NP-MRD: Showing NP-Card for Tyrosylglycine (NP0136688)

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Record Information

Version

1.0

Created at

2022-05-12 15:20:57 UTC

Updated at

2022-05-12 15:20:57 UTC

NP-MRD ID

NP0136688

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tyrosylglycine

Description

Tyrosylglycine, also known as YG or L-tyr-gly, 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. Tyrosylglycine is a very strong basic compound (based on its pKa). It was first documented in 1966 (PMID: 5938633). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 18963488) (PMID: 5965096) (PMID: 6313725) (PMID: 2795003) (PMID: 22305362) (PMID: 949476).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -0.0719    0.1634   -1.4556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4269   -0.4920   -0.2177 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2439    0.1601    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7016    0.0771    0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4056    1.0752    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7808    0.9790    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4654   -0.1168    0.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8428   -0.2450    0.3143 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413   -1.1161    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744   -1.0248    1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8862   -0.5312   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -1.1165    0.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254    0.0596   -1.0758 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642    0.0298   -0.9801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5515    0.7092    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6731    1.1785    1.0192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8858    0.8091    0.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594    0.2483   -1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5265   -0.3717   -2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0482   -1.5494   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0495   -0.3208    1.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126    1.2317    1.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9094    1.9593   -0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3465    1.7666   -0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4069    0.1284    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2256   -2.0011    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404   -1.8464    1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920    0.5332   -1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5618   -1.0140   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    0.6046   -1.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4235    0.0326    0.9553 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 10  4  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 17 31  1  0
M  END


  Mrv1652304062014222D          

 17 17  0  0  0  0            999 V2000
    1.4289   -1.6499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136688

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O4/c12-9(11(17)13-6-10(15)16)5-7-1-3-8(14)4-2-7/h1-4,9,14H,5-6,12H2,(H,13,17)(H,15,16)/t9-/m0/s1

> <INCHI_KEY>
HPYDSVWYXXKHRD-VIFPVBQESA-N

> <FORMULA>
C11H14N2O4

> <MOLECULAR_WEIGHT>
238.243

> <EXACT_MASS>
238.095356939

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.76010787000185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetic acid

> <ALOGPS_LOGP>
-2.32

> <JCHEM_LOGP>
-2.596497657952923

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.518648414519804

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5147773710925465

> <JCHEM_PKA_STRONGEST_BASIC>
8.020997917844086

> <JCHEM_POLAR_SURFACE_AREA>
112.65

> <JCHEM_REFRACTIVITY>
59.9007

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    1   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
L-Tyr-gly	ChEBI
Tyrosyl-glycine	ChEBI
YG	ChEBI
L-Tyr-ile	HMDB
L-Tyrosylglycine	HMDB
N-L-Tyrosylglycine	HMDB
N-Tyrosylglycine	HMDB
Tyr-ile	HMDB
Tyrosine glycine dipeptide	HMDB
Tyrosine-glycine dipeptide	HMDB
Y-g dipeptide	HMDB
YG dipeptide	HMDB

Chemical Formula

C₁₁H₁₄N₂O₄

Average Mass

238.2430 Da

Monoisotopic Mass

238.09536 Da

IUPAC Name

2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetic acid

Traditional Name

[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H14N2O4/c12-9(11(17)13-6-10(15)16)5-7-1-3-8(14)4-2-7/h1-4,9,14H,5-6,12H2,(H,13,17)(H,15,16)/t9-/m0/s1

InChI Key

HPYDSVWYXXKHRD-VIFPVBQESA-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

Not Available

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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic salt
Hydrocarbon derivative
Primary aliphatic amine
Organic nitrogen compound
Amine
Organic oxygen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic zwitterion
Primary amine
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:74990 )

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	-2.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	8.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.65 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.9 m³·mol⁻¹	ChemAxon
Polarizability	23.76 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

HMDB0029105

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7021853

PDB ID

Not Available

ChEBI ID

74990

Good Scents ID

Not Available

References

General References

Ishimitsu T, Sakurai H: Structure-ionization relationship of tyrosine-containing peptides. Talanta. 1983 Nov;30(11):879-83. doi: 10.1016/0039-9140(83)80204-5. [PubMed:18963488 ]
Jones JG, Scotland SM, Dodgson KS: The biological sulphation of L-tyrosyl peptides. Biochem J. 1966 Jan;98(1):138-41. doi: 10.1042/bj0980138. [PubMed:5938633 ]
Basford JM, Jones JG, Rose FA, Dodgson KS: A possible route to the production of free L-tyrosine O-sulphate by the rat. Biochem J. 1966 Jun;99(3):534-7. doi: 10.1042/bj0990534. [PubMed:5965096 ]
Mousa S, Couri D: Analysis of enkephalins, beta-endorphins and small peptides in their sequences by highly sensitive high-performance liquid chromatography with electrochemical detection: implications in opioid peptide metabolism. J Chromatogr. 1983 Sep 2;267(1):191-8. doi: 10.1016/s0021-9673(01)90832-5. [PubMed:6313725 ]
Zlokovic BV, Mackic JB, Djuricic B, Davson H: Kinetic analysis of leucine-enkephalin cellular uptake at the luminal side of the blood-brain barrier of an in situ perfused guinea-pig brain. J Neurochem. 1989 Nov;53(5):1333-40. doi: 10.1111/j.1471-4159.1989.tb08522.x. [PubMed:2795003 ]
Schiesel S, Lammerhofer M, Leitner A, Lindner W: Quantitative high-performance liquid chromatography-tandem mass spectrometry impurity profiling methods for the analysis of parenteral infusion solutions for amino acid supplementation containing L-alanyl-L-glutamine. J Chromatogr A. 2012 Oct 12;1259:111-20. doi: 10.1016/j.chroma.2012.01.020. Epub 2012 Jan 18. [PubMed:22305362 ]
Stohrer G, Brown GB: Adduct of tyrosine and the oncogen 3-acetoxyxanthine. Biochemistry. 1976 Jun 29;15(13):2772-5. doi: 10.1021/bi00658a010. [PubMed:949476 ]
Krause JA, Eggleston DS: Linear tripeptide conformation. Crystal structures of Cbz-glycylglycyltyrosine methyl ester and Cbz-glycyl(D,L)tyrosylglycine ethyl ester. Int J Pept Protein Res. 1993 Feb;41(2):133-40. [PubMed:8458686 ]
Crooks PA, Krechniak JW, Olson JW, Gillespie MN: High-performance liquid chromatographic analysis of pulmonary metabolites of Leu- and Met-enkephalins in isolated perfused rat lung. J Pharm Sci. 1985 Sep;74(9):1010-2. doi: 10.1002/jps.2600740923. [PubMed:4067842 ]
Anderson L, Bussler B, Martins H, Dufton M: Enkephalin-processing oligopeptidases in cobra venom: inhibition by thiorphan and bestatin reveals co-operative actions. Toxicon. 1998 May;36(5):719-28. doi: 10.1016/s0041-0101(97)00134-7. [PubMed:9655632 ]

Showing NP-Card for Tyrosylglycine (NP0136688)

MOL for NP0136688 (Tyrosylglycine)

3D MOL for NP0136688 (Tyrosylglycine)

3D SDF for NP0136688 (Tyrosylglycine)

3D-SDF for NP0136688 (Tyrosylglycine)

PDB for NP0136688 (Tyrosylglycine)

3D PDB for NP0136688 (Tyrosylglycine)

SMILES for NP0136688 (Tyrosylglycine)

INCHI for NP0136688 (Tyrosylglycine)

Structure for NP0136688 (Tyrosylglycine)

3D Structure for NP0136688 (Tyrosylglycine)