| Record Information |
|---|
| Version | 5.0 |
|---|
| Status | Expected but not Quantified |
|---|
| Creation Date | 2006-08-13 01:22:37 UTC |
|---|
| Update Date | 2023-02-21 17:16:45 UTC |
|---|
| HMDB ID | HMDB0003609 |
|---|
| Secondary Accession Numbers | - HMDB0006356
- HMDB03609
- HMDB06356
|
|---|
| Metabolite Identification |
|---|
| Common Name | 2-Aminoacrylic acid |
|---|
| Description | 2-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 | InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6) |
|---|
| Synonyms | | Value | Source |
|---|
| 2,3-Didehydroalanine | ChEBI | | 2-Aminoacrylate | ChEBI | | alpha,beta-Dehydroalanine | ChEBI | | Anhydroserine2-aminopropenoic acid | ChEBI | | Dehydroalanine | ChEBI | | 2-Aminoprop-2-enoate | Kegg | | a,b-Dehydroalanine | Generator | | Α,β-dehydroalanine | Generator | | Anhydroserine2-aminopropenoate | Generator | | 2-Aminoprop-2-enoic acid | Generator | | (alpha)-(beta)-Di-dehydroalanine | HMDB | | a-b-Di-dehydroalanine | HMDB | | alpha-beta-Di-dehydroalanine | HMDB | | alpha-Aminoacrylate | HMDB | | 2-Amino-2-propenoic acid | HMDB | | Aminoacrylic acid | HMDB | | Dehydro-L-alanine | HMDB | | alpha,beta-Didehydroalanine | HMDB | | alpha-Aminoacrylic acid | HMDB | | α,β-Didehydroalanine | HMDB | | α-Aminoacrylic acid | HMDB |
|
|---|
| Chemical Formula | C3H5NO2 |
|---|
| Average Molecular Weight | 87.0773 |
|---|
| Monoisotopic Molecular Weight | 87.032028409 |
|---|
| IUPAC Name | 2-aminoprop-2-enoic acid |
|---|
| Traditional Name | dehydroalanine |
|---|
| CAS Registry Number | 28453-71-6 |
|---|
| SMILES | NC(=C)C(O)=O |
|---|
| InChI Identifier | InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6) |
|---|
| InChI Key | UQBOJOOOTLPNST-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). |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic acids and derivatives |
|---|
| Class | Carboxylic acids and derivatives |
|---|
| Sub Class | Amino acids, peptides, and analogues |
|---|
| Direct Parent | Alpha 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 Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Physiological effect | Not Available |
|---|
| Disposition | |
|---|
| Process | Not Available |
|---|
| Role | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Molecular Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | -2.651 | Not Available |
|
|---|
| Experimental Chromatographic Properties | Not Available |
|---|
| Predicted Molecular Properties | |
|---|
| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
|---|
| 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 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 8.7902 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 4.61 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 338.9 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 524.0 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 360.6 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 75.5 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 259.1 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 106.4 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 281.9 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 245.4 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 770.5 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 579.7 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 39.1 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 684.7 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 219.5 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 318.1 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 656.3 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 408.6 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 383.9 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
|---|
| 2-Aminoacrylic acid,1TMS,isomer #1 | C=C(N)C(=O)O[Si](C)(C)C | 1027.4 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,1TMS,isomer #2 | C=C(N[Si](C)(C)C)C(=O)O | 1123.8 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,2TMS,isomer #1 | C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1215.4 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,2TMS,isomer #1 | C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1260.8 | Standard non polar | 33892256 | | 2-Aminoacrylic acid,2TMS,isomer #1 | C=C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1388.4 | Standard polar | 33892256 | | 2-Aminoacrylic acid,2TMS,isomer #2 | C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1326.1 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,2TMS,isomer #2 | C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1237.1 | Standard non polar | 33892256 | | 2-Aminoacrylic acid,2TMS,isomer #2 | C=C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1493.0 | Standard polar | 33892256 | | 2-Aminoacrylic acid,3TMS,isomer #1 | C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1353.6 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,3TMS,isomer #1 | C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1315.2 | Standard non polar | 33892256 | | 2-Aminoacrylic acid,3TMS,isomer #1 | C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1338.2 | Standard polar | 33892256 | | 2-Aminoacrylic acid,1TBDMS,isomer #1 | C=C(N)C(=O)O[Si](C)(C)C(C)(C)C | 1257.8 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,1TBDMS,isomer #2 | C=C(N[Si](C)(C)C(C)(C)C)C(=O)O | 1369.7 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,2TBDMS,isomer #1 | C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1634.0 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,2TBDMS,isomer #1 | C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1620.2 | Standard non polar | 33892256 | | 2-Aminoacrylic acid,2TBDMS,isomer #1 | C=C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1641.0 | Standard polar | 33892256 | | 2-Aminoacrylic acid,2TBDMS,isomer #2 | C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1760.8 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,2TBDMS,isomer #2 | C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1634.4 | Standard non polar | 33892256 | | 2-Aminoacrylic acid,2TBDMS,isomer #2 | C=C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1680.3 | Standard polar | 33892256 | | 2-Aminoacrylic acid,3TBDMS,isomer #1 | C=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)C | 1961.5 | Semi standard non polar | 33892256 | | 2-Aminoacrylic acid,3TBDMS,isomer #1 | C=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)C | 1929.2 | Standard non polar | 33892256 | | 2-Aminoacrylic acid,3TBDMS,isomer #1 | C=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)C | 1735.7 | Standard polar | 33892256 |
|
|---|