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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:51:52 UTC

Update Date

2021-09-26 22:52:39 UTC

HMDB ID

HMDB0244725

Secondary Accession Numbers

None

Metabolite Identification

Common Name

16-Mercaptohexadecanoic acid

Description

16-Mercaptohexadecanoic acid, also known as 16-mha CPD or 16-sulfanylhexadecanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Based on a literature review a significant number of articles have been published on 16-Mercaptohexadecanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 16-mercaptohexadecanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 16-Mercaptohexadecanoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0244725
     RDKit          3D
16-Mercaptohexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    8.4710   -1.5452    1.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0556   -0.7543    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8063   -0.4847   -0.5481 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -0.1002    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6996   -1.1057    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -0.5978    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112    0.5850   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016    1.2276   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    0.5939   -0.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -0.6119   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4198   -1.0545   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4923   -0.0379   -0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -0.6496   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433    0.2890   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2314    0.6456    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    1.5643    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945    1.0391    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2597   -0.1568    0.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2494   -1.6342    0.7950 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8204    0.3636   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6397    0.7875    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139    0.2141    1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -1.9984    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8355   -1.4826   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -0.4061    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585   -1.4601    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588    1.3815    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800    0.4093   -1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102    2.1976   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    1.6918    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138    0.4013   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    1.3847   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467   -0.4761    1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716   -1.5314   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.3364   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702   -1.9767   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    0.9479   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059    0.1054    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -1.5214   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -0.9960   -1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120   -0.1817   -1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    1.2549   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3508    1.2623    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2480   -0.2195    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5173    1.9076    1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325    2.4783    0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4622    1.8582    0.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6635    0.8644   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5748    0.0585    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2313   -0.3973    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0115   -2.7971    0.8647 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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
M  END


  Mrv1652309102123522D          

 19 18  0  0  0  0            999 V2000
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2336    5.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9480    6.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 S   0  0  0  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  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  2  0  0  0  0
  9 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244725

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCCCCCCCCCCCCCCS

> <INCHI_IDENTIFIER>
InChI=1S/C16H32O2S/c17-16(18)14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-19/h19H,1-15H2,(H,17,18)

> <INCHI_KEY>
INOAASCWQMFJQA-UHFFFAOYSA-N

> <FORMULA>
C16H32O2S

> <MOLECULAR_WEIGHT>
288.49

> <EXACT_MASS>
288.212301444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.60191950948961

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-sulfanylhexadecanoic acid

> <ALOGPS_LOGP>
6.77

> <JCHEM_LOGP>
6.071273557

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.200826388716463

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9520172062848555

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
85.0409

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.25e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-sulfanylhexadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244725
     RDKit          3D
16-Mercaptohexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    8.4710   -1.5452    1.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0556   -0.7543    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8063   -0.4847   -0.5481 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -0.1002    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6996   -1.1057    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -0.5978    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112    0.5850   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016    1.2276   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    0.5939   -0.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -0.6119   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4198   -1.0545   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4923   -0.0379   -0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -0.6496   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433    0.2890   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2314    0.6456    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    1.5643    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945    1.0391    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2597   -0.1568    0.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2494   -1.6342    0.7950 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8204    0.3636   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6397    0.7875    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139    0.2141    1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -1.9984    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8355   -1.4826   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -0.4061    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585   -1.4601    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588    1.3815    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800    0.4093   -1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102    2.1976   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    1.6918    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138    0.4013   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    1.3847   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467   -0.4761    1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716   -1.5314   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.3364   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702   -1.9767   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    0.9479   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059    0.1054    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -1.5214   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -0.9960   -1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120   -0.1817   -1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    1.2549   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3508    1.2623    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2480   -0.2195    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5173    1.9076    1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325    2.4783    0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4622    1.8582    0.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6635    0.8644   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5748    0.0585    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2313   -0.3973    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0115   -2.7971    0.8647 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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.504  10.106   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.836  10.106   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.503   9.336   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      14.836  11.646   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.840  10.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.842   9.336   0.000  0.00  0.00           C+0
HETATM   19  S   UNK     0      36.175  10.106   0.000  0.00  0.00           S+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0244725
HETATM    1  O1  UNL     1       8.471  -1.545   1.428  1.00  0.00           O  
HETATM    2  C1  UNL     1       8.056  -0.754   0.566  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.806  -0.485  -0.548  1.00  0.00           O  
HETATM    4  C2  UNL     1       6.741  -0.100   0.747  1.00  0.00           C  
HETATM    5  C3  UNL     1       5.700  -1.106   0.356  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.267  -0.598   0.503  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.011   0.585  -0.337  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.702   1.228  -0.293  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.449   0.594  -0.696  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.944  -0.612  -0.006  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.420  -1.054  -0.549  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.492  -0.038  -0.388  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.768  -0.650  -0.967  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.943   0.289  -0.868  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.231   0.646   0.581  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.410   1.564   0.665  1.00  0.00           C  
HETATM   17  C15 UNL     1      -6.694   1.039   0.150  1.00  0.00           C  
HETATM   18  C16 UNL     1      -7.260  -0.157   0.829  1.00  0.00           C  
HETATM   19  S1  UNL     1      -6.249  -1.634   0.795  1.00  0.00           S  
HETATM   20  H1  UNL     1       8.820   0.364  -1.074  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.640   0.788   0.076  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.614   0.214   1.810  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.753  -1.998   1.035  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.835  -1.483  -0.657  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.046  -0.406   1.566  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.659  -1.460   0.199  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.759   1.381   0.025  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.380   0.409  -1.393  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.810   2.198  -0.920  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.618   1.692   0.758  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.514   0.401  -1.830  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.616   1.385  -0.689  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.947  -0.476   1.080  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.572  -1.531  -0.218  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.247  -1.336  -1.599  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.670  -1.977  -0.006  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.311   0.948  -0.807  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.706   0.105   0.711  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.007  -1.521  -0.304  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.576  -0.996  -1.981  1.00  0.00           H  
HETATM   41  H22 UNL     1      -4.812  -0.182  -1.323  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.738   1.255  -1.392  1.00  0.00           H  
HETATM   43  H24 UNL     1      -3.351   1.262   0.930  1.00  0.00           H  
HETATM   44  H25 UNL     1      -4.248  -0.219   1.248  1.00  0.00           H  
HETATM   45  H26 UNL     1      -5.517   1.908   1.730  1.00  0.00           H  
HETATM   46  H27 UNL     1      -5.133   2.478   0.062  1.00  0.00           H  
HETATM   47  H28 UNL     1      -7.462   1.858   0.269  1.00  0.00           H  
HETATM   48  H29 UNL     1      -6.663   0.864  -0.951  1.00  0.00           H  
HETATM   49  H30 UNL     1      -7.575   0.059   1.879  1.00  0.00           H  
HETATM   50  H31 UNL     1      -8.231  -0.397   0.307  1.00  0.00           H  
HETATM   51  H32 UNL     1      -7.011  -2.797   0.865  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   47   48
CONECT   18   19   49   50
CONECT   19   51
END

HMDB0244725
     RDKit          3D
16-Mercaptohexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    8.4710   -1.5452    1.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0556   -0.7543    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8063   -0.4847   -0.5481 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7409   -0.1002    0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6996   -1.1057    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672   -0.5978    0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112    0.5850   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016    1.2276   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492    0.5939   -0.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -0.6119   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4198   -1.0545   -0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4923   -0.0379   -0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7683   -0.6496   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433    0.2890   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2314    0.6456    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4097    1.5643    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945    1.0391    0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2597   -0.1568    0.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2494   -1.6342    0.7950 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8204    0.3636   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6397    0.7875    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139    0.2141    1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532   -1.9984    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8355   -1.4826   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -0.4061    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585   -1.4601    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588    1.3815    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3800    0.4093   -1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102    2.1976   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6179    1.6918    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138    0.4013   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    1.3847   -0.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467   -0.4761    1.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716   -1.5314   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -1.3364   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702   -1.9767   -0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    0.9479   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7059    0.1054    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -1.5214   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756   -0.9960   -1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120   -0.1817   -1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    1.2549   -1.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3508    1.2623    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2480   -0.2195    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5173    1.9076    1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325    2.4783    0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4622    1.8582    0.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6635    0.8644   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5748    0.0585    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2313   -0.3973    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0115   -2.7971    0.8647 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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16-Mercaptohexadecanoate	Generator
16-Sulfanylhexadecanoate	HMDB
16-Sulphanylhexadecanoate	HMDB
16-Sulphanylhexadecanoic acid	HMDB
16-MHA CPD	HMDB

Chemical Formula

C₁₆H₃₂O₂S

Average Molecular Weight

288.49

Monoisotopic Molecular Weight

288.212301444

IUPAC Name

16-sulfanylhexadecanoic acid

Traditional Name

16-sulfanylhexadecanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCCCCCCCCCCCCCCS

InChI Identifier

InChI=1S/C16H32O2S/c17-16(18)14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-19/h19H,1-15H2,(H,17,18)

InChI Key

INOAASCWQMFJQA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Thia fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alkylthiol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.77	ALOGPS
logP	6.07	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	85.04 m³·mol⁻¹	ChemAxon
Polarizability	37.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	169.559	30932474
DeepCCS	[M-H]-	167.201	30932474
DeepCCS	[M-2H]-	202.125	30932474
DeepCCS	[M+Na]+	176.732	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.4	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.8	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	179.4	32859911
AllCCS	[M+HCOO]-	181.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	23.4866 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.19 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3412.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	692.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	253.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	377.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	570.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	968.8 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	1022.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	169.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2161.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	568.3 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	1845.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	803.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	801.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	645.9 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	18.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16-Mercaptohexadecanoic acid	OC(=O)CCCCCCCCCCCCCCCS	3415.0	Standard polar	33892256
16-Mercaptohexadecanoic acid	OC(=O)CCCCCCCCCCCCCCCS	2250.1	Standard non polar	33892256
16-Mercaptohexadecanoic acid	OC(=O)CCCCCCCCCCCCCCCS	2336.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16-Mercaptohexadecanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCS[Si](C)(C)C	2599.8	Semi standard non polar	33892256
16-Mercaptohexadecanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCS[Si](C)(C)C	2591.5	Standard non polar	33892256
16-Mercaptohexadecanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCS[Si](C)(C)C	2572.8	Standard polar	33892256
16-Mercaptohexadecanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCS[Si](C)(C)C(C)(C)C	3115.3	Semi standard non polar	33892256
16-Mercaptohexadecanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCS[Si](C)(C)C(C)(C)C	3002.8	Standard non polar	33892256
16-Mercaptohexadecanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCS[Si](C)(C)C(C)(C)C	2790.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Mercaptohexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-2950000000-eff30c43ca2c1ddb7704	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Mercaptohexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Mercaptohexadecanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Mercaptohexadecanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Mercaptohexadecanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16-Mercaptohexadecanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Mercaptohexadecanoic acid 10V, Positive-QTOF	splash10-0079-0190000000-750e0f57ed9794bea082	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Mercaptohexadecanoic acid 20V, Positive-QTOF	splash10-00di-9550000000-3106b3d24be535bf389c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Mercaptohexadecanoic acid 40V, Positive-QTOF	splash10-0a5d-9000000000-c941b1b4069184332275	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Mercaptohexadecanoic acid 10V, Negative-QTOF	splash10-000i-0090000000-be55d789826033db08e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Mercaptohexadecanoic acid 20V, Negative-QTOF	splash10-00kr-0090000000-1b282d5dfb4345f1e440	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16-Mercaptohexadecanoic acid 40V, Negative-QTOF	splash10-00kf-9540000000-1454e058224c4d3311d7	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2761790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3522585

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 16-Mercaptohexadecanoic acid (HMDB0244725)

MOL for HMDB0244725 (16-Mercaptohexadecanoic acid)

3D MOL for HMDB0244725 (16-Mercaptohexadecanoic acid)

3D SDF for HMDB0244725 (16-Mercaptohexadecanoic acid)

3D-SDF for HMDB0244725 (16-Mercaptohexadecanoic acid)

PDB for HMDB0244725 (16-Mercaptohexadecanoic acid)

3D PDB for HMDB0244725 (16-Mercaptohexadecanoic acid)

SMILES for HMDB0244725 (16-Mercaptohexadecanoic acid)

INCHI for HMDB0244725 (16-Mercaptohexadecanoic acid)

Structure for HMDB0244725 (16-Mercaptohexadecanoic acid)

3D Structure for HMDB0244725 (16-Mercaptohexadecanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra