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Showing NP-Card for L-Asparagine (NP0000653)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-25 01:14:25 UTC
NP-MRD IDNP0000653
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Asparagine
DescriptionAsparagine (Asn) or L-asparagine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-asparagine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Asparagine is found in all organisms ranging from bacteria to plants to animals. In humans, asparagine is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. The precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. This enzyme transfers the amino group from glutamate to oxaloacetate producing alpha-ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming beta-aspartyl-AMP. Glutamine donates an ammonium group which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Since the asparagine side chain can make efficient hydrogen bond interactions with the peptide backbone, asparagines are often found near the beginning and end of alpha-helices, and in turn motifs in beta sheets. Its role can be thought as "capping" the hydrogen bond interactions which would otherwise need to be satisfied by the polypeptide backbone. Asparagine also provides key sites for N-linked glycosylation, a modification of the protein chain that is characterized by the addition of carbohydrate chains. A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature (i.E. Baking). These occur primarily in baked goods such as French fries, potato chips, and roasted coffee. Asparagine was first isolated in 1806 from asparagus juice --hence its name. Asparagine was the first amino acid to be isolated. The smell observed in the urine of some individuals after the consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. However, some scientists disagree and implicate other substances in the smell, especially methanethiol.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000653 (L-Asparagine)

174
  Mrv1652309032023552D          

  9  8  0  0  1  0            999 V2000
    5.6655   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.0784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  8  2  0  0  0  0
  3  9  2  0  0  0  0
  6  4  1  1  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for NP0000653 (L-Asparagine)

HMDB0000168
     RDKit          3D
L-Asparagine
 17 16  0  0  0  0  0  0  0  0999 V2000
    3.0118    0.0585    0.1453 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6464    0.3601    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3443    0.9974    1.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5912   -0.0606   -0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590    0.3934   -0.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0169   -0.1883    1.2122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055    0.0373   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    0.4553   -2.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8410   -0.7744   -0.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4628    0.4712   -0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -0.5572    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    0.3882   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017   -1.1687   -0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070    1.5134   -0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -0.5724    1.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3344   -0.9505    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476   -0.4027   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  1
  6 15  1  0
  6 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0000653 (L-Asparagine)

174
  Mrv1652309032023552D          

  9  8  0  0  1  0            999 V2000
    5.6655   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.0784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2  8  2  0  0  0  0
  3  9  2  0  0  0  0
  6  4  1  1  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC(N)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1

> <INCHI_KEY>
DCXYFEDJOCDNAF-REOHCLBHSA-N

> <FORMULA>
C4H8N2O3

> <MOLECULAR_WEIGHT>
132.1179

> <EXACT_MASS>
132.053492132

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.677080187792834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-carbamoylpropanoic acid

> <ALOGPS_LOGP>
-3.36

> <JCHEM_LOGP>
-4.287830841089268

> <ALOGPS_LOGS>
0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.09048069675879

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9985390993927763

> <JCHEM_PKA_STRONGEST_BASIC>
8.433487205020553

> <JCHEM_POLAR_SURFACE_AREA>
106.41

> <JCHEM_REFRACTIVITY>
28.354899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-asparagine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000653 (L-Asparagine)

HMDB0000168
     RDKit          3D
L-Asparagine
 17 16  0  0  0  0  0  0  0  0999 V2000
    3.0118    0.0585    0.1453 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6464    0.3601    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3443    0.9974    1.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5912   -0.0606   -0.5672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590    0.3934   -0.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0169   -0.1883    1.2122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8055    0.0373   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    0.4553   -2.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8410   -0.7744   -0.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4628    0.4712   -0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -0.5572    0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660    0.3882   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017   -1.1687   -0.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070    1.5134   -0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -0.5724    1.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3344   -0.9505    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476   -0.4027   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  1
  6 15  1  0
  6 16  1  0
  9 17  1  0
M  END
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PDB for NP0000653 (L-Asparagine)

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 174                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0      10.576  -0.146   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.242   2.164   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.241  -1.686   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.908  -1.686   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       3.907   0.624   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.908  -0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574   0.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.242   0.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.241  -0.146   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    6                                                            
CONECT    5    9                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    1    2    6                                                  
CONECT    9    3    5    7                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000653 (L-Asparagine)

COMPND    HMDB0000168
HETATM    1  N1  UNL     1       3.012   0.058   0.145  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.646   0.360   0.378  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.344   0.997   1.411  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.591  -0.061  -0.567  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.759   0.393  -0.069  1.00  0.00           C  
HETATM    6  N2  UNL     1      -1.017  -0.188   1.212  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.805   0.037  -1.070  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.745   0.455  -2.241  1.00  0.00           O  
HETATM    9  O3  UNL     1      -2.841  -0.774  -0.640  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.463   0.471  -0.698  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.515  -0.557   0.815  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.766   0.388  -1.563  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.602  -1.169  -0.669  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.707   1.513  -0.003  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.983  -0.572   1.227  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.334  -0.951   1.467  1.00  0.00           H  
HETATM   17  H8  UNL     1      -3.748  -0.403  -0.395  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3    3    4
CONECT    4    5   12   13
CONECT    5    6    7   14
CONECT    6   15   16
CONECT    7    8    8    9
CONECT    9   17
END
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SMILES for NP0000653 (L-Asparagine)

N[C@@H](CC(N)=O)C(O)=O
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INCHI for NP0000653 (L-Asparagine)

InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
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View in JSmol
Synonyms
ValueSource
(2S)-2,4-Diamino-4-oxobutanoic acidChEBI
(2S)-2-Amino-3-carbamoylpropanoic acidChEBI
(S)-2-Amino-3-carbamoylpropanoic acidChEBI
(S)-AsparagineChEBI
2-Aminosuccinamic acidChEBI
alpha-Aminosuccinamic acidChEBI
AsnChEBI
ASPARAGINEChEBI
Aspartamic acidChEBI
L-2-Aminosuccinamic acidChEBI
L-AsparaginChEBI
L-Aspartic acid beta-amideChEBI
NChEBI
(2S)-2,4-Diamino-4-oxobutanoateGenerator
(2S)-2-Amino-3-carbamoylpropanoateGenerator
(S)-2-Amino-3-carbamoylpropanoateGenerator
2-AminosuccinamateGenerator
a-AminosuccinamateGenerator
a-Aminosuccinamic acidGenerator
alpha-AminosuccinamateGenerator
Α-aminosuccinamateGenerator
Α-aminosuccinamic acidGenerator
AspartamateGenerator
L-2-AminosuccinamateGenerator
L-Aspartate b-amideGenerator
L-Aspartate beta-amideGenerator
L-Aspartate β-amideGenerator
L-Aspartic acid b-amideGenerator
L-Aspartic acid β-amideGenerator
(-)-AsparagineHMDB
(S)-2,4-Diamino-4-oxobutanoateHMDB
(S)-2,4-Diamino-4-oxobutanoic acidHMDB
AgedoiteHMDB
alpha AmminosuccinamateHMDB
alpha Amminosuccinamic acidHMDB
AltheineHMDB
Asparagine acidHMDB
AsparamideHMDB
Aspartic acid amideHMDB
Aspartic acid b-amideHMDB
Aspartic acid beta amideHMDB
b2,4-(S)-Diamino-4-oxo-utanoateHMDB
b2,4-(S)-Diamino-4-oxo-utanoic acidHMDB
Crystal VIHMDB
L-2,4-Diamino-4-oxobutanoateHMDB
L-2,4-Diamino-4-oxobutanoic acidHMDB
L-AspartamineHMDB
L-b-AsparagineHMDB
L-beta-AsparagineHMDB
Chemical FormulaC4H8N2O3
Average Mass132.1179 Da
Monoisotopic Mass132.05349 Da
IUPAC Name(2S)-2-amino-3-carbamoylpropanoic acid
Traditional NameL-asparagine
CAS Registry Number70-47-3
SMILES
N[C@@H](CC(N)=O)C(O)=O
InChI Identifier
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
InChI KeyDCXYFEDJOCDNAF-REOHCLBHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-11-12View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-27View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-27View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-10-22View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-11-12View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-07View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica gigasLOTUS Database
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia absinthiumLOTUS Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
Astragalus falcatusLOTUS Database
Atalantia buxifoliaLOTUS Database
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Bambusa vulgarisLOTUS Database
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Calendula officinalisLOTUS Database
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumKNApSAcK Database
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catha edulisLOTUS Database
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Convolvulus arvensisLOTUS Database
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaPlant
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daphnia pulexLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Ficus septicaLOTUS Database
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Gossypium hirsutumLOTUS Database
Grifola frondosaFooDB
Hedera helixLOTUS Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lotus corniculatusLOTUS Database
Lotus uliginosusLOTUS Database
Luffa aegyptiacaFooDB
Lunaria annuaLOTUS Database
LupinusFooDB
Lupinus albusFooDB
Lupinus luteusLOTUS Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
Melolontha hippocastaniLOTUS Database
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus australisLOTUS Database
Morus nigraFooDB
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
Ocotea vellozianaLOTUS Database
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia ficus-indicaLOTUS Database
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus densifloraLOTUS Database
Pinus edulisFooDB
Pinus ponderosaLOTUS Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pleurotus ostreatusFooDB
Polygonum alpinumFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scorzonera hispanicaFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Stangeria eriopusLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Telekia speciosaLOTUS Database
Tetragonia tetragonioidesFooDB
Thalassiosira pseudonanaLOTUS Database
ThelespermaFooDB
Thymus pulegioidesFooDB
Thymus transcaucasicusLOTUS Database
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trifolium pratense L.KNApSAcK Database
Trifolium repensPlant
Trifolium repens L.KNApSAcK Database
Trigonella foenum-graecumFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valeriana officinalisLOTUS Database
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Withania somniferaLOTUS Database
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine 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 ParentAsparagine and derivatives
Alternative Parents
Substituents
  • Asparagine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • Carboxamide group
  • Amino acid
  • Primary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 - 235 °CNot Available
Boiling Point438.03 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility29.4 mg/mLNot Available
LogP-3.82Chmelík, J., Hudecek, J., Putyera, K., Makovicka, J., Kalous, V., & Chmelíková, J. (1991). Characterization of the hydrophobic properties of amino acids on the basis of their partition and distribution coefficients in the 1-octanol-water system. Collection of Czechoslovak chemical communications, 56(10), 2030-2041.
Predicted Properties
PropertyValueSource
Water Solubility168 g/LALOGPS
logP-3.4ALOGPS
logP-4.3ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.35 m³·mol⁻¹ChemAxon
Polarizability11.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000168
DrugBank IDDB00174
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000787
KNApSAcK IDC00001341
Chemspider ID6031
KEGG Compound IDC00152
BioCyc IDASN
BiGG ID34055
Wikipedia LinkAsparagine
METLIN ID14
PubChem Compound6267
PDB IDNot Available
ChEBI ID17196
Good Scents IDrw1039271
References
General References
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  2. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
  4. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
  5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
  6. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
  7. Starczynowski DT, Reynolds JG, Gilmore TD: Mutations of tumor necrosis factor alpha-responsive serine residues within the C-terminal transactivation domain of human transcription factor REL enhance its in vitro transforming ability. Oncogene. 2005 Nov 10;24(49):7355-68. [PubMed:16027730 ]
  8. Fischer D, Schroers A, Blumcke I, Urbach H, Zerres K, Mortier W, Vorgerd M, Schroder R: Consequences of a novel caveolin-3 mutation in a large German family. Ann Neurol. 2003 Feb;53(2):233-41. [PubMed:12557291 ]
  9. Filho JC, Bergstrom J, Stehle P, Furst P: Simultaneous measurements of free amino acid patterns of plasma, muscle and erythrocytes in healthy human subjects. Clin Nutr. 1997 Dec;16(6):299-305. [PubMed:16844612 ]
  10. Sun S, Han J, Ralph WM Jr, Chandrasekaran A, Liu K, Auborn KJ, Carter TH: Endoplasmic reticulum stress as a correlate of cytotoxicity in human tumor cells exposed to diindolylmethane in vitro. Cell Stress Chaperones. 2004 Mar;9(1):76-87. [PubMed:15270080 ]
  11. Takamatsu S, Inoue N, Katsumata T, Nakamura K, Fujibayashi Y, Takeuchi M: The relationship between the branch-forming glycosyltransferases and cell surface sugar chain structures. Biochemistry. 2005 Apr 26;44(16):6343-9. [PubMed:15835923 ]
  12. Chiara F, Goumans MJ, Forsberg H, Ahgren A, Rasola A, Aspenstrom P, Wernstedt C, Hellberg C, Heldin CH, Heuchel R: A gain of function mutation in the activation loop of platelet-derived growth factor beta-receptor deregulates its kinase activity. J Biol Chem. 2004 Oct 8;279(41):42516-27. Epub 2004 Jul 28. [PubMed:15284236 ]
  13. Xu L, Wang Y, Gillespie D, Meissner G: Two rings of negative charges in the cytosolic vestibule of type-1 ryanodine receptor modulate ion fluxes. Biophys J. 2006 Jan 15;90(2):443-53. Epub 2005 Oct 20. [PubMed:16239337 ]
  14. Poon CJ, Plaas AH, Keene DR, McQuillan DJ, Last K, Fosang AJ: N-linked keratan sulfate in the aggrecan interglobular domain potentiates aggrecanase activity. J Biol Chem. 2005 Jun 24;280(25):23615-21. Epub 2005 Apr 22. [PubMed:15849197 ]
  15. Ahlman B, Andersson K, Leijonmarck CE, Ljungqvist O, Hedenborg L, Wernerman J: Short-term starvation alters the free amino acid content of the human intestinal mucosa. Clin Sci (Lond). 1994 Jun;86(6):653-62. [PubMed:7914846 ]
  16. Avramis VI, Panosyan EH: Pharmacokinetic/pharmacodynamic relationships of asparaginase formulations: the past, the present and recommendations for the future. Clin Pharmacokinet. 2005;44(4):367-93. [PubMed:15828851 ]
  17. Mohrmann K, van Eijndhoven MA, Schinkel AH, Schellens JH: Absence of N-linked glycosylation does not affect plasma membrane localization of breast cancer resistance protein (BCRP/ABCG2). Cancer Chemother Pharmacol. 2005 Oct;56(4):344-50. Epub 2005 May 5. [PubMed:15875186 ]
  18. Socher E, Conrad M, Heger L, Paulsen F, Sticht H, Zunke F, Arnold P: Computational decomposition reveals reshaping of the SARS-CoV-2-ACE2 interface among viral variants expressing the N501Y mutation. J Cell Biochem. 2021 Dec;122(12):1863-1872. doi: 10.1002/jcb.30142. Epub 2021 Sep 13. [PubMed:34516024 ]