NP-MRD: Showing NP-Card for Aspartyl-Glutamine (NP0136388)

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Record Information

Version

2.0

Created at

2022-05-12 15:13:15 UTC

Updated at

2022-05-12 15:13:15 UTC

NP-MRD ID

NP0136388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspartyl-Glutamine

Description

Aspartyl-Glutamine, also known as D-Q dipeptide or asp-GLN, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Aspartyl-Glutamine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. Aspartyl-Glutamine is a dipeptide composed of aspartate and glutamine. Aspartyl-Glutamine was first documented in 1986 (PMID: 3818845). This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.0870    2.7029   -1.5985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    1.5478   -0.7637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0557    1.3369   -0.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    0.6429   -0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1677   -0.4540    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0421   -1.4598    0.3674 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1847   -0.8454    0.8152 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348   -0.9884    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -1.6664   -1.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6822   -0.4362    0.2969 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6715   -1.3708   -0.3280 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580    0.8572   -0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1246    1.9793    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3109    1.8599    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    3.2293   -0.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684   -2.4203    1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673   -2.5475    2.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6183   -3.1892    1.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4805    3.5317   -1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7552    2.7075   -2.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9640    1.2308   -0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7426    0.2675   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3740   -0.0655    1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0449   -1.0097   -0.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8837   -1.9966   -0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1387   -0.3457    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9216   -0.3913    1.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570   -1.7842   -1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9596   -2.0748    0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792    0.7421   -1.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    1.1283   -0.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627    3.4595   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6636   -4.1781    1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 16  1  0
 16 18  1  0
 16 17  2  0
 11 28  1  0
 11 29  1  0
 10 27  1  1
 12 30  1  0
 12 31  1  0
 15 32  1  0
  7 26  1  0
  6 25  1  6
  5 23  1  0
  5 24  1  0
  4 21  1  0
  4 22  1  0
  1 19  1  0
  1 20  1  0
 18 33  1  0
M  END


  Mrv1652304062013292D          

 18 17  0  0  0  0            999 V2000
    7.8079    2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    4.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    4.5079    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136388

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H15N3O6/c10-4(3-7(14)15)8(16)12-5(9(17)18)1-2-6(11)13/h4-5H,1-3,10H2,(H2,11,13)(H,12,16)(H,14,15)(H,17,18)

> <INCHI_KEY>
GSMPSRPMQQDRIB-UHFFFAOYSA-N

> <FORMULA>
C9H15N3O6

> <MOLECULAR_WEIGHT>
261.2319

> <EXACT_MASS>
261.096085227

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.200305298616662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-amino-3-carboxypropanamido)-4-carbamoylbutanoic acid

> <ALOGPS_LOGP>
-3.59

> <JCHEM_LOGP>
-5.449729285425411

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.671991604202899

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9786709178506126

> <JCHEM_PKA_STRONGEST_BASIC>
8.526425804304235

> <JCHEM_POLAR_SURFACE_AREA>
172.80999999999997

> <JCHEM_REFRACTIVITY>
56.44270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-amino-3-carboxypropanamido)-4-carbamoylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0      14.575   5.335   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.241   7.645   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      11.907   3.795   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.906   6.105   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      21.243   6.105   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      15.908   7.645   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.242   8.415   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      14.575   8.415   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
Asp-GLN	HMDB
Aspartate glutamine dipeptide	HMDB
Aspartate-glutamine dipeptide	HMDB
Aspartylglutamine	HMDB
D-Q Dipeptide	HMDB
DQ Dipeptide	HMDB
L-Aspartyl-L-glutamine	HMDB
2-[(2-Amino-3-carboxy-1-hydroxypropylidene)amino]-4-(C-hydroxycarbonimidoyl)butanoate	Generator

Chemical Formula

C₉H₁₅N₃O₆

Average Mass

261.2319 Da

Monoisotopic Mass

261.09609 Da

IUPAC Name

2-(2-amino-3-carboxypropanamido)-4-carbamoylbutanoic acid

Traditional Name

2-(2-amino-3-carboxypropanamido)-4-carbamoylbutanoic acid

CAS Registry Number

Not Available

SMILES

NC(CC(O)=O)C(=O)NC(CCC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C9H15N3O6/c10-4(3-7(14)15)8(16)12-5(9(17)18)1-2-6(11)13/h4-5H,1-3,10H2,(H2,11,13)(H,12,16)(H,14,15)(H,17,18)

InChI Key

GSMPSRPMQQDRIB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Glutamine or derivatives
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acyl-amine
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Fatty amide
Primary carboxylic acid amide
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Amino acid or derivatives
Carboxylic acid
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.6	ALOGPS
logP	-5.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	8.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	56.44 m³·mol⁻¹	ChemAxon
Polarizability	24.2 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0028751

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22169419

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

van der Leij FR, Welling GW: Determination of beta-aspartylpeptidase activity in human faeces by high-performance liquid chromatography using pre-column derivatization with phenyl isothiocyanate. J Chromatogr. 1986 Nov 28;383(1):35-42. doi: 10.1016/s0378-4347(00)83438-6. [PubMed:3818845 ]

Showing NP-Card for Aspartyl-Glutamine (NP0136388)

MOL for NP0136388 (Aspartyl-Glutamine)

3D MOL for NP0136388 (Aspartyl-Glutamine)

3D SDF for NP0136388 (Aspartyl-Glutamine)

3D-SDF for NP0136388 (Aspartyl-Glutamine)

PDB for NP0136388 (Aspartyl-Glutamine)

3D PDB for NP0136388 (Aspartyl-Glutamine)

SMILES for NP0136388 (Aspartyl-Glutamine)

INCHI for NP0136388 (Aspartyl-Glutamine)

Structure for NP0136388 (Aspartyl-Glutamine)

3D Structure for NP0136388 (Aspartyl-Glutamine)