MiMeDB: Showing metabocard for 4-(gamma-L-glutamylamino)butanoic acid (MMDBc0055457)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:52:32 UTC

Update Date

2022-08-12 20:09:22 UTC

Metabolite ID

MMDBc0055457

Metabolite Identification

Common Name

4-(gamma-L-glutamylamino)butanoic acid

Description

4-(gamma-L-glutamylamino)butanoate, also known as N(5)-(3-carboxylatopropyl)-L-glutamine, 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. Based on a literature review very few articles have been published on 4-(gamma-L-glutamylamino)butanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221522D          

 17 16  0  0  1  0            999 V2000
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.4783    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  9  6  1  0  0  0  0
  6 10  1  1  0  0  0
 11  5  1  4  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16  9  1  0  0  0  0
  6 17  1  1  0  0  0
M  CHG  1  12  -1
M  END
> <DATABASE_ID>
MMDBc0055457

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCC([O-])=NCCCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O5/c10-6(9(15)16)3-4-7(12)11-5-1-2-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/p-1/t6-/m0/s1

> <INCHI_KEY>
MKYPKZSGLSOGLL-LURJTMIESA-M

> <FORMULA>
C9H15N2O5

> <MOLECULAR_WEIGHT>
231.229

> <EXACT_MASS>
231.098645171

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.951908638848202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-amino-4-carboxy-N-(3-carboxypropyl)butanecarboximidate

> <JCHEM_LOGP>
-4.130502042090055

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9069857479759746

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1441058399663753

> <JCHEM_PKA_STRONGEST_BASIC>
9.536417999012231

> <JCHEM_POLAR_SURFACE_AREA>
136.04

> <JCHEM_REFRACTIVITY>
64.61760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-amino-4-carboxy-N-(3-carboxypropyl)butanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.692   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.025   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.026   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -1.691   2.104   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -0.357  -0.206   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0      -8.359   1.334   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -7.026   3.644   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       3.644   0.564   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    8                                                       
CONECT    3    4    6                                                       
CONECT    4    3    7                                                       
CONECT    5    1   11                                                       
CONECT    6    3    9   10   17                                             
CONECT    7    4   11   12                                                  
CONECT    8    2   13   14                                                  
CONECT    9    6   15   16                                                  
CONECT   10    6                                                            
CONECT   11    5    7                                                       
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16    9                                                            
CONECT   17    6                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

Synonyms

Value	Source
(2S)-2-Ammonio-5-[(3-carboxylatopropyl)amino]-5-oxopentanoate	ChEBI
(2S)-2-Azaniumyl-4-[(3-carboxylatopropyl)carbamoyl]butanoate	ChEBI
N(5)-(3-Carboxylatopropyl)-L-glutamine	ChEBI
(2S)-2-Ammonio-5-[(3-carboxylatopropyl)amino]-5-oxopentanoic acid	Generator
(2S)-2-Azaniumyl-4-[(3-carboxylatopropyl)carbamoyl]butanoic acid	Generator
4-(g-L-Glutamylamino)butanoate	Generator
4-(g-L-Glutamylamino)butanoic acid	Generator
4-(gamma-L-Glutamylamino)butanoic acid	Generator
4-(Γ-L-glutamylamino)butanoate	Generator
4-(Γ-L-glutamylamino)butanoic acid	Generator

Molecular Formula

C₉H₁₅N₂O₅

Average Mass

231.229

Monoisotopic Mass

231.098645171

IUPAC Name

(4S)-4-amino-4-carboxy-N-(3-carboxypropyl)butanecarboximidate

Traditional Name

(4S)-4-amino-4-carboxy-N-(3-carboxypropyl)butanecarboximidate

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCC([O-])=NCCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C9H16N2O5/c10-6(9(15)16)3-4-7(12)11-5-1-2-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/p-1/t6-/m0/s1

InChI Key

MKYPKZSGLSOGLL-LURJTMIESA-M

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino-acid anion (CHEBI:58800 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-4.1	ChemAxon
pKa (Strongest Acidic)	2.14	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	136.04 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	64.62 m³·mol⁻¹	ChemAxon
Polarizability	22.95 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

Not Available

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	4	Human ; Human feces

Exposure Sources

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

26331368

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245457

PDB ID

Not Available

ChEBI ID

58800

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 4-(gamma-L-glutamylamino)butanoic acid (MMDBc0055457)

MOL for #<Metabolite:0x00007fdb306fc558>

3D MOL for #<Metabolite:0x00007fdb306fc558>

3D SDF for #<Metabolite:0x00007fdb306fc558>

3D-SDF for #<Metabolite:0x00007fdb306fc558>

PDB for #<Metabolite:0x00007fdb306fc558>

3D PDB for #<Metabolite:0x00007fdb306fc558>

SMILES for #<Metabolite:0x00007fdb306fc558>

INCHI for #<Metabolite:0x00007fdb306fc558>

Structure for #<Metabolite:0x00007fdb306fc558>

3D Structure for #<Metabolite:0x00007fdb306fc558>