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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 00:50:12 UTC

Update Date

2021-09-14 15:41:33 UTC

HMDB ID

HMDB0003581

Secondary Accession Numbers

HMDB03581

Metabolite Identification

Common Name

Dethiobiotin

Description

Dethiobiotin belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a significant number of articles have been published on Dethiobiotin.

Structure

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

HMDB0003581
     RDKit          3D
Dethiobiotin
 33 33  0  0  0  0  0  0  0  0999 V2000
   -3.6392    1.3524   -0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3562    0.0165   -0.0738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5279    0.0013    1.3471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -1.1569    1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -1.8361    2.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -1.3773    0.8350 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -0.4721   -0.2823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9183    0.5965   -0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317   -0.0773   -0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    0.9784   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    0.4519   -0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -0.5948    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5678   -1.1310    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990   -1.9308   -0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213   -0.7902    1.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7757    1.2371   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8830    2.1102   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100    1.7049   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0622   -0.7314   -0.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0522    0.6698    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000   -2.0837    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -0.9917   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541    1.3740   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958    1.0734    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5683   -0.8753    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4480   -0.5174   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533    1.7701   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    1.4556    0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302    0.0495   -1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6030    1.2831   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1691   -0.1035    1.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5146   -1.4588    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888    0.0035    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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
  7  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END


  Mrv1652306242023492D          

 15 15  0  0  0  0            999 V2000
 9999.288710000.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.003310000.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.717710000.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.433110000.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7789 9999.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.146410000.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.452710000.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.861810000.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.577210000.8697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8618 9999.6321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.902110000.9510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.234710000.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4896 9999.6814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3146 9999.6814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.569510000.4660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15  1  1  6  0  0  0
 14  5  1  6  0  0  0
 12  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003581

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1NC(=O)N[C@@H]1CCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1

> <INCHI_KEY>
AUTOLBMXDDTRRT-JGVFFNPUSA-N

> <FORMULA>
C10H18N2O3

> <MOLECULAR_WEIGHT>
214.2615

> <EXACT_MASS>
214.131742452

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.15226202416082

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
0.7256986656666673

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.825802330845217

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.634655499494166

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7681297551220103

> <JCHEM_POLAR_SURFACE_AREA>
78.43

> <JCHEM_REFRACTIVITY>
54.398

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5S)-dethiobiotin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003581
     RDKit          3D
Dethiobiotin
 33 33  0  0  0  0  0  0  0  0999 V2000
   -3.6392    1.3524   -0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3562    0.0165   -0.0738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5279    0.0013    1.3471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -1.1569    1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -1.8361    2.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -1.3773    0.8350 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -0.4721   -0.2823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9183    0.5965   -0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317   -0.0773   -0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    0.9784   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    0.4519   -0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -0.5948    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5678   -1.1310    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990   -1.9308   -0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213   -0.7902    1.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7757    1.2371   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8830    2.1102   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100    1.7049   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0622   -0.7314   -0.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0522    0.6698    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000   -2.0837    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -0.9917   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541    1.3740   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958    1.0734    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5683   -0.8753    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4480   -0.5174   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533    1.7701   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    1.4556    0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302    0.0495   -1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6030    1.2831   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1691   -0.1035    1.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5146   -1.4588    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888    0.0035    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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
  7  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 24-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-20         0                                  
HETATM    1  C   UNK     0    8665.3398668.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.6738667.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.0068668.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.3428667.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8664.3878664.818   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.6738668.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8660.0458667.994   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8672.0098667.520   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8673.3448668.290   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8672.0098665.980   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8662.7518668.442   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    8661.5058667.537   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0    8661.9818666.072   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8663.5218666.072   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9968667.537   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5   14                                                            
CONECT    6    4    8                                                       
CONECT    7   12                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12   15                                                       
CONECT   12   11   13    7                                                  
CONECT   13   12   14                                                       
CONECT   14   15   13    5                                                  
CONECT   15   14   11    1                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0003581
HETATM    1  C1  UNL     1      -3.639   1.352  -0.703  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.356   0.017  -0.074  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.528   0.001   1.347  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.811  -1.157   1.797  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.064  -1.836   2.847  1.00  0.00           O  
HETATM    6  N2  UNL     1      -1.776  -1.377   0.835  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.969  -0.472  -0.282  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.918   0.596  -0.195  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.432  -0.077  -0.434  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.485   0.978  -0.352  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.879   0.452  -0.572  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.207  -0.595   0.477  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.568  -1.131   0.287  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.799  -1.931  -0.679  1.00  0.00           O  
HETATM   15  O3  UNL     1       5.621  -0.790   1.133  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.776   1.237  -1.782  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.883   2.110  -0.418  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.610   1.705  -0.293  1.00  0.00           H  
HETATM   19  H4  UNL     1      -4.062  -0.731  -0.521  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.052   0.670   1.948  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.000  -2.084   0.923  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.818  -0.992  -1.252  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.054   1.374  -0.954  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.896   1.073   0.794  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.568  -0.875   0.332  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.448  -0.517  -1.451  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.253   1.770  -1.100  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.447   1.456   0.645  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.030   0.049  -1.588  1.00  0.00           H  
HETATM   30  H15 UNL     1       3.603   1.283  -0.418  1.00  0.00           H  
HETATM   31  H16 UNL     1       3.169  -0.103   1.484  1.00  0.00           H  
HETATM   32  H17 UNL     1       2.515  -1.459   0.448  1.00  0.00           H  
HETATM   33  H18 UNL     1       6.189   0.004   0.938  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    7   19
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7   21
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   14   15
CONECT   15   33
END

HMDB0003581
     RDKit          3D
Dethiobiotin
 33 33  0  0  0  0  0  0  0  0999 V2000
   -3.6392    1.3524   -0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3562    0.0165   -0.0738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5279    0.0013    1.3471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -1.1569    1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0643   -1.8361    2.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -1.3773    0.8350 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -0.4721   -0.2823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9183    0.5965   -0.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317   -0.0773   -0.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    0.9784   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788    0.4519   -0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -0.5948    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5678   -1.1310    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7990   -1.9308   -0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213   -0.7902    1.1328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7757    1.2371   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8830    2.1102   -0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6100    1.7049   -0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0622   -0.7314   -0.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0522    0.6698    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000   -2.0837    0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -0.9917   -1.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541    1.3740   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958    1.0734    0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5683   -0.8753    0.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4480   -0.5174   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2533    1.7701   -1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    1.4556    0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302    0.0495   -1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6030    1.2831   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1691   -0.1035    1.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5146   -1.4588    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888    0.0035    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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
  7  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Dethiobiotin	ChEBI
(4R,5S)-5-Methyl-2-oxo-4-imidazolidinehexanoic acid	ChEBI
(4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoic acid	ChEBI
D-Dethiobiotin	ChEBI
Desthiobiotin	ChEBI
(4R,5S)-5-Methyl-2-oxo-4-imidazolidinehexanoate	Generator
(4R-cis)-5-Methyl-2-oxo-4-imidazolidinehexanoate	Generator
Desthiobiotin, (4R-cis)-isomer	MeSH
Desthiobiotin, (cis)-(+-)-isomer	MeSH
4-Methyl-5-(omega-carboxyamyl)imidazolidone-2	HMDB
4-Methyl-5-(ω-carboxyamyl)imidazolidone-2	HMDB
5-Methyl-2-oxo-4-imidazolidinecaproic acid	HMDB
Dethiobiotin	HMDB
epsilon-(4-Methyl-5-imidazolidone-2)caproic acid	HMDB
ε-(4-Methyl-5-imidazolidone-2)caproic acid	HMDB

Chemical Formula

C₁₀H₁₈N₂O₃

Average Molecular Weight

214.2615

Monoisotopic Molecular Weight

214.131742452

IUPAC Name

6-[(4R,5S)-5-methyl-2-oxoimidazolidin-4-yl]hexanoic acid

Traditional Name

(4R,5S)-dethiobiotin

CAS Registry Number

533-48-2

SMILES

C[C@@H]1NC(=O)N[C@@H]1CCCCCC(O)=O

InChI Identifier

InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1

InChI Key

AUTOLBMXDDTRRT-JGVFFNPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Imidazolidinone
Imidazolidine
Carbonic acid derivative
Urea
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dethiobiotin (CHEBI:42280 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0003581)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003581)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003581)

Source

Exogenous

Exogenous (HMDB: HMDB0003581)

Food

Food (HMDB: HMDB0003581)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Endogenous (HMDB: HMDB0003581)

Plant

Animal

Animal (HMDB: HMDB0003581)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003581)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003581)
Biotin Metabolism (PathBank: SMP0000785)

Lipid metabolism pathway (HMDB: HMDB0003581)

Cellular process

Cell signaling (HMDB: HMDB0003581)

Biochemical process

Lipid transport (HMDB: HMDB0003581)

Role

Biological role

Energy source (HMDB: HMDB0003581)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003581)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003581)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	157 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	144.136	30932474
[M+H]+	Not Available	144.26	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000453

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.27 g/L	ALOGPS
logP	0.72	ALOGPS
logP	0.73	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-1.8	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	6	ChemAxon
Refractivity	54.4 m³·mol⁻¹	ChemAxon
Polarizability	23.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.74	31661259
DarkChem	[M-H]-	148.896	31661259
DeepCCS	[M+H]+	149.554	30932474
DeepCCS	[M-H]-	147.158	30932474
DeepCCS	[M-2H]-	180.437	30932474
DeepCCS	[M+Na]+	155.519	30932474
AllCCS	[M+H]+	150.8	32859911
AllCCS	[M+H-H2O]+	147.1	32859911
AllCCS	[M+NH4]+	154.3	32859911
AllCCS	[M+Na]+	155.3	32859911
AllCCS	[M-H]-	152.0	32859911
AllCCS	[M+Na-2H]-	152.7	32859911
AllCCS	[M+HCOO]-	153.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.53 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6785 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.61 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	236.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	840.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	216.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	82.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	261.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	284.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	640.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	643.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	211.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	735.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	152.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	637.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	372.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	268.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dethiobiotin	C[C@@H]1NC(=O)N[C@@H]1CCCCCC(O)=O	3090.6	Standard polar	33892256
Dethiobiotin	C[C@@H]1NC(=O)N[C@@H]1CCCCCC(O)=O	2092.9	Standard non polar	33892256
Dethiobiotin	C[C@@H]1NC(=O)N[C@@H]1CCCCCC(O)=O	2204.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dethiobiotin,1TMS,isomer #1	C[C@@H]1NC(=O)N[C@@H]1CCCCCC(=O)O[Si](C)(C)C	2116.6	Semi standard non polar	33892256
Dethiobiotin,1TMS,isomer #2	C[C@H]1[C@@H](CCCCCC(=O)O)NC(=O)N1[Si](C)(C)C	2111.1	Semi standard non polar	33892256
Dethiobiotin,1TMS,isomer #3	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O	2106.2	Semi standard non polar	33892256
Dethiobiotin,2TMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)NC(=O)N1[Si](C)(C)C	2157.1	Semi standard non polar	33892256
Dethiobiotin,2TMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)NC(=O)N1[Si](C)(C)C	2130.6	Standard non polar	33892256
Dethiobiotin,2TMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)NC(=O)N1[Si](C)(C)C	3519.8	Standard polar	33892256
Dethiobiotin,2TMS,isomer #2	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C	2155.3	Semi standard non polar	33892256
Dethiobiotin,2TMS,isomer #2	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C	2129.6	Standard non polar	33892256
Dethiobiotin,2TMS,isomer #2	C[C@@H]1NC(=O)N([Si](C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C	3517.4	Standard polar	33892256
Dethiobiotin,2TMS,isomer #3	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	2002.2	Semi standard non polar	33892256
Dethiobiotin,2TMS,isomer #3	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	2085.1	Standard non polar	33892256
Dethiobiotin,2TMS,isomer #3	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	2685.8	Standard polar	33892256
Dethiobiotin,3TMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	2002.5	Semi standard non polar	33892256
Dethiobiotin,3TMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	2134.2	Standard non polar	33892256
Dethiobiotin,3TMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	2434.7	Standard polar	33892256
Dethiobiotin,1TBDMS,isomer #1	C[C@@H]1NC(=O)N[C@@H]1CCCCCC(=O)O[Si](C)(C)C(C)(C)C	2348.6	Semi standard non polar	33892256
Dethiobiotin,1TBDMS,isomer #2	C[C@H]1[C@@H](CCCCCC(=O)O)NC(=O)N1[Si](C)(C)C(C)(C)C	2349.6	Semi standard non polar	33892256
Dethiobiotin,1TBDMS,isomer #3	C[C@@H]1NC(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1CCCCCC(=O)O	2350.4	Semi standard non polar	33892256
Dethiobiotin,2TBDMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C(C)(C)C)NC(=O)N1[Si](C)(C)C(C)(C)C	2611.8	Semi standard non polar	33892256
Dethiobiotin,2TBDMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C(C)(C)C)NC(=O)N1[Si](C)(C)C(C)(C)C	2543.9	Standard non polar	33892256
Dethiobiotin,2TBDMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C(C)(C)C)NC(=O)N1[Si](C)(C)C(C)(C)C	3337.9	Standard polar	33892256
Dethiobiotin,2TBDMS,isomer #2	C[C@@H]1NC(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C(C)(C)C	2601.6	Semi standard non polar	33892256
Dethiobiotin,2TBDMS,isomer #2	C[C@@H]1NC(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C(C)(C)C	2538.6	Standard non polar	33892256
Dethiobiotin,2TBDMS,isomer #2	C[C@@H]1NC(=O)N([Si](C)(C)C(C)(C)C)[C@@H]1CCCCCC(=O)O[Si](C)(C)C(C)(C)C	3312.4	Standard polar	33892256
Dethiobiotin,2TBDMS,isomer #3	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2427.4	Semi standard non polar	33892256
Dethiobiotin,2TBDMS,isomer #3	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2562.9	Standard non polar	33892256
Dethiobiotin,2TBDMS,isomer #3	C[C@H]1[C@@H](CCCCCC(=O)O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2714.1	Standard polar	33892256
Dethiobiotin,3TBDMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2647.9	Semi standard non polar	33892256
Dethiobiotin,3TBDMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2762.6	Standard non polar	33892256
Dethiobiotin,3TBDMS,isomer #1	C[C@H]1[C@@H](CCCCCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2669.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Dethiobiotin GC-MS (3 TMS)	splash10-0006-3790100000-c94f58473d108e2927a3	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dethiobiotin GC-EI-TOF (Non-derivatized)	splash10-0006-1690000000-1bda89bfc3811fd0846b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Dethiobiotin GC-MS (Non-derivatized)	splash10-0006-3790100000-c94f58473d108e2927a3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dethiobiotin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9500000000-0f385ef69a9d53ba7904	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dethiobiotin GC-MS (1 TMS) - 70eV, Positive	splash10-00ba-9200000000-19b608dc5ef3430fb0b4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dethiobiotin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dethiobiotin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin LC-ESI-qTof , Positive-QTOF	splash10-056s-4910000000-2e5662744c4e67149ef8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin LC-ESI-QQ , positive-QTOF	splash10-004i-9200000000-03c3baa9836a6b78a20b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin LC-ESI-QQ , positive-QTOF	splash10-004i-9100000000-b90f330888cd6165f177	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin LC-ESI-QQ , positive-QTOF	splash10-056r-9000000000-7330a6fde54cd5afd3d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin LC-ESI-QQ , positive-QTOF	splash10-0a4i-9000000000-42126ce46ca1e187b36a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin LC-ESI-IT , positive-QTOF	splash10-0002-0900000000-2f9eaf52d9aa20dfeb5d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin , positive-QTOF	splash10-056s-4910000000-2e5662744c4e67149ef8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 35V, Positive-QTOF	splash10-0002-0900000000-d8e78a6d347413a0f682	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 10V, Positive-QTOF	splash10-0002-0910000000-b2dd4a92e38e38ef8a7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 40V, Positive-QTOF	splash10-066r-9000000000-b2eb519e2e0e5ad91911	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 20V, Positive-QTOF	splash10-002b-4900000000-cf863dd0f0baea9dbe85	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 20V, Negative-QTOF	splash10-0006-9210000000-a459410fa0babb81e6b9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 40V, Negative-QTOF	splash10-0006-9000000000-178bc9c95d917ad3ea55	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 10V, Negative-QTOF	splash10-03di-1190000000-d73931a407641bc332ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dethiobiotin 35V, Negative-QTOF	splash10-03di-0490000000-ae866fa9d32aecb5a67d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 10V, Positive-QTOF	splash10-00kb-0920000000-12242f12c8a3476fe52c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 20V, Positive-QTOF	splash10-014j-1910000000-bca8247f7dffe184f262	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 40V, Positive-QTOF	splash10-00kf-9100000000-a1befeec39f013c667cc	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 10V, Negative-QTOF	splash10-03di-0490000000-fbb5b60d4417d32465c9	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 20V, Negative-QTOF	splash10-0006-9520000000-9247557ea0c296d0d2ad	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 40V, Negative-QTOF	splash10-0006-9000000000-a9e635f12ade363f1ca8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 10V, Negative-QTOF	splash10-03di-1090000000-7406e098948885bf0fa7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 20V, Negative-QTOF	splash10-01ox-5930000000-26072ff1fff5e748d959	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 40V, Negative-QTOF	splash10-0006-9200000000-47fd1748a2d47287944d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dethiobiotin 10V, Positive-QTOF	splash10-014j-0980000000-f238d4cd8c859f72d3bc	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03775

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3351

PubChem Compound

445027

PDB ID

Not Available

ChEBI ID

42280

Food Biomarker Ontology

Not Available

VMH ID

DTBT

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kuzuhara, Hiroyoshi; Ohrui, Hiroshi; Emoto, Sakae. Syntheses with azido sugars. II. Conversion of D-glucose to (+)-dethiobiotin. Agricultural and Biological Chemistry (1971), 35(1), 8-17.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Rodriguez-Melendez R, Lewis B, McMahon RJ, Zempleni J: Diaminobiotin and desthiobiotin have biotin-like activities in Jurkat cells. J Nutr. 2003 May;133(5):1259-64. [PubMed:12730407 ]

Showing metabocard for Dethiobiotin (HMDB0003581)

MOL for HMDB0003581 (Dethiobiotin)

3D MOL for HMDB0003581 (Dethiobiotin)

3D SDF for HMDB0003581 (Dethiobiotin)

3D-SDF for HMDB0003581 (Dethiobiotin)

PDB for HMDB0003581 (Dethiobiotin)

3D PDB for HMDB0003581 (Dethiobiotin)

SMILES for HMDB0003581 (Dethiobiotin)

INCHI for HMDB0003581 (Dethiobiotin)

Structure for HMDB0003581 (Dethiobiotin)

3D Structure for HMDB0003581 (Dethiobiotin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra