MiMeDB: Showing metabocard for Biotin (MMDBc0000006)

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Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:13:29 UTC

Update Date

2024-04-30 19:30:51 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

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f76-1960000000-b21ddd69490cac3254f8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0f76-3960000000-a8a94e2de123f66979d8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f76-1960000000-b21ddd69490cac3254f8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f76-3960000000-a8a94e2de123f66979d8	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6910000000-11bfe0a5a77f7dfaa8c5	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9680000000-eb01d8147a82f7982b54	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0090000000-6d956bb533d353d449c9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0190000000-01f67d1bdf8c742e48c8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9400000000-107f2a44f521c2513578	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-1a3f65d909dc40055e87	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004i-0090000000-c928e8d0a18f3f848262	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-066s-1920000000-5f795e0b7f1d7cf986e5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0ar1-1920000000-c298be862857cb3bbc7f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000t-0900000000-cdc4a4c359ff765fd32d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05xs-1920000000-3be430b63e9c748c681a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0090000000-bcffb0dcf77e8fd727a4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f6x-0390000000-c209523d36e9a7681f44	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0090000000-c0f81ee86772310db415	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0190000000-016eb89528e564c74720	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9400000000-107f2a44f521c2513578	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d08e1b3709844e1e91b0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0190000000-21d0f2512788276bbb89	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udj-0690000000-dc372934024e58bdcc60	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0290000000-43932f104dea28cbdfb8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1960000000-d3673c6bc624b97f35be	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-00a4e152d89024a9b423	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1390000000-3f4b512cfa57b894ff94	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6y-7890000000-ea1e647fc5b31e42af0b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e139c928dcc46b225bdb	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01pt-9500000000-a1e1ec56cf32236ac6b1	2018-05-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

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 feces; Human ; Human vaginal secretion; Human mucosa; Human saliva; Human subgingival plaque; Goat feces; Sheep feces; Human stool; Human supragingival plaque; Human urine; Human sputum; 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 stool; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque; 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 stool; Human saliva; Human mucosa; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human supragingival plaque; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria	Verrucomicrobia	3	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	9	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	153	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	7	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		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		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Source Name	Data Source	Reference
	Not Available	Clupeinae (herring, sardine, sprat)	FooDB	DTU
	Not Available	Common dab	FooDB	DTU
	Not Available	Lemon sole	FooDB	DTU
	Not Available	Lingonberry	FooDB	DTU
Animal	Not Available	Atlantic halibut	FooDB	DTU
Animal	Not Available	Clawed lobster	FooDB	DTU
Animal	Not Available	Clupeinae (herring, sardine, sprat)	FooDB	DTU
Animal	Not Available	Flatfish	FooDB	DTU
Animal	Not Available	Garfish	FooDB	DTU
Animal	Not Available	Haddock	FooDB	DTU
Animal	Not Available	Lemon sole	FooDB	DTU
Animal	Not Available	Norway lobster	FooDB	DTU
Animal	Not Available	Oyster mushroom	FooDB	DTU
Animal	Not Available	Pleuronectidae (dab, halibut, plaice)	FooDB	DTU
Animal	Not Available	Salmonidae (salmon, trout)	FooDB	DTU
Animal	Not Available	Scombridae (bonito, mackerel, tuna)	FooDB	DTU
Animal	Not Available	Shrimp	FooDB	DTU
Animal	Not Available	Thunnus	FooDB	DTU
Animal	Filet	Scombridae (bonito, mackerel, tuna)	FooDB	DTU
Animal	Fillet	Gadus (common cod)	FooDB	DTU
Animal	Gizzard	Chicken	FooDB	DTU
Animal	Heart	Cow	FooDB	DTU
Animal	Heart	Pig	FooDB	DTU
Animal	Kidney	Cow	FooDB	DTU
Animal	Kidney	Pig	FooDB	DTU
Animal	Liver	Chicken	FooDB	DTU
Animal	Liver	Cow	FooDB	DTU
Animal	Liver	Pig	FooDB	DTU
Animal	Meat	Chicken	FooDB	DTU
Animal	Meat	Cow	FooDB	DTU
Animal	Meat	Mountain hare	FooDB	DTU
Animal	Meat	Pig	FooDB	DTU
Animal	Meat	Rabbit	FooDB	DTU
Animal	Meat	Sheep (mutton, lamb)	FooDB	DTU
Animal	Meat	Turkey	FooDB	DTU
Animal	Meat and skin	Anatidae	FooDB	DTU
Animal	Meat and skin	Chicken	FooDB	DTU
Animal	Meat and skin	Turkey	FooDB	DTU
Animal	Roe	Gadus (common cod)	FooDB	DTU
Animal	Thymus	Sheep (mutton, lamb)	FooDB	DTU
Animal	Tongue	Cow	FooDB	DTU
Animal	Tongue	Pig	FooDB	DTU
Plant	Not Available	Broccoli	FooDB	DTU
Plant	Not Available	Brussel sprouts	FooDB	DTU
Plant	Not Available	Cauliflower	FooDB	DTU
Plant	Not Available	Common cabbage	FooDB	DTU
Plant	Not Available	Common mushroom	FooDB	DTU
Plant	Not Available	Common wheat	FooDB	DUKE
Plant	Not Available	Corn	FooDB	DTU
Plant	Not Available	Cottonseed	FooDB	DUKE
Plant	Not Available	Dill	FooDB	DTU
Plant	Not Available	Garden cress	FooDB	DTU
Plant	Not Available	Gooseberry	FooDB	DTU
Plant	Not Available	Jerusalem artichoke	FooDB	DTU
Plant	Not Available	Oat	FooDB	DTU
Plant	Not Available	Potato	FooDB	DTU
Plant	Not Available	Rice	FooDB	DTU
Plant	Not Available	Sesame	FooDB	DUKE
Plant	Not Available	Swede	FooDB	DTU
Plant	Not Available	Sweet potato	FooDB	DTU
Plant	Not Available	Turnip	FooDB	DTU
Plant	Not Available	Wild celery	FooDB	DTU
Plant	Bean	Broad bean	FooDB	DUKE
Plant	Bean	Common bean	FooDB	DTU
Plant	Bean	Common pea	FooDB	DTU
Plant	Bean	Soy bean	FooDB	DTU
Plant	Bulb	Allium	FooDB	DTU
Plant	Bulb	Garlic	FooDB	DUKE
Plant	Flour	Common buckwheat	FooDB	DTU
Plant	Flour	Rice	FooDB	DTU
Plant	Flour	Rye	FooDB	DTU
Plant	Flour	Wheat	FooDB	DTU
Plant	Fruit	Apple	FooDB	DTU
Plant	Fruit	Apricot	FooDB	DTU
Plant	Fruit	Avocado	FooDB	DTU
Plant	Fruit	Black elderberry	FooDB	DUKE
Plant	Fruit	Blackcurrant	FooDB	DTU
Plant	Fruit	Coconut	FooDB	DTU
Plant	Fruit	Cucumber	FooDB	DTU
Plant	Fruit	Cucurbita	FooDB	DTU
Plant	Fruit	Elderberry	FooDB	DTU
Plant	Fruit	Fig	FooDB	DTU
Plant	Fruit	Garden tomato	FooDB	DTU
Plant	Fruit	Gooseberry	FooDB	DTU
Plant	Fruit	Grape	FooDB	DTU
Plant	Fruit	Grapefruit	FooDB	DTU
Plant	Fruit	Lemon	FooDB	DTU
Plant	Fruit	Mandarin orange (clementine, tangerine)	FooDB	DTU
Plant	Fruit	Peach	FooDB	DTU
Plant	Fruit	Pear	FooDB	DTU
Plant	Fruit	Pepper	FooDB	DTU
Plant	Fruit	Pineapple	FooDB	DTU
Plant	Fruit	Prunus (cherry, plum)	FooDB	DTU
Plant	Fruit	Redcurrant	FooDB	DTU
Plant	Fruit	Strawberry	FooDB	DTU
Plant	Fruit	Sweet orange	FooDB	DTU
Plant	Juice	Grapefruit	FooDB	DTU
Plant	Juice	Lemon	FooDB	DTU
Plant	Juice	Sweet orange	FooDB	DTU
Plant	Kernel	Corn	FooDB	DTU
Plant	Kernel	Rice	FooDB	DTU
Plant	Kernel	Rye	FooDB	DTU
Plant	Kernel	Wheat	FooDB	DTU
Plant	Leaves	Chervil	FooDB	DTU
Plant	Leaves	Chicory	FooDB	DTU
Plant	Leaves	Chives	FooDB	DTU
Plant	Leaves	Common cabbage	FooDB	DTU
Plant	Leaves	Lettuce	FooDB	DTU
Plant	Leaves	Parsley	FooDB	DTU
Plant	Leaves	Spinach	FooDB	DTU
Plant	Nut	Almond	FooDB	DTU
Plant	Nut	Black walnut	FooDB	DTU
Plant	Nut	Brazil nut	FooDB	DTU
Plant	Nut	Common walnut	FooDB	DUKE
Plant	Nut	Hazelnut	FooDB	DTU
Plant	Nut	Peanut	FooDB	DTU
Plant	Root	Carrots	FooDB	DTU
Plant	Root	Celery	FooDB	DTU
Plant	Root	Parsnip	FooDB	DTU
Plant	Seed	Barley	FooDB	DUKE
Plant	Seed	Lentils	FooDB	DUKE
Plant	Shoot	Asparagus	FooDB	DTU
Plant	Tuber	Chestnut	FooDB	DTU

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.08198		0.00033	0.421	uM	Not Specified	Not Specified	Acute lymphoblastic leukemia	HMDB	18996865
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000447	0.000217			uM	Not Specified	Not Specified	Dementia	HMDB	10577274
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000336	0.00008603			uM	Not Specified	Not Specified	Epilepsy	HMDB	10577274
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0229				uM	Not Specified	Not Specified	Head injury	HMDB	18996865
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000545		0.00004799	0.00192	uM	Not Specified	Not Specified	Motor neuron disease (MND)	HMDB	10577274
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000324	0.000107			uM	Not Specified	Not Specified	Multiple sclerosis	HMDB	10577274
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0005	0.0002			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	10701954
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.000557	0.000307			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	10577274
Human Blood	Detected and Quantified	0.00127	0.00067			uM	Adult (>18 years old)	Both	Normal	HMDB	1814646
Human Urine	Detected and Quantified	0.023		0.013	0.032	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	9022537
Human Urine	Detected and Quantified	0.049	0.035			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	1814646
Human Urine	Detected and Quantified	58.242	21.921			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	0.0016		0.0009	0.0028	uM	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 Blood	Detected and Quantified	0.0024		0.0008	0.0041	uM	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 Blood	Detected and Quantified	0.0034		0.002	0.0051	uM	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 Urine	Detected and Quantified	0.014		0.002	0.044	umol/mmol creatinine	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 Saliva	Detected and Quantified	0.123	0.141			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.296	0.150			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.071	0.041			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human Blood	Detected and Quantified			0.11	0.13	uM	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

References

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 ]
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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 ]
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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 ]
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Showing metabocard for Biotin (MMDBc0000006)

MOL for #<Metabolite:0x00007f53983e85a8>

3D MOL for #<Metabolite:0x00007f53983e85a8>

3D SDF for #<Metabolite:0x00007f53983e85a8>

3D-SDF for #<Metabolite:0x00007f53983e85a8>

PDB for #<Metabolite:0x00007f53983e85a8>

3D PDB for #<Metabolite:0x00007f53983e85a8>

SMILES for #<Metabolite:0x00007f53983e85a8>

INCHI for #<Metabolite:0x00007f53983e85a8>

Structure for #<Metabolite:0x00007f53983e85a8>

3D Structure for #<Metabolite:0x00007f53983e85a8>