MiMeDB: Showing metabocard for Biotin (MMDBc0000006)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:13:29 UTC

Update Date

2022-08-30 23:01:51 UTC

Metabolite ID

MMDBc0000006

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>
MMDBc0000006

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₀H₁₆N₂O₃S

Average Mass

244.311

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Nucleus

Biospecimen Locations

All Tissues
Blood
Cerebrospinal Fluid (CSF)
Feces
Prostate
Saliva
Urine

Tissue Locations

All Tissues
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191694	Acetyl-CoA carboxylase 2	Unknown	O00763	Homo_sapiens
MMDBp0191695	Pyruvate carboxylase, mitochondrial	Unknown	P11498	Homo_sapiens
MMDBp0191721	Acetyl-CoA carboxylase 1	Unknown	Q13085	Homo_sapiens
MMDBp0191928	Propionyl-CoA carboxylase beta chain, mitochondrial	Enzyme	P05166	Homo_sapiens
MMDBp0191929	Propionyl-CoA carboxylase alpha chain, mitochondrial	Enzyme	P05165	Homo_sapiens
MMDBp0192162	Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial	Enzyme	Q9HCC0	Homo_sapiens
MMDBp0192163	Biotin--protein ligase	Enzyme	P50747	Homo_sapiens
MMDBp0192164	Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial	Enzyme	Q96RQ3	Homo_sapiens
MMDBp0192193	Biotinidase	Enzyme	P43251	Homo_sapiens
MMDBp0193102	Cytochrome P450 1B1	Unknown	Q16678	Homo_sapiens
MMDBp0193609	Sodium-dependent multivitamin transporter	Unknown	Q9Y289	Homo_sapiens
MMDBp0196344	Putative uncharacterized protein DKFZp686B20267	Unknown	Q68D27	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Acylcarnitine (1‐{[1‐carboxylato‐3‐(trimethylammonio)propan‐2‐ yl]oxy}‐1‐oxoicosa‐5,7,11,14‐tetraen‐9‐yl)peroxy
Acylcarnitine (10E,12E,14E)-16-hydroxy-9-oxooctadeca-10,12,14-trienoylcarnitine
Acylcarnitine (10E,12E,14E)-9-hydroxy-16-oxooctadeca-10,12,14-trienoylcarnitine
Acylcarnitine (10E,12Z)-9-hydroxyoctadeca-10,12-dienoylcarnitine
Acylcarnitine (10E,13E)-Nonadeca-10,13-dienoylcarnitine

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

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

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Acute Lymphoblastic Leukemia	Association	Human Cerebrospinal Fluid (CSF)	HMDB	18996865
Dementia	Association	Human Cerebrospinal Fluid (CSF)	HMDB	10577274
Epilepsy	Association	Human Cerebrospinal Fluid (CSF)	HMDB	10577274
Motor neuron disease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	10577274
Multiple sclerosis	Association	Human Cerebrospinal Fluid (CSF)	HMDB	10577274
Eosinophilic esophagitis	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Fibrobacteres	1		Microbial culture
Eukaryota	Apicomplexa	1		Microbial culture
Bacteria	Firmicutes	740	Human ; Human feces; Human vaginal secretion; Goat feces; Sheep feces; Human pleural fluid plaque; Pig ; Cattle	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Spirochaetes	2	Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	244	Human feces; Human ; Human feces; pleural fluid plaque; bal; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Deinococcus-Thermus	1		Microbial culture
Bacteria	Actinobacteria	222	Human feces; Human ; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque	Microbial culture; Metabolic reconstruction
Bacteria	Verrucomicrobia	3	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	9	Human feces; Cattle ; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	153	Human feces; Human appendix biopsy; Human	Metabolic reconstruction
Bacteria	Synergistetes	7	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	36	Human feces; Human	Metabolic reconstruction
Bacteria	Candidatus Melainabacteria	2	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human	Detected and Quantified	0.08198		0.00033	0.421	Not Specified	Not Specified	Acute lymphoblastic leukemia	HMDB	18996865
Human	Detected and Quantified	0.000447	0.000217			Not Specified	Not Specified	Dementia	HMDB	10577274
Human	Detected and Quantified	0.000336	0.00008603			Not Specified	Not Specified	Epilepsy	HMDB	10577274
Human	Detected and Quantified	0.0229				Not Specified	Not Specified	Head injury	HMDB	18996865
Human	Detected and Quantified	0.000545		0.00004799	0.00192	Not Specified	Not Specified	Motor neuron disease (MND)	HMDB	10577274
Human	Detected and Quantified	0.000324	0.000107			Not Specified	Not Specified	Multiple sclerosis	HMDB	10577274
Human	Detected and Quantified	0.0005	0.0002			Adult (>18 years old)	Not Specified	Normal	HMDB	10701954
Human	Detected and Quantified	0.000557	0.000307			Adult (>18 years old)	Not Specified	Normal	HMDB	10577274
Human	Detected and Quantified	0.00127	0.00067			Adult (>18 years old)	Both	Normal	HMDB	1814646
Human	Detected and Quantified	0.023		0.013	0.032	Adult (>18 years old)	Both	Normal	HMDB	9022537
Human	Detected and Quantified	0.049	0.035			Adult (>18 years old)	Both	Normal	HMDB	1814646
Human	Detected and Quantified	58.242	21.921			Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified	0.0016		0.0009	0.0028	Children (1-13 years old)	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	0.0024		0.0008	0.0041	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	0.0034		0.002	0.0051	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	0.014		0.002	0.044	Children (1-13 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human	Detected and Quantified	0.123	0.141			Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human	Detected and Quantified	0.296	0.150			Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human	Detected and Quantified	0.071	0.041			Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human	Detected and Quantified			0.11	0.13	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human All Tissues	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000030

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

CMMC Knowledgebase

Not Available

General References

Thuy LP, Belmont J, Nyhan WL: Prenatal diagnosis and treatment of holocarboxylase synthetase deficiency. Prenat Diagn. 1999 Feb;19(2):108-12. doi: 10.1002/(sici)1097-0223(199902)19:2<108::aid-pd476>3.0.co;2-e. [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. doi: 10.1093/ajcn/65.2.508. [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. doi: 10.1046/j.1365-2559.1997.3020895.x. [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. doi: 10.1093/jn/127.5.710. [PubMed:9164991 ]
Thuy LP, Sweetman L, Nyhan WL: A new immunochemical assay for biotin. Clin Chim Acta. 1991 Oct 31;202(3):191-7. doi: 10.1016/0009-8981(91)90049-i. [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. doi: 10.1007/BF02505040. [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. doi: 10.1080/07315724.1997.10718682. [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. doi: 10.1021/bc060002u. [PubMed:16704206 ]
Mock DM: Biotin status: which are valid indicators and how do we know? J Nutr. 1999 Feb;129(2S Suppl):498S-503S. doi: 10.1093/jn/129.2.498S. [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. doi: 10.1212/wnl.49.5.1444. [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. doi: 10.1093/jn/131.8.2208. [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. doi: 10.1172/JCI13138. [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. doi: 10.1152/ajpendo.1997.272.1.E83. [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. doi: 10.1111/j.1346-8138.2005.tb00758.x. [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. doi: 10.1111/j.1530-0277.1993.tb00801.x. [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. doi: 10.1093/ajcn/65.4.951. [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. doi: 10.1046/j.1523-1747.2003.12058.x. [PubMed:12603856 ]
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 ]
Gravel RA, Narang MA: Molecular genetics of biotin metabolism: old vitamin, new science. J Nutr Biochem. 2005 Jul;16(7):428-31. doi: 10.1016/j.jnutbio.2005.03.020. [PubMed:15992684 ]
Zempleni J: Uptake, localization, and noncarboxylase roles of biotin. Annu Rev Nutr. 2005;25:175-96. doi: 10.1146/annurev.nutr.25.121304.131724. [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. doi: 10.1002/elps.200410070. [PubMed:15690449 ]

Showing metabocard for Biotin (MMDBc0000006)

MOL for #<Metabolite:0x00007f1240e4ce70>

3D MOL for #<Metabolite:0x00007f1240e4ce70>

3D SDF for #<Metabolite:0x00007f1240e4ce70>

3D-SDF for #<Metabolite:0x00007f1240e4ce70>

PDB for #<Metabolite:0x00007f1240e4ce70>

3D PDB for #<Metabolite:0x00007f1240e4ce70>

SMILES for #<Metabolite:0x00007f1240e4ce70>

INCHI for #<Metabolite:0x00007f1240e4ce70>

Structure for #<Metabolite:0x00007f1240e4ce70>

3D Structure for #<Metabolite:0x00007f1240e4ce70>