Compounds > glycyl-glycyl-proline
Page last updated: 2024-12-07

glycyl-glycyl-proline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Glycyl-glycyl-proline (GGPro) is a tripeptide composed of the amino acids glycine, glycine, and proline. It is known for its unique conformational properties, particularly its ability to adopt a stable type II β-turn conformation. This conformational preference makes GGPro a valuable building block for peptides and proteins, and it has been extensively studied for its potential applications in drug discovery and biomaterials.

GGPro has been shown to exhibit various biological activities, including:

- **Antioxidant activity:** GGPro has been found to protect cells from oxidative damage by scavenging free radicals.
- **Anti-inflammatory activity:** Studies suggest that GGPro can suppress inflammation by inhibiting the production of pro-inflammatory cytokines.
- **Neuroprotective activity:** GGPro has been shown to protect neurons from damage induced by various stressors, such as oxidative stress and excitotoxicity.

Furthermore, GGPro has been investigated for its potential applications in:

- **Drug delivery:** GGPro-based peptides have been explored as carriers for drug delivery systems, owing to their ability to cross cell membranes.
- **Biomaterial development:** GGPro's unique conformational properties have led to its use in the development of biomaterials for tissue engineering and drug delivery.

The importance of GGPro lies in its versatility and potential for diverse applications. Its conformational flexibility and biological activities make it an attractive target for further research and development in various fields.'

Gly-Gly-Pro : A tripeptide composed of glycine, glycine and L-proline amino acids joined in sequence by peptide linkages. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
GlycinegenusA non-essential amino acid. It is found primarily in gelatin and silk fibroin and used therapeutically as a nutrient. It is also a fast inhibitory neurotransmitter.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID97051
CHEMBL ID1221709
CHEBI ID155880
SCHEMBL ID15756757
MeSH IDM0171534

Synonyms (27)

Synonym
CHEMBL1221709
14379-76-1
GGP ,
g-g-p
glycylglycylproline
gly-gly-l-pro
1-(n-glycylglycyl)-l-proline
glycylglycyl-l-proline
gly-gly-pro
CHEBI:155880
glycyl-glycyl-proline
(2s)-1-[(2-aminoacetamido)acetyl]pyrrolidine-2-carboxylic acid
h-gly-gly-pro-oh
(2s)-1-[2-[(2-aminoacetyl)amino]acetyl]pyrrolidine-2-carboxylic acid
nsc 97938
l-proline, 1-(n-glycylglycyl)-
AKOS010421474
glycylglycyl-l-prolin
SCHEMBL15756757
mfcd00237937
glycyl-glycyl-l-proline
HY-111922
glycyl-glycyl-l-prolineglycyl-glycyl-l-proline
CS-0094055
MS-23299
STARBLD0000769
(2s)-1-[2-(2-aminoacetamido)acetyl]pyrrolidine-2-carboxylic acid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
tripeptideAny oligopeptide that consists of three amino-acid residues connected by peptide linkages.
tripeptide zwitterionA peptide zwitterion obtained from the tranfer of a proton from the carboxy group to the amino group of any tripeptide. It contains an equal number of positively-charged and negatively-charged functional groups. Major structure at pH 7.3.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID680853TP_TRANSPORTER: inhibition of Gly-Sar uptake (Gly-Sar: 20 uM, Gly-Gly-Pro: 10000 uM) in PEPT1-expressing HeLa cells1995The Journal of biological chemistry, Mar-24, Volume: 270, Issue:12
Human intestinal H+/peptide cotransporter. Cloning, functional expression, and chromosomal localization.
AID500816Inhibition of nitrogen-starved wild type sigma1278b yeast Gap1-mediated amino acid uptake at 5 mM after 60 secs relative to L-citrulline2009Nature chemical biology, Jan, Volume: 5, Issue:1
Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's1 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.60

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.60 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (20.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pipecolic acid
pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.		2.0510piperidinemonocarboxylic acid
pentachlorophenol
PENTA: structure given in first source		3.5111aromatic fungicide;
chlorophenol;
organochlorine pesticide;
pentachlorobenzenes		human xenobiotic metabolite
taurine
[no description available]		2.0510amino sulfonic acid;
zwitterion		antioxidant;
Escherichia coli metabolite;
glycine receptor agonist;
human metabolite;
mouse metabolite;
nutrient;
radical scavenger;
Saccharomyces cerevisiae metabolite
serine
Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.		2.0510L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid;
serine zwitterion;
serine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
aspartic acid
Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.		2.0510aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		2.0510aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		2.0510amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		2.0510amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
histidine
Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.		2.0510amino acid zwitterion;
histidine;
L-alpha-amino acid;
polar amino acid zwitterion;
proteinogenic amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
threonine
Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.		2.0510amino acid zwitterion;
aspartate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
threonine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		2.0510erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
citrulline
citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.		2.0510amino acid zwitterion;
citrulline		Daphnia magna metabolite;
EC 1.14.13.39 (nitric oxide synthase) inhibitor;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
protective agent;
Saccharomyces cerevisiae metabolite
glycyl-glycyl-glycine
glycyl-glycyl-glycine : A tripeptide in which three glycine units are linked via peptide bonds in a linear sequence.		2.0510tripeptide zwitterion;
tripeptide
glycylglycine
[no description available]		2.0510dipeptide zwitterion;
dipeptide		human metabolite
cephalexin
Cephalexin: A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of CEPHALORIDINE or CEPHALOTHIN, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms.. cephalexin : A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.		1.9810beta-lactam antibiotic allergen;
cephalosporin;
semisynthetic derivative		antibacterial drug
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.0510glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
cefadroxil anhydrous
Cefadroxil: Long-acting, broad-spectrum, water-soluble, CEPHALEXIN derivative.. cefadroxil : A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.		1.9810cephalosporinantibacterial drug
leucyltyrosine
leucyltyrosine: RN given refers to L-Tyr,L-Leu-isomer; RN for cpd without isomeric designation not avail 4/93		2.0510dipeptidemetabolite
leucyl-glycyl-glycine
leucyl-glycyl-glycine: RN given refers to (L-Leu)-isomer. Leu-Gly-Gly : A tripeptide composed of one L-leucine and two glycine residues joined in sequence.		2.0510tripeptidemetabolite
leucylleucine
Leu-Leu : A dipeptide formed from two L-leucine residues.		2.0510dipeptide;
L-aminoacyl-L-amino acid zwitterion		human metabolite;
Mycoplasma genitalium metabolite
leucyl-alanine
Leu-Ala : A dipeptide composed of L-leucine and L-alanine joined by a peptide linkage.		2.0510dipeptidemetabolite
leucyl-leucyl-leucine
leucyl-leucyl-leucine: RN given refers to (L-Leu-L-Leu-L-Leu)-isomer. Leu-Leu-Leu : A tripeptide formed from three L-leucine residues.		2.0510tripeptidemetabolite
alanylproline
alanylproline: RN given refers to all (L)-isomer		1.9810dipeptide zwitterion;
dipeptide		metabolite
glycyltryptophan
glycyltryptophan: RN given refers to (L)-isomer. Gly-Trp : A dipeptide formed from glycine and L-tryptophan residues.		2.0510dipeptidemetabolite
glycylleucine
Gly-Leu : A dipeptide composed of glycine and L-leucine joined by a peptide linkage.		2.0510dipeptide zwitterion;
dipeptide		metabolite
glycyl-l-phenylalanine
glycylphenylalanine: RN given refers to (DL)-isomer. Gly-Phe : A dipeptide formed from glycine and L-phenylalanine residues.		2.0510dipeptide zwitterion;
dipeptide		human metabolite;
metabolite
aspartyl-phenylalanine
aspartyl-phenylalanine: metabolite of aspartame; may inhibit angiotensin converting enzyme; RN given refers to all (L)-isomer		2.0510dipeptidehuman blood serum metabolite;
human xenobiotic metabolite
glycylsarcosine
glycylsarcosine : A dipeptide obtained by formal condensation of the carboxy group of glycine with the amino group of sarcosine.		2.4120dipeptide zwitterion;
dipeptide
leucylleucine
leucylleucine: RN given refers to (DL-Leu-DL-Leu)-isomer		2.0510peptide
glycyl-leucyl-tyrosine
glycyl-leucyl-tyrosine: structure given in first source		2.0510oligopeptide
glycylaspartic acid
glycylaspartic acid: RN given refers to (L)-isomer		2.0510dipeptidemetabolite
glycyl-histidyl-glycine
[no description available]		2.0510oligopeptide
n-glycylglutamic acid
N-glycylglutamic acid: RN given refers to (L)-isomer. Gly-Glu : A dipeptide formed from glycyl and L-glutamic acid residues.		2.0510dipeptidemetabolite
histidylglycine
histidylglycine: RN given refers to all (L)-isomer. His-Gly : A dipeptide formed from L-histidine and glycine residues.		2.0510dipeptidemetabolite
valylvaline
valylvaline: RN given refers to (L)-isomer. Val-Val : A dipeptide formed from two L-valine residues.		2.0510dipeptideMycoplasma genitalium metabolite
alpha-methylphenylalanine
alpha-methylphenylalanine: induces chronic hyperphenylalaninemia in suckling rats; models for the study of inborn errors of metabolism; RN given refers to parent cpd without isomeric designation		2.0510benzenes;
monocarboxylic acid
prolinamide
prolinamide: RN given refers to cpd without isomeric designation. L-prolinamide : The carboxamide derivative of L-proline.		2.0510amino acid amide;
L-proline derivative;
pyrrolidinecarboxamide
tyrosyl-glycyl-glycine
tyrosyl-glycyl-glycine: RN given refers to L-isomer; this may not be the same as IMREG-1. Tyr-Gly-Gly : A tripeptide composed of one L-tyrosine and two glycine residues joined in sequence.		2.0510tripeptide zwitterion;
tripeptide		metabolite
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		2.0510amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
arginylarginine 2-naphthylamide
arginylarginine 2-naphthylamide: substrate for dipeptidyl peptidase III		2.0510
histidylphenylalanine
His-Phe : A dipeptide obtained by formal condensation of the carboxy group of L-histidine with the amino group of L-phenylalanine.		2.0510dipeptide
glycyl-glycyl-valine
[no description available]		2.0510oligopeptide
glycyl-glycyl-sarcosine
glycyl-glycyl-sarcosine: structure given in first source		2.0510
cysteinylglycine
cysteinylglycine: RN given refers to (L)-isomer; RN for cpd without isomeric designation not in Chemlne 7/13/83. L-cysteinylglycine : A dipeptide consisting of glycine having an L-cysteinyl attached to its alpha-amino group. It is an intermediate metabolite in glutathione metabolism.		2.0510dipeptide zwitterion;
dipeptide		Escherichia coli metabolite;
human metabolite;
Saccharomyces cerevisiae metabolite
glutamyl-glutamic acid
glutamyl-glutamic acid: RN given for (L,L)-isomer. Glu-Glu : A dipeptide composed of two L-glutamic acid units joined by a peptide linkage.		2.0510dipeptideMycoplasma genitalium metabolite
n-acetyltryptophan
N-acetyl-L-tryptophan : A N-acetyl-L-amino acid that is the N-acetyl derivative of L-tryptophan.		2.0510L-tryptophan derivative;
N-acetyl-L-amino acid		metabolite
n-glycylalanine
Gly-Ala : A dipeptide formed from glycine and L-alanine residues.		2.0510dipeptidemetabolite
glycylvaline
glycylvaline: RN given refers to (DL)-isomer		2.0510dipeptidehuman metabolite
epsilon-tert-butyloxycarbonyl-lysine
epsilon-tert-butyloxycarbonyl-lysine: RN given refers to (L)-isomer		2.0510
glycylproline
Gly-Pro : A dipeptide consisting of L-proline having a glycyl residue attached to its alpha-amino group.		4.1131dipeptide zwitterion;
dipeptide		metabolite
tryptophanol
tryptophanol: RN given refers to cpd without isomeric designation		2.0510
phenylalanylglycine
phenylalanylglycine: RN given refers to (DL)-isomer. Phe-Gly : A dipeptide formed from L-phenylalanine and glycine residues.		2.0510dipeptidemetabolite
glycyl-alanyl-phenylalanine
[no description available]		2.0510oligopeptide
methionylglycine
methionylglycine: RN given refers to (L)-isomer. Met-Gly : A dipeptide formed from L-methionine and glycine residues.		2.0510dipeptidemetabolite
histidylhistidine
histidylhistidine: RN given for L-,L-isomer		2.0510dipeptideMycoplasma genitalium metabolite
valylleucine
valylleucine: RN given refers to all L-isomer. Val-Leu : A dipeptide formed from L-valine and L-leucine residues.		2.0510dipeptidemetabolite
alanylglycine
[no description available]		2.0510dipeptide zwitterion;
dipeptide		metabolite
alpha-glutamyltryptophan
Trp-Glu : A dipeptide formed from L-tryptophan and L-glutamic acid residues.		2.0510dipeptidemetabolite
methionylglutamic acid
Met-Glu : A dipeptide formed from L-methionine and L-glutamic acid residues.		2.0510dipeptidemetabolite
phenylalanyl-valine
phenylalanyl-valine: structure in first source. Phe-Val : A dipeptide formed from L-phenylalanine and L-valine residues.		2.0510dipeptidemetabolite
homocarnosine
homocarnosine: RN given refers to parent cpd. homocarnosine : A histidine derivative that is histidine in which one of the hydrogens attached to the alpha-amino group has been replaced by a 4-aminobutanoyl group.		2.0510dipeptide zwitterion;
dipeptide;
homocarnosine;
L-histidine derivative;
N-acyl-L-alpha-amino acid anion;
N-acyl-L-alpha-amino acid		human metabolite
clove
Madagascar: One of the Indian Ocean Islands off the southeast coast of Africa. Its capital is Antananarivo. It was formerly called the Malagasy Republic. Discovered by the Portuguese in 1500, its history has been tied predominantly to the French, becoming a French protectorate in 1882, a French colony in 1896, and a territory within the French union in 1946. The Malagasy Republic was established in the French Community in 1958 but it achieved independence in 1960. Its name was changed to Madagascar in 1975. (From Webster's New Geographical Dictionary, 1988, p714)		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Alopecia Cicatrisata
[description not available]		03.5111
Alopecia
Absence of hair from areas where it is normally present.		03.5111