of this enzyme in yeast would be detoxification of naturally occuring 3-hydroxyaspartate. [PMID: 12951240]
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • L-threo-3-Hydroxyaspartate
  • threo-3-Hydroxy-L-aspartate
  • DL-Threo-beta-hydroxyaspartic acid
  • DL-Threo-b-hydroxyaspartate
  • DL-Threo-b-hydroxyaspartic acid
  • DL-Threo-beta-hydroxyaspartate
  • DL-Threo-β-hydroxyaspartate
  • DL-Threo-β-hydroxyaspartic acid
  • L-Threo-3-hydroxyaspartic acid
  • (3S)-3-Hydroxy-L-aspartate
  • Erythro-beta-hydroxyaspartic acid
  • Threo-beta-aspartate
  • L-Threo-beta-hydroxyaspartic acid
  • beta-Hydroxyaspartic acid
  • Threo-hydroxyaspartic acid
  • 3-Hydroxyaspartic acid
  • 3-Hydroxyaspartic acid, (erythro-L)-isomer
  • DL-Threo-3-hydroxyaspartic acid
  • 3-Hydroxyaspartic acid, (threo-L)-isomer
  • 3-Hydroxyaspartic acid, (threo-DL)-isomer
  • 3-Hydroxyaspartic acid, (erythro-D)-isomer
  • 3-Hydroxyaspartic acid, (erythro-DL)-isomer
  • 3-Hydroxyaspartic acid, (erythro)-isomer
  • Threo-tha
  • L-Erythro-3-hydroxyaspartate
  • threo-3-Hydroxy-L-aspartic acid
CAS number7298-99-9
WeightAverage: 149.1021
Monoisotopic: 149.032422339
InChI KeyYYLQUHNPNCGKJQ-LWMBPPNESA-N
InChIInChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1
IUPAC Name(2S,3S)-2-amino-3-hydroxybutanedioic acid
Traditional IUPAC Name3-hydroxyaspartic acid
Chemical FormulaC4H7NO5
SMILESN[C@@H]([C@H](O)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid 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 ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Hydroxy acid
  • Monosaccharide
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility111 g/LALOGPS
logP-3.4ALOGPS
logP-4.4ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.87 m³·mol⁻¹ChemAxon
Polarizability12.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-af8204a8797562a5e1a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-2900000000-3532e53b3a0b32d5b387JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-17b233107605486b5b32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0570-9000000000-b4d1e0a4cedd017f9bb4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-4900000000-b4e20ff53fc1f019de14JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-9700000000-446a91507f281401574dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-e8a8b69125b8407a7211JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID10696
HMDB IDNot Available
Pubchem Compound ID191652
Kegg IDC11511
ChemSpider ID391503
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Threo-3-hydroxyaspartate ammonia-lyase
General function:
Involved in catalytic activity
Specific function:
Exhibits dehydratase activity specific for L-threo-3- hydroxyaspartate
Gene Name:
SRY1
Uniprot ID:
P36007
Molecular weight:
34898.69922
Reactions
Threo-3-hydroxy-L-aspartate → oxaloacetate + NH(3).