MiMeDB: Showing metabocard for N-isopropyl-L-glutamine zwitterion (MMDBc0032846)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:02:12 UTC

Update Date

2022-08-31 21:44:24 UTC

Metabolite ID

MMDBc0032846

Metabolite Identification

Common Name

N-isopropyl-L-glutamine zwitterion

Description

An amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of N-isopropyl-L-glutamine; major species at pH 7.3.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304301923472D          

 13 12  0  0  1  0            999 V2000
   13.4448  -11.5601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4448  -12.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1593  -12.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7304  -12.7976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7304  -13.6225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0160  -12.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5871  -12.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5871  -11.5600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8725  -12.7974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3015  -12.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1580  -12.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1580  -11.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4436  -12.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  1  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032846

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O3/c1-5(2)10-7(11)4-3-6(9)8(12)13/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1

> <INCHI_KEY>
CABXGBMKSVRWOG-LURJTMIESA-N

> <FORMULA>
C8H16N2O3

> <MOLECULAR_WEIGHT>
188.227

> <EXACT_MASS>
188.116092383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.616975182732446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(propan-2-yl)carbamoyl]butanoic acid

> <ALOGPS_LOGP>
-2.39

> <JCHEM_LOGP>
-3.003654249690879

> <ALOGPS_LOGS>
-0.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.853280744795818

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4309061638520966

> <JCHEM_PKA_STRONGEST_BASIC>
9.312088877667565

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
47.17400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-(isopropylcarbamoyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-APR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-19         0                                  
HETATM    1  O   UNK     0      25.097 -21.579   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      25.097 -23.119   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      26.431 -23.888   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      23.763 -23.889   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      23.763 -25.429   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      22.430 -23.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.763 -23.118   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      19.763 -21.579   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      18.429 -23.888   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      21.096 -23.889   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.095 -23.118   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.095 -21.578   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.761 -23.888   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4   10                                                       
CONECT    7    8    9   10                                                  
CONECT    8    7                                                            
CONECT    9    7   11                                                       
CONECT   10    7    6                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
gamma-L-Glutamyl-isopropylamide	ChEBI
N(5)-Isopropyl-L-glutamine zwitterion	ChEBI
g-L-Glutamyl-isopropylamide	Generator
Γ-L-glutamyl-isopropylamide	Generator
gamma-Glutamyl-isopropylamide	ChEBI
g-Glutamyl-isopropylamide	Generator
Γ-glutamyl-isopropylamide	Generator

Molecular Formula

C₈H₁₆N₂O₃

Average Mass

188.227

Monoisotopic Mass

188.116092383

IUPAC Name

(2S)-2-amino-4-[(propan-2-yl)carbamoyl]butanoic acid

Traditional Name

(2S)-2-amino-4-(isopropylcarbamoyl)butanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H16N2O3/c1-5(2)10-7(11)4-3-6(9)8(12)13/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1

InChI Key

CABXGBMKSVRWOG-LURJTMIESA-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
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic salt
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N(5)-alkyl-L-glutamine (CHEBI:85891 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	21.2 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	2.43	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.17 m³·mol⁻¹	ChemAxon
Polarizability	19.62 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	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	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

5361284

KEGG Compound ID

Not Available

BioCyc ID

CPD-9372

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6993183

PDB ID

Not Available

ChEBI ID

85420

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-isopropyl-L-glutamine zwitterion (MMDBc0032846)

MOL for #<Metabolite:0x00007fecc402f7e8>

3D MOL for #<Metabolite:0x00007fecc402f7e8>

3D SDF for #<Metabolite:0x00007fecc402f7e8>

3D-SDF for #<Metabolite:0x00007fecc402f7e8>

PDB for #<Metabolite:0x00007fecc402f7e8>

3D PDB for #<Metabolite:0x00007fecc402f7e8>

SMILES for #<Metabolite:0x00007fecc402f7e8>

INCHI for #<Metabolite:0x00007fecc402f7e8>

Structure for #<Metabolite:0x00007fecc402f7e8>

3D Structure for #<Metabolite:0x00007fecc402f7e8>