NP-MRD: Showing NP-Card for Asparaginylglycine (NP0136370)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:48 UTC

Updated at

2022-05-12 15:12:48 UTC

NP-MRD ID

NP0136370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asparaginylglycine

Description

Asparaginylglycine, also known as L-asn-gly or NG, 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. Asparaginylglycine is a very strong basic compound (based on its pKa). Asparaginylglycine was first documented in 1978 (PMID: 728426). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 6838831).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062013262D          

 13 12  0  0  0  0            999 V2000
 2500.2753 2499.7653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.5605 2499.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.8458 2499.7653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.1309 2499.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4159 2499.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.6990 2499.3537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4159 2500.5908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.5605 2498.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.9901 2499.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7052 2499.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4199 2499.3537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7052 2500.5908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.2753 2500.5908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 13  1  1  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136370

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H11N3O4/c7-3(1-4(8)10)6(13)9-2-5(11)12/h3H,1-2,7H2,(H2,8,10)(H,9,13)(H,11,12)/t3-/m0/s1

> <INCHI_KEY>
KLKHFFMNGWULBN-VKHMYHEASA-N

> <FORMULA>
C6H11N3O4

> <MOLECULAR_WEIGHT>
189.171

> <EXACT_MASS>
189.074955846

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.257594134364155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S)-2-amino-3-carbamoylpropanamido]acetic acid

> <ALOGPS_LOGP>
-3.37

> <JCHEM_LOGP>
-5.397239611697938

> <ALOGPS_LOGS>
-1.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.036769938212988

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.429800945039131

> <JCHEM_PKA_STRONGEST_BASIC>
7.347071219264442

> <JCHEM_POLAR_SURFACE_AREA>
135.51000000000002

> <JCHEM_REFRACTIVITY>
41.1584

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-2-amino-3-carbamoylpropanamido]acetic 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  C   UNK     0    4667.1814666.229   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4665.8464665.460   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4664.5124666.229   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4663.1784665.460   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4661.8434666.229   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4660.5054665.460   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4661.8434667.769   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4665.8464663.919   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4668.5154665.460   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4669.8504666.229   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    4671.1844665.460   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    4669.8504667.769   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0    4667.1814667.769   0.000  0.00  0.00           N+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
L-Asn-gly	ChEBI
N-G	ChEBI
NG	ChEBI
Asn-gly	HMDB
Asparagine glycine dipeptide	HMDB
Asparagine-glycine dipeptide	HMDB
Asparaginyl-glycine	HMDB
L-Asparaginylglycine	HMDB
N-Asparaginylglycine	HMDB
N-g Dipeptide	HMDB
N-L-Asparaginylglycine	HMDB
NG Dipeptide	HMDB

Chemical Formula

C₆H₁₁N₃O₄

Average Mass

189.1710 Da

Monoisotopic Mass

189.07496 Da

IUPAC Name

2-[(2S)-2-amino-3-carbamoylpropanamido]acetic acid

Traditional Name

[(2S)-2-amino-3-carbamoylpropanamido]acetic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CC(N)=O)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C6H11N3O4/c7-3(1-4(8)10)6(13)9-2-5(11)12/h3H,1-2,7H2,(H2,8,10)(H,9,13)(H,11,12)/t3-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73422 )

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	-3.4	ALOGPS
logP	-5.4	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	7.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	135.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	41.16 m³·mol⁻¹	ChemAxon
Polarizability	17.26 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

HMDB0028731

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

9899050

PDB ID

Not Available

ChEBI ID

73422

Good Scents ID

Not Available

References

General References

Titani K, Koide A, Ericsson LH, Kumar S, Hermann J, Wade RD, Walsh KA, Neurath H, Fischer EH: Sequence of the carboxyl-terminal 492 residues of rabbit muscle glycogen phosphorylase including the pyridoxal 5'-phosphate binding site. Biochemistry. 1978 Dec 26;17(26):5680-93. doi: 10.1021/bi00619a014. [PubMed:728426 ]
Furuta H, Kajita A: Dimeric hemoglobin of the bivalve mollusc Anadara broughtonii: complete amino acid sequence of the globin chain. Biochemistry. 1983 Feb 15;22(4):917-22. doi: 10.1021/bi00273a032. [PubMed:6838831 ]

Showing NP-Card for Asparaginylglycine (NP0136370)

MOL for NP0136370 (Asparaginylglycine)

3D MOL for NP0136370 (Asparaginylglycine)

3D SDF for NP0136370 (Asparaginylglycine)

3D-SDF for NP0136370 (Asparaginylglycine)

PDB for NP0136370 (Asparaginylglycine)

3D PDB for NP0136370 (Asparaginylglycine)

SMILES for NP0136370 (Asparaginylglycine)

INCHI for NP0136370 (Asparaginylglycine)

Structure for NP0136370 (Asparaginylglycine)

3D Structure for NP0136370 (Asparaginylglycine)