MiMeDB: Showing metabocard for Yersiniabactin (MMDBc0016055)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:46:55 UTC

Update Date

2025-01-17 02:28:24 UTC

Metabolite ID

MMDBc0016055

Metabolite Identification

Common Name

Yersiniabactin

Description

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₂₁H₂₇N₃O₄S₃

Average Mass

481.64

Monoisotopic Mass

481.116369883

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C21H27N3O4S3/c1-20(2,18-24-21(3,10-31-18)19(27)28)15(26)12-8-30-17(22-12)13-9-29-16(23-13)11-6-4-5-7-14(11)25/h4-7,12-13,15,17,22,25-26H,8-10H2,1-3H3,(H,27,28)

InChI Key

JHYVWAMMAMCUIR-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	150.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	54.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	470.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	583.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	498.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	195.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2346.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	116.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	385.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	270.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	141.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	146.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	154.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	28.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	233.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	99.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	323.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1565.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	950.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Yersiniabactin_TMS_1	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2)=N1	standard non polar	2025-10-23	1991.17
Gas Chromatography	Yersiniabactin_TMS_2	CC1(C(=O)O)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard non polar	2025-10-23	2135.97
Gas Chromatography	Yersiniabactin_TMS_3	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2)=N1	standard non polar	2025-10-23	1965.58
Gas Chromatography	Yersiniabactin_TMS_4	CC1(C(=O)O)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	1540.53
Gas Chromatography	Yersiniabactin_TMS_5	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2)=N1	standard non polar	2025-10-23	2767.67
Gas Chromatography	Yersiniabactin_TMS_6	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard non polar	2025-10-23	2554.02
Gas Chromatography	Yersiniabactin_TMS_7	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	785.459
Gas Chromatography	Yersiniabactin_TMS_8	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard non polar	2025-10-23	2987.52
Gas Chromatography	Yersiniabactin_TMS_9	CC1(C(=O)O)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	1692.24
Gas Chromatography	Yersiniabactin_TMS_10	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	1047.09
Gas Chromatography	Yersiniabactin_TMS_11	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard non polar	2025-10-23	719.602
Gas Chromatography	Yersiniabactin_TMS_12	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	1332.61
Gas Chromatography	Yersiniabactin_TMS_13	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	2552.51
Gas Chromatography	Yersiniabactin_TMS_14	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	1782.46
Gas Chromatography	Yersiniabactin_TMS_15	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard non polar	2025-10-23	1923.34
Gas Chromatography	Yersiniabactin_TMS_1	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2)=N1	standard polar	2025-10-23	2151.1
Gas Chromatography	Yersiniabactin_TMS_2	CC1(C(=O)O)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard polar	2025-10-23	2653.24
Gas Chromatography	Yersiniabactin_TMS_3	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2)=N1	standard polar	2025-10-23	1722.3
Gas Chromatography	Yersiniabactin_TMS_4	CC1(C(=O)O)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	2496.33
Gas Chromatography	Yersiniabactin_TMS_5	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2)=N1	standard polar	2025-10-23	1412.5
Gas Chromatography	Yersiniabactin_TMS_6	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard polar	2025-10-23	1733.6
Gas Chromatography	Yersiniabactin_TMS_7	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	3328.23
Gas Chromatography	Yersiniabactin_TMS_8	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard polar	2025-10-23	2422.16
Gas Chromatography	Yersiniabactin_TMS_9	CC1(C(=O)O)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	2350.91
Gas Chromatography	Yersiniabactin_TMS_10	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	2071.71
Gas Chromatography	Yersiniabactin_TMS_11	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2)=N1	standard polar	2025-10-23	2353.45
Gas Chromatography	Yersiniabactin_TMS_12	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	1990.17
Gas Chromatography	Yersiniabactin_TMS_13	CC1(C(=O)O)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	1481.66
Gas Chromatography	Yersiniabactin_TMS_14	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	1935.43
Gas Chromatography	Yersiniabactin_TMS_15	CC1(C(=O)O[Si](C)(C)C)CSC(C(C)(C)C(O[Si](C)(C)C)C2CSC(C3CSC(C4=CC=CC=C4O[Si](C)(C)C)=N3)N2[Si](C)(C)C)=N1	standard polar	2025-10-23	1309.58

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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/Eubacteria	Proteobacteria	3	Human ; Human feces; Human feces; pleural fluid plaque; bal	Metabolic reconstruction; Microbial culture

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Yersiniabactin (MMDBc0016055)

MOL for #<Metabolite:0x00007f2e51742670>

3D MOL for #<Metabolite:0x00007f2e51742670>

3D SDF for #<Metabolite:0x00007f2e51742670>

3D-SDF for #<Metabolite:0x00007f2e51742670>

PDB for #<Metabolite:0x00007f2e51742670>

3D PDB for #<Metabolite:0x00007f2e51742670>

SMILES for #<Metabolite:0x00007f2e51742670>

INCHI for #<Metabolite:0x00007f2e51742670>

Structure for #<Metabolite:0x00007f2e51742670>

3D Structure for #<Metabolite:0x00007f2e51742670>