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Showing NP-Card for asparagine (NP0209059)

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Record Information
Version2.0
Created at2022-09-05 06:19:07 UTC
Updated at2022-09-05 06:19:07 UTC
NP-MRD IDNP0209059
Secondary Accession NumbersNone
Natural Product Identification
Common Nameasparagine
DescriptionAsparagine, also known as Asn or hasp, 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. Asparagine is a very strong basic compound (based on its pKa). asparagine is found in Arabidopsis thaliana, Atalantia buxifolia, Bambusa vulgaris, Caenorhabditis elegans, Castanea sativa, Catha edulis, Chlamydomonas reinhardtii, Lates calcarifer, Lemna aequinoctialis, Lotus burttii, Lunaria annua, Lupinus luteus, Medicago sativa, Melolontha hippocastani, Mycoplasma bovis, Panax ginseng, Paris fargesii, Pseudostellaria heterophylla and Withania somnifera. asparagine was first documented in 2012 (PMID: 22770225). An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 2-amino-2-oxoethyl group (PMID: 22264337).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0209059 (asparagine)

Structure #1
  Mrv0541 02241206012D          

  9  8  0  0  0  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
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3D MOL for NP0209059 (asparagine)

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3D SDF for NP0209059 (asparagine)
Structure #1
  Mrv0541 02241206012D          

  9  8  0  0  0  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC(O)=N)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)

> <INCHI_KEY>
DCXYFEDJOCDNAF-UHFFFAOYSA-N

> <FORMULA>
C4H8N2O3

> <MOLECULAR_WEIGHT>
132.1179

> <EXACT_MASS>
132.053492132

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
11.721718741917872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(C-hydroxycarbonimidoyl)propanoic acid

> <ALOGPS_LOGP>
-3.37

> <JCHEM_LOGP>
-4.375117513713448

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.679677810144658

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7183940751206768

> <JCHEM_PKA_STRONGEST_BASIC>
9.623245446777423

> <JCHEM_POLAR_SURFACE_AREA>
107.40000000000002

> <JCHEM_REFRACTIVITY>
39.2915

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asparagine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0209059 (asparagine)
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PDB for NP0209059 (asparagine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.540  -1.540   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.541   0.770   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       4.207  -1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.127   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1    6    7                                                  
CONECT    4    2    8    9                                                  
CONECT    5    2                                                            
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0209059 (asparagine)
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SMILES for NP0209059 (asparagine)
NC(CC(O)=N)C(O)=O
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INCHI for NP0209059 (asparagine)
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)
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Synonyms
ValueSource
2,4-Diamino-4-oxobutanoic acidChEBI
2-Amino-3-carbamoylpropanoic acidChEBI
AsnChEBI
AsparaginChEBI
AsparaginaChEBI
DL-AsparagineChEBI
HaspChEBI
NChEBI
2,4-Diamino-4-oxobutanoateGenerator
2-Amino-3-carbamoylpropanoateGenerator
L-AsparagineMeSH
AsparagineMeSH
Chemical FormulaC4H8N2O3
Average Mass132.1179 Da
Monoisotopic Mass132.05349 Da
IUPAC Name2-amino-3-(C-hydroxycarbonimidoyl)propanoic acid
Traditional Nameasparagine
CAS Registry NumberNot Available
SMILES
NC(CC(O)=N)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)
InChI KeyDCXYFEDJOCDNAF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 22.5 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaLOTUS Database
Atalantia buxifoliaLOTUS Database
Bambusa vulgarisLOTUS Database
Caenorhabditis elegansLOTUS Database
Castanea sativaLOTUS Database
Catha edulisLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Lates calcariferLOTUS Database
Lemna aequinoctialisLOTUS Database
Lotus burttiiLOTUS Database
Lunaria annuaLOTUS Database
Lupinus luteusLOTUS Database
Medicago sativaLOTUS Database
Melolontha hippocastaniLOTUS Database
Mycoplasmopsis bovisLOTUS Database
Panax ginsengLOTUS Database
Paris fargesiiLOTUS Database
Pseudostellaria heterophyllaLOTUS Database
Withania somniferaLOTUS 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
    • 

  • Fatty amide
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Carboxamide group
    • 

  • Primary carboxylic acid amide
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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-3.4ALOGPS
logP-4.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)9.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity39.29 m³·mol⁻¹ChemAxon
Polarizability11.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16438  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAsparagine  
METLIN IDNot Available
PubChem Compound236  
PDB IDNot Available
ChEBI ID22653  
Good Scents IDNot Available
References
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225  ] 
  2. Castro C, Sar F, Shaw WR, Mishima M, Miska EA, Griffin JL: A metabolomic strategy defines the regulation of lipid content and global metabolism by Delta9 desaturases in Caenorhabditis elegans. BMC Genomics. 2012 Jan 20;13:36. doi: 10.1186/1471-2164-13-36. [PubMed:22264337  ] 
  3. LOTUS database [Link]