Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:19 UTC

Update Date

2023-02-21 17:18:45 UTC

HMDB ID

HMDB0029419

Secondary Accession Numbers

HMDB29419

Metabolite 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 3D MOL SDF 3D SDF PDB 3D 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>
HMDB0029419

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 Molecular Weight

189.1692

Monoisotopic Molecular Weight

189.074955855

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029419)

Source

Endogenous

Endogenous (HMDB: HMDB0029419)

Plant

Plant (HMDB: HMDB0029419)

Exogenous

Food

Food (HMDB: HMDB0029419)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0029419)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Propionic Acidemia (HMDB: HMDB0029419)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.673	31661259
DarkChem	[M-H]-	137.373	31661259
DeepCCS	[M+H]+	138.912	30932474
DeepCCS	[M-H]-	135.084	30932474
DeepCCS	[M-2H]-	172.608	30932474
DeepCCS	[M+Na]+	148.147	30932474
AllCCS	[M+H]+	140.5	32859911
AllCCS	[M+H-H2O]+	136.9	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	144.8	32859911
AllCCS	[M-H]-	139.1	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	142.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycylglycylglycine	NC\C(O)=N\C\C(O)=N\CC(O)=O	2641.0	Standard polar	33892256
Glycylglycylglycine	NC\C(O)=N\C\C(O)=N\CC(O)=O	1813.0	Standard non polar	33892256
Glycylglycylglycine	NC\C(O)=N\C\C(O)=N\CC(O)=O	2179.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycylglycylglycine,1TMS,isomer #1	C[Si](C)(C)O/C(CN)=N\C/C(O)=N/CC(=O)O	1986.2	Semi standard non polar	33892256
Glycylglycylglycine,1TMS,isomer #2	C[Si](C)(C)O/C(C/N=C(\O)CN)=N\CC(=O)O	2017.7	Semi standard non polar	33892256
Glycylglycylglycine,1TMS,isomer #3	C[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(\O)CN	2051.3	Semi standard non polar	33892256
Glycylglycylglycine,1TMS,isomer #4	C[Si](C)(C)NC/C(O)=N/C/C(O)=N/CC(=O)O	2099.2	Semi standard non polar	33892256
Glycylglycylglycine,2TMS,isomer #1	C[Si](C)(C)O/C(CN)=N\C/C(=N/CC(=O)O)O[Si](C)(C)C	2004.9	Semi standard non polar	33892256
Glycylglycylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(/CN)O[Si](C)(C)C	1981.5	Semi standard non polar	33892256
Glycylglycylglycine,2TMS,isomer #3	C[Si](C)(C)NC/C(=N/C/C(O)=N/CC(=O)O)O[Si](C)(C)C	2046.9	Semi standard non polar	33892256
Glycylglycylglycine,2TMS,isomer #4	C[Si](C)(C)OC(=O)C/N=C(/C/N=C(\O)CN)O[Si](C)(C)C	2010.8	Semi standard non polar	33892256
Glycylglycylglycine,2TMS,isomer #5	C[Si](C)(C)NC/C(O)=N/C/C(=N/CC(=O)O)O[Si](C)(C)C	2095.6	Semi standard non polar	33892256
Glycylglycylglycine,2TMS,isomer #6	C[Si](C)(C)NC/C(O)=N/C/C(O)=N/CC(=O)O[Si](C)(C)C	2104.3	Semi standard non polar	33892256
Glycylglycylglycine,2TMS,isomer #7	C[Si](C)(C)N(C/C(O)=N/C/C(O)=N/CC(=O)O)[Si](C)(C)C	2220.8	Semi standard non polar	33892256
Glycylglycylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C/N=C(/C/N=C(/CN)O[Si](C)(C)C)O[Si](C)(C)C	2021.9	Semi standard non polar	33892256
Glycylglycylglycine,3TMS,isomer #2	C[Si](C)(C)NC/C(=N/C/C(=N/CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2074.2	Semi standard non polar	33892256
Glycylglycylglycine,3TMS,isomer #3	C[Si](C)(C)NC/C(=N/C/C(O)=N/CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2050.8	Semi standard non polar	33892256
Glycylglycylglycine,3TMS,isomer #4	C[Si](C)(C)O/C(CN([Si](C)(C)C)[Si](C)(C)C)=N\C/C(O)=N/CC(=O)O	2188.3	Semi standard non polar	33892256
Glycylglycylglycine,3TMS,isomer #5	C[Si](C)(C)NC/C(O)=N/C/C(=N/CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2077.5	Semi standard non polar	33892256
Glycylglycylglycine,3TMS,isomer #6	C[Si](C)(C)O/C(C/N=C(\O)CN([Si](C)(C)C)[Si](C)(C)C)=N\CC(=O)O	2212.9	Semi standard non polar	33892256
Glycylglycylglycine,3TMS,isomer #7	C[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(\O)CN([Si](C)(C)C)[Si](C)(C)C	2214.8	Semi standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #1	C[Si](C)(C)NC/C(=N/C/C(=N/CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2086.3	Semi standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #1	C[Si](C)(C)NC/C(=N/C/C(=N/CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2083.9	Standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #2	C[Si](C)(C)O/C(C/N=C(/CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=N\CC(=O)O	2238.6	Semi standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #2	C[Si](C)(C)O/C(C/N=C(/CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=N\CC(=O)O	2177.9	Standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(/CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2218.3	Semi standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #3	C[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(/CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2174.7	Standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #4	C[Si](C)(C)OC(=O)C/N=C(/C/N=C(\O)CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2229.3	Semi standard non polar	33892256
Glycylglycylglycine,4TMS,isomer #4	C[Si](C)(C)OC(=O)C/N=C(/C/N=C(\O)CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	2202.1	Standard non polar	33892256
Glycylglycylglycine,5TMS,isomer #1	C[Si](C)(C)OC(=O)C/N=C(/C/N=C(/CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2270.8	Semi standard non polar	33892256
Glycylglycylglycine,5TMS,isomer #1	C[Si](C)(C)OC(=O)C/N=C(/C/N=C(/CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	2167.1	Standard non polar	33892256
Glycylglycylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O/C(CN)=N\C/C(O)=N/CC(=O)O	2191.9	Semi standard non polar	33892256
Glycylglycylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O/C(C/N=C(\O)CN)=N\CC(=O)O	2209.6	Semi standard non polar	33892256
Glycylglycylglycine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(\O)CN	2223.5	Semi standard non polar	33892256
Glycylglycylglycine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC/C(O)=N/C/C(O)=N/CC(=O)O	2310.3	Semi standard non polar	33892256
Glycylglycylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O/C(CN)=N\C/C(=N/CC(=O)O)O[Si](C)(C)C(C)(C)C	2388.6	Semi standard non polar	33892256
Glycylglycylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(/CN)O[Si](C)(C)C(C)(C)C	2404.4	Semi standard non polar	33892256
Glycylglycylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC/C(=N/C/C(O)=N/CC(=O)O)O[Si](C)(C)C(C)(C)C	2470.5	Semi standard non polar	33892256
Glycylglycylglycine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(/C/N=C(\O)CN)O[Si](C)(C)C(C)(C)C	2403.3	Semi standard non polar	33892256
Glycylglycylglycine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC/C(O)=N/C/C(=N/CC(=O)O)O[Si](C)(C)C(C)(C)C	2488.4	Semi standard non polar	33892256
Glycylglycylglycine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC/C(O)=N/C/C(O)=N/CC(=O)O[Si](C)(C)C(C)(C)C	2510.9	Semi standard non polar	33892256
Glycylglycylglycine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C/C(O)=N/C/C(O)=N/CC(=O)O)[Si](C)(C)C(C)(C)C	2543.5	Semi standard non polar	33892256
Glycylglycylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(/C/N=C(/CN)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2520.6	Semi standard non polar	33892256
Glycylglycylglycine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC/C(=N/C/C(=N/CC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2633.7	Semi standard non polar	33892256
Glycylglycylglycine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC/C(=N/C/C(O)=N/CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2647.1	Semi standard non polar	33892256
Glycylglycylglycine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O/C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N\C/C(O)=N/CC(=O)O	2769.2	Semi standard non polar	33892256
Glycylglycylglycine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC/C(O)=N/C/C(=N/CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2644.3	Semi standard non polar	33892256
Glycylglycylglycine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O/C(C/N=C(\O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N\CC(=O)O	2758.8	Semi standard non polar	33892256
Glycylglycylglycine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(\O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2767.1	Semi standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC/C(=N/C/C(=N/CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2748.4	Semi standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC/C(=N/C/C(=N/CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2658.2	Standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O/C(C/N=C(/CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=N\CC(=O)O	2987.0	Semi standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O/C(C/N=C(/CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=N\CC(=O)O	2744.8	Standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(/CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2978.0	Semi standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(\O)C/N=C(/CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2807.3	Standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(/C/N=C(\O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2963.2	Semi standard non polar	33892256
Glycylglycylglycine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(/C/N=C(\O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2845.6	Standard non polar	33892256
Glycylglycylglycine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(/C/N=C(/CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3180.6	Semi standard non polar	33892256
Glycylglycylglycine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/N=C(/C/N=C(/CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2885.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (3 TMS)	splash10-00di-2920000000-c79f40a9740fc25b3f1c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (5 TMS)	splash10-00di-3910000000-4555ddf2ff8c000d0010	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (4 TMS)	splash10-00di-2900000000-624925570b3a64cc957d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (3 TMS)	splash10-00di-2900000000-c27bc3ac23a84247a718	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (Non-derivatized)	splash10-00di-2920000000-c79f40a9740fc25b3f1c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (Non-derivatized)	splash10-00di-3910000000-4555ddf2ff8c000d0010	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (Non-derivatized)	splash10-00di-2900000000-624925570b3a64cc957d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Glycylglycylglycine GC-MS (Non-derivatized)	splash10-00di-2900000000-c27bc3ac23a84247a718	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylglycylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-d38148835b5d52efffd3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylglycylglycine GC-MS (3 TMS) - 70eV, Positive	splash10-0ul0-9545000000-57ef53c37c0fd6201b85	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycylglycylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9100000000-b943e0e1caf180c452cf	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycylglycylglycine 35V, Negative-QTOF	splash10-0079-9200000000-916e62984f4337bfbf61	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 10V, Positive-QTOF	splash10-008l-9700000000-e6fcfff45e998c9a367a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 20V, Positive-QTOF	splash10-00e9-9100000000-489ffcb6bc99d93eec83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 40V, Positive-QTOF	splash10-00e9-9000000000-92a2d71d3481d78dfe82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 10V, Negative-QTOF	splash10-000i-3900000000-1fdbc86e4c25c94ab8ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 20V, Negative-QTOF	splash10-00di-9700000000-c86ca89521d958d72d1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 40V, Negative-QTOF	splash10-05fu-9000000000-9f260afc01f2c85261c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 10V, Negative-QTOF	splash10-0079-9600000000-43f39811659f82264e12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 20V, Negative-QTOF	splash10-05fr-9000000000-0697279a1de5b7dfc77a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 40V, Negative-QTOF	splash10-0a4l-9000000000-d44908d71ad0ce830f08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 10V, Positive-QTOF	splash10-0006-0900000000-dd285350baadfe693484	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 20V, Positive-QTOF	splash10-000i-9200000000-0a9dac7c24acf2949799	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycylglycylglycine 40V, Positive-QTOF	splash10-0ab9-9000000000-3220a8dea8459edb6b6b	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000517

KNApSAcK ID

C00055469

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 metabocard for Glycylglycylglycine (HMDB0029419)

MOL for HMDB0029419 (Glycylglycylglycine)

3D MOL for HMDB0029419 (Glycylglycylglycine)

3D SDF for HMDB0029419 (Glycylglycylglycine)

3D-SDF for HMDB0029419 (Glycylglycylglycine)

PDB for HMDB0029419 (Glycylglycylglycine)

3D PDB for HMDB0029419 (Glycylglycylglycine)

SMILES for HMDB0029419 (Glycylglycylglycine)

INCHI for HMDB0029419 (Glycylglycylglycine)

Structure for HMDB0029419 (Glycylglycylglycine)

3D Structure for HMDB0029419 (Glycylglycylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra