MiMeDB: Showing metabocard for epsilon-(gamma-Glutamyl)lysine (MMDBc0000428)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:37:32 UTC

Update Date

2022-08-31 06:06:51 UTC

MiMeDB ID

MMDBc0000428

Metabolite Identification

Common Name

epsilon-(gamma-Glutamyl)lysine

Description

In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688 ). In Parkinson's disease (PD), conformational changes in the alpha-synuclein monomer precede the formation of Lewy bodies. Both tTG and its substrate-characteristic N(epsilon)-(gamma-glutamyl)-lysine crosslink are increased in PD nigral dopamine neurons. (PMID 15001552 ). Expression of tissue transglutaminase (tTgase) and epsilon-(gamma-glutamyl)-lysine was present in all scarring of the blebs sites, being the main cause of failure in glaucoma filtration surgery. Transglutaminases are calcium-dependent enzymes that catalyze the posttranslational modification of proteins through an acyl transfer reaction between the gamma-carboxamide group of a peptide-bound glutaminyl residue and various amines. Covalent cross-linking using epsilon-(gamma-glutamyl)-lysine bonds is stable and resistant to enzymatic, chemical, and mechanical disruption. (PMID: 16936095 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₁H₂₁N₃O₅

Average Molecular Weight

275.3015

Monoisotopic Molecular Weight

275.148120797

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

InChI Key

JPKNLFVGUZRHOB-YUMQZZPRSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
Alzheimer's disease		This associated disease is originally imported from HMDB metabolite HMDB0003869 concentration id 16837	Association	Human Blood		17031479	details
Huntington's disease		This associated disease is originally imported from HMDB metabolite HMDB0003869 concentration id 15023	Association	Human Cerebrospinal Fluid (CSF)		11739625	details

Microbial Sources

Phylum	Total species	Hosts and Body Sites	Microbial Links
Verrucomicrobia	1	Human Feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteroidetes	4	Human Feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen
Firmicutes	13	Human Feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Proteobacteria	1	Human Feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Euryarchaeota	1	Human Feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	0.1629	0.0392			Elderly (>65 years old)	Both	Alzheimer's disease	HMDB	17031479	details
Human	Detected and Quantified	0.70		0.66	0.74	Adult (>18 years old)	Not Specified	Huntington's disease	HMDB	11739625	details
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620	details
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Jeitner TM, Bogdanov MB, Matson WR, Daikhin Y, Yudkoff M, Folk JE, Steinman L, Browne SE, Beal MF, Blass JP, Cooper AJ: N(epsilon)-(gamma-L-glutamyl)-L-lysine (GGEL) is increased in cerebrospinal fluid of patients with Huntington's disease. J Neurochem. 2001 Dec;79(5):1109-12. doi: 10.1046/j.1471-4159.2001.00673.x. [PubMed:11739625 ]
Andringa G, Lam KY, Chegary M, Wang X, Chase TN, Bennett MC: Tissue transglutaminase catalyzes the formation of alpha-synuclein crosslinks in Parkinson's disease. FASEB J. 2004 May;18(7):932-4. doi: 10.1096/fj.03-0829fje. Epub 2004 Mar 4. [PubMed:15001552 ]
El Nahas AM, Abo-Zenah H, Skill NJ, Bex S, Wild G, Griffin M, Johnson TS: Elevated epsilon-(gamma-glutamyl)lysine in human diabetic nephropathy results from increased expression and cellular release of tissue transglutaminase. Nephron Clin Pract. 2004;97(3):c108-17. doi: 10.1159/000078639. [PubMed:15292688 ]
Priglinger SG, Alge CS, Kook D, Thiel M, Schumann R, Eibl K, Yu A, Neubauer AS, Kampik A, Welge-Lussen U: Potential role of tissue transglutaminase in glaucoma filtering surgery. Invest Ophthalmol Vis Sci. 2006 Sep;47(9):3835-45. doi: 10.1167/iovs.05-0960. [PubMed:16936095 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for epsilon-(gamma-Glutamyl)lysine (MMDBc0000428)

MOL for #<Metabolite:0x000055b76e0e53c8>

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3D PDB for #<Metabolite:0x000055b76e0e53c8>

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Structure for #<Metabolite:0x000055b76e0e53c8>

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