Record Information |
---|
Version | 1.0 |
---|
Creation Date | 2016-07-13 19:22:16 UTC |
---|
Update Date | 2016-09-23 18:44:27 UTC |
---|
Lmdb | LMDB00009 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | Biotin |
---|
Description | Biotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as vitamin H or B7 or coenzyme R. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the 'biotin cycle'. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various animal tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; at least seven biotinylation sites have been identified in animal histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signaling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology. (PMID: 15992684 , 16011464 ). |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
(+)-cis-hexahydro-2-oxo-1H-thieno[3,4]Imidazole-4-valeric acid | ChEBI | (3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acid | ChEBI | 5-(2-oxohexahydro-1H-thieno[3,4-D]Imidazol-4-yl)pentanoic acid | ChEBI | Biotina | ChEBI | Biotine | ChEBI | Biotinum | ChEBI | cis-(+)-tetrahydro-2-oxothieno[3,4]Imidazoline-4-valeric acid | ChEBI | cis-hexahydro-2-oxo-1H-thieno(3,4)Imidazole-4-valeric acid | ChEBI | cis-tetrahydro-2-oxothieno(3,4-D)Imidazoline-4-valeric acid | ChEBI | Coenzyme R | ChEBI | D-(+)-Biotin | ChEBI | D-Biotin | ChEBI | Vitamin b7 | ChEBI | Vitamin H | ChEBI | (+)-cis-hexahydro-2-oxo-1H-thieno[3,4]Imidazole-4-valerate | Generator | (3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerate | Generator | 5-(2-oxohexahydro-1H-thieno[3,4-D]Imidazol-4-yl)pentanoate | Generator | cis-(+)-tetrahydro-2-oxothieno[3,4]Imidazoline-4-valerate | Generator | cis-hexahydro-2-oxo-1H-thieno(3,4)Imidazole-4-valerate | Generator | cis-tetrahydro-2-oxothieno(3,4-D)Imidazoline-4-valerate | Generator | (+)-Biotin | HMDB | -(+)-Biotin | HMDB | 1SWK | HMDB | 1SWN | HMDB | 1SWR | HMDB | Biodermatin | HMDB | Bioepiderm | HMDB | Bios H | HMDB | Bios II | HMDB | D(+)-Biotin | HMDB | D-Biotin factor S | HMDB | delta-(+)-Biotin | HMDB | delta-Biotin | HMDB | delta-Biotin factor S | HMDB | Factor S | HMDB | Factor S (vitamin) | HMDB | hexahydro-2-oxo-1H-thieno(3,4-D)Imidazole-4-pentanoate | HMDB | hexahydro-2-oxo-1H-thieno(3,4-D)Imidazole-4-pentanoic acid | HMDB | hexahydro-2-oxo-[3AS-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoate | HMDB | hexahydro-2-oxo-[3AS-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid | HMDB | hexahydro-2-oxo-[3As-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoate | HMDB | hexahydro-2-oxo-[3As-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid | HMDB | Lutavit H2 | HMDB | Meribin | HMDB | Rovimix H 2 | HMDB | Vitamin-H | HMDB | Biotin hermes brand | MeSH | Biotin roche brand | MeSH | Biotin simons brand | MeSH | Biotin strathmann brand | MeSH | Biotin ziethen brand | MeSH | Biotin ratiopharm | MeSH | Roche brand OF biotin | MeSH | Roche, biotine | MeSH | E+b pharma brand OF biotin | MeSH | Medobiotin | MeSH | Biokur | MeSH | Biotinratiopharm | MeSH | Gelfert, biotin | MeSH | Hermes brand OF biotin | MeSH | Hermes, biotin | MeSH | Medopharm brand OF biotin | MeSH | Ratiopharm brand OF biotin | MeSH | Biocur brand OF biotin | MeSH | Biotin dermapharm brand | MeSH | Biotine roche | MeSH | Deacura | MeSH | Dermapharm brand OF biotin | MeSH | Gabunat | MeSH | Medebiotin | MeSH | Rombellin | MeSH | Ziethen brand OF biotin | MeSH | Biotin biocur brand | MeSH | Biotin gelfert | MeSH | Biotin hermes | MeSH | Biotin medopharm brand | MeSH | Biotin ratiopharm brand | MeSH | Biotin-ratiopharm | MeSH | H, Vitamin | MeSH | Medea brand OF biotin sodium salt | MeSH | Simons brand OF biotin | MeSH | Strathmann brand OF biotin | MeSH |
|
---|
Chemical Formula | C10H16N2O3S |
---|
Average Molecular Weight | 244.311 |
---|
Monoisotopic Molecular Weight | 244.088163078 |
---|
IUPAC Name | 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid |
---|
Traditional Name | biotin |
---|
CAS Registry Number | 58-85-5 |
---|
SMILES | [H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2 |
---|
InChI Identifier | InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1 |
---|
InChI Key | YBJHBAHKTGYVGT-ZKWXMUAHSA-N |
---|
Chemical Taxonomy |
---|
Description | This compound belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Biotin and derivatives |
---|
Sub Class | Not Available |
---|
Direct Parent | Biotin and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Biotin
- Imidazolyl carboxylic acid derivative
- Medium-chain fatty acid
- Heterocyclic fatty acid
- Thia fatty acid
- Fatty acid
- Fatty acyl
- Thiolane
- 2-imidazoline
- Isourea
- Azacycle
- Dialkylthioether
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Carboxylic acid derivative
- Thioether
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organonitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Aliphatic heteropolycyclic compound
|
---|
Molecular Framework | Aliphatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Status | Detected and Quantified |
---|
Origin | Not Available |
---|
Biofunction | Not Available |
---|
Application | Not Available |
---|
Cellular locations | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | splash10-0f76-1960000000-b21ddd69490cac3254f8 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-0f76-3960000000-a8a94e2de123f66979d8 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-MS | splash10-0006-6910000000-11bfe0a5a77f7dfaa8c5 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF | splash10-0f76-1960000000-b21ddd69490cac3254f8 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-MS | splash10-0f76-3960000000-a8a94e2de123f66979d8 | View in MoNA |
---|
GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-00dl-9680000000-eb01d8147a82f7982b54 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0006-0090000000-6d956bb533d353d449c9 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0006-0190000000-01f67d1bdf8c742e48c8 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0fxx-3920000000-f0b9613cbd9371e4be92 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9400000000-107f2a44f521c2513578 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-1a3f65d909dc40055e87 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-004i-0090000000-c928e8d0a18f3f848262 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-066s-1920000000-5f795e0b7f1d7cf986e5 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-0ar1-1920000000-c298be862857cb3bbc7f | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-000t-0900000000-cdc4a4c359ff765fd32d | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-05xs-1920000000-3be430b63e9c748c681a | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0006-0090000000-bcffb0dcf77e8fd727a4 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0f6x-0390000000-c209523d36e9a7681f44 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0090000000-c0f81ee86772310db415 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0190000000-016eb89528e564c74720 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0fxx-3920000000-f0b9613cbd9371e4be92 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9400000000-107f2a44f521c2513578 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-d08e1b3709844e1e91b0 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-0190000000-21d0f2512788276bbb89 | View in MoNA |
---|
LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0udj-0690000000-dc372934024e58bdcc60 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-0290000000-43932f104dea28cbdfb8 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-1960000000-d3673c6bc624b97f35be | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9600000000-00a4e152d89024a9b423 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-1390000000-3f4b512cfa57b894ff94 | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f6y-7890000000-ea1e647fc5b31e42af0b | View in MoNA |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-e139c928dcc46b225bdb | View in MoNA |
---|
1D NMR | 1H NMR Spectrum | Not Available |
---|
1D NMR | 1H NMR Spectrum | Not Available |
---|
1D NMR | 13C NMR Spectrum | Not Available |
---|
2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
---|
2D NMR | [1H,1H] 2D NMR Spectrum | Not Available |
---|
|
---|