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Showing NP-Card for 2,3-didehydroalanine (NP0274036)

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Record Information
Version2.0
Created at2022-09-08 21:16:52 UTC
Updated at2022-09-08 21:16:52 UTC
NP-MRD IDNP0274036
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,3-didehydroalanine
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. 2,3-didehydroalanine is found in Arabidopsis thaliana and Trypanosoma brucei. 2,3-didehydroalanine was first documented in 2006 (PMID: 16734454). A 2,3-dehydroamino acid that is alanine which has been dehydrogenated to introduce a double bond between positions 2 and 3 (PMID: 18585427) (PMID: 23749972) (PMID: 23815688).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0274036 (2,3-didehydroalanine)


  Mrv1652309152017102D          

  6  5  0  0  0  0            999 V2000
    1.0717    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
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3D MOL for NP0274036 (2,3-didehydroalanine)

     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
    0.0112   -1.3193   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2786   -0.0320   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303    0.3516    0.1708 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7650    0.9641   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793    2.1708    0.0460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0817    0.6168   -0.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7604   -2.0715   -0.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069   -1.6231   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2577    0.5479   -0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    0.4280    1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -0.0333    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  6  1  0
  4  5  2  0
  3  9  1  0
  3 10  1  0
  1  7  1  0
  1  8  1  0
  6 11  1  0
M  END
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3D SDF for NP0274036 (2,3-didehydroalanine)


  Mrv1652309152017102D          

  6  5  0  0  0  0            999 V2000
    1.0717    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0274036

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C3H5NO2

> <MOLECULAR_WEIGHT>
87.0773

> <EXACT_MASS>
87.032028409

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.719046717395206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-aminoprop-2-enoic acid

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
-2.882087225726914

> <ALOGPS_LOGS>
0.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5832095700972584

> <JCHEM_PKA_STRONGEST_BASIC>
8.64381918712956

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
20.9163

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dehydroalanine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0274036 (2,3-didehydroalanine)

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PDB for NP0274036 (2,3-didehydroalanine)
HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  N   UNK     0       2.001   0.385   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.667  -1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.000  -0.385   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.667   1.925   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0274036 (2,3-didehydroalanine)
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SMILES for NP0274036 (2,3-didehydroalanine)
NC(=C)C(O)=O
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INCHI for NP0274036 (2,3-didehydroalanine)
InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6)
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View in JSmol
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 Mass87.0773 Da
Monoisotopic Mass87.03203 Da
IUPAC Name2-aminoprop-2-enoic acid
Traditional Namedehydroalanine
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaLOTUS Database
Trypanosoma bruceiLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0003609  
DrugBank IDDB02688  
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Seebeck FP, Szostak JW: Ribosomal synthesis of dehydroalanine-containing peptides. J Am Chem Soc. 2006 Jun 7;128(22):7150-1. doi: 10.1021/ja060966w. [PubMed:16734454  ] 
  2. Corpet DE, Tache S, Archer MC, Bruce WR: Dehydroalanine and lysinoalanine in thermolyzed casein do not promote colon cancer in the rat. Food Chem Toxicol. 2008 Sep;46(9):3037-42. doi: 10.1016/j.fct.2008.06.002. Epub  2008 Jun 10. [PubMed:18585427  ] 
  3. Flynn JM, Downs DM: In the absence of RidA, endogenous 2-aminoacrylate inactivates alanine racemases by modifying the pyridoxal 5'-phosphate cofactor. J Bacteriol. 2013 Aug;195(16):3603-9. doi: 10.1128/JB.00463-13. Epub 2013 Jun 7. [PubMed:23749972  ] 
  4. Flynn JM, Christopherson MR, Downs DM: Decreased coenzyme A levels in ridA mutant strains of Salmonella enterica result from inactivated serine hydroxymethyltransferase. Mol Microbiol. 2013 Aug;89(4):751-9. doi: 10.1111/mmi.12313. Epub 2013 Jul 19. [PubMed:23815688  ] 
  5. LOTUS database [Link]