MiMeDB: Showing metabocard for N-(gamma-L-glutamyl)-L-alaninol zwitterion (MMDBc0032884)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:56:14 UTC

Update Date

2022-08-31 21:45:05 UTC

Metabolite ID

MMDBc0032884

Metabolite Identification

Common Name

N-(gamma-L-glutamyl)-L-alaninol zwitterion

Description

An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of N-(γ-L-glutamyl)-L-alaninol; major species at pH 7.3.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311182123562D          

 14 13  0  0  1  0            999 V2000
    3.7125    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  CHG  2  11   1  13  -1
M  END
> <DATABASE_ID>
MMDBc0032884

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@@H](CO)NC(=O)CC[C@H]([NH3+])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O4/c1-5(4-11)10-7(12)3-2-6(9)8(13)14/h5-6,11H,2-4,9H2,1H3,(H,10,12)(H,13,14)/t5-,6-/m0/s1

> <INCHI_KEY>
JJWXGBABENFUNJ-WDSKDSINSA-N

> <FORMULA>
C8H16N2O4

> <MOLECULAR_WEIGHT>
204.226

> <EXACT_MASS>
204.111007003

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.69946753210824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-azaniumyl-4-{[(2S)-1-hydroxypropan-2-yl]carbamoyl}butanoate

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-4.0508831140632156

> <ALOGPS_LOGS>
-0.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.978620169155437

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2342463849268266

> <JCHEM_PKA_STRONGEST_BASIC>
9.312085953384488

> <JCHEM_POLAR_SURFACE_AREA>
117.1

> <JCHEM_REFRACTIVITY>
70.8476

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-ammonio-4-{[(2S)-1-hydroxypropan-2-yl]carbamoyl}butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-NOV-21         0                                  
HETATM    1  C   UNK     0       6.930   2.461   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.263   4.001   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.264   4.771   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.597   2.461   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      13.598   6.311   0.000  0.00  0.00           N+1
HETATM   12  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
gamma-L-Glutamyl-L-alaninol	ChEBI
g-L-Glutamyl-L-alaninol	Generator
Γ-L-glutamyl-L-alaninol	Generator
N-(g-L-Glutamyl)-L-alaninol zwitterion	Generator
N-(Γ-L-glutamyl)-L-alaninol zwitterion	Generator
g-Glutamyl-L-alaninol	Generator
Γ-glutamyl-L-alaninol	Generator

Molecular Formula

C₈H₁₆N₂O₄

Average Mass

204.226

Monoisotopic Mass

204.111007003

IUPAC Name

(2S)-2-azaniumyl-4-{[(2S)-1-hydroxypropan-2-yl]carbamoyl}butanoate

Traditional Name

(2S)-2-ammonio-4-{[(2S)-1-hydroxypropan-2-yl]carbamoyl}butanoate

CAS Registry Number

Not Available

SMILES

C[C@@H](CO)NC(=O)CC[C@H]([NH3+])C([O-])=O

InChI Identifier

InChI=1S/C8H16N2O4/c1-5(4-11)10-7(12)3-2-6(9)8(13)14/h5-6,11H,2-4,9H2,1H3,(H,10,12)(H,13,14)/t5-,6-/m0/s1

InChI Key

JJWXGBABENFUNJ-WDSKDSINSA-N

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
L-alpha-amino acid
Fatty amide
N-acyl-amine
Fatty acyl
Fatty acid
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Alcohol
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Organic salt
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N(5)-alkyl-L-glutamine (CHEBI:85894 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	33.1 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-4.1	ChemAxon
logS	-0.89	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.1 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.85 m³·mol⁻¹	ChemAxon
Polarizability	20.7 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

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34999695

KEGG Compound ID

Not Available

BioCyc ID

CPD-9373

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25202985

PDB ID

Not Available

ChEBI ID

85421

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N-(gamma-L-glutamyl)-L-alaninol zwitterion (MMDBc0032884)

MOL for #<Metabolite:0x00007fecd0092c10>

3D MOL for #<Metabolite:0x00007fecd0092c10>

3D SDF for #<Metabolite:0x00007fecd0092c10>

3D-SDF for #<Metabolite:0x00007fecd0092c10>

PDB for #<Metabolite:0x00007fecd0092c10>

3D PDB for #<Metabolite:0x00007fecd0092c10>

SMILES for #<Metabolite:0x00007fecd0092c10>

INCHI for #<Metabolite:0x00007fecd0092c10>

Structure for #<Metabolite:0x00007fecd0092c10>

3D Structure for #<Metabolite:0x00007fecd0092c10>