NP-MRD: Showing NP-Card for N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine (NP0048405)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:55:57 UTC

Updated at

2022-03-17 20:55:57 UTC

NP-MRD ID

NP0048405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine

Description

N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine, also known as gamma-L-glutaminyl-3,4-benzoquinone, belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine is a very strong basic compound (based on its pKa). Outside of the human body, N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine has been detected, but not quantified in, mushrooms. This could make N5-(3,4-dioxo-1,5-cyclohexadien-1-yl)-L-glutamine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215472D          

 18 18  0  0  0  0            999 V2000
   -2.0233    0.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8485    0.0852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    1.3232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3080    1.3232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400   -1.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -1.3232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.0852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -1.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -0.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207    0.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -0.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207    1.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    0.3260    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
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCC(=O)NC1=CC(=O)C(=O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O5/c12-7(11(17)18)2-4-10(16)13-6-1-3-8(14)9(15)5-6/h1,3,5,7H,2,4,12H2,(H,13,16)(H,17,18)

> <INCHI_KEY>
PIJUAYKLMIQQRF-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O5

> <MOLECULAR_WEIGHT>
252.2234

> <EXACT_MASS>
252.074621504

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
23.041851138151266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[(3,4-dioxocyclohexa-1,5-dien-1-yl)carbamoyl]butanoic acid

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-3.1313071377922808

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.574256729507923

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9894035110576938

> <JCHEM_PKA_STRONGEST_BASIC>
8.912073114180355

> <JCHEM_POLAR_SURFACE_AREA>
126.56

> <JCHEM_REFRACTIVITY>
62.81660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-[(3,4-dioxocyclohexa-1,5-dien-1-yl)carbamoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.777   0.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.777   1.700   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -5.317   0.159   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.777  -1.381   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.112   2.470   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.442   2.470   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.688  -2.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.353  -1.700   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.018  -2.470   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -1.353  -0.159   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.317  -1.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.652  -2.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.985  -1.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.985  -0.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.652   0.606   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.317  -0.162   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.652   2.146   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.317   0.609   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1                                                            
CONECT    4    1    7                                                       
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   11   15                                                       
CONECT   17   15                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
gamma-L-Glutaminyl-3,4-benzoquinone	HMDB
N-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine	HMDB
2-Amino-4-[(3,4-dioxocyclohexa-1,5-dien-1-yl)-C-hydroxycarbonimidoyl]butanoate	Generator

Chemical Formula

C₁₁H₁₂N₂O₅

Average Mass

252.2234 Da

Monoisotopic Mass

252.07462 Da

IUPAC Name

2-amino-4-[(3,4-dioxocyclohexa-1,5-dien-1-yl)carbamoyl]butanoic acid

Traditional Name

2-amino-4-[(3,4-dioxocyclohexa-1,5-dien-1-yl)carbamoyl]butanoic acid

CAS Registry Number

30382-25-3

SMILES

NC(CCC(=O)NC1=CC(=O)C(=O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C11H12N2O5/c12-7(11(17)18)2-4-10(16)13-6-1-3-8(14)9(15)5-6/h1,3,5,7H,2,4,12H2,(H,13,16)(H,17,18)

InChI Key

PIJUAYKLMIQQRF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Alpha-amino acid
O-benzoquinone
Quinone
Fatty amide
N-acyl-amine
Fatty acyl
Vinylogous amide
Amino acid
Cyclic ketone
Secondary carboxylic acid amide
Carboxamide group
Ketone
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	ALOGPS
logP	-3.1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.99	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	126.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.82 m³·mol⁻¹	ChemAxon
Polarizability	23.04 Å³	ChemAxon
Number of Rings	1	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

HMDB0035993

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014801

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

131751895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine (NP0048405)

MOL for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

3D MOL for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

3D SDF for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

3D-SDF for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

PDB for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

3D PDB for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

SMILES for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

INCHI for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

Structure for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)

3D Structure for NP0048405 (N5-(3,4-Dioxo-1,5-cyclohexadien-1-yl)-L-glutamine)