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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (12) Show 12 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000030

Secondary Accession Numbers

HMDB00030

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 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000030
     RDKit          3D
Biotin
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.5260    1.0153   -1.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.0044   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3170    2.2164   -0.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582   -0.2628   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.0572    0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -1.1680    1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4203   -1.8425    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502   -1.1698   -0.4508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2127    0.3276   -1.3780 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186    1.0135   -1.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184   -0.0840   -0.7978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7041    0.5915    0.0447 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367    1.1338    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3431    2.0119    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    0.4975    1.1034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.6793    0.3065 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2398    3.0246   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7298   -0.9573    0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575   -0.7250   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    0.3863    1.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    0.9037    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -1.8536    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313   -0.8898    2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8070    0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -2.2137   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690   -1.8661   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    1.0902   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    1.9757   -0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1306   -0.8258   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    0.6418   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.9079    1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4311   -1.4545    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16  8  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  6
 12 30  1  0
 15 31  1  0
 16 32  1  1
M  END


  Mrv1652309032023502D          

 18 19  0  0  1  0            999 V2000
    0.4125   -1.2695    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4125   -1.2695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6674   -2.0541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675   -2.0541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -1.2695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -1.2695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3818   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -0.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398    0.7526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -0.4849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 18  1  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
 18  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  1  9  1  6  0  0  0
  2 10  1  6  0  0  0
 18 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000030

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C10H16N2O3S

> <MOLECULAR_WEIGHT>
244.311

> <EXACT_MASS>
244.088163078

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.919241786433474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
0.31942364800000006

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.546990539562877

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.4043165776835425

> <JCHEM_PKA_STRONGEST_BASIC>
-1.863639696129737

> <JCHEM_POLAR_SURFACE_AREA>
78.42999999999999

> <JCHEM_REFRACTIVITY>
60.0509

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000030
     RDKit          3D
Biotin
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.5260    1.0153   -1.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.0044   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3170    2.2164   -0.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582   -0.2628   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.0572    0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -1.1680    1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4203   -1.8425    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502   -1.1698   -0.4508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2127    0.3276   -1.3780 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186    1.0135   -1.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184   -0.0840   -0.7978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7041    0.5915    0.0447 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367    1.1338    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3431    2.0119    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    0.4975    1.1034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.6793    0.3065 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2398    3.0246   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7298   -0.9573    0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575   -0.7250   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    0.3863    1.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    0.9037    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -1.8536    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313   -0.8898    2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8070    0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -2.2137   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690   -1.8661   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    1.0902   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    1.9757   -0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1306   -0.8258   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    0.6418   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.9079    1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4311   -1.4545    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16  8  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  6
 12 30  1  0
 15 31  1  0
 16 32  1  1
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       0.770  -2.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -2.370   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.246  -3.834   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -1.246  -3.834   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       0.000  -4.740   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000  -6.280   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0       2.310  -2.370   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0      -2.310  -2.370   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       2.579  -0.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.913  -0.905   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.247  -0.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.581  -0.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.914  -0.135   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.248  -0.905   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.914   1.405   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.246  -0.905   0.000  0.00  0.00           C+0
CONECT    1    2   18    3    9                                             
CONECT    2    1    4    5   10                                             
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    2    6                                                       
CONECT    6   18    5                                                       
CONECT    7    3    8    4                                                  
CONECT    8    7                                                            
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11   18   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1    6   11                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0000030
HETATM    1  O1  UNL     1       4.526   1.015  -1.531  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.626   1.004  -0.633  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.317   2.216  -0.051  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.958  -0.263  -0.251  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.952   0.057   0.827  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.200  -1.168   1.295  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.420  -1.842   0.248  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.650  -1.170  -0.451  1.00  0.00           C  
HETATM    9  S1  UNL     1      -0.213   0.328  -1.378  1.00  0.00           S  
HETATM   10  C7  UNL     1      -1.919   1.013  -1.460  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.718  -0.084  -0.798  1.00  0.00           C  
HETATM   12  N1  UNL     1      -3.704   0.592   0.045  1.00  0.00           N  
HETATM   13  C9  UNL     1      -2.937   1.134   1.115  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.343   2.012   1.916  1.00  0.00           O  
HETATM   15  N2  UNL     1      -1.638   0.497   1.103  1.00  0.00           N  
HETATM   16  C10 UNL     1      -1.827  -0.679   0.307  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.240   3.025  -0.657  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.730  -0.957   0.146  1.00  0.00           H  
HETATM   19  H3  UNL     1       2.558  -0.725  -1.148  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.573   0.386   1.711  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.329   0.904   0.551  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.008  -1.854   1.697  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.631  -0.890   2.205  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.027  -2.807   0.684  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.157  -2.214  -0.528  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.069  -1.866  -1.244  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.146   1.090  -2.543  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.975   1.976  -0.949  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.131  -0.826  -1.462  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.727   0.642  -0.133  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.825   0.908   1.605  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.431  -1.455   0.786  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9   16   26
CONECT    9   10
CONECT   10   11   27   28
CONECT   11   12   16   29
CONECT   12   13   30
CONECT   13   14   14   15
CONECT   15   16   31
CONECT   16   32
END

HMDB0000030
     RDKit          3D
Biotin
 32 33  0  0  0  0  0  0  0  0999 V2000
    4.5260    1.0153   -1.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.0044   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3170    2.2164   -0.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9582   -0.2628   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.0572    0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -1.1680    1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4203   -1.8425    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502   -1.1698   -0.4508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2127    0.3276   -1.3780 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186    1.0135   -1.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7184   -0.0840   -0.7978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7041    0.5915    0.0447 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367    1.1338    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3431    2.0119    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    0.4975    1.1034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.6793    0.3065 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2398    3.0246   -0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7298   -0.9573    0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575   -0.7250   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5727    0.3863    1.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    0.9037    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083   -1.8536    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313   -0.8898    2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0272   -2.8070    0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -2.2137   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690   -1.8661   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    1.0902   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747    1.9757   -0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1306   -0.8258   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    0.6418   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.9079    1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4311   -1.4545    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16  8  1  0
 16 11  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  6
 12 30  1  0
 15 31  1  0
 16 32  1  1
M  END

View in JSmol View Stereo Labels

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
Bioepiderm	Kegg
(+)-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
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	HMDB
Biotin roche brand	HMDB
Biotin simons brand	HMDB
Biotin strathmann brand	HMDB
Biotin ziethen brand	HMDB
Biotin ratiopharm	HMDB
Roche brand OF biotin	HMDB
Roche, biotine	HMDB
E+b pharma brand OF biotin	HMDB
Medobiotin	HMDB
Biokur	HMDB
Biotinratiopharm	HMDB
Gelfert, biotin	HMDB
Hermes brand OF biotin	HMDB
Hermes, biotin	HMDB
Medopharm brand OF biotin	HMDB
Ratiopharm brand OF biotin	HMDB
Biocur brand OF biotin	HMDB
Biotin dermapharm brand	HMDB
Biotine roche	HMDB
Deacura	HMDB
Dermapharm brand OF biotin	HMDB
Gabunat	HMDB
Medebiotin	HMDB
Rombellin	HMDB
Ziethen brand OF biotin	HMDB
Biotin biocur brand	HMDB
Biotin gelfert	HMDB
Biotin hermes	HMDB
Biotin medopharm brand	HMDB
Biotin ratiopharm brand	HMDB
Biotin-ratiopharm	HMDB
H, Vitamin	HMDB
Medea brand OF biotin sodium salt	HMDB
Simons brand OF biotin	HMDB
Strathmann brand OF biotin	HMDB

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]imidazol-4-yl]pentanoic acid

Traditional Name

5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid

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

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

biotins (CHEBI:15956 )
Water-soluble vitamins (C00120 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	232 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.22 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	156.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000313
[M+H]+	Not Available	151.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000313

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	0.17	ALOGPS
logP	0.32	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	60.05 m³·mol⁻¹	ChemAxon
Polarizability	24.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.455	31661259
DarkChem	[M-H]-	153.682	31661259
AllCCS	[M+H]+	154.571	32859911
AllCCS	[M-H]-	158.737	32859911
DeepCCS	[M-2H]-	189.082	30932474
DeepCCS	[M+Na]+	164.497	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	151.1	32859911
AllCCS	[M+NH4]+	157.8	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	159.0	32859911
AllCCS	[M+HCOO]-	159.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Biotin	[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2	3865.4	Standard polar	33892256
Biotin	[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2	2275.7	Standard non polar	33892256
Biotin	[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2	2588.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Biotin,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12	2520.5	Semi standard non polar	33892256
Biotin,1TMS,isomer #2	C[Si](C)(C)N1C(=O)N[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]21	2546.8	Semi standard non polar	33892256
Biotin,1TMS,isomer #3	C[Si](C)(C)N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21	2539.2	Semi standard non polar	33892256
Biotin,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C	2580.1	Semi standard non polar	33892256
Biotin,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C	2306.2	Standard non polar	33892256
Biotin,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2[Si](C)(C)C	4188.6	Standard polar	33892256
Biotin,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]12	2568.5	Semi standard non polar	33892256
Biotin,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]12	2298.2	Standard non polar	33892256
Biotin,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N([Si](C)(C)C)[C@H]12	4247.6	Standard polar	33892256
Biotin,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]21	2481.3	Semi standard non polar	33892256
Biotin,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]21	2311.0	Standard non polar	33892256
Biotin,2TMS,isomer #3	C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]21	3326.8	Standard polar	33892256
Biotin,3TMS,isomer #1	C[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)C	2459.9	Semi standard non polar	33892256
Biotin,3TMS,isomer #1	C[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)C	2378.7	Standard non polar	33892256
Biotin,3TMS,isomer #1	C[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)C	2983.0	Standard polar	33892256
Biotin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12	2759.9	Semi standard non polar	33892256
Biotin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)N[C@H]2CS[C@@H](CCCCC(=O)O)[C@H]21	2768.2	Semi standard non polar	33892256
Biotin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21	2758.9	Semi standard non polar	33892256
Biotin,2TBDMS,isomer #1	CC(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)C	3055.6	Semi standard non polar	33892256
Biotin,2TBDMS,isomer #1	CC(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)C	2787.2	Standard non polar	33892256
Biotin,2TBDMS,isomer #1	CC(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)C	3987.0	Standard polar	33892256
Biotin,2TBDMS,isomer #2	CC(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]12	3049.0	Semi standard non polar	33892256
Biotin,2TBDMS,isomer #2	CC(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]12	2779.6	Standard non polar	33892256
Biotin,2TBDMS,isomer #2	CC(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]12	4008.6	Standard polar	33892256
Biotin,2TBDMS,isomer #3	CC(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]21	2897.2	Semi standard non polar	33892256
Biotin,2TBDMS,isomer #3	CC(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]21	2819.9	Standard non polar	33892256
Biotin,2TBDMS,isomer #3	CC(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]21	3231.0	Standard polar	33892256
Biotin,3TBDMS,isomer #1	CC(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)C	3112.9	Semi standard non polar	33892256
Biotin,3TBDMS,isomer #1	CC(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)C	3053.8	Standard non polar	33892256
Biotin,3TBDMS,isomer #1	CC(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)C	3092.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Biotin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f76-1960000000-b21ddd69490cac3254f8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Biotin GC-MS (3 TMS)	splash10-0f76-3960000000-a8a94e2de123f66979d8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Biotin GC-EI-TOF (Non-derivatized)	splash10-0f76-1960000000-b21ddd69490cac3254f8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Biotin GC-MS (Non-derivatized)	splash10-0f76-3960000000-a8a94e2de123f66979d8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6910000000-11bfe0a5a77f7dfaa8c5	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9680000000-eb01d8147a82f7982b54	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biotin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01pt-9500000000-a1e1ec56cf32236ac6b1	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0006-0090000000-6d956bb533d353d449c9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0006-0190000000-01f67d1bdf8c742e48c8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0006-9400000000-107f2a44f521c2513578	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0006-9000000000-1a3f65d909dc40055e87	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-004i-0090000000-c928e8d0a18f3f848262	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-066s-1920000000-5f795e0b7f1d7cf986e5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0ar1-1920000000-c298be862857cb3bbc7f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-000t-0900000000-cdc4a4c359ff765fd32d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-qTof , Positive-QTOF	splash10-05xs-1920000000-3be430b63e9c748c681a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QTOF , negative-QTOF	splash10-0006-0090000000-bcffb0dcf77e8fd727a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QTOF , negative-QTOF	splash10-0f6x-0390000000-c209523d36e9a7681f44	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOF	splash10-0006-0090000000-c0f81ee86772310db415	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOF	splash10-0006-0190000000-016eb89528e564c74720	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOF	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOF	splash10-0006-9400000000-107f2a44f521c2513578	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-QQ , negative-QTOF	splash10-0006-9000000000-d08e1b3709844e1e91b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin LC-ESI-ITFT , negative-QTOF	splash10-0006-0190000000-21d0f2512788276bbb89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biotin Linear Ion Trap , negative-QTOF	splash10-0udj-0690000000-dc372934024e58bdcc60	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin 10V, Positive-QTOF	splash10-002b-0290000000-43932f104dea28cbdfb8	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin 20V, Positive-QTOF	splash10-0002-1960000000-d3673c6bc624b97f35be	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin 40V, Positive-QTOF	splash10-052f-9600000000-00a4e152d89024a9b423	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin 10V, Negative-QTOF	splash10-0006-1390000000-3f4b512cfa57b894ff94	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin 20V, Negative-QTOF	splash10-0f6y-7890000000-ea1e647fc5b31e42af0b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biotin 40V, Negative-QTOF	splash10-0006-9100000000-e139c928dcc46b225bdb	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Nucleus

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

All Tissues
Prostate

Pathways

Name	SMPDB/PathBank	KEGG
Biotin Metabolism
Alanine, aspartate and glutamate metabolism	Not Available
Primary Hyperoxaluria Type I		Not Available
Pyruvate Carboxylase Deficiency		Not Available
Lactic Acidemia		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0034 (0.002 - 0.0051) uM	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.0016 (0.0009 - 0.0028) uM	Children (1-13 years old)	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.0024 (0.0008 - 0.0041) uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.11-0.13 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.00127 +/- 0.00067 uM	Adult (>18 years old)	Both	Normal	1814646	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000557 +/- 0.000307 uM	Adult (>18 years old)	Not Specified	Normal	10577274	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0005 +/- 0.0002 uM	Adult (>18 years old)	Not Specified	Normal	10701954	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	0.123 +/- 0.141 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.071 +/- 0.041 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	0.296 +/- 0.150 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	0.014 (0.002-0.044) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.049 +/- 0.035 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	1814646	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.023 (0.013-0.032) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9022537	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.08198 (0.00033-0.421) uM	Not Specified	Not Specified	Acute lymphoblastic leukemia	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.16 uM	Not Specified	Not Specified	Bronchopulmonary dysplasia	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00039 uM	Not Specified	Not Specified	Burkitt's lymphoma	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000447 +/- 0.000217 uM	Not Specified	Not Specified	Dementia	10577274	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000336 +/- 0.00008603 uM	Not Specified	Not Specified	Epilepsy	10577274	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0229 uM	Not Specified	Not Specified	Head injury	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0273 (0.0247-0.0299) uM	Not Specified	Not Specified	Lymphoblastic lymphoma	18996865	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000545 (0.00004799-0.00192) uM	Not Specified	Not Specified	Motor neuron disease (MND)	10577274	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000324 +/- 0.000107 uM	Not Specified	Not Specified	Multiple sclerosis	10577274	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000692 +/- 0.000602 uM	Not Specified	Not Specified	Polyneuropathy	10577274	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000438 +/- 0.000156 uM	Not Specified	Not Specified	Vascular encephalopathies	10577274	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	58.242 +/- 21.921 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Acute Lymphoblastic Leukemia
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
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
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
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
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
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
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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

167320 (Dementia)
126200 (Multiple sclerosis)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB00121

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15956

Food Biomarker Ontology

Not Available

VMH ID

BTN

MarkerDB ID

MDB00000015

Good Scents ID

Not Available

References

Synthesis Reference

Corey, 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

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 ]
Thuy LP, Belmont J, Nyhan WL: Prenatal diagnosis and treatment of holocarboxylase synthetase deficiency. Prenat Diagn. 1999 Feb;19(2):108-12. [PubMed:10215065 ]
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 ]
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 ]
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 ]
Thuy LP, Sweetman L, Nyhan WL: A new immunochemical assay for biotin. Clin Chim Acta. 1991 Oct 31;202(3):191-7. [PubMed:1814646 ]
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 ]
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 ]
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 ]
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 ]
Mock DM: Biotin status: which are valid indicators and how do we know? J Nutr. 1999 Feb;129(2S Suppl):498S-503S. [PubMed:10064317 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Gravel RA, Narang MA: Molecular genetics of biotin metabolism: old vitamin, new science. J Nutr Biochem. 2005 Jul;16(7):428-31. [PubMed:15992684 ]
Zempleni J: Uptake, localization, and noncarboxylase roles of biotin. Annu Rev Nutr. 2005;25:175-96. [PubMed:16011464 ]
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.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Acetyl-CoA carboxylase 2

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

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 ]

Enzyme Details

2. Pyruvate carboxylase, mitochondrial

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

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 ]
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 ]
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 ]
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 ]
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 ]

Enzyme Details

3. Acetyl-CoA carboxylase 1

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

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 ]
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 ]
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 ]
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 ]
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 ]

Enzyme Details

4. Propionyl-CoA carboxylase beta chain, mitochondrial

General function:: Involved in ligase activity
Specific function:: Not Available
Gene Name:: PCCB
Uniprot ID:: P05166
Molecular weight:: 58215.13

References

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 ]
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 ]
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 ]
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 ]
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 ]

Enzyme Details

5. Propionyl-CoA carboxylase alpha chain, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: PCCA
Uniprot ID:: P05165
Molecular weight:: 80058.295

References

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 ]
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 ]
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 ]
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 ]
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 ]

Enzyme Details

6. Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial

General function:: Involved in ligase activity
Specific function:: Not Available
Gene Name:: MCCC2
Uniprot ID:: Q9HCC0
Molecular weight:: 61332.65

References

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 ]
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 ]
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 ]
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 ]

Enzyme Details

7. Biotin--protein ligase

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'-AMP	details

References

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 ]
Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [PubMed:16772434 ]
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 ]

Enzyme Details

8. Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: MCCC1
Uniprot ID:: Q96RQ3
Molecular weight:: 80472.45

References

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 ]

Enzyme Details

9. Biotinidase

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 + Ammonia	details
Biocytin + Water → Biotin + L-Lysine	details

Enzyme Details

10. Cytochrome P450 1B1

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

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.

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Showing metabocard for Biotin (HMDB0000030)

MOL for HMDB0000030 (Biotin)

3D MOL for HMDB0000030 (Biotin)

3D SDF for HMDB0000030 (Biotin)

3D-SDF for HMDB0000030 (Biotin)

PDB for HMDB0000030 (Biotin)

3D PDB for HMDB0000030 (Biotin)

SMILES for HMDB0000030 (Biotin)

INCHI for HMDB0000030 (Biotin)

Structure for HMDB0000030 (Biotin)

3D Structure for HMDB0000030 (Biotin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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