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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000030
Secondary Accession Numbers
  • HMDB00030
Metabolite Identification
Common NameBiotin
DescriptionBiotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as coenzyme R and vitamin H or B7. 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. Humans fulfill their biotin requirement through their diet through endogenous reutilization of biotin and perhaps through the 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. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signalling, 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 signalling: 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 human 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 signalling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to the 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 human 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 signalling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology (PMID: 15992684 , 16011464 ).
Structure
Data?1584032999
Synonyms
ValueSource
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acidChEBI
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acidChEBI
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acidChEBI
BiotinaChEBI
BiotineChEBI
BiotinumChEBI
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acidChEBI
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acidChEBI
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acidChEBI
Coenzyme RChEBI
D-(+)-BiotinChEBI
D-BiotinChEBI
Vitamin b7ChEBI
Vitamin HChEBI
BioepidermKegg
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerateGenerator
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerateGenerator
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoateGenerator
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerateGenerator
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valerateGenerator
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerateGenerator
(+)-BiotinHMDB
-(+)-BiotinHMDB
1SWKHMDB
1SWNHMDB
1SWRHMDB
BiodermatinHMDB
Bios HHMDB
Bios IIHMDB
D(+)-BiotinHMDB
D-Biotin factor SHMDB
delta-(+)-BiotinHMDB
delta-BiotinHMDB
delta-Biotin factor SHMDB
Factor SHMDB
Factor S (vitamin)HMDB
Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoateHMDB
Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoic acidHMDB
Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
Lutavit H2HMDB
MeribinHMDB
Rovimix H 2HMDB
Vitamin-HHMDB
Biotin hermes brandHMDB
Biotin roche brandHMDB
Biotin simons brandHMDB
Biotin strathmann brandHMDB
Biotin ziethen brandHMDB
Biotin ratiopharmHMDB
Roche brand OF biotinHMDB
Roche, biotineHMDB
E+b pharma brand OF biotinHMDB
MedobiotinHMDB
BiokurHMDB
BiotinratiopharmHMDB
Gelfert, biotinHMDB
Hermes brand OF biotinHMDB
Hermes, biotinHMDB
Medopharm brand OF biotinHMDB
Ratiopharm brand OF biotinHMDB
Biocur brand OF biotinHMDB
Biotin dermapharm brandHMDB
Biotine rocheHMDB
DeacuraHMDB
Dermapharm brand OF biotinHMDB
GabunatHMDB
MedebiotinHMDB
RombellinHMDB
Ziethen brand OF biotinHMDB
Biotin biocur brandHMDB
Biotin gelfertHMDB
Biotin hermesHMDB
Biotin medopharm brandHMDB
Biotin ratiopharm brandHMDB
Biotin-ratiopharmHMDB
H, VitaminHMDB
Medea brand OF biotin sodium saltHMDB
Simons brand OF biotinHMDB
Strathmann brand OF biotinHMDB
Chemical FormulaC10H16N2O3S
Average Molecular Weight244.311
Monoisotopic Molecular Weight244.088163078
IUPAC Name5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
Traditional Name5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
CAS Registry Number58-85-5
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 KeyYBJHBAHKTGYVGT-ZKWXMUAHSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBiotin and derivatives
Sub ClassNot Available
Direct ParentBiotin 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 FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point232 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.22 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available156.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000313
[M+H]+Not Available151.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000313
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP0.17ALOGPS
logP0.32ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.05 m³·mol⁻¹ChemAxon
Polarizability24.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.45531661259
DarkChem[M-H]-153.68231661259
AllCCS[M+H]+154.57132859911
AllCCS[M-H]-158.73732859911
DeepCCS[M-2H]-189.08230932474
DeepCCS[M+Na]+164.49730932474
AllCCS[M+H]+154.632859911
AllCCS[M+H-H2O]+151.132859911
AllCCS[M+NH4]+157.832859911
AllCCS[M+Na]+158.732859911
AllCCS[M-H]-158.732859911
AllCCS[M+Na-2H]-159.032859911
AllCCS[M+HCOO]-159.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Biotin[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N23865.4Standard polar33892256
Biotin[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N22275.7Standard non polar33892256
Biotin[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N22588.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Biotin,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]122520.5Semi standard non polar33892256
Biotin,1TMS,isomer #2C[Si](C)(C)N1C(=O)N[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]212546.8Semi standard non polar33892256
Biotin,1TMS,isomer #3C[Si](C)(C)N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]212539.2Semi standard non polar33892256
Biotin,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C2580.1Semi standard non polar33892256
Biotin,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C2306.2Standard non polar33892256
Biotin,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C4188.6Standard polar33892256
Biotin,2TMS,isomer #2C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]122568.5Semi standard non polar33892256
Biotin,2TMS,isomer #2C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]122298.2Standard non polar33892256
Biotin,2TMS,isomer #2C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]124247.6Standard polar33892256
Biotin,2TMS,isomer #3C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]212481.3Semi standard non polar33892256
Biotin,2TMS,isomer #3C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]212311.0Standard non polar33892256
Biotin,2TMS,isomer #3C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]213326.8Standard polar33892256
Biotin,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2459.9Semi standard non polar33892256
Biotin,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2378.7Standard non polar33892256
Biotin,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2983.0Standard polar33892256
Biotin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]122759.9Semi standard non polar33892256
Biotin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)N[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]212768.2Semi standard non polar33892256
Biotin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]212758.9Semi standard non polar33892256
Biotin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C(C)(C)C3055.6Semi standard non polar33892256
Biotin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C(C)(C)C2787.2Standard non polar33892256
Biotin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C(C)(C)C3987.0Standard polar33892256
Biotin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C(C)(C)C)[C@H]123049.0Semi standard non polar33892256
Biotin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C(C)(C)C)[C@H]122779.6Standard non polar33892256
Biotin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C(C)(C)C)[C@H]124008.6Standard polar33892256
Biotin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]212897.2Semi standard non polar33892256
Biotin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]212819.9Standard non polar33892256
Biotin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]213231.0Standard polar33892256
Biotin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3112.9Semi standard non polar33892256
Biotin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3053.8Standard non polar33892256
Biotin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3092.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Biotin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f76-1960000000-b21ddd69490cac3254f82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Biotin GC-MS (3 TMS)splash10-0f76-3960000000-a8a94e2de123f66979d82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Biotin GC-EI-TOF (Non-derivatized)splash10-0f76-1960000000-b21ddd69490cac3254f82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Biotin GC-MS (Non-derivatized)splash10-0f76-3960000000-a8a94e2de123f66979d82017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6910000000-11bfe0a5a77f7dfaa8c52016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9680000000-eb01d8147a82f7982b542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biotin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01pt-9500000000-a1e1ec56cf32236ac6b12018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0006-0090000000-6d956bb533d353d449c92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0006-0190000000-01f67d1bdf8c742e48c82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0fxx-3920000000-f0b9613cbd9371e4be922012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0006-9400000000-107f2a44f521c25135782012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0006-9000000000-1a3f65d909dc40055e872012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-004i-0090000000-c928e8d0a18f3f8482622012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-066s-1920000000-5f795e0b7f1d7cf986e52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0ar1-1920000000-c298be862857cb3bbc7f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-000t-0900000000-cdc4a4c359ff765fd32d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-qTof , Positive-QTOFsplash10-05xs-1920000000-3be430b63e9c748c681a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QTOF , negative-QTOFsplash10-0006-0090000000-bcffb0dcf77e8fd727a42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QTOF , negative-QTOFsplash10-0f6x-0390000000-c209523d36e9a7681f442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOFsplash10-0006-0090000000-c0f81ee86772310db4152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOFsplash10-0006-0190000000-016eb89528e564c747202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOFsplash10-0fxx-3920000000-f0b9613cbd9371e4be922017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOFsplash10-0006-9400000000-107f2a44f521c25135782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-d08e1b3709844e1e91b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin LC-ESI-ITFT , negative-QTOFsplash10-0006-0190000000-21d0f2512788276bbb892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biotin Linear Ion Trap , negative-QTOFsplash10-0udj-0690000000-dc372934024e58bdcc602017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biotin 10V, Positive-QTOFsplash10-002b-0290000000-43932f104dea28cbdfb82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biotin 20V, Positive-QTOFsplash10-0002-1960000000-d3673c6bc624b97f35be2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biotin 40V, Positive-QTOFsplash10-052f-9600000000-00a4e152d89024a9b4232016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biotin 10V, Negative-QTOFsplash10-0006-1390000000-3f4b512cfa57b894ff942016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biotin 20V, Negative-QTOFsplash10-0f6y-7890000000-ea1e647fc5b31e42af0b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biotin 40V, Negative-QTOFsplash10-0006-9100000000-e139c928dcc46b225bdb2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0034 (0.002 - 0.0051) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0016 (0.0009 - 0.0028) uMChildren (1-13 years old)Not SpecifiedNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0024 (0.0008 - 0.0041) uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.11-0.13 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00127 +/- 0.00067 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000557 +/- 0.000307 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0005 +/- 0.0002 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.123 +/- 0.141 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.071 +/- 0.041 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified0.296 +/- 0.150 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
UrineDetected and Quantified0.014 (0.002-0.044) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.049 +/- 0.035 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.023 (0.013-0.032) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.08198 (0.00033-0.421) uMNot SpecifiedNot SpecifiedAcute lymphoblastic leukemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.16 uMNot SpecifiedNot SpecifiedBronchopulmonary dysplasia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00039 uMNot SpecifiedNot SpecifiedBurkitt's lymphoma details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000447 +/- 0.000217 uMNot SpecifiedNot SpecifiedDementia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000336 +/- 0.00008603 uMNot SpecifiedNot SpecifiedEpilepsy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0229 uMNot SpecifiedNot SpecifiedHead injury details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0273 (0.0247-0.0299) uMNot SpecifiedNot SpecifiedLymphoblastic lymphoma details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000545 (0.00004799-0.00192) uMNot SpecifiedNot SpecifiedMotor neuron disease (MND) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000324 +/- 0.000107 uMNot SpecifiedNot SpecifiedMultiple sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000692 +/- 0.000602 uMNot SpecifiedNot SpecifiedPolyneuropathy details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000438 +/- 0.000156 uMNot SpecifiedNot SpecifiedVascular encephalopathies details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified58.242 +/- 21.921 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Acute Lymphoblastic Leukemia
  1. Bogusiewicz A, Stratton SL, Ellison DA, Mock DM: Biotin accounts for less than half of all biotin and biotin metabolites in the cerebrospinal fluid of children. Am J Clin Nutr. 2008 Nov;88(5):1291-6. [PubMed:18996865 ]
Dementia
  1. Anagnostouli M, Livaniou E, Nyalala JO, Evangelatos G, Zournas C, Ithakissios DS, Papageorgiou C: Cerebrospinal fluid levels of biotin in various neurological disorders. Acta Neurol Scand. 1999 Jun;99(6):387-92. [PubMed:10577274 ]
Epilepsy
  1. Anagnostouli M, Livaniou E, Nyalala JO, Evangelatos G, Zournas C, Ithakissios DS, Papageorgiou C: Cerebrospinal fluid levels of biotin in various neurological disorders. Acta Neurol Scand. 1999 Jun;99(6):387-92. [PubMed:10577274 ]
Head injury
  1. Bogusiewicz A, Stratton SL, Ellison DA, Mock DM: Biotin accounts for less than half of all biotin and biotin metabolites in the cerebrospinal fluid of children. Am J Clin Nutr. 2008 Nov;88(5):1291-6. [PubMed:18996865 ]
Motor neuron disease
  1. Anagnostouli M, Livaniou E, Nyalala JO, Evangelatos G, Zournas C, Ithakissios DS, Papageorgiou C: Cerebrospinal fluid levels of biotin in various neurological disorders. Acta Neurol Scand. 1999 Jun;99(6):387-92. [PubMed:10577274 ]
Multiple sclerosis
  1. Anagnostouli M, Livaniou E, Nyalala JO, Evangelatos G, Zournas C, Ithakissios DS, Papageorgiou C: Cerebrospinal fluid levels of biotin in various neurological disorders. Acta Neurol Scand. 1999 Jun;99(6):387-92. [PubMed:10577274 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB00121
Phenol Explorer Compound IDNot Available
FooDB IDFDB014510
KNApSAcK IDC00000756
Chemspider ID149962
KEGG Compound IDC00120
BioCyc IDBIOTIN
BiGG ID33931
Wikipedia LinkBiotin
METLIN ID243
PubChem Compound171548
PDB IDNot Available
ChEBI ID15956
Food Biomarker OntologyNot Available
VMH IDBTN
MarkerDB IDMDB00000015
Good Scents IDNot Available
References
Synthesis ReferenceCorey, E. J.; Mehrotra, Mukund M. A simple and enantioselective synthesis of (+)-biotin. Tetrahedron Letters (1988), 29(1), 57-60.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Thuy LP, Belmont J, Nyhan WL: Prenatal diagnosis and treatment of holocarboxylase synthetase deficiency. Prenat Diagn. 1999 Feb;19(2):108-12. [PubMed:10215065 ]
  3. Zempleni J, McCormick DB, Mock DM: Identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-l-sulfoxide in human urine. Am J Clin Nutr. 1997 Feb;65(2):508-11. [PubMed:9022537 ]
  4. Bussolati G, Gugliotta P, Volante M, Pace M, Papotti M: Retrieved endogenous biotin: a novel marker and a potential pitfall in diagnostic immunohistochemistry. Histopathology. 1997 Nov;31(5):400-7. [PubMed:9416479 ]
  5. Mock DM, Stadler DD, Stratton SL, Mock NI: Biotin status assessed longitudinally in pregnant women. J Nutr. 1997 May;127(5):710-6. [PubMed:9164991 ]
  6. Thuy LP, Sweetman L, Nyhan WL: A new immunochemical assay for biotin. Clin Chim Acta. 1991 Oct 31;202(3):191-7. [PubMed:1814646 ]
  7. Limat A, Suormala T, Hunziker T, Waelti ER, Braathen LR, Baumgartner R: Proliferation and differentiation of cultured human follicular keratinocytes are not influenced by biotin. Arch Dermatol Res. 1996;288(1):31-8. [PubMed:8750932 ]
  8. Bigham SL, Ballard JD, Giles KD, Clelland CS, Jeffcoat R, Griffin KS, Farley TD, Bushman DR, Wright JR: Synthesis and possible applications of biotin-linked copper clusters. Physiol Chem Phys Med NMR. 1990;22(2):63-72. [PubMed:2100006 ]
  9. Mock DM, Stadler DD: Conflicting indicators of biotin status from a cross-sectional study of normal pregnancy. J Am Coll Nutr. 1997 Jun;16(3):252-7. [PubMed:9176832 ]
  10. Bingham JP, Bian S, Tan ZY, Takacs Z, Moczydlowski E: Synthesis of a biotin derivative of iberiotoxin: binding interactions with streptavidin and the BK Ca2+-activated K+ channel expressed in a human cell line. Bioconjug Chem. 2006 May-Jun;17(3):689-99. [PubMed:16704206 ]
  11. Mock DM: Biotin status: which are valid indicators and how do we know? J Nutr. 1999 Feb;129(2S Suppl):498S-503S. [PubMed:10064317 ]
  12. Mock DM, Dyken ME: Biotin catabolism is accelerated in adults receiving long-term therapy with anticonvulsants. Neurology. 1997 Nov;49(5):1444-7. [PubMed:9371938 ]
  13. Mock DM, Nyalala JO, Raguseo RM: A direct streptavidin-binding assay does not accurately quantitate biotin in human urine. J Nutr. 2001 Aug;131(8):2208-14. [PubMed:11481419 ]
  14. Mardach R, Zempleni J, Wolf B, Cannon MJ, Jennings ML, Cress S, Boylan J, Roth S, Cederbaum S, Mock DM: Biotin dependency due to a defect in biotin transport. J Clin Invest. 2002 Jun;109(12):1617-23. [PubMed:12070309 ]
  15. Mock DM, Heird GM: Urinary biotin analogs increase in humans during chronic supplementation: the analogs are biotin metabolites. Am J Physiol. 1997 Jan;272(1 Pt 1):E83-5. [PubMed:9038855 ]
  16. Fujimoto W, Inaoki M, Fukui T, Inoue Y, Kuhara T: Biotin deficiency in an infant fed with amino acid formula. J Dermatol. 2005 Apr;32(4):256-61. [PubMed:15863846 ]
  17. Schenker S, Hu ZQ, Johnson RF, Yang Y, Frosto T, Elliott BD, Henderson GI, Mock DM: Human placental biotin transport: normal characteristics and effect of ethanol. Alcohol Clin Exp Res. 1993 Jun;17(3):566-75. [PubMed:8333586 ]
  18. Mock NI, Malik MI, Stumbo PJ, Bishop WP, Mock DM: Increased urinary excretion of 3-hydroxyisovaleric acid and decreased urinary excretion of biotin are sensitive early indicators of decreased biotin status in experimental biotin deficiency. Am J Clin Nutr. 1997 Apr;65(4):951-8. [PubMed:9094878 ]
  19. Grafe F, Wohlrab W, Neubert RH, Brandsch M: Transport of biotin in human keratinocytes. J Invest Dermatol. 2003 Mar;120(3):428-33. [PubMed:12603856 ]
  20. Gravel RA, Narang MA: Molecular genetics of biotin metabolism: old vitamin, new science. J Nutr Biochem. 2005 Jul;16(7):428-31. [PubMed:15992684 ]
  21. Zempleni J: Uptake, localization, and noncarboxylase roles of biotin. Annu Rev Nutr. 2005;25:175-96. [PubMed:16011464 ]
  22. Holmberg A, Blomstergren A, Nord O, Lukacs M, Lundeberg J, Uhlen M: The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis. 2005 Feb;26(3):501-10. [PubMed:15690449 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Enzymes

General function:
Involved in acetyl-CoA carboxylase activity
Specific function:
ACC-beta may be involved in the provision of malonyl-CoA or in the regulation of fatty acid oxidation, rather than fatty acid biosynthesis. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name:
ACACB
Uniprot ID:
O00763
Molecular weight:
276538.575
References
  1. Liu Y, Zalameda L, Kim KW, Wang M, McCarter JD: Discovery of acetyl-coenzyme A carboxylase 2 inhibitors: comparison of a fluorescence intensity-based phosphate assay and a fluorescence polarization-based ADP Assay for high-throughput screening. Assay Drug Dev Technol. 2007 Apr;5(2):225-35. [PubMed:17477831 ]
General function:
Involved in catalytic activity
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:
PC
Uniprot ID:
P11498
Molecular weight:
129632.565
References
  1. Liu L, Li Y, Zhu Y, Du G, Chen J: Redistribution of carbon flux in Torulopsis glabrata by altering vitamin and calcium level. Metab Eng. 2007 Jan;9(1):21-9. Epub 2006 Aug 12. [PubMed:17008113 ]
  2. Ferreira G, Weiss WP: Effect of biotin on activity and gene expression of biotin-dependent carboxylases in the liver of dairy cows. J Dairy Sci. 2007 Mar;90(3):1460-6. [PubMed:17297119 ]
  3. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. [PubMed:17659996 ]
  4. Jitrapakdee S, Adina-Zada A, Besant PG, Surinya KH, Cleland WW, Wallace JC, Attwood PV: Differential regulation of the yeast isozymes of pyruvate carboxylase and the locus of action of acetyl CoA. Int J Biochem Cell Biol. 2007;39(6):1211-23. Epub 2007 Mar 30. [PubMed:17478118 ]
  5. Ozimek PZ, Klompmaker SH, Visser N, Veenhuis M, van der Klei IJ: The transcarboxylase domain of pyruvate carboxylase is essential for assembly of the peroxisomal flavoenzyme alcohol oxidase. FEMS Yeast Res. 2007 Oct;7(7):1082-92. Epub 2007 Feb 20. [PubMed:17316367 ]
General function:
Involved in acetyl-CoA carboxylase activity
Specific function:
Catalyzes the rate-limiting reaction in the biogenesis of long-chain fatty acids. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name:
ACACA
Uniprot ID:
Q13085
Molecular weight:
269997.01
References
  1. Bilder P, Lightle S, Bainbridge G, Ohren J, Finzel B, Sun F, Holley S, Al-Kassim L, Spessard C, Melnick M, Newcomer M, Waldrop GL: The structure of the carboxyltransferase component of acetyl-coA carboxylase reveals a zinc-binding motif unique to the bacterial enzyme. Biochemistry. 2006 Feb 14;45(6):1712-22. [PubMed:16460018 ]
  2. Brownsey RW, Boone AN, Elliott JE, Kulpa JE, Lee WM: Regulation of acetyl-CoA carboxylase. Biochem Soc Trans. 2006 Apr;34(Pt 2):223-7. [PubMed:16545081 ]
  3. Aoki H, Kimura K, Igarashi K, Takenaka A: Soy protein suppresses gene expression of acetyl-coA carboxylase alpha from promoter PI in rat liver. Biosci Biotechnol Biochem. 2006 Apr;70(4):843-9. [PubMed:16636450 ]
  4. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. [PubMed:16707089 ]
  5. Leonard E, Lim KH, Saw PN, Koffas MA: Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microbiol. 2007 Jun;73(12):3877-86. Epub 2007 Apr 27. [PubMed:17468269 ]
General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
PCCB
Uniprot ID:
P05166
Molecular weight:
58215.13
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. [PubMed:15623830 ]
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. [PubMed:9311592 ]
  5. Ishii M, Chuakrut S, Arai H, Igarashi Y: Occurrence, biochemistry and possible biotechnological application of the 3-hydroxypropionate cycle. Appl Microbiol Biotechnol. 2004 Jun;64(5):605-10. Epub 2004 Feb 28. [PubMed:14997352 ]
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PCCA
Uniprot ID:
P05165
Molecular weight:
80058.295
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Clavero S, Martinez MA, Perez B, Perez-Cerda C, Ugarte M, Desviat LR: Functional characterization of PCCA mutations causing propionic acidemia. Biochim Biophys Acta. 2002 Nov 20;1588(2):119-25. [PubMed:12385775 ]
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. [PubMed:9311592 ]
  5. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. [PubMed:15623830 ]
General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
MCCC2
Uniprot ID:
Q9HCC0
Molecular weight:
61332.65
References
  1. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. [PubMed:16707089 ]
  2. de Queiroz MS, Waldrop GL: Modeling and numerical simulation of biotin carboxylase kinetics: implications for half-sites reactivity. J Theor Biol. 2007 May 7;246(1):167-75. Epub 2006 Dec 28. [PubMed:17266990 ]
  3. Ludke A, Kramer R, Burkovski A, Schluesener D, Poetsch A: A proteomic study of Corynebacterium glutamicum AAA+ protease FtsH. BMC Microbiol. 2007 Jan 25;7:6. [PubMed:17254330 ]
  4. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. [PubMed:17659996 ]
General function:
Involved in biotin-[acetyl-CoA-carboxylase] ligase activity
Specific function:
Post-translational modification of specific protein by attachment of biotin. Acts on various carboxylases such as acetyl-CoA-carboxylase, pyruvate carboxylase, propionyl CoA carboxylase, and 3-methylcrotonyl CoA carboxylase.
Gene Name:
HLCS
Uniprot ID:
P50747
Molecular weight:
80759.345
Reactions
Adenosine triphosphate + Biotin + apo-[methylmalonyl-CoA:pyruvate carboxytransferase] → Adenosine monophosphate + Pyrophosphate + [methylmalonyl-CoA:pyruvate carboxytransferase]details
Adenosine triphosphate + Biotin + apo-[propionyl-CoA:carbon-dioxide ligase (ADP-forming)] → Adenosine monophosphate + Pyrophosphate + [propionyl-CoA:carbon-dioxide ligase (ADP-forming)]details
Adenosine triphosphate + Biotin + apo-[3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)] → Adenosine monophosphate + Pyrophosphate + [3-methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)]details
Adenosine triphosphate + Biotin + apo-[acetyl-CoA:carbon-dioxide ligase (ADP-forming)] → Adenosine monophosphate + Pyrophosphate + [acetyl-CoA:carbon-dioxide ligase (ADP-forming)]details
Adenosine triphosphate + Biotin → Pyrophosphate + Biotinyl-5'-AMPdetails
References
  1. Velazquez-Arellano A: From an inborn error patient to a search for regulatory meaning: a biotin conducted voyage. Mol Genet Metab. 2006 Mar;87(3):194-7. Epub 2005 Dec 15. [PubMed:16359899 ]
  2. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [PubMed:16772434 ]
  3. Camporeale G, Giordano E, Rendina R, Zempleni J, Eissenberg JC: Drosophila melanogaster holocarboxylase synthetase is a chromosomal protein required for normal histone biotinylation, gene transcription patterns, lifespan, and heat tolerance. J Nutr. 2006 Nov;136(11):2735-42. [PubMed:17056793 ]
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MCCC1
Uniprot ID:
Q96RQ3
Molecular weight:
80472.45
References
  1. Friebel D, von der Hagen M, Baumgartner ER, Fowler B, Hahn G, Feyh P, Heubner G, Baumgartner MR, Hoffmann GF: The first case of 3-methylcrotonyl-CoA carboxylase (MCC) deficiency responsive to biotin. Neuropediatrics. 2006 Apr;37(2):72-8. [PubMed:16773504 ]
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Catalytic release of biotin from biocytin, the product of biotin-dependent carboxylases degradation.
Gene Name:
BTD
Uniprot ID:
P43251
Molecular weight:
61132.43
Reactions
Biotin amide + Water → Biotin + Ammoniadetails
Biocytin + Water → Biotin + L-Lysinedetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Only showing the first 10 proteins. There are 12 proteins in total.