NP-MRD: Showing NP-Card for Glycylglycylglycine (NP0000388)

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Record Information

Version

2.0

Created at

2012-09-11 17:30:19 UTC

Updated at

2024-09-03 04:22:16 UTC

NP-MRD ID

NP0000388

Natural Product DOI

https://doi.org/10.57994/2796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glycylglycylglycine

Description

Glycylglycylglycine, also known as GGG or triglycine, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. A tripeptide in which three glycine units are linked via peptide bonds in a linear sequence. Glycylglycylglycine has been detected, but not quantified, in fruits. This could make glycylglycylglycine a potential biomarker for the consumption of these foods. Glycylglycylglycine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305271900142D          

 13 12  0  0  0  0            999 V2000
    3.3000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC\C(O)=N\C\C(O)=N\CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11N3O4/c7-1-4(10)8-2-5(11)9-3-6(12)13/h1-3,7H2,(H,8,10)(H,9,11)(H,12,13)

> <INCHI_KEY>
XKUKSGPZAADMRA-UHFFFAOYSA-N

> <FORMULA>
C6H11N3O4

> <MOLECULAR_WEIGHT>
189.1692

> <EXACT_MASS>
189.074955855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.722159929678153

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid

> <ALOGPS_LOGP>
-3.15

> <JCHEM_LOGP>
-4.335925583246738

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.821399711617057

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1878933417298563

> <JCHEM_PKA_STRONGEST_BASIC>
9.334722221231386

> <JCHEM_POLAR_SURFACE_AREA>
128.5

> <JCHEM_REFRACTIVITY>
42.6538

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       6.160   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.930  -1.334   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    4    7                                                       
CONECT    2    5    8                                                       
CONECT    3    6    9                                                       
CONECT    4    1    8   10                                                  
CONECT    5    2    9   11                                                  
CONECT    6    3   12   13                                                  
CONECT    7    1                                                            
CONECT    8    2    4                                                       
CONECT    9    3    5                                                       
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
(Gly)3	ChEBI
Diglycylglycine	ChEBI
GGG	ChEBI
Gly-gly-gly	ChEBI
GlyGlyGly	ChEBI
N-(N-Glycylglycyl)glycine	ChEBI
Triglycine	ChEBI
(([(Aminoacetyl)amino]acetyl)amino)acetic acid	HMDB
Glycine, N-(N-glycylglycyl)- (8ci)(9ci)	HMDB
GLYCYL-glycyl-glycine	HMDB
Glycylpeptide	HMDB
N-(N-GLYCYLGLYCYL)-glycine	HMDB
GGG Peptide	HMDB
Triglycine sulfate	HMDB
Diglycyl-glycine	HMDB

Chemical Formula

C₆H₁₁N₃O₄

Average Mass

189.1692 Da

Monoisotopic Mass

189.07496 Da

IUPAC Name

2-[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid

Traditional Name

[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid

CAS Registry Number

556-33-2

SMILES

NC\C(O)=N\C\C(O)=N\CC(O)=O

InChI Identifier

InChI=1S/C6H11N3O4/c7-1-4(10)8-2-5(11)9-3-6(12)13/h1-3,7H2,(H,8,10)(H,9,11)(H,12,13)

InChI Key

XKUKSGPZAADMRA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, D₂O, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-10	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Blighia sapida	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organonitrogen compound
Organic oxygen compound
Organic oxide
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Amine
Organooxygen compound
Primary amine
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tripeptide (CHEBI:63961 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	246 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	58.5 mg/mL at 25 °C	Not Available
LogP	-2.68	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.63 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-4.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	42.65 m³·mol⁻¹	ChemAxon
Polarizability	17.72 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

HMDB0029419

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000517

KNApSAcK ID

Not Available

Chemspider ID

10688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11161

PDB ID

GGG

ChEBI ID

63961

Good Scents ID

Not Available

References

General References

Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
Li J, Hidalgo IJ: Molecular modeling study of structural requirements for the oligopeptide transporter. J Drug Target. 1996;4(1):9-17. [PubMed:8798874 ]
Liu S, Edwards DS, Looby RJ, Poirier MJ, Rajopadhye M, Bourque JP, Carroll TR: Labeling cyclic glycoprotein IIb/IIIa receptor antagonists with 99mTc by the preformed chelate approach: effects of chelators on properties of [99mTc]chelator-peptide conjugates. Bioconjug Chem. 1996 Mar-Apr;7(2):196-202. [PubMed:8983341 ]
Hedwig GR, Hoiland H: Thermodynamic properties of peptide solutions. Part 11. Partial molar isentropic pressure coefficients in aqueous solutions of some tripeptides that model protein side-chains. Biophys Chem. 1994 Mar;49(2):175-81. [PubMed:8155817 ]
Lipowska M, Hansen L, Xu X, Marzilli PA, Taylor A Jr, Marzilli LG: New N(3)S donor ligand small peptide analogues of the N-mercaptoacetyl-glycylglycylglycine ligand in the clinically used Tc-99m renal imaging agent: evidence for unusual amide oxygen coordination by two new ligands. Inorg Chem. 2002 Jun 3;41(11):3032-41. [PubMed:12033915 ]
Bokatzian-Johnson SS, Stover ML, Dixon DA, Cassady CJ: Gas-phase deprotonation of the peptide backbone for tripeptides and their methyl esters with hydrogen and methyl side chains. J Phys Chem B. 2012 Dec 27;116(51):14844-58. doi: 10.1021/jp3113528. Epub 2012 Dec 14. [PubMed:23194315 ]
Rios A, Richard JP, Amyes TL: Formation and stability of peptide enolates in aqueous solution. J Am Chem Soc. 2002 Jul 17;124(28):8251-9. [PubMed:12105903 ]
El Aribi H, Rodriquez CF, Almeida DR, Ling Y, Mak WW, Hopkinson AC, Siu KW: Elucidation of fragmentation mechanisms of protonated Peptide ions and their products: a case study on glycylglycylglycine using density functional theory and threshold collision-induced dissociation. J Am Chem Soc. 2003 Jul 30;125(30):9229-36. [PubMed:15369379 ]
Poschet JF, Hammond SM, Fairclough PD: Characterisation of penicillin-G uptake in rabbit small-intestinal brush-border membrane vesicles. Biochim Biophys Acta. 1996 Jan 31;1278(2):233-40. [PubMed:8593281 ]
Rodriquez CF, Cunje A, Shoeib T, Chu IK, Hopkinson AC, Siu KW: Proton migration and tautomerism in protonated triglycine. J Am Chem Soc. 2001 Apr 4;123(13):3006-12. [PubMed:11457011 ]
Ma L, Yu P, Veerendra B, Rold TL, Retzloff L, Prasanphanich A, Sieckman G, Hoffman TJ, Volkert WA, Smith CJ: In vitro and in vivo evaluation of Alexa Fluor 680-bombesin[7-14]NH2 peptide conjugate, a high-affinity fluorescent probe with high selectivity for the gastrin-releasing peptide receptor. Mol Imaging. 2007 May-Jun;6(3):171-80. [PubMed:17532883 ]
Gunji H, Kochi H, Hiraiwa K: Comparison of kinetic property between human seminal and renal gamma-glutamyltransferase. Fukushima J Med Sci. 1994 Dec;40(2):119-32. [PubMed:7642163 ]
Tsukagoshi K, Sawanoi K, Nakajima R: Capillary electrophoretic system incorporating an UV/CL dual detector. Talanta. 2006 Feb 15;68(4):1071-5. doi: 10.1016/j.talanta.2005.06.070. Epub 2005 Aug 16. [PubMed:18970433 ]
Cheng J, Khin KT, Jensen GS, Liu A, Davis ME: Synthesis of linear, beta-cyclodextrin-based polymers and their camptothecin conjugates. Bioconjug Chem. 2003 Sep-Oct;14(5):1007-17. [PubMed:13129405 ]
Ye SJ, Armentrout PB: Absolute thermodynamic measurements of alkali metal cation interactions with a simple dipeptide and tripeptide. J Phys Chem A. 2008 Apr 24;112(16):3587-96. doi: 10.1021/jp710709j. Epub 2008 Mar 26. [PubMed:18363386 ]
Alves S, Correia JD, Santos I, Veerendra B, Sieckman GL, Hoffman TJ, Rold TL, Figueroa SD, Retzloff L, McCrate J, Prasanphanich A, Smith CJ: Pyrazolyl conjugates of bombesin: a new tridentate ligand framework for the stabilization of fac-[M(CO)3]+ moiety. Nucl Med Biol. 2006 Jul;33(5):625-34. Epub 2006 May 2. [PubMed:16843837 ]
Asakura T, Takahashi N, Takada K, Inoue T, Ohkawa K: Drug conjugate of doxorubicin with glutathione is a potent reverser of multidrug resistance in rat hepatoma cells. Anticancer Drugs. 1997 Feb;8(2):199-203. [PubMed:9073316 ]
Koleva BB, Kolev TM, Spiteller M: Structural and spectroscopic analysis of hydrogensquarates of glycine-containing tripeptides. Biopolymers. 2006 Dec 5;83(5):498-507. [PubMed:16886213 ]
Downes CJ, Hedwig GR: Partial molar heat capacities of the peptides glycylglycylglycine, glycyl-L-alanylglycine and glycyl-DL-threonylglycine in aqueous solution over the temperature range 50 to 125 degrees C. Biophys Chem. 1995 Aug;55(3):279-88. [PubMed:17020871 ]
Martin NH, Loveless DM, Main KL, Pyles AK: Computation of through-space NMR shielding effects by functional groups common to peptides. J Mol Graph Model. 2006 Sep;25(1):1-9. Epub 2005 Nov 18. [PubMed:16300978 ]
Ogawa K, Mukai T, Arano Y, Ono M, Hanaoka H, Ishino S, Hashimoto K, Nishimura H, Saji H: Development of a rhenium-186-labeled MAG3-conjugated bisphosphonate for the palliation of metastatic bone pain based on the concept of bifunctional radiopharmaceuticals. Bioconjug Chem. 2005 Jul-Aug;16(4):751-7. [PubMed:16029015 ]
Danyi P, Varnagy K, Sovago I, Schon I, Sanna D, Micera G: Potentiometric and spectroscopic studies on the copper(II) complexes of peptide hormones containing disulfide bridges. J Inorg Biochem. 1995 Oct;60(1):69-78. [PubMed:7595472 ]
Chu IK, Shoeib T, Guo X, Rodriquez CF, Lau TC, Hopkinson AC, Siu KW: Characterization of the product ions from the collision-induced dissociation of argentinated peptides. J Am Soc Mass Spectrom. 2001 Feb;12(2):163-75. [PubMed:11212001 ]
Akao T, Kobashi K: Inhibitory effect of glycine on ethanol absorption from gastrointestinal tract. Biol Pharm Bull. 1995 Dec;18(12):1653-6. [PubMed:8787782 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Glycylglycylglycine (NP0000388)

MOL for NP0000388 (Glycylglycylglycine)

3D MOL for NP0000388 (Glycylglycylglycine)

3D SDF for NP0000388 (Glycylglycylglycine)

3D-SDF for NP0000388 (Glycylglycylglycine)

PDB for NP0000388 (Glycylglycylglycine)

3D PDB for NP0000388 (Glycylglycylglycine)

SMILES for NP0000388 (Glycylglycylglycine)

INCHI for NP0000388 (Glycylglycylglycine)

Structure for NP0000388 (Glycylglycylglycine)

3D Structure for NP0000388 (Glycylglycylglycine)