NP-MRD: Showing NP-Card for Glutaminylmethionine (NP0136431)

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Record Information

Version

2.0

Created at

2022-05-12 15:14:22 UTC

Updated at

2022-05-12 15:14:22 UTC

NP-MRD ID

NP0136431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutaminylmethionine

Description

Glutaminylmethionine, also known as Q-m dipeptide or GLN-met, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Glutaminylmethionine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
    2.2028    2.1087   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5235    1.1227   -1.6659 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -0.4113   -1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071   -1.5618   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021   -1.7007    0.4622 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9943   -0.8379    0.7770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -1.2438    0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -2.3837    0.1239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4601   -0.3415    0.9155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9404    0.9002    1.4119 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3796   -0.1016   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4923    0.8383    0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4206    1.1104   -0.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5218    1.9777   -0.7764 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2225    0.5705   -2.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0191   -1.7501    1.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560   -1.0955    2.6362 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839   -2.4939    1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5582    3.1531   -0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955    1.7829    0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    2.2254    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147   -0.7359   -2.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -0.2031   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3599   -2.5146   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -1.8355   -1.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -2.7591    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    0.0926    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0812   -0.8214    1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    1.6555    0.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3185    1.1665    2.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203   -1.0333   -0.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7992    0.4020   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0920    1.7943    0.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082    0.3842    0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9425    2.4625   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8714    2.0991    0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174   -2.0220    1.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 18  1  0
 16 17  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  0
  9 28  1  1
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 18 37  1  0
M  END


  Mrv1652304062013372D          

 18 17  0  0  0  0            999 V2000
 2501.0699 2500.0010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.3559 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6419 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9279 2499.5877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.2139 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4999 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7859 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0719 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7859 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9279 2498.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6419 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7839 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4979 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2119 2499.5877    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9280 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0699 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7839 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3559 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  1 16  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCC[C@H](NC(=O)[C@@H](N)CCC(N)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H19N3O4S/c1-18-5-4-7(10(16)17)13-9(15)6(11)2-3-8(12)14/h6-7H,2-5,11H2,1H3,(H2,12,14)(H,13,15)(H,16,17)/t6-,7-/m0/s1

> <INCHI_KEY>
SIGGQAHUPUBWNF-BQBZGAKWSA-N

> <FORMULA>
C10H19N3O4S

> <MOLECULAR_WEIGHT>
277.34

> <EXACT_MASS>
277.109627278

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.35564055632128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-4-(methylsulfanyl)butanoic acid

> <ALOGPS_LOGP>
-2.64

> <JCHEM_LOGP>
-3.8883992866040153

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.57818572798461

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6621115423323403

> <JCHEM_PKA_STRONGEST_BASIC>
8.225660352885372

> <JCHEM_POLAR_SURFACE_AREA>
135.51000000000002

> <JCHEM_REFRACTIVITY>
67.496

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-4-(methylsulfanyl)butanoic 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    4668.6644666.669   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4667.3314665.897   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4665.9984666.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4664.6654665.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4663.3334666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4662.0004665.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4660.6674666.669   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    4659.3344665.897   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0    4660.6674668.208   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4664.6654664.358   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4665.9984668.208   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4669.9974665.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4671.3294666.669   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0    4672.6624665.897   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0    4673.9994666.669   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4668.6644668.208   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    4669.9974668.975   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    4667.3314668.975   0.000  0.00  0.00           O+0
CONECT    1    2   12   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
CONECT   11    3                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    1   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
GLN-Met	HMDB
L-Glutaminyl-L-methionine	HMDB
N-Glutaminylmethionine	HMDB
N-L-Glutaminyl-L-methionine	HMDB
Glutaminyl-methionine	HMDB
Glutamine methionine dipeptide	HMDB
Glutamine-methionine dipeptide	HMDB
Q-m Dipeptide	HMDB
QM Dipeptide	HMDB
L-GLN-L-Met	HMDB
Glutaminylmethionine	HMDB
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-(methylsulfanyl)butanoate	Generator
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-(methylsulphanyl)butanoate	Generator
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-(methylsulphanyl)butanoic acid	Generator

Chemical Formula

C₁₀H₁₉N₃O₄S

Average Mass

277.3400 Da

Monoisotopic Mass

277.10963 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-4-(methylsulfanyl)butanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-4-(methylsulfanyl)butanoic acid

CAS Registry Number

Not Available

SMILES

CSCC[C@H](NC(=O)[C@@H](N)CCC(N)=O)C(O)=O

InChI Identifier

InChI=1S/C10H19N3O4S/c1-18-5-4-7(10(16)17)13-9(15)6(11)2-3-8(12)14/h6-7H,2-5,11H2,1H3,(H2,12,14)(H,13,15)(H,16,17)/t6-,7-/m0/s1

InChI Key

SIGGQAHUPUBWNF-BQBZGAKWSA-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 peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Thia fatty acid
Fatty acyl
Fatty acid
Amino acid or derivatives
Amino acid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkylthioether
Thioether
Sulfenyl compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Primary amine
Carbonyl group
Organic nitrogen compound
Amine
Primary aliphatic amine
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	-2.6	ALOGPS
logP	-3.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	8.23	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	9	ChemAxon
Refractivity	67.5 m³·mol⁻¹	ChemAxon
Polarizability	28.36 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

HMDB0028803

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

54307034

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glutaminylmethionine (NP0136431)

MOL for NP0136431 (Glutaminylmethionine)

3D MOL for NP0136431 (Glutaminylmethionine)

3D SDF for NP0136431 (Glutaminylmethionine)

3D-SDF for NP0136431 (Glutaminylmethionine)

PDB for NP0136431 (Glutaminylmethionine)

3D PDB for NP0136431 (Glutaminylmethionine)

SMILES for NP0136431 (Glutaminylmethionine)

INCHI for NP0136431 (Glutaminylmethionine)

Structure for NP0136431 (Glutaminylmethionine)

3D Structure for NP0136431 (Glutaminylmethionine)