MiMeDB: Showing metabocard for Hexadecanedioic acid (MMDBc0009404)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:55:35 UTC

Update Date

2024-04-30 19:34:16 UTC

Metabolite ID

MMDBc0009404

Metabolite Identification

Common Name

Hexadecanedioic acid

Description

Hexadecanedioic acid, also known as thapsic acid, 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. Hexadecanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in the liver (PMID: 4372285 ). It has antitumor activity (PMID: 14987827 ).

Structure

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

HMDB0000672
     RDKit          3D
Hexadecanedioic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
    7.2092   -0.0386    1.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1956   -0.5604    1.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -1.4976    2.8972 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453   -0.1479    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    0.8552    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9939    1.5022   -0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    0.7021   -1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.3846   -0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4325   -0.0095    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.0134    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4435    0.5116   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -0.7590   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019   -0.5532    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    0.5171    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.1657   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5974   -1.1185   -0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4665   -1.1516    0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793   -0.1810    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7274    0.5563   -0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4703   -0.0458    1.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7112   -2.3978    2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -1.0598    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3021    0.3642    2.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810    0.4518   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.6935    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982    2.3814   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    2.1210    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280    0.1868   -2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    1.3480   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -0.8047   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -1.2558   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.9291    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    0.3562    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013    1.9885   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086    1.3103    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    0.3572   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1933    1.2972   -1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -1.5810   -0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.1219   -1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3532   -0.2395    1.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798   -1.5215    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5152    1.5096    0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.6734    1.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5957    1.0049   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988    0.0398   -1.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419   -1.3151   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8483   -1.9320   -0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9242   -2.1680    0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -1.0025    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8357    0.8692    1.7900 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  2  0
 18 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END


  Mrv1652309042000052D          

 20 19  0  0  0  0            999 V2000
10009.534410005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.249710005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.963010005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.678410005.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.963010004.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.819010005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.105710005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.390410005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.675010005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.961810005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.246810005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.532310005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.817510005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.103010005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.388510005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.674010005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.959210005.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.242610005.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.528110005.3826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.242610006.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  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  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
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009404

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CCCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)

> <INCHI_KEY>
QQHJDPROMQRDLA-UHFFFAOYSA-N

> <FORMULA>
C16H30O4

> <MOLECULAR_WEIGHT>
286.407

> <EXACT_MASS>
286.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.370636137216245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
hexadecanedioic acid

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
4.9363410126666665

> <ALOGPS_LOGS>
-4.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.253049650892543

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650989659564581

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
78.74899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexadecanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000672
     RDKit          3D
Hexadecanedioic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
    7.2092   -0.0386    1.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1956   -0.5604    1.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -1.4976    2.8972 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453   -0.1479    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    0.8552    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9939    1.5022   -0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    0.7021   -1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.3846   -0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4325   -0.0095    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.0134    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4435    0.5116   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -0.7590   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019   -0.5532    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    0.5171    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.1657   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5974   -1.1185   -0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4665   -1.1516    0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793   -0.1810    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7274    0.5563   -0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4703   -0.0458    1.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7112   -2.3978    2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -1.0598    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3021    0.3642    2.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810    0.4518   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.6935    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982    2.3814   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    2.1210    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280    0.1868   -2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    1.3480   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -0.8047   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -1.2558   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.9291    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    0.3562    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013    1.9885   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086    1.3103    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    0.3572   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1933    1.2972   -1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -1.5810   -0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.1219   -1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3532   -0.2395    1.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798   -1.5215    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5152    1.5096    0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.6734    1.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5957    1.0049   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988    0.0398   -1.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419   -1.3151   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8483   -1.9320   -0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9242   -2.1680    0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -1.0025    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8357    0.8692    1.7900 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  2  0
 18 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8684.4648676.714   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8685.7998677.483   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8687.1318676.714   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8688.4668677.483   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8687.1318675.174   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8683.1298677.483   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8681.7978676.714   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8680.4628677.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8679.1278676.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8677.7958677.483   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8676.4618676.714   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8675.1278677.483   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8673.7938676.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8672.4598677.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.1258676.714   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.7918677.483   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.4578676.714   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.1208677.483   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8665.7868676.714   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8667.1208679.022   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   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   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0000672
HETATM    1  O1  UNL     1       7.209  -0.039   1.427  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.196  -0.560   1.899  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.251  -1.498   2.897  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.845  -0.148   1.353  1.00  0.00           C  
HETATM    5  C3  UNL     1       5.086   0.855   0.310  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.994   1.502  -0.414  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.138   0.702  -1.283  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.351  -0.385  -0.684  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.432  -0.009   0.430  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.403   1.013   0.037  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.444   0.512  -1.086  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.137  -0.759  -0.711  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.002  -0.553   0.489  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.012   0.517   0.238  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.891   0.166  -0.928  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.597  -1.118  -0.664  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.467  -1.152   0.545  1.00  0.00           C  
HETATM   18  C16 UNL     1      -6.579  -0.181   0.538  1.00  0.00           C  
HETATM   19  O3  UNL     1      -6.727   0.556  -0.463  1.00  0.00           O  
HETATM   20  O4  UNL     1      -7.470  -0.046   1.589  1.00  0.00           O  
HETATM   21  H1  UNL     1       6.711  -2.398   2.736  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.317  -1.060   1.135  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.302   0.364   2.196  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.881   0.452  -0.411  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.682   1.693   0.810  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.398   2.381  -1.056  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.356   2.121   0.338  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.828   0.187  -2.051  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.516   1.348  -1.984  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.669  -0.805  -1.520  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.955  -1.256  -0.442  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.936  -0.929   0.802  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.006   0.356   1.331  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.901   1.988  -0.246  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.209   1.310   0.928  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.155   0.357  -2.015  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.193   1.297  -1.397  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.382  -1.581  -0.496  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.756  -1.122  -1.589  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.353  -0.239   1.357  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.480  -1.522   0.794  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.515   1.510   0.108  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.661   0.673   1.156  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.596   1.005  -1.172  1.00  0.00           H  
HETATM   45  H25 UNL     1      -3.299   0.040  -1.862  1.00  0.00           H  
HETATM   46  H26 UNL     1      -5.242  -1.315  -1.565  1.00  0.00           H  
HETATM   47  H27 UNL     1      -3.848  -1.932  -0.578  1.00  0.00           H  
HETATM   48  H28 UNL     1      -5.924  -2.168   0.592  1.00  0.00           H  
HETATM   49  H29 UNL     1      -4.897  -1.002   1.484  1.00  0.00           H  
HETATM   50  H30 UNL     1      -7.836   0.869   1.790  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8   28   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   19   20
CONECT   20   50
END

HMDB0000672
     RDKit          3D
Hexadecanedioic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
    7.2092   -0.0386    1.4271 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1956   -0.5604    1.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -1.4976    2.8972 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453   -0.1479    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0857    0.8552    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9939    1.5022   -0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    0.7021   -1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.3846   -0.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4325   -0.0095    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4031    1.0134    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4435    0.5116   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375   -0.7590   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019   -0.5532    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0124    0.5171    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    0.1657   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5974   -1.1185   -0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4665   -1.1516    0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793   -0.1810    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7274    0.5563   -0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4703   -0.0458    1.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7112   -2.3978    2.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -1.0598    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3021    0.3642    2.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8810    0.4518   -0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.6935    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982    2.3814   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564    2.1210    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280    0.1868   -2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    1.3480   -1.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -0.8047   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -1.2558   -0.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.9291    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    0.3562    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013    1.9885   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086    1.3103    0.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    0.3572   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1933    1.2972   -1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -1.5810   -0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.1219   -1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3532   -0.2395    1.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798   -1.5215    0.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5152    1.5096    0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6615    0.6734    1.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5957    1.0049   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988    0.0398   -1.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2419   -1.3151   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8483   -1.9320   -0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9242   -2.1680    0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -1.0025    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8357    0.8692    1.7900 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  2  0
 18 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
M  END

Synonyms

Value	Source
1,14-Tetradecanedicarboxylic acid	ChEBI
1,16-Hexadecanedioic acid	ChEBI
Thapsic acid	ChEBI
1,14-Tetradecanedicarboxylate	Generator
1,16-Hexadecanedioate	Generator
Thapsate	Generator
Hexadecanedioate	Generator
Α,ω-tetrαdecαnedicαrboxylαte	HMDB
N-Tetradecane-ω,ω'-dicarboxylate	HMDB
N-Tetradecane-ω,ω'-dicarboxylic acid	HMDB
alpha,Omega-tetradecanedicarboxylic acid	HMDB
N-Tetradecane-omega,omega'-dicarboxylic acid	HMDB
N-Tetradecane-ω,ω’-dicarboxylic acid	HMDB
Α,ω-tetradecanedicarboxylic acid	HMDB
Hexadecanedioic acid	MeSH

Molecular Formula

C₁₆H₃₀O₄

Average Mass

286.407

Monoisotopic Mass

286.214409448

IUPAC Name

hexadecanedioic acid

Traditional Name

hexadecanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)

InChI Key

QQHJDPROMQRDLA-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
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:73722 )
Dicarboxylic acids (LMFA01170022 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0057 g/L	ALOGPS
logP	4.68	ALOGPS
logP	4.94	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	35.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-07do-2940000000-8c28631b1022d3318936	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0109-7691100000-587f0a395c2991f76096	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0090000000-2311edb5a21bc7c11854	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-01b9-0090000000-29b1e4612ce1b89fe132	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-9000000000-cb4b2bb791cf66c26ad1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 20V, positive	splash10-014r-0490000000-dacc672eeb75f850682b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-014i-0090000000-9e4148fba4082bf62e1e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-014i-2590000000-8bc2ce9bfb76d9bb26b7	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-066s-4950000000-47159163bf80115de8b2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-053b-6920000000-8a0094cbb6f9d1650566	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0012-8910000000-2a109bc90ccab90ea68b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-00l2-9700000000-d514011d0869df067d52	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-05o1-9500000000-983b1d8b6bb3f3f63b35	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-015a-9300000000-69f141c415f5b32f3403	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-067j-9200000000-7b8fa454eb425f3e106e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, positive	splash10-067i-9100000000-a8b8484850ff331b59c4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, positive	splash10-067i-9000000000-2d72212014cb905b53ba	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, positive	splash10-066r-9000000000-5f4d3971357b080285ef	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, positive	splash10-0aor-9000000000-1f5e11f8710cbd1da2c2	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 39V, positive	splash10-0ar0-9100000000-203172aa59c73e588123	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 49V, positive	splash10-0ar0-9200000000-2f3b6e1eff5a4c95e99b	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-21fd3982c0181bc06670	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014u-0390000000-67df6952912c86a0cd98	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-5900000000-ff60e3a81da2e330db67	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-6c700a9c0357a7d235a8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-0090000000-fb79a4abfe50390ddb88	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9140000000-7aba6aa5bd7692dcc532	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01ow-9210000000-ae9c39d4b07c3e8cb742	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)		2015-03-12	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0005254	Hexadecanedioic acid	Hexadecanedioyl Coenzyme A	acyl-CoA synthetase long-chain family member 5	VMH	15060085 4062873
MMDBr0005311	16-Hydroxy hexadecanoic acid	Hexadecanedioic acid	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH	15060085 4062873
MMDBr0005325	Hexadecanedioic acid	Hexadecanedioic acid	Not Available	VMH	10331655 11478366

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Archaea	Euryarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Fruit	Prunus avium	FooDB	24285751
Plant	Leaves	Solanum tuberosum	FooDB	DUKE

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000672

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Thapsic acid

METLIN ID

5642

PubChem Compound

10459

PDB ID

Not Available

ChEBI ID

73722

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Pettersen JE, Aas M: Subcellular localization of hexadecanedioic acid activation in human liver. J Lipid Res. 1974 Nov;15(6):551-6. [PubMed:4372285 ]
You YJ, Kim Y, Nam NH, Bang SC, Ahn BZ: Alkyl and carboxylalkyl esters of 4'-demethyl-4-deoxypodophyllotoxin: synthesis, cytotoxic, and antitumor activity. Eur J Med Chem. 2004 Feb;39(2):189-93. doi: 10.1016/j.ejmech.2003.10.002. [PubMed:14987827 ]

Showing metabocard for Hexadecanedioic acid (MMDBc0009404)

MOL for #<Metabolite:0x00007fdb4c53f460>

3D MOL for #<Metabolite:0x00007fdb4c53f460>

3D SDF for #<Metabolite:0x00007fdb4c53f460>

3D-SDF for #<Metabolite:0x00007fdb4c53f460>

PDB for #<Metabolite:0x00007fdb4c53f460>

3D PDB for #<Metabolite:0x00007fdb4c53f460>

SMILES for #<Metabolite:0x00007fdb4c53f460>

INCHI for #<Metabolite:0x00007fdb4c53f460>

Structure for #<Metabolite:0x00007fdb4c53f460>

3D Structure for #<Metabolite:0x00007fdb4c53f460>