NP-MRD: Showing NP-Card for Glutamyltyrosine (NP0046704)

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Record Information

Version

2.0

Created at

2022-03-17 20:11:31 UTC

Updated at

2022-03-17 20:11:31 UTC

NP-MRD ID

NP0046704

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutamyltyrosine

Description

Glutamyltyrosine, also known as alpha-L-glu-L-tyr or E-Y, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Glutamyltyrosine is a very strong basic compound (based on its pKa). Glutamyltyrosine is a dipeptide composed of glutamate and tyrosine, and is a proteolytic breakdown product of larger proteins. Outside of the human body, Glutamyltyrosine has been detected, but not quantified in, soy beans. This could make glutamyltyrosine a potential biomarker for the consumption of these foods. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamyltyrosine is found in Trypanosoma brucei. Glutamyltyrosine was first documented in 1973 (PMID: 4796163). Glutamyltyrosine is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 3123118) (PMID: 10638694) (PMID: 1263081) (PMID: 27275383) (PMID: 1966886).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303032020272D          

 22 22  0  0  0  0            999 V2000
 2500.1774 2501.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.8923 2500.8483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.8923 2500.0229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6133 2499.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3282 2500.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6133 2498.7978    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2500.8984 2498.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.1836 2498.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.4687 2498.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.7539 2498.7978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.4687 2497.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3282 2498.3841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6071 2501.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3220 2500.8483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.6071 2502.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.3159 2499.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.4621 2500.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.7478 2501.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.0332 2500.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.0332 2500.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.7477 2499.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.4621 2500.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 20 16  1  0  0  0  0
  1 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046704

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O6/c15-10(5-6-12(18)19)13(20)16-11(14(21)22)7-8-1-3-9(17)4-2-8/h1-4,10-11,17H,5-7,15H2,(H,16,20)(H,18,19)(H,21,22)/t10-,11-/m0/s1

> <INCHI_KEY>
YSWHPLCDIMUKFE-QWRGUYRKSA-N

> <FORMULA>
C14H18N2O6

> <MOLECULAR_WEIGHT>
310.306

> <EXACT_MASS>
310.116486308

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.553704790560225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-amino-4-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-2.36

> <JCHEM_LOGP>
-2.7174016991533407

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.960805191352627

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.165447731298546

> <JCHEM_PKA_STRONGEST_BASIC>
8.413060628824018

> <JCHEM_POLAR_SURFACE_AREA>
149.95

> <JCHEM_REFRACTIVITY>
75.18500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-amino-4-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAR-20         0                                  
HETATM    1  C   UNK     0    4666.9984669.019   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4668.3324668.250   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4668.3324666.709   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4669.6784665.963   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    4671.0134666.732   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4669.6784664.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4668.3444663.650   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4667.0094664.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4665.6754663.650   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    4664.3414664.423   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    4665.6754662.109   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0    4671.0134663.650   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    4669.6674669.019   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    4671.0014668.250   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4669.6674670.560   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    4661.6564665.937   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    4665.6634668.249   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4664.3294669.019   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4662.9954668.249   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4662.9954666.709   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4664.3294665.939   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4665.6634666.709   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   20                                                            
CONECT   17   18   22    1                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   16                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
alpha-Glu-tyr	ChEBI
alpha-Glutamyltyrosine	ChEBI
alpha-L-Glu-L-tyr	ChEBI
E-Y	ChEBI
EY	ChEBI
L-Glu-L-tyr	ChEBI
a-Glu-tyr	Generator
Α-glu-tyr	Generator
a-Glutamyltyrosine	Generator
Α-glutamyltyrosine	Generator
a-L-Glu-L-tyr	Generator
Α-L-glu-L-tyr	Generator
Α-L-glutamyl-L-tyrosine	HMDB
L-Α-glutamyl-L-tyrosine	HMDB
N-Α-glutamyltyrosine	HMDB
N-Α-L-glutamyl-L-tyrosine	HMDB
N-L-Α-glutamyltyrosine	HMDB
N-L-Α-glutamyl-L-tyrosine	HMDB
alpha-L-Glutamyl-L-tyrosine	HMDB
L-alpha-Glutamyl-L-tyrosine	HMDB
N-alpha-Glutamyltyrosine	HMDB
N-alpha-L-Glutamyl-L-tyrosine	HMDB
N-L-alpha-Glutamyltyrosine	HMDB
N-L-alpha-Glutamyl-L-tyrosine	HMDB
NSC 523821	HMDB
Glu-tyr	HMDB
L-Glutamyl-L-tyrosine	HMDB
N-Glutamyltyrosine	HMDB
N-L-Glutamyl-L-tyrosine	HMDB
Glutamyl-tyrosine	HMDB
Glutamic acid tyrosine dipeptide	HMDB
Glutamate tyrosine dipeptide	HMDB
Glutamic acid-tyrosine dipeptide	HMDB
Glutamate-tyrosine dipeptide	HMDB
e-Y dipeptide	HMDB
EY dipeptide	HMDB
Glutamyltyrosine	HMDB, ChEBI

Chemical Formula

C₁₄H₁₈N₂O₆

Average Mass

310.3060 Da

Monoisotopic Mass

310.11649 Da

IUPAC Name

(4S)-4-amino-4-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}butanoic acid

Traditional Name

(4S)-4-amino-4-{[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C14H18N2O6/c15-10(5-6-12(18)19)13(20)16-11(14(21)22)7-8-1-3-9(17)4-2-8/h1-4,10-11,17H,5-7,15H2,(H,16,20)(H,18,19)(H,21,22)/t10-,11-/m0/s1

InChI Key

YSWHPLCDIMUKFE-QWRGUYRKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Tyrosine or derivatives
Phenylalanine or derivatives
Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Amino fatty acid
Phenol
Hydroxy fatty acid
N-acyl-amine
Monocyclic benzene moiety
Fatty amide
Benzenoid
Fatty acyl
Dicarboxylic acid or derivatives
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organic oxygen compound
Organic oxide
Organopnictogen compound
Primary amine
Primary aliphatic amine
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:73513 )

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	-2.4	ALOGPS
logP	-2.7	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.95 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	75.18 m³·mol⁻¹	ChemAxon
Polarizability	30.55 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

HMDB0028831

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005571

KNApSAcK ID

Not Available

Chemspider ID

449883

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

515717

PDB ID

Not Available

ChEBI ID

73513

Good Scents ID

Not Available

References

General References

Jeffrey RF, MacDonald TM, Lee MR: A comparison of the renal actions of gamma-L-glutamyl-L-dopa and gamma-L-glutamyl-L-tyrosine in normal man. Clin Sci (Lond). 1988 Jan;74(1):37-40. doi: 10.1042/cs0740037. [PubMed:3123118 ]
Ichishima E, Yamane A, Nitta T, Kinoshita M, Nikkuni S: Production of a new type of acid carboxypeptidase of molds of the Aspergillus niger group. Appl Microbiol. 1973 Sep;26(3):327-31. doi: 10.1128/am.26.3.327-331.1973. [PubMed:4796163 ]
Sadiq S, Berndt TJ, Nath KA, Knox FG: Effect of gamma-L-glutamyl-L-dopa on phosphate excretion. J Lab Clin Med. 2000 Jan;135(1):52-6. doi: 10.1016/s0022-2143(00)70020-5. [PubMed:10638694 ]
Izaddoost M, Harris BG, Gracy RW: Structure and toxicity of alkaloids and amino acids of Sophora secundiflora. J Pharm Sci. 1976 Mar;65(3):352-4. doi: 10.1002/jps.2600650309. [PubMed:1263081 ]
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Kwok CF, Jap TS, Ho LT: Changes of insulin receptor in aortic endothelial cells from diabetic rats. Diabetes Res. 1990 May;14(1):27-31. [PubMed:1966886 ]

Showing NP-Card for Glutamyltyrosine (NP0046704)

MOL for NP0046704 (Glutamyltyrosine)

3D MOL for NP0046704 (Glutamyltyrosine)

3D SDF for NP0046704 (Glutamyltyrosine)

3D-SDF for NP0046704 (Glutamyltyrosine)

PDB for NP0046704 (Glutamyltyrosine)

3D PDB for NP0046704 (Glutamyltyrosine)

SMILES for NP0046704 (Glutamyltyrosine)

INCHI for NP0046704 (Glutamyltyrosine)

Structure for NP0046704 (Glutamyltyrosine)

3D Structure for NP0046704 (Glutamyltyrosine)