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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 01:22:37 UTC
Update Date2023-02-21 17:16:45 UTC
HMDB IDHMDB0003609
Secondary Accession Numbers
  • HMDB0006356
  • HMDB03609
  • HMDB06356
Metabolite Identification
Common Name2-Aminoacrylic acid
Description2-Aminoacrylic acid, also known as 2,3-didehydroalanine or 2-aminoacrylate, 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). 2-Aminoacrylic acid is a very strong basic compound (based on its pKa). 2-Aminoacrylic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 2-Aminoacrylic acid has been detected, but not quantified in, several different foods, such as wax gourds, soursops, durians, green beans, and grapes. This could make 2-aminoacrylic acid a potential biomarker for the consumption of these foods. A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3.
Structure
Data?1676999805
Synonyms
ValueSource
2,3-DidehydroalanineChEBI
2-AminoacrylateChEBI
alpha,beta-DehydroalanineChEBI
Anhydroserine2-aminopropenoic acidChEBI
DehydroalanineChEBI
2-Aminoprop-2-enoateKegg
a,b-DehydroalanineGenerator
Α,β-dehydroalanineGenerator
Anhydroserine2-aminopropenoateGenerator
2-Aminoprop-2-enoic acidGenerator
(alpha)-(beta)-Di-dehydroalanineHMDB
a-b-Di-dehydroalanineHMDB
alpha-beta-Di-dehydroalanineHMDB
alpha-AminoacrylateHMDB
2-Amino-2-propenoic acidHMDB
Aminoacrylic acidHMDB
Dehydro-L-alanineHMDB
alpha,beta-DidehydroalanineHMDB
alpha-Aminoacrylic acidHMDB
α,β-DidehydroalanineHMDB
α-Aminoacrylic acidHMDB
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 KeyUQBOJOOOTLPNST-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
  • Amino acid
  • Carboxylic acid
  • Enamine
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.651Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility233 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.92 m³·mol⁻¹ChemAxon
Polarizability7.72 ųChemAxon
Number of Rings0ChemAxon
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]+115.67431661259
DarkChem[M-H]-109.7431661259
DeepCCS[M+H]+122.830932474
DeepCCS[M-H]-120.00230932474
DeepCCS[M-2H]-156.3830932474
DeepCCS[M+Na]+130.95130932474
AllCCS[M+H]+124.932859911
AllCCS[M+H-H2O]+120.532859911
AllCCS[M+NH4]+129.032859911
AllCCS[M+Na]+130.232859911
AllCCS[M-H]-121.732859911
AllCCS[M+Na-2H]-126.432859911
AllCCS[M+HCOO]-131.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.0.95 minutes32390414
Predicted by Siyang on May 30, 20228.7902 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.61 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid338.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid524.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid360.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid75.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid259.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid106.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid281.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid245.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)770.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid579.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid39.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid684.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid219.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid318.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate656.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA408.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water383.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Aminoacrylic acidNC(=C)C(O)=O2001.7Standard polar33892256
2-Aminoacrylic acidNC(=C)C(O)=O1005.6Standard non polar33892256
2-Aminoacrylic acidNC(=C)C(O)=O1058.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Aminoacrylic acid,1TMS,isomer #1C=C(N)C(=O)O[Si](C)(C)C1027.4Semi standard non polar33892256
2-Aminoacrylic acid,1TMS,isomer #2C=C(N[Si](C)(C)C)C(=O)O1123.8Semi standard non polar33892256
2-Aminoacrylic acid,2TMS,isomer #1C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1215.4Semi standard non polar33892256
2-Aminoacrylic acid,2TMS,isomer #1C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1260.8Standard non polar33892256
2-Aminoacrylic acid,2TMS,isomer #1C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1388.4Standard polar33892256
2-Aminoacrylic acid,2TMS,isomer #2C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1326.1Semi standard non polar33892256
2-Aminoacrylic acid,2TMS,isomer #2C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1237.1Standard non polar33892256
2-Aminoacrylic acid,2TMS,isomer #2C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1493.0Standard polar33892256
2-Aminoacrylic acid,3TMS,isomer #1C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1353.6Semi standard non polar33892256
2-Aminoacrylic acid,3TMS,isomer #1C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1315.2Standard non polar33892256
2-Aminoacrylic acid,3TMS,isomer #1C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1338.2Standard polar33892256
2-Aminoacrylic acid,1TBDMS,isomer #1C=C(N)C(=O)O[Si](C)(C)C(C)(C)C1257.8Semi standard non polar33892256
2-Aminoacrylic acid,1TBDMS,isomer #2C=C(N[Si](C)(C)C(C)(C)C)C(=O)O1369.7Semi standard non polar33892256
2-Aminoacrylic acid,2TBDMS,isomer #1C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1634.0Semi standard non polar33892256
2-Aminoacrylic acid,2TBDMS,isomer #1C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1620.2Standard non polar33892256
2-Aminoacrylic acid,2TBDMS,isomer #1C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1641.0Standard polar33892256
2-Aminoacrylic acid,2TBDMS,isomer #2C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1760.8Semi standard non polar33892256
2-Aminoacrylic acid,2TBDMS,isomer #2C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1634.4Standard non polar33892256
2-Aminoacrylic acid,2TBDMS,isomer #2C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1680.3Standard polar33892256
2-Aminoacrylic acid,3TBDMS,isomer #1C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1961.5Semi standard non polar33892256
2-Aminoacrylic acid,3TBDMS,isomer #1C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1929.2Standard non polar33892256
2-Aminoacrylic acid,3TBDMS,isomer #1C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1735.7Standard polar33892256
Spectra
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 IDDB02688
Phenol Explorer Compound IDNot Available
FooDB IDFDB023206
KNApSAcK IDNot Available
Chemspider ID110510
KEGG Compound IDC02218
BioCyc ID2-AMINOACRYLATE
BiGG ID39352
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound123991
PDB IDNot Available
ChEBI ID17123
Food Biomarker OntologyNot Available
VMH ID2AMAC
MarkerDB IDNot Available
Good Scents IDNot Available
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
Serine → 2-Aminoacrylic acid + Waterdetails