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Record Information
Version3.6
Creation Date2006-08-13 01:22:37 UTC
Update Date2016-02-11 01:06:24 UTC
HMDB IDHMDB03609
Secondary Accession Numbers
  • HMDB06356
Metabolite Identification
Common Name2-Aminoacrylic acid
DescriptionDehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid).
Structure
Thumb
Synonyms
ValueSource
2-AminoacrylateKegg
2-Aminoprop-2-enoateKegg
2-Aminoprop-2-enoic acidGenerator
(alpha)-(beta)-Di-dehydroalanineHMDB
a-b-Di-dehydroalanineHMDB
alpha-beta-Di-dehydroalanineHMDB
DehydroalanineHMDB
Chemical FormulaC3H5NO2
Average Molecular Weight87.0773
Monoisotopic Molecular Weight87.032028409
IUPAC Name2-aminoprop-2-enoic acid
Traditional Namedehydroalanine
CAS Registry Number28453-71-6
SMILES
NC(=C)C(O)=O
InChI Identifier
InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6)
InChI KeyInChIKey=UQBOJOOOTLPNST-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Microbial
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.651Not Available
Predicted Properties
PropertyValueSource
Water Solubility233.0 mg/mLALOGPS
logP-0.13ALOGPS
logP-2.9ChemAxon
logS0.43ALOGPS
pKa (Strongest Acidic)2.58ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.92 m3·mol-1ChemAxon
Polarizability7.72 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9000000000-15dc8dc52e98be913462View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-dc312ec6c67a0557dea5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6abf262be2b6f2447777View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-8d7c53619f483f86f61aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-e78e6283f6f0fd640c07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-9000000000-f45341969a54a57e8b77View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Thyroid hormone synthesisSMP00716Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023206
KNApSAcK IDNot Available
Chemspider ID110510
KEGG Compound IDC02218
BioCyc IDNot Available
BiGG ID39352
Wikipedia LinkDehydroalanine
NuGOwiki LinkHMDB03609
Metagene LinkHMDB03609
METLIN IDNot Available
PubChem Compound123991
PDB IDDHA
ChEBI ID17123
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63
Reactions
3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Thyroxine + 2-Aminoacrylic acid + Waterdetails
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
SDS
Uniprot ID:
P20132
Molecular weight:
34625.105
Reactions
L-Serine → 2-Aminoacrylic acid + Waterdetails