NP-MRD: Showing NP-Card for 5-L-Glutamyl-taurine (NP0087152)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:41:36 UTC

Updated at

2022-05-11 16:41:36 UTC

NP-MRD ID

NP0087152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-L-Glutamyl-taurine

Description

5-L-Glutamyl-taurine, also known as gamma-L-glutamyltaurine or glutaurina, 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. 5-L-Glutamyl-taurine is a very strong basic compound (based on its pKa). 5-L-Glutamyl-taurine exists in all living organisms, ranging from bacteria to humans. 5-L-glutamyl-taurine can be biosynthesized from taurine through its interaction with the enzyme Gamma-glutamyltransferase 6. 5-L-Glutamyl-taurine was first documented in 1978 (PMID: 157672). In humans, 5-L-glutamyl-taurine is involved in taurine and hypotaurine metabolism (PMID: 1450962) (PMID: 15838590) (PMID: 2875599) (PMID: 3185869).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
    4.0175    0.1737    1.4684 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499    0.0328    0.2237 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8692   -0.3634    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9585   -0.5541   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4103   -0.9804   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5615   -1.1013    1.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4406   -1.2197   -0.9355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7522   -1.6239   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3781   -0.5974    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502    0.9627   -0.4541 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.3770    0.8170   -1.6956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086    1.4872   -0.8080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2645    2.0378    0.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    1.3091   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    1.3783   -1.6516 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6992    2.4526    0.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7120    1.0903    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224    0.1450    1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7480   -0.7637   -0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013   -1.3358    1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4905    0.4036    1.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191    0.4300   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -1.3275   -1.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -1.0932   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4349   -1.7924   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6647   -2.5665    0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7781   -0.4753    1.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861   -0.9911    0.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0467    1.6139    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6242    2.4517    0.5326 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 13  1  1
 10 11  2  0
 10 12  2  0
  2 14  1  0
 14 16  1  0
 14 15  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv0541 02231219542D          

 16 15  0  0  1  0            999 V2000
   -2.8157    0.0799    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -0.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    0.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2305   -0.6316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048    0.7990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3812    0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6621   -0.3387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7648   -0.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0457    0.9018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763    0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -0.3387    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8995    0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1841   -1.1644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6148   -0.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956    0.9018    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  2  0  0  0  0
  1  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  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
 12 13  1  0  0  0  0
 12 14  1  1  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087152

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O6S/c8-5(7(11)12)1-2-6(10)9-3-4-16(13,14)15/h5H,1-4,8H2,(H,9,10)(H,11,12)(H,13,14,15)/t5-/m0/s1

> <INCHI_KEY>
WGXUDTHMEITUBO-YFKPBYRVSA-N

> <FORMULA>
C7H14N2O6S

> <MOLECULAR_WEIGHT>
254.261

> <EXACT_MASS>
254.05725688

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
23.236422345381698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-3.616801198005179

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.5895014283267166

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.268893735412334

> <JCHEM_PKA_STRONGEST_BASIC>
9.312083141824443

> <JCHEM_POLAR_SURFACE_AREA>
146.79

> <JCHEM_REFRACTIVITY>
52.6929

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-[(2-sulfoethyl)carbamoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      -5.256   0.149   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      -3.914  -0.625   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.591   0.923   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -6.030  -1.179   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -4.489   1.491   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.578   0.142   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.236  -0.632   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.092   0.142   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.428  -0.632   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.085   1.683   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.756   0.142   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.084  -0.632   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.412   0.142   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.077  -2.174   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       6.748  -0.632   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.405   1.683   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
5-Glutamyl-taurine	ChEBI
gamma-Glutamyltaurine	ChEBI
gamma-GT	ChEBI
gamma-L-Glutamyltaurine	ChEBI
Glutaurina	ChEBI
Glutaurinum	ChEBI
Litoralon	ChEBI
Glutaurine	Kegg
g-Glutamyltaurine	Generator
Γ-glutamyltaurine	Generator
g-GT	Generator
Γ-GT	Generator
g-L-Glutamyltaurine	Generator
Γ-L-glutamyltaurine	Generator
alpha-Glutamyl taurine	HMDB
gamma-L-Glutamyl-taurine	HMDB
Glautaurine	HMDB
Glutaurin	HMDB
Glutaurin, (D)-isomer	HMDB
alpha-Glutamyltaurine	HMDB

Chemical Formula

C₇H₁₄N₂O₆S

Average Mass

254.2610 Da

Monoisotopic Mass

254.05726 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(=O)NCCS(O)(=O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H14N2O6S/c8-5(7(11)12)1-2-6(10)9-3-4-16(13,14)15/h5H,1-4,8H2,(H,9,10)(H,11,12)(H,13,14,15)/t5-/m0/s1

InChI Key

WGXUDTHMEITUBO-YFKPBYRVSA-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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 acid
Fatty acyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary amine
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:27694 )

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	-2.3	ALOGPS
logP	-3.6	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.79 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	52.69 m³·mol⁻¹	ChemAxon
Polarizability	23.24 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

HMDB0004195

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023332

KNApSAcK ID

Not Available

Chemspider ID

62003

KEGG Compound ID

C05844

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glutaurine

METLIN ID

Not Available

PubChem Compound

68759

PDB ID

Not Available

ChEBI ID

27694

Good Scents ID

Not Available

References

General References

Uemura S, Ienaga K, Higashiura K, Kimura H: Gamma-glutamyltaurine has potent and long-lasting antiepileptic action as demonstrated by intra-amygdaloid injection in amygdala-kindled rats. Brain Res. 1992 Oct 30;594(2):347-50. doi: 10.1016/0006-8993(92)91150-d. [PubMed:1450962 ]
Feuer L, Torok LJ, Csaba G: Effect of Litoralon on the development of goblet cells of the intestinal mucosa during metamorphosis of the frog. Acta Morphol Acad Sci Hung. 1978;26(3-4):319-24. [PubMed:157672 ]
Bittner S, Win T, Gupta R: gamma-L-glutamyltaurine. Amino Acids. 2005 Jun;28(4):343-56. doi: 10.1007/s00726-005-0196-7. Epub 2005 Apr 21. [PubMed:15838590 ]
Schulz H, Feuer L: Anticonflict properties of the dipeptide Litoralon and of diazepam in rats. Acta Physiol Hung. 1986;67(3):331-8. [PubMed:2875599 ]
Balazs M, Telegdy G: Effects of glutaurine treatment on electroshock-induced amnesia. Antiamnesic action of glutaurine. Neuropeptides. 1988 Aug-Sep;12(2):55-8. doi: 10.1016/0143-4179(88)90031-5. [PubMed:3185869 ]

Showing NP-Card for 5-L-Glutamyl-taurine (NP0087152)

MOL for NP0087152 (5-L-Glutamyl-taurine)

3D MOL for NP0087152 (5-L-Glutamyl-taurine)

3D SDF for NP0087152 (5-L-Glutamyl-taurine)

3D-SDF for NP0087152 (5-L-Glutamyl-taurine)

PDB for NP0087152 (5-L-Glutamyl-taurine)

3D PDB for NP0087152 (5-L-Glutamyl-taurine)

SMILES for NP0087152 (5-L-Glutamyl-taurine)

INCHI for NP0087152 (5-L-Glutamyl-taurine)

Structure for NP0087152 (5-L-Glutamyl-taurine)

3D Structure for NP0087152 (5-L-Glutamyl-taurine)