Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (85)transporters (1) Show 86 proteins XML

enzymes (85)transporters (1) Show 86 proteins

Show more...Show more...Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000220

Secondary Accession Numbers

HMDB00220
HMDB0060083
HMDB60083

Metabolite Identification

Common Name

Palmitic acid

Description

Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30% (molar) of human depot fat (PMID: 13756126 ), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132 ). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia ). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent.

Structure

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

HMDB0000220
     RDKit          3D
Palmitic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -3.5104   -0.8661   -3.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -0.0759   -1.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7882    0.0744   -1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0815    0.8250    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5592    0.4304    1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930    0.4086    1.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4410    1.7570    1.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726    1.7322    1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947    0.7739    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609    0.9118    1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534   -0.0113    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5610    0.2120    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5892   -0.6495    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6101   -0.3841   -1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -1.1957   -2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084   -2.6249   -1.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -3.0517   -1.3756 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573   -3.5467   -2.5893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536   -0.1120   -3.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264   -1.6901   -2.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5213   -1.2600   -3.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.8581   -1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8379   -0.7713   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2330   -0.9757   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3614    0.5655   -2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313    0.8393    0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8734    1.9228   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9264   -0.6116    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200    1.0972    2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208   -0.3755    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    0.2740    2.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898    2.4522    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    2.1628    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414    1.4022    2.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399    2.7406    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348   -0.2660    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374    1.0572   -0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867    0.6731    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689    1.9398    0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -1.0656    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273    0.2761   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448    0.0139    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    1.2650    0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -0.3091    0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4872   -1.6899    0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6106   -0.6106   -1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8784    0.6862   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6623   -0.9641   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4946   -0.8949   -3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882   -3.3484   -3.5125 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  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  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 18 50  1  0
M  END

  Mrv1652309272007342D          

 18 17  0  0  0  0            999 V2000
   19.3778    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6634    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9490    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2345    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5202    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8058    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0913    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3770    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6626    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9481    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2338    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5193    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8049    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0904    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3760    4.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6617    4.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9473    4.1758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6617    5.4132    0.0000 O   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  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
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000220

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

> <INCHI_KEY>
IPCSVZSSVZVIGE-UHFFFAOYSA-N

> <FORMULA>
C16H32O2

> <MOLECULAR_WEIGHT>
256.4241

> <EXACT_MASS>
256.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
34.35684664668638

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexadecanoic acid

> <ALOGPS_LOGP>
7.23

> <JCHEM_LOGP>
6.256582777666667

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
77.08359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.07e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000220
     RDKit          3D
Palmitic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -3.5104   -0.8661   -3.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -0.0759   -1.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7882    0.0744   -1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0815    0.8250    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5592    0.4304    1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930    0.4086    1.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4410    1.7570    1.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726    1.7322    1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947    0.7739    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609    0.9118    1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534   -0.0113    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5610    0.2120    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5892   -0.6495    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6101   -0.3841   -1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -1.1957   -2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084   -2.6249   -1.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -3.0517   -1.3756 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573   -3.5467   -2.5893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536   -0.1120   -3.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264   -1.6901   -2.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5213   -1.2600   -3.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.8581   -1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8379   -0.7713   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2330   -0.9757   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3614    0.5655   -2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313    0.8393    0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8734    1.9228   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9264   -0.6116    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200    1.0972    2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208   -0.3755    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    0.2740    2.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898    2.4522    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    2.1628    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414    1.4022    2.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399    2.7406    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348   -0.2660    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374    1.0572   -0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867    0.6731    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689    1.9398    0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -1.0656    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273    0.2761   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448    0.0139    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    1.2650    0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -0.3091    0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4872   -1.6899    0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6106   -0.6106   -1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8784    0.6862   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6623   -0.9641   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4946   -0.8949   -3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882   -3.3484   -3.5125 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  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  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 18 50  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      36.172   7.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.838   8.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.505   7.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.171   8.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.838   7.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.504   8.565   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.170   7.795   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.837   8.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.504   7.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.170   8.565   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.836   7.795   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.503   8.565   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.169   7.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.835   8.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.502   7.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.169   8.565   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.835   7.795   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      16.169  10.105   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
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                                                       
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   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0000220
HETATM    1  C1  UNL     1      -3.510  -0.866  -3.010  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.398  -0.076  -1.671  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.788   0.074  -1.193  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.082   0.825   0.031  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.559   0.430   1.341  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.093   0.409   1.583  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.441   1.757   1.338  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.973   1.732   1.586  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.195   0.774   0.728  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.261   0.912   1.137  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.153  -0.011   0.336  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.561   0.212   0.825  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.589  -0.649   0.125  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.610  -0.384  -1.340  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.611  -1.196  -2.115  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.308  -2.625  -1.994  1.00  0.00           C  
HETATM   17  O1  UNL     1       4.317  -3.052  -1.376  1.00  0.00           O  
HETATM   18  O2  UNL     1       6.157  -3.547  -2.589  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.854  -0.112  -3.743  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.226  -1.690  -2.853  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.521  -1.260  -3.270  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.861   0.858  -1.883  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.838  -0.771  -1.005  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.233  -0.976  -1.168  1.00  0.00           H  
HETATM   25  H7  UNL     1      -5.361   0.566  -2.037  1.00  0.00           H  
HETATM   26  H8  UNL     1      -6.231   0.839   0.106  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.873   1.923  -0.184  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.926  -0.612   1.613  1.00  0.00           H  
HETATM   29  H11 UNL     1      -5.020   1.097   2.136  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.521  -0.376   1.130  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.003   0.274   2.731  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.890   2.452   2.079  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.713   2.163   0.340  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.841   1.402   2.660  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.540   2.741   1.553  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.535  -0.266   0.805  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.237   1.057  -0.347  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.387   0.673   2.192  1.00  0.00           H  
HETATM   39  H21 UNL     1       1.569   1.940   0.931  1.00  0.00           H  
HETATM   40  H22 UNL     1       1.881  -1.066   0.402  1.00  0.00           H  
HETATM   41  H23 UNL     1       2.127   0.276  -0.756  1.00  0.00           H  
HETATM   42  H24 UNL     1       3.645   0.014   1.911  1.00  0.00           H  
HETATM   43  H25 UNL     1       3.892   1.265   0.684  1.00  0.00           H  
HETATM   44  H26 UNL     1       5.574  -0.309   0.542  1.00  0.00           H  
HETATM   45  H27 UNL     1       4.487  -1.690   0.430  1.00  0.00           H  
HETATM   46  H28 UNL     1       3.611  -0.611  -1.791  1.00  0.00           H  
HETATM   47  H29 UNL     1       4.878   0.686  -1.499  1.00  0.00           H  
HETATM   48  H30 UNL     1       6.662  -0.964  -1.772  1.00  0.00           H  
HETATM   49  H31 UNL     1       5.495  -0.895  -3.185  1.00  0.00           H  
HETATM   50  H32 UNL     1       6.488  -3.348  -3.513  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   17   18
CONECT   18   50
END

HMDB0000220
     RDKit          3D
Palmitic acid
 50 49  0  0  0  0  0  0  0  0999 V2000
   -3.5104   -0.8661   -3.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -0.0759   -1.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7882    0.0744   -1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0815    0.8250    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5592    0.4304    1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930    0.4086    1.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4410    1.7570    1.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726    1.7322    1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947    0.7739    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2609    0.9118    1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534   -0.0113    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5610    0.2120    0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5892   -0.6495    0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6101   -0.3841   -1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -1.1957   -2.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084   -2.6249   -1.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -3.0517   -1.3756 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573   -3.5467   -2.5893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8536   -0.1120   -3.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264   -1.6901   -2.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5213   -1.2600   -3.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.8581   -1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8379   -0.7713   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2330   -0.9757   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3614    0.5655   -2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313    0.8393    0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8734    1.9228   -0.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9264   -0.6116    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200    1.0972    2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208   -0.3755    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    0.2740    2.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8898    2.4522    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7126    2.1628    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414    1.4022    2.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399    2.7406    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348   -0.2660    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374    1.0572   -0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867    0.6731    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689    1.9398    0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8809   -1.0656    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273    0.2761   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448    0.0139    1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    1.2650    0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -0.3091    0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4872   -1.6899    0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6106   -0.6106   -1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8784    0.6862   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6623   -0.9641   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4946   -0.8949   -3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882   -3.3484   -3.5125 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  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  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 18 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Hexyldecanoic acid	ChEBI
1-Pentadecanecarboxylic acid	ChEBI
16:00	ChEBI
C16	ChEBI
C16 Fatty acid	ChEBI
C16:0	ChEBI
Cetylic acid	ChEBI
CH3-[CH2]14-COOH	ChEBI
FA 16:0	ChEBI
Hexadecanoate	ChEBI
Hexadecoic acid	ChEBI
Hexadecylic acid	ChEBI
Hexaectylic acid	ChEBI
N-Hexadecanoic acid	ChEBI
N-Hexadecoic acid	ChEBI
Palmitate	ChEBI
Palmitinic acid	ChEBI
Palmitinsaeure	ChEBI
Pentadecanecarboxylic acid	ChEBI
1-Hexyldecanoate	Generator
1-Pentadecanecarboxylate	Generator
Cetylate	Generator
Hexadecanoic acid	Generator
Hexadecoate	Generator
Hexadecylate	Generator
Hexaectylate	Generator
N-Hexadecanoate	Generator
N-Hexadecoate	Generator
Palmitinate	Generator
Pentadecanecarboxylate	Generator
Acid, hexadecanoic	MeSH
Acid, palmitic	MeSH
Edenor C16	HMDB
Emersol 140	HMDB
Emersol 143	HMDB
Glycon P-45	HMDB
Hexadecanoate (N-C16:0)	HMDB
Hexadecanoic acid palmitic acid	HMDB
Hydrofol	HMDB
Hydrofol acid 1690	HMDB
Hystrene 8016	HMDB
Hystrene 9016	HMDB
Industrene 4516	HMDB
Kortacid 1698	HMDB
Loxiol ep 278	HMDB
Lunac P 95	HMDB
Lunac P 95KC	HMDB
Lunac P 98	HMDB
Palmitoate	HMDB
Palmitoic acid	HMDB
PAM	HMDB
PLM	HMDB
Prifac 2960	HMDB
Prifrac 2960	HMDB
Pristerene 4934	HMDB
Univol u332	HMDB
FA(16:0)	HMDB

Chemical Formula

C₁₆H₃₂O₂

Average Molecular Weight

256.4241

Monoisotopic Molecular Weight

256.240230268

IUPAC Name

hexadecanoic acid

Traditional Name

palmitic acid

CAS Registry Number

57-10-3

SMILES

CCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

InChI Key

IPCSVZSSVZVIGE-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
Straight chain fatty acid
Monocarboxylic 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

long-chain fatty acid (CHEBI:15756 )
straight-chain saturated fatty acid (CHEBI:15756 )
Straight chain fatty acids (C00249 )
Saturated fatty acids (C00249 )
Straight chain fatty acids (LMFA01010001 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.0e-05 mg/mL	Not Available
LogP	7.17	SANGSTER (1993)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	167.516	30932474
[M-H]-	Not Available	168.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000184

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00041 g/L	ALOGPS
logP	7.23	ALOGPS
logP	6.26	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	77.08 m³·mol⁻¹	ChemAxon
Polarizability	34.36 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
DarkChem	[M+H]+	167.423	31661259
DarkChem	[M-H]-	167.331	31661259
AllCCS	[M+H]+	172.157	32859911
AllCCS	[M-H]-	171.289	32859911
DeepCCS	[M+H]+	165.936	30932474
DeepCCS	[M-H]-	161.916	30932474
DeepCCS	[M-2H]-	199.074	30932474
DeepCCS	[M+Na]+	174.954	30932474
AllCCS	[M+H]+	172.2	32859911
AllCCS	[M+H-H2O]+	169.0	32859911
AllCCS	[M+NH4]+	175.1	32859911
AllCCS	[M+Na]+	175.9	32859911
AllCCS	[M-H]-	171.3	32859911
AllCCS	[M+Na-2H]-	172.4	32859911
AllCCS	[M+HCOO]-	173.8	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.	10.77 minutes	32390414
Predicted by Siyang on May 30, 2022	22.9766 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Palmitic acid	CCCCCCCCCCCCCCCC(O)=O	2904.2	Standard polar	33892256
Palmitic acid	CCCCCCCCCCCCCCCC(O)=O	1929.4	Standard non polar	33892256
Palmitic acid	CCCCCCCCCCCCCCCC(O)=O	1976.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Palmitic acid,1TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C	2044.7	Semi standard non polar	33892256
Palmitic acid,1TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2291.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Adipose Tissue
Bladder
Epidermis
Fibroblasts
Kidney
Placenta
Platelet
Prostate
Skeletal Muscle

Pathways

Name	SMPDB/PathBank	KEGG
Glycerolipid Metabolism
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Fatty Acid Biosynthesis		Not Available
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	129 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22061338	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Blood	Detected and Quantified	1060.743 +/- 35.0981 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	1064.643 +/- 50.697 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	1052.943 +/- 54.597 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	1029.544 +/- 62.397 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	52 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	53 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	74 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	80 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	95 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	114 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Blood	Detected and Quantified	131 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	147 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	347 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	366 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	424 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	1415.468 +/- 323.410 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	1215.798 +/- 212.0316 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	2500 +/- 630 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	2360 +/- 430 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected and Quantified	22.3-31.1 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	22.7-32.9 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	25.0 +/- 2.8 uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	25.5 +/- 2.8 uM	Adolescent (13-18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	26.7 +/- 4.4 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	30.49 +/- 2.64 uM	Adult (>18 years old)	Both	Normal	14634727	details
Blood	Detected and Quantified	66.010 +/- 9.879 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	63.8 +/- 0.400 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	122 +/- 48 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	18.0 +/- 12.0 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected and Quantified	122.219 +/- 200.254 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected and Quantified	421.957 +/- 602.517 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Saliva	Detected and Quantified	11.09 +/- 2.5 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	22727327	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	1268322	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	3.5-7.2 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	3.0-8.7 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	4-10.5 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	1.4 (0.1-3.8) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	4.0-9.3 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	10.8 (2.6-32.7) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	2.2 (0.8-8.2) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.4 (0.1-7.3) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	0.30 +/- 0.09 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	11 (6.0-23) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	6.7(2.6-24.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	11.2 (6.0-26.1) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	0.45-0.73 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.46-1.1 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	16.903 +/- 12.225 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	22061338	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22007635	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Inflammatory bowel disease	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	22.852 +/- 19.074 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	10.703 +/- 11.558 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Lv W, Yang T: Identification of possible biomarkers for breast cancer from free fatty acid profiles determined by GC-MS and multivariate statistical analysis. Clin Biochem. 2012 Jan;45(1-2):127-33. doi: 10.1016/j.clinbiochem.2011.10.011. Epub 2011 Oct 26. [PubMed:22061338 ]
Colorectal cancer
Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Schizophrenia
Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ] Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8. [PubMed:22007635 ]
Inflammatory bowel disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
181500 (Schizophrenia)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB03796

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15756

Food Biomarker Ontology

Not Available

VMH ID

HDCA

MarkerDB ID

MDB00000104

Good Scents ID

rw1009101

References

Synthesis Reference

Xu, Yan; Ling, Li. A method for preparing conjugated linoleic acid and palmitic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. [PubMed:16351159 ]
Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. [PubMed:11124748 ]
Lloyd B, Halter RJ, Kuchan MJ, Baggs GE, Ryan AS, Masor ML: Formula tolerance in postbreastfed and exclusively formula-fed infants. Pediatrics. 1999 Jan;103(1):E7. [PubMed:9917487 ]
Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. [PubMed:15854043 ]
Mensink RP: Nutrition in lipid disorders. Ther Umsch. 1995 Aug;52(8):509-14. [PubMed:7676394 ]
Mesiha MS, Ponnapula S, Plakogiannis F: Oral absorption of insulin encapsulated in artificial chyles of bile salts, palmitic acid and alpha-tocopherol dispersions. Int J Pharm. 2002 Dec 5;249(1-2):1-5. [PubMed:12433429 ]
Dubinin DM, Naidina VP, Zaloguev SN: [Evaluation of human skin function in a sealed room by a chromatographic method]. Kosm Biol Aviakosm Med. 1985 Nov-Dec;19(6):69-73. [PubMed:2868151 ]
Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [PubMed:12385891 ]
Otsuki T, Oku M: [A study on the effect of cortisol and progesterone on cytosolic arachidonic and palmitic acid concentrations in cultured human myometrial cells]. Nihon Sanka Fujinka Gakkai Zasshi. 1995 Jun;47(6):531-8. [PubMed:7608616 ]
Draisey TF, Gagneja GL, Thibert RJ: Pulmonary surfactant and amniotic fluid insulin. Obstet Gynecol. 1977 Aug;50(2):197-9. [PubMed:577607 ]
Florentin E, Athias A, Lagrost L: Modulation of the activity of the human cholesteryl ester transfer protein by carboxylated derivatives. Evidence for 13-cis-retinoic acid as a potent activator of the protein's activity in plasma. Eur J Biochem. 1996 Sep 15;240(3):699-706. [PubMed:8856073 ]
Urien S, Morin D, Tillement JP: Effect of alpha-1-acid glycoprotein, albumin and palmitic acid on the brain and salivary gland extraction of warfarin in rats. J Pharmacol Exp Ther. 1989 Feb;248(2):781-5. [PubMed:2918479 ]
Wang J, Zhu F, Pan G: [Diagnosis of chylous ascites with oral administration of 13C-palmitic acid]. Zhonghua Nei Ke Za Zhi. 1996 Jun;35(6):382-4. [PubMed:9387625 ]
Ip MP, Draisey TF, Thibert RJ, Gagneja GL, Jasey GM: Fetal lung maturity, as assessed by gas-liquid chromatographic determination of phospholipid palmitic acid in amniotic fluid. Clin Chem. 1977 Jan;23(1):35-40. [PubMed:832370 ]
Messner T, Erkstam UB, Gustafsson IB, Nilsson SB, Vessby B: Diet and dietary markers in Kiruna and Uppsala, Sweden--a comparison. Int J Circumpolar Health. 1997 Apr;56(1-2):21-9. [PubMed:9300843 ]
Vessby B, Tengblad S, Lithell H: Insulin sensitivity is related to the fatty acid composition of serum lipids and skeletal muscle phospholipids in 70-year-old men. Diabetologia. 1994 Oct;37(10):1044-50. [PubMed:7851683 ]
Liau YH, Slomiany BL, Slomiany A, Piasek A, Palmer D, Rosenthal WS: Identification of mucus glycoprotein fatty acyltransferase activity in human gastric mucosa. Digestion. 1985;32(1):57-62. [PubMed:4018446 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
KINGSBURY KJ, PAUL S, CROSSLEY A, MORGAN DM: The fatty acid composition of human depot fat. Biochem J. 1961 Mar;78:541-50. [PubMed:13756126 ]
Jensen RG, Hagerty MM, McMahon KE: Lipids of human milk and infant formulas: a review. Am J Clin Nutr. 1978 Jun;31(6):990-1016. doi: 10.1093/ajcn/31.6.990. [PubMed:352132 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 86 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Reactions

Hexadecanoyl-[acp] + Water → Acyl-carrier protein + Palmitic acid	details

Enzyme Details

2. Acyl-protein thioesterase 1

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:: LYPLA1
Uniprot ID:: O75608
Molecular weight:: 24669.355

Reactions

Palmitoyl-protein + Water → Palmitic acid + protein	details

Enzyme Details

3. Calcium-dependent phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:: PLA2G5
Uniprot ID:: P39877
Molecular weight:: 15674.065

Enzyme Details

4. Group IIF secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:: PLA2G2F
Uniprot ID:: Q9BZM2
Molecular weight:: 23256.29

Enzyme Details

5. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Enzyme Details

6. Phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G1B
Uniprot ID:: P04054
Molecular weight:: 16359.535

Enzyme Details

7. Group 10 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:: PLA2G10
Uniprot ID:: O15496
Molecular weight:: 18153.04

Enzyme Details

8. Galactoside-binding soluble lectin 13

General function:: Involved in sugar binding
Specific function:: Has lysophospholipase activity.
Gene Name:: LGALS13
Uniprot ID:: Q9UHV8
Molecular weight:: 16118.44

Enzyme Details

9. Group IIE secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:: PLA2G2E
Uniprot ID:: Q9NZK7
Molecular weight:: 15988.525

Enzyme Details

10. Acyl-protein thioesterase 2

General function:: Involved in hydrolase activity
Specific function:: May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:: LYPLA2
Uniprot ID:: O95372
Molecular weight:: 24736.71

Reactions

Palmitoyl-protein + Water → Palmitic acid + protein	details

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 86 proteins in total.

Show all enzymes and transporters

Showing metabocard for Palmitic acid (HMDB0000220)

MOL for HMDB0000220 (Palmitic acid)

3D MOL for HMDB0000220 (Palmitic acid)

3D SDF for HMDB0000220 (Palmitic acid)

3D-SDF for HMDB0000220 (Palmitic acid)

PDB for HMDB0000220 (Palmitic acid)

3D PDB for HMDB0000220 (Palmitic acid)

SMILES for HMDB0000220 (Palmitic acid)

INCHI for HMDB0000220 (Palmitic acid)

Structure for HMDB0000220 (Palmitic acid)

3D Structure for HMDB0000220 (Palmitic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Transporters