MiMeDB: Showing metabocard for Glutathionylspermidine (MMDBc0030065)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:52:36 UTC

Update Date

2024-10-13 07:16:25 UTC

Metabolite ID

MMDBc0030065

Metabolite Identification

Common Name

Glutathionylspermidine

Description

Glutathionylspermidine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Glutathionylspermidine (Gsp) is a metabolite common to Escherichia coli and protozoal parasites of the Trypanosoma family. (PMID 9398217 ) Glutathionylspermidine is an intermediate formed in the biosynthesis of trypanothione, an essential metabolite in defence against chemical and oxidative stress in the Kinetoplastida. (PMID 18959765 ) Glutathionylspermidine is formed as end product and the enzyme lacks TryS activity. (PMID 12049631 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N1-(gamma-L-Glutamyl-L-cysteinyl-glycyl)-spermidine	ChEBI
N1-(g-L-Glutamyl-L-cysteinyl-glycyl)-spermidine	Generator
N1-(Γ-L-glutamyl-L-cysteinyl-glycyl)-spermidine	Generator
N'-glutathionylspermidine disulfide	MeSH

Molecular Formula

C₁₇H₃₄N₆O₅S

Average Mass

434.554

Monoisotopic Mass

434.231138918

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

33932-35-3

SMILES

Not Available

InChI Identifier

InChI=1S/C17H34N6O5S/c18-6-1-2-7-20-8-3-9-21-15(25)10-22-16(26)13(11-29)23-14(24)5-4-12(19)17(27)28/h12-13,20,29H,1-11,18-19H2,(H,21,25)(H,22,26)(H,23,24)(H,27,28)/t12-,13-/m0/s1

InChI Key

NEDQLXHBVHSKNV-STQMWFEESA-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
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
L-alpha-amino acid
Alpha-amino acid or derivatives
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Secondary amine
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Alkylthiol
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Primary amine
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutathione derivative (CHEBI:16613 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007850	Glutathionylspermidine	Glutathione	Not Available		VMH	30371894
MMDBr0007851	Glutathione	Glutathionylspermidine	Not Available		VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	52	Human ; Human feces; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human sputum; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	10	Pig ; Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	1	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

DB03295

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05730

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440772

PDB ID

Not Available

ChEBI ID

16613

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Glutathionylspermidine (MMDBc0030065)

MOL for #<Metabolite:0x0000556b6ab7bf08>

3D MOL for #<Metabolite:0x0000556b6ab7bf08>

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3D-SDF for #<Metabolite:0x0000556b6ab7bf08>

PDB for #<Metabolite:0x0000556b6ab7bf08>

3D PDB for #<Metabolite:0x0000556b6ab7bf08>

SMILES for #<Metabolite:0x0000556b6ab7bf08>

INCHI for #<Metabolite:0x0000556b6ab7bf08>

Structure for #<Metabolite:0x0000556b6ab7bf08>

3D Structure for #<Metabolite:0x0000556b6ab7bf08>