MiMeDB: Showing metabocard for Dethiobiotin (MMDBc0029726)

Microbial

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:39:09 UTC

Update Date

2024-10-13 09:38:29 UTC

Metabolite ID

MMDBc0029726

Metabolite Identification

Common Name

Dethiobiotin

Description

Dethiobiotin is a synthetic metabolite that mimic the effects of biotin on gene expression and thus have biotin-like activities. It is an intermediate in biotin metabolism, and converted to biotin via biotin synthase (EC:2.8.1.6). (KEGG) Biotin serves as a coenzyme for carboxylases such as propionyl-CoA carboxylase. (PMID 12730407 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₁₀H₁₈N₂O₃

Average Mass

214.2615

Monoisotopic Mass

214.131742452

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

533-48-2

SMILES

Not Available

InChI Identifier

InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1

InChI Key

AUTOLBMXDDTRRT-JGVFFNPUSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

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	389.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	276.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	157.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	280.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	252.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	219.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	757.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	752.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	370.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	153.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	352.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	160.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	81.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	385.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	645.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	74.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	199.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	841.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	614.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Dethiobiotin_TMS_1	C[C@@H]1NC(=O)N[C@@H]1CCCCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1805.26
Gas Chromatography	Dethiobiotin_TMS_2	C[C@H]1[C@@H](CCCCCC(=O)O)NC(=O)N1[Si](C)(C)C	standard non polar	2025-10-23	2251.78
Gas Chromatography	Dethiobiotin_TMS_3	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O	standard non polar	2025-10-23	2076.59
Gas Chromatography	Dethiobiotin_TMS_4	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)NC(=O)N1[Si](C)(C)C	standard non polar	2025-10-23	1972.1
Gas Chromatography	Dethiobiotin_TMS_5	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1076.97
Gas Chromatography	Dethiobiotin_TMS_6	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	standard non polar	2025-10-23	2255.41
Gas Chromatography	Dethiobiotin_TMS_7	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	standard non polar	2025-10-23	1958.92
Gas Chromatography	Dethiobiotin_TMS_1	C[C@@H]1NC(=O)N[C@@H]1CCCCCC(=O)O[Si](C)(C)C	standard polar	2025-10-23	1390.85
Gas Chromatography	Dethiobiotin_TMS_2	C[C@H]1[C@@H](CCCCCC(=O)O)NC(=O)N1[Si](C)(C)C	standard polar	2025-10-23	2006.82
Gas Chromatography	Dethiobiotin_TMS_3	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O	standard polar	2025-10-23	2904.73
Gas Chromatography	Dethiobiotin_TMS_4	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)NC(=O)N1[Si](C)(C)C	standard polar	2025-10-23	2320.45
Gas Chromatography	Dethiobiotin_TMS_5	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C	standard polar	2025-10-23	1809.25
Gas Chromatography	Dethiobiotin_TMS_6	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	standard polar	2025-10-23	1937.75
Gas Chromatography	Dethiobiotin_TMS_7	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	standard polar	2025-10-23	1982.31

Biological Properties

Cellular Locations

Extracellular
Membrane

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

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
MMDBr0018046	7,8-Diaminononanoate	Dethiobiotin	ATP-dependent dethiobiotin synthetase BioD 1	Synthesis	PathBank	31602464
MMDBr0018047	S-Adenosylmethionine	Biotin	Biotin synthase	Synthesis	PathBank	31602464
MMDBr0019421	Diaminopimelic acid	Dethiobiotin	Dethiobiotin synthetase	Synthesis	PathBank	31602464
MMDBr0019422	S-Adenosylmethionine	Biotin	Biotin synthase, mitochondrial	Synthesis	PathBank	31602464
MMDBr0024707	di-mu-Sulfido-diiron(1+)	5'-Deoxyadenosine	Biotin synthase	Synthesis	RHEA	34755880
MMDBr0024708	di-mu-Sulfido-diiron(1+)	5'-Deoxyadenosine	Biotin synthase	Synthesis	RHEA	34755880

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	4	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Turkey ; Cattle ; River trout ; Sheep ; Chicken	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	299	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Turkey ; Cattle ; River trout ; Sheep ; Chicken	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	201	Pig ; Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	81	Human feces; Human ; Human saliva; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	6	Human feces; Pig ; Human	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	66	Human feces; Human ; Cattle	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Aquificae	2
Bacteria/Eubacteria	Chlamydiae	3	Human ; Sheep ; Cat
Bacteria/Eubacteria	Chlorobi	1
Bacteria/Eubacteria	Cyanobacteria	6	Human
Bacteria/Eubacteria	Elusimicrobia	1
Archaea/Archaea	nah	1
Archaea/Archaea	Euryarchaeota	3		Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	nah	1
Bacteria/Eubacteria	Nitrospirae	1
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Rodriguez-Melendez R, Lewis B, McMahon RJ, Zempleni J: Diaminobiotin and desthiobiotin have biotin-like activities in Jurkat cells. J Nutr. 2003 May;133(5):1259-64. doi: 10.1093/jn/133.5.1259. [PubMed:12730407 ]

Showing metabocard for Dethiobiotin (MMDBc0029726)

MOL for #<Metabolite:0x00007f2e20cd05a0>

3D MOL for #<Metabolite:0x00007f2e20cd05a0>

3D SDF for #<Metabolite:0x00007f2e20cd05a0>

3D-SDF for #<Metabolite:0x00007f2e20cd05a0>

PDB for #<Metabolite:0x00007f2e20cd05a0>

3D PDB for #<Metabolite:0x00007f2e20cd05a0>

SMILES for #<Metabolite:0x00007f2e20cd05a0>

INCHI for #<Metabolite:0x00007f2e20cd05a0>

Structure for #<Metabolite:0x00007f2e20cd05a0>

3D Structure for #<Metabolite:0x00007f2e20cd05a0>