NP-MRD: Showing NP-Card for Tryptophyl-Glycine (NP0136667)

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Record Information

Version

2.0

Created at

2022-05-12 15:20:25 UTC

Updated at

2022-05-12 15:20:25 UTC

NP-MRD ID

NP0136667

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tryptophyl-Glycine

Description

Tryptophyl-Glycine, also known as W-g dipeptide or TRP-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. Tryptophyl-Glycine is a very strong basic compound (based on its pKa). Tryptophyl-Glycine is a dipeptide composed of tryptophan and glycine. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. 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. Tryptophyl-Glycine was first documented in 1965 (PMID: 5879901). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 18950135) (PMID: 14323609) (PMID: 231893) (PMID: 14290281) (PMID: 5943437) (PMID: 210982).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    0.3922   -0.8986    0.7819 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8095    0.3796    0.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0660    1.0163   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4568    1.1456   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    2.3226    0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    2.0271    0.6633 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5743    0.7467    0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7006   -0.0198    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521   -1.3602    0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6253   -1.9232   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929   -1.1626   -0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    0.1674   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237    0.3440   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    1.4069   -0.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0050   -0.8344   -0.0328 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3691   -0.8679   -0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1822    0.0378    0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6242    0.6907    1.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5457    0.2174    0.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1772   -1.0969    1.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -1.6754    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040    1.0395    1.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0253    0.3962   -1.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3361    2.0217   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253    3.2766    0.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    2.7611    1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5970    0.4256    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6914   -1.9041    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6491   -2.9583   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268   -1.6298   -0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -1.7108    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7909   -1.8852   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -0.6170   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9678    0.1214   -0.7015 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  1  0
  7 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  2 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 12  4  1  0
  8  7  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
 11 30  1  0
 10 29  1  0
  9 28  1  0
  8 27  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
M  END


  Mrv1652304062014182D          

 19 20  0  0  0  0            999 V2000
   -0.2461    0.4041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605    0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605    1.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750   -0.4209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895    0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8576    0.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4097    0.1266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9972   -0.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1902   -0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382   -1.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -1.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7001   -1.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2521   -1.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    0.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973    0.8166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829   -0.4209    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  0  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  1  0  0  0  0
 10 11  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136667

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H15N3O3/c14-10(13(19)16-7-12(17)18)5-8-6-15-11-4-2-1-3-9(8)11/h1-4,6,10,15H,5,7,14H2,(H,16,19)(H,17,18)

> <INCHI_KEY>
UYKREHOKELZSPB-UHFFFAOYSA-N

> <FORMULA>
C13H15N3O3

> <MOLECULAR_WEIGHT>
261.2765

> <EXACT_MASS>
261.111341361

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.81032131027468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid

> <ALOGPS_LOGP>
-0.94

> <JCHEM_LOGP>
-2.1933012878640943

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.474728930085679

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7201495143070713

> <JCHEM_PKA_STRONGEST_BASIC>
7.9595349763807

> <JCHEM_POLAR_SURFACE_AREA>
108.21000000000001

> <JCHEM_REFRACTIVITY>
69.0063

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-amino-3-(1H-indol-3-yl)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      -0.459   0.754   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.793   1.524   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.793   3.064   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.127   0.754   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -3.127  -0.786   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -4.460   1.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.794   0.754   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.201   1.381   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -8.231   0.236   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -7.461  -1.097   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.955  -0.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.925  -1.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.400  -3.386   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.907  -3.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.937  -2.562   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.874   1.524   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.208   0.754   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.542   1.524   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.208  -0.786   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    1   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
L-Tryptophyl-L-glycine	HMDB
TRP-Gly	HMDB
Tryptophan glycine dipeptide	HMDB
Tryptophan-glycine dipeptide	HMDB
Tryptophylglycine	HMDB
W-g Dipeptide	HMDB
WG Dipeptide	HMDB
Tryptophanylglycine	HMDB
2-{[2-amino-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}acetate	Generator

Chemical Formula

C₁₃H₁₅N₃O₃

Average Mass

261.2765 Da

Monoisotopic Mass

261.11134 Da

IUPAC Name

2-[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid

Traditional Name

[2-amino-3-(1H-indol-3-yl)propanamido]acetic acid

CAS Registry Number

Not Available

SMILES

NC(CC1=CNC2=C1C=CC=C2)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C13H15N3O3/c14-10(13(19)16-7-12(17)18)5-8-6-15-11-4-2-1-3-9(8)11/h1-4,6,10,15H,5,7,14H2,(H,16,19)(H,17,18)

InChI Key

UYKREHOKELZSPB-UHFFFAOYSA-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Triptan
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Fatty amide
Substituted pyrrole
Fatty acyl
Benzenoid
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Amine
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.94	ALOGPS
logP	-2.2	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	7.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.01 m³·mol⁻¹	ChemAxon
Polarizability	26.81 Å³	ChemAxon
Number of Rings	2	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

HMDB0029083

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

263471

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pan Y, Birkedal H, Pattison P, Brown D, Chapuis G: Molecular dynamics study of tryptophylglycine: a dipeptide nanotube with confined water. J Phys Chem B. 2004 May 20;108(20):6458-66. doi: 10.1021/jp037219v. [PubMed:18950135 ]
Yajima H, Kubo K: Studies on peptides. IV. The synthesis of D-histidyl-L-phenylalanyl-L- arginyl-L-tryptophylglycine and L-histidyl-L-phenylalanyl-L-arginyl-D-tryptophylglycine and their physiological properties in frog melanocyte in vitro. Chem Pharm Bull (Tokyo). 1965 Jul;13(7):759-64. doi: 10.1248/cpb.13.759. [PubMed:5879901 ]
YAJIMA H, KUBO K: THE SYNTHESIS OF D-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYLGLYCINE AND L-HISTIDYL-L-PHENYLALANYL-L-ARGINYL-D-TRYPTOPHYLGLYCINE AND THEIR PHYSIOLOGICAL PROPERTIES IN FROG MELANOCYTE. Biochim Biophys Acta. 1965 Mar 8;97:596-7. doi: 10.1016/0304-4165(65)90176-5. [PubMed:14323609 ]
Partanen S, Kaakkola S, Kaariainen I: Tryptophylglycine dipeptide in ACTH/MSH cells of the human hypophysis: its identification and studies on its antinociceptive effects in mice. Acta Physiol Scand. 1979 Nov;107(3):213-18. doi: 10.1111/j.1748-1716.1979.tb06465.x. [PubMed:231893 ]
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Showing NP-Card for Tryptophyl-Glycine (NP0136667)

MOL for NP0136667 (Tryptophyl-Glycine)

3D MOL for NP0136667 (Tryptophyl-Glycine)

3D SDF for NP0136667 (Tryptophyl-Glycine)

3D-SDF for NP0136667 (Tryptophyl-Glycine)

PDB for NP0136667 (Tryptophyl-Glycine)

3D PDB for NP0136667 (Tryptophyl-Glycine)

SMILES for NP0136667 (Tryptophyl-Glycine)

INCHI for NP0136667 (Tryptophyl-Glycine)

Structure for NP0136667 (Tryptophyl-Glycine)

3D Structure for NP0136667 (Tryptophyl-Glycine)