NP-MRD: Showing NP-Card for Biotin (NP0001135)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:50 UTC

NP-MRD ID

NP0001135

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Biotin

Description

Biotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as vitamin H or B7 or coenzyme R. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the 'biotin cycle'. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: Those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. There are four biotin-dependent carboxylases in mammals: Those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: Cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various 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 signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; at least seven biotinylation sites have been identified in 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 signaling 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


  Mrv1652306242117433D          

 32 33  0  0  0  0            999 V2000
    4.2249    0.8332    0.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717    0.4975   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235    0.8735   -0.9481 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999   -0.2973   -0.9435 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1616   -0.5660    0.0215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0635   -1.3627   -0.6120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0688   -1.6410    0.3230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6987   -0.3848    0.8255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0856   -0.7634    1.9695 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866    0.4650    1.3173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3673    1.3311    0.4847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1744    1.7794   -0.6614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988    0.5879   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428    0.4591   -2.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -0.3675   -1.0205 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4039    0.4071   -0.2135 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6062    1.7489   -1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533    0.2875   -1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -1.2514   -1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7578    0.4477    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320   -1.0380    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -0.8866   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -2.3603   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793   -2.1597    1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7588   -2.3427   -0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    0.2432    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968   -0.0475    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    1.0195    2.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9088    2.1487    1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    2.7204   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -1.3616   -1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684    0.9810   -0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
  3 17  1  0  0  0  0
  4 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8 26  1  1  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  1  0  0  0
 12 30  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  6  0  0  0
M  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


  Mrv1652306242117433D          

 32 33  0  0  0  0            999 V2000
    4.2249    0.8332    0.9278 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3717    0.4975   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5235    0.8735   -0.9481 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2999   -0.2973   -0.9435 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1616   -0.5660    0.0215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0635   -1.3627   -0.6120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0688   -1.6410    0.3230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6987   -0.3848    0.8255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0856   -0.7634    1.9695 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866    0.4650    1.3173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3673    1.3311    0.4847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1744    1.7794   -0.6614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988    0.5879   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1428    0.4591   -2.3861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -0.3675   -1.0205 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4039    0.4071   -0.2135 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6062    1.7489   -1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533    0.2875   -1.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307   -1.2514   -1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7578    0.4477    0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320   -1.0380    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -0.8866   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141   -2.3603   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793   -2.1597    1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7588   -2.3427   -0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    0.2432    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968   -0.0475    0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212    1.0195    2.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9088    2.1487    1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    2.7204   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -1.3616   -1.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684    0.9810   -0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
  3 17  1  0  0  0  0
  4 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 20  1  0  0  0  0
  5 21  1  0  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8 26  1  1  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  1  0  0  0
 12 30  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0001135

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]1([H])SC([H])([H])[C@]2([H])N([H])C(=O)N([H])[C@]12[H]

> <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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0       4.225   0.833   0.928  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.372   0.498  -0.275  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.524   0.874  -0.948  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.300  -0.297  -0.944  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.162  -0.566   0.022  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.063  -1.363  -0.612  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.069  -1.641   0.323  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.699  -0.385   0.826  0.00  0.00           C+0
HETATM    9  S   UNK     0      -2.086  -0.763   1.970  0.00  0.00           S+0
HETATM   10  C   UNK     0      -3.287   0.465   1.317  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.367   1.331   0.485  0.00  0.00           C+0
HETATM   12  N   UNK     0      -3.174   1.779  -0.661  0.00  0.00           N+0
HETATM   13  C   UNK     0      -3.299   0.588  -1.462  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.143   0.459  -2.386  0.00  0.00           O+0
HETATM   15  N   UNK     0      -2.323  -0.368  -1.020  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.404   0.407  -0.214  0.00  0.00           C+0
HETATM   17  H   UNK     0       5.606   1.749  -1.458  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.953   0.288  -1.802  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.731  -1.251  -1.296  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.758   0.448   0.285  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.532  -1.038   0.948  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.747  -0.887  -1.555  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.514  -2.360  -0.891  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.379  -2.160   1.222  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.759  -2.343  -0.144  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.029   0.243   1.334  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.997  -0.048   0.670  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.721   1.020   2.158  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.909   2.149   1.024  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.547   2.720  -0.827  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.343  -1.362  -1.266  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.768   0.981  -0.882  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2   17                                                       
CONECT    4    2    5   18   19                                             
CONECT    5    4    6   20   21                                             
CONECT    6    5    7   22   23                                             
CONECT    7    6    8   24   25                                             
CONECT    8    7    9   16   26                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   27   28                                             
CONECT   11   10   12   16   29                                             
CONECT   12   11   13   30                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   31                                                  
CONECT   16   15    8   11   32                                             
CONECT   17    3                                                            
CONECT   18    4                                                            
CONECT   19    4                                                            
CONECT   20    5                                                            
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    7                                                            
CONECT   26    8                                                            
CONECT   27   10                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    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

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 Mass

244.3110 Da

Monoisotopic Mass

244.08816 Da

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]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]1([H])SC([H])([H])[C@]2([H])N([H])C(=O)N([H])[C@]12[H]

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	DTU Food
Abramis brama	FooDB	DTU Food
Acipenseridae	FooDB	DTU Food
Actinidia chinensis	FooDB	DTU Food
Agaricus bisporus	FooDB	DTU Food
Agave	FooDB	FooDB
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	DTU Food
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium schoenoprasum	FooDB	DTU Food
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	Wikipedia
Anacardium occidentale	FooDB	DTU Food
Ananas comosus	FooDB	DTU Food
Anarhichas lupus	FooDB	DTU Food
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	DTU Food
Angelica keiskei	FooDB	FooDB
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	DTU Food
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anthriscus cerefolium	FooDB	DTU Food
Apium graveolens	FooDB	DTU Food
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	DTU Food
Artemia salina	LOTUS Database	35616633
Artemisia dracunculus	FooDB	FooDB
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	DTU Food
Astacidea	FooDB	DTU Food
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Averrhoa carambola	FooDB	DTU Food
Basella alba	FooDB	FooDB
Belone belone	FooDB	DTU Food
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	DTU Food
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	DTU Food
Borago officinalis	FooDB	FooDB
Bos taurus	FooDB	DTU Food
Brachyura	FooDB	DTU Food
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	DTU Food
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	DTU Food
Brassica oleracea var. gongylodes	FooDB	DTU Food
Brassica oleracea var. italica	FooDB	DTU Food
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	DTU Food
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	DTU Food
Capparis spinosa	FooDB	FooDB
Capsicum annuum	FooDB	DTU Food
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	DTU Food
Caridea	FooDB	DTU Food
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	DTU Food
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Ceratonia siliqua	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	DTU Food
Cichorium endivia	FooDB	DTU Food
Cichorium intybus	FooDB	DTU Food
Cinnamomum	FooDB	DTU Food
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	DTU Food
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	DTU Food
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	DTU Food
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	DTU Food
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	DTU Food
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	DTU Food
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Colocasia esculenta	FooDB	FooDB
Columbidae	FooDB	DTU Food
Corchorus olitorius	FooDB	FooDB
Coregonus	FooDB	DTU Food
Coriandrum sativum L.	FooDB	DTU Food
Corylus	FooDB	DTU Food
Corylus avellana	FooDB	FooDB
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cucumis melo	FooDB	DTU Food
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	DTU Food
Cucurbita	FooDB	DTU Food
Cucurbita maxima	FooDB	CalorieSlism
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	DTU Food
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	DTU Food
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	DTU Food
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	DTU Food
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	DTU Food
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	DTU Food
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Engraulidae	FooDB	DTU Food
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	DTU Food
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	DTU Food
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	DTU Food
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	DTU Food
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gallus gallus	FooDB	DTU Food
Garcinia mangostana	FooDB	FooDB
Gastropoda	FooDB	DTU Food
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	DTU Food
Helianthus tuberosus	FooDB	DTU Food
Hibiscus sabbariffa	FooDB	FooDB
Hippoglossus hippoglossus	FooDB	DTU Food
Hippophae rhamnoides	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hyssopus officinalis L.	FooDB	FooDB
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	DTU Food
Juglans	FooDB	DTU Food
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	DTU Food
Juglans regia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	DG. Criossby. The Organic Constituents of Food. I. Lettuce. J. Food Sci. 1963, 28(3):347-355
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	DTU Food
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	DTU Food
Leporidae	FooDB	DTU Food
Lepus timidus	FooDB	DTU Food
Levisticum officinale	FooDB	FooDB
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	FooDB	DTU Food
Lipomyces starkeyi	LOTUS Database	35616633
Litchi chinensis	FooDB	DTU Food
Lota lota	FooDB	DTU Food
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Lysinibacillus sphaericus	LOTUS Database	35616633
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	DTU Food
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	DTU Food
Manihot esculenta	FooDB	DTU Food
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	KNApSAcK Database	22123792
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	FooDB
Mentha x piperita	FooDB	FooDB
Merlangius merlangus	FooDB	DTU Food
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Micromesistius poutassou	FooDB	DTU Food
Microstomus kitt	FooDB	DTU Food
Molva molva	FooDB	DTU Food
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	DTU Food
Mytilidae	FooDB	DTU Food
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nephelium lappaceum	FooDB	FooDB
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	FooDB
Octopus vulgaris	FooDB	DTU Food
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	DTU Food
Oncorhynchus mykiss	FooDB	DTU Food
Opuntia	FooDB	DTU Food
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	DTU Food
Ovis aries	FooDB	DTU Food
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Paraburkholderia phymatum	-	KNApSAcK
Passiflora edulis	FooDB	DTU Food
Pastinaca sativa	FooDB	DTU Food
Pediomelum esculentum	FooDB	FooDB
Perciformes	FooDB	DTU Food
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	DTU Food
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phoenix dactylifera	FooDB	DTU Food
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	DTU Food
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	DTU Food
Pistacia vera	FooDB	DTU Food
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Polygonum alpinum	FooDB	FooDB
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	DTU Food
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	DTU Food
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	DTU Food
Prunus dulcis	FooDB	DTU Food
Prunus persica	FooDB	DTU Food
Prunus persica var. nucipersica	FooDB	DTU Food
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	DTU Food
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	DTU Food
Pyrus communis	FooDB	DTU Food
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Ranidae	FooDB	DTU Food
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Raphanus sativus var. sativus	FooDB	FooDB
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	DTU Food
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	DTU Food
Ribes rubrum	FooDB	DTU Food
Ribes uva-crispa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rosa	FooDB	DTU Food
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	DTU Food
Rumex articus	FooDB	FooDB
Saccharina japonica	FooDB	DTU Food
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	DTU Food
Sechium edule	FooDB	DTU Food
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sesbania bispinosa	FooDB	FooDB
Siluriformes	FooDB	DTU Food
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	DTU Food
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum melongena	FooDB	DTU Food
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	DTU Food
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	DTU Food
Squalus acanthias	FooDB	DTU Food
Sus scrofa domestica	FooDB	DTU Food
Synechococcus elongatus	LOTUS Database	35616633
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	DTU Food
Taraxacum officinale	FooDB	DTU Food
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Thunnus	FooDB	DTU Food
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum durum	FooDB	DTU Food
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Typha angustifolia	FooDB	FooDB
Vaccinium	FooDB	DTU Food
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	DTU Food
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	DTU Food
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	DTU Food
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	DTU Food
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vitis	FooDB	DTU Food
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	DTU Food
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	232 °C	Not Available
Boiling Point	573.58 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.22 mg/mL at 25 °C	Not Available
LogP	0.861 (est)	The Good Scents Company Information System

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

External Links

HMDB ID

HMDB0000030

DrugBank ID

DB00121

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1068841

References

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 ]

Showing NP-Card for Biotin (NP0001135)

MOL for NP0001135 (Biotin)

3D MOL for NP0001135 (Biotin)

3D SDF for NP0001135 (Biotin)

3D-SDF for NP0001135 (Biotin)

PDB for NP0001135 (Biotin)

3D PDB for NP0001135 (Biotin)

SMILES for NP0001135 (Biotin)

INCHI for NP0001135 (Biotin)

Structure for NP0001135 (Biotin)

3D Structure for NP0001135 (Biotin)