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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (71)transporters (1) Show 72 proteins XML

enzymes (71)transporters (1) Show 72 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:31:55 UTC

HMDB ID

HMDB0000827

Secondary Accession Numbers

HMDB00827

Metabolite Identification

Common Name

Stearic acid

Description

Stearic acid, also known as octadecanoic acid or C18:0, 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. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801 ). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309272007362D          

 20 19  0  0  0  0            999 V2000
   22.0460    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3314    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6169    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4735    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7590    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3301    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6156    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9012    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4722    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7577    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3288    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6143    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999    5.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1854    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999    6.1283    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
 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>
HMDB0000827

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)

> <INCHI_KEY>
QIQXTHQIDYTFRH-UHFFFAOYSA-N

> <FORMULA>
C18H36O2

> <MOLECULAR_WEIGHT>
284.4772

> <EXACT_MASS>
284.271530396

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.635591048723384

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octadecanoic acid

> <ALOGPS_LOGP>
8.02

> <JCHEM_LOGP>
7.145720107666667

> <ALOGPS_LOGS>
-6.63

> <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>
86.28559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.61e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stearic acid

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCCCCCCC(O)=O/file?fo...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:55})
 56 55  0  0  0  0  0  0  0  0999 V2000
   11.8091   -0.2823   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5423    0.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3111   -0.3326   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0443    0.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8131   -0.3829   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5463    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3152   -0.4332   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0484    0.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8172   -0.4836   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504    0.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -0.5340   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9476    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1788   -0.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4455    0.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6767   -0.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9435    0.2234   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1747   -0.6850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4224    0.1601   -0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6300   -0.4260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3359    1.3653   -0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8218   -0.9114    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8218   -0.9114   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6862    0.3649    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5296    1.2050    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5296    1.2050   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3238   -0.9618   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3238   -0.9618    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0316    1.1546    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0316    1.1546   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8258   -1.0121   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8258   -1.0121    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5337    1.1043    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5337    1.1043   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3278   -1.0624   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3278   -1.0624    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    1.0539    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    1.0539   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299   -1.1128   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299   -1.1128    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5377    1.0036    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5377    1.0036   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6681   -1.1631   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6681   -1.1631    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9603    0.9532    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9603    0.9532   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -1.2135   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -1.2135    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4582    0.9029    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4582    0.9029   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6640   -1.2638   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6640   -1.2638    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9562    0.8525    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9562    0.8525   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1620   -1.3142   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1620   -1.3142    0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4012    0.1574   -0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  1  0  0  0  0
  2 24  1  0  0  0  0
  2 25  1  0  0  0  0
  3  4  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4  5  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5  6  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6  7  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  7  8  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  8  9  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  9 10  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
 10 11  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 11 12  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
 12 13  1  0  0  0  0
 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
 13 14  1  0  0  0  0
 13 46  1  0  0  0  0
 13 47  1  0  0  0  0
 14 15  1  0  0  0  0
 14 48  1  0  0  0  0
 14 49  1  0  0  0  0
 15 16  1  0  0  0  0
 15 50  1  0  0  0  0
 15 51  1  0  0  0  0
 16 17  1  0  0  0  0
 16 52  1  0  0  0  0
 16 53  1  0  0  0  0
 17 18  1  0  0  0  0
 17 54  1  0  0  0  0
 17 55  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 56  1  0  0  0  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      41.153   9.129   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      39.819   9.899   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      38.485   9.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      37.152   9.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      35.818   9.129   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.484   9.899   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.150   9.129   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.817   9.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.483   9.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.149   9.899   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.816   9.129   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.482   9.899   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.148   9.129   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.814   9.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.481   9.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.147   9.899   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.813   9.129   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.480   9.899   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.146   9.129   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      18.480  11.439   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                                                       
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    https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCCCCCCC(O)=O/file?fo... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      11.809  -0.282   0.000  1.00  0.00           C  
HETATM    2  C   UNL     1      10.542   0.576   0.000  1.00  0.00           C  
HETATM    3  C   UNL     1       9.311  -0.333   0.000  1.00  0.00           C  
HETATM    4  C   UNL     1       8.044   0.525   0.000  1.00  0.00           C  
HETATM    5  C   UNL     1       6.813  -0.383   0.000  1.00  0.00           C  
HETATM    6  C   UNL     1       5.546   0.475   0.000  1.00  0.00           C  
HETATM    7  C   UNL     1       4.315  -0.433   0.000  1.00  0.00           C  
HETATM    8  C   UNL     1       3.048   0.425   0.000  1.00  0.00           C  
HETATM    9  C   UNL     1       1.817  -0.484   0.000  1.00  0.00           C  
HETATM   10  C   UNL     1       0.550   0.374   0.000  1.00  0.00           C  
HETATM   11  C   UNL     1      -0.681  -0.534   0.000  1.00  0.00           C  
HETATM   12  C   UNL     1      -1.948   0.324   0.000  1.00  0.00           C  
HETATM   13  C   UNL     1      -3.179  -0.584   0.000  1.00  0.00           C  
HETATM   14  C   UNL     1      -4.446   0.274   0.000  1.00  0.00           C  
HETATM   15  C   UNL     1      -5.677  -0.635   0.000  1.00  0.00           C  
HETATM   16  C   UNL     1      -6.944   0.223   0.000  1.00  0.00           C  
HETATM   17  C   UNL     1      -8.175  -0.685   0.000  1.00  0.00           C  
HETATM   18  C   UNL     1      -9.422   0.160   0.000  1.00  0.00           C  
HETATM   19  O   UNL     1     -10.630  -0.426   0.000  1.00  0.00           O  
HETATM   20  O   UNL     1      -9.336   1.365   0.000  1.00  0.00           O  
HETATM   21  H   UNL     1      11.822  -0.911   0.890  1.00  0.00           H  
HETATM   22  H   UNL     1      11.822  -0.911  -0.890  1.00  0.00           H  
HETATM   23  H   UNL     1      12.686   0.365   0.000  1.00  0.00           H  
HETATM   24  H   UNL     1      10.530   1.205   0.890  1.00  0.00           H  
HETATM   25  H   UNL     1      10.530   1.205  -0.890  1.00  0.00           H  
HETATM   26  H   UNL     1       9.324  -0.962  -0.890  1.00  0.00           H  
HETATM   27  H   UNL     1       9.324  -0.962   0.890  1.00  0.00           H  
HETATM   28  H   UNL     1       8.032   1.155   0.890  1.00  0.00           H  
HETATM   29  H   UNL     1       8.032   1.155  -0.890  1.00  0.00           H  
HETATM   30  H   UNL     1       6.826  -1.012  -0.890  1.00  0.00           H  
HETATM   31  H   UNL     1       6.826  -1.012   0.890  1.00  0.00           H  
HETATM   32  H   UNL     1       5.534   1.104   0.890  1.00  0.00           H  
HETATM   33  H   UNL     1       5.534   1.104  -0.890  1.00  0.00           H  
HETATM   34  H   UNL     1       4.328  -1.062  -0.890  1.00  0.00           H  
HETATM   35  H   UNL     1       4.328  -1.062   0.890  1.00  0.00           H  
HETATM   36  H   UNL     1       3.036   1.054   0.890  1.00  0.00           H  
HETATM   37  H   UNL     1       3.036   1.054  -0.890  1.00  0.00           H  
HETATM   38  H   UNL     1       1.830  -1.113  -0.890  1.00  0.00           H  
HETATM   39  H   UNL     1       1.830  -1.113   0.890  1.00  0.00           H  
HETATM   40  H   UNL     1       0.538   1.004   0.890  1.00  0.00           H  
HETATM   41  H   UNL     1       0.538   1.004  -0.890  1.00  0.00           H  
HETATM   42  H   UNL     1      -0.668  -1.163  -0.890  1.00  0.00           H  
HETATM   43  H   UNL     1      -0.668  -1.163   0.890  1.00  0.00           H  
HETATM   44  H   UNL     1      -1.960   0.953   0.890  1.00  0.00           H  
HETATM   45  H   UNL     1      -1.960   0.953  -0.890  1.00  0.00           H  
HETATM   46  H   UNL     1      -3.166  -1.214  -0.890  1.00  0.00           H  
HETATM   47  H   UNL     1      -3.166  -1.214   0.890  1.00  0.00           H  
HETATM   48  H   UNL     1      -4.458   0.903   0.890  1.00  0.00           H  
HETATM   49  H   UNL     1      -4.458   0.903  -0.890  1.00  0.00           H  
HETATM   50  H   UNL     1      -5.664  -1.264  -0.890  1.00  0.00           H  
HETATM   51  H   UNL     1      -5.664  -1.264   0.890  1.00  0.00           H  
HETATM   52  H   UNL     1      -6.956   0.853   0.890  1.00  0.00           H  
HETATM   53  H   UNL     1      -6.956   0.853  -0.890  1.00  0.00           H  
HETATM   54  H   UNL     1      -8.162  -1.314  -0.890  1.00  0.00           H  
HETATM   55  H   UNL     1      -8.162  -1.314   0.890  1.00  0.00           H  
HETATM   56  H   UNL     1     -11.401   0.157   0.000  1.00  0.00           H  
CONECT    1    2   21   22   23                                       
CONECT    2    1    3   24   25                                       
CONECT    3    2    4   26   27                                       
CONECT    4    3    5   28   29                                       
CONECT    5    4    6   30   31                                       
CONECT    6    5    7   32   33                                       
CONECT    7    6    8   34   35                                       
CONECT    8    7    9   36   37                                       
CONECT    9    8   10   38   39                                       
CONECT   10    9   11   40   41                                       
CONECT   11   10   12   42   43                                       
CONECT   12   11   13   44   45                                       
CONECT   13   12   14   46   47                                       
CONECT   14   13   15   48   49                                       
CONECT   15   14   16   50   51                                       
CONECT   16   15   17   52   53                                       
CONECT   17   16   18   54   55                                       
CONECT   18   17   19   20   20                                       
CONECT   19   18   56                                                 
CONECT   20   18   18                                                 
CONECT   21    1                                                      
CONECT   22    1                                                      
CONECT   23    1                                                      
CONECT   24    2                                                      
CONECT   25    2                                                      
CONECT   26    3                                                      
CONECT   27    3                                                      
CONECT   28    4                                                      
CONECT   29    4                                                      
CONECT   30    5                                                      
CONECT   31    5                                                      
CONECT   32    6                                                      
CONECT   33    6                                                      
CONECT   34    7                                                      
CONECT   35    7                                                      
CONECT   36    8                                                      
CONECT   37    8                                                      
CONECT   38    9                                                      
CONECT   39    9                                                      
CONECT   40   10                                                      
CONECT   41   10                                                      
CONECT   42   11                                                      
CONECT   43   11                                                      
CONECT   44   12                                                      
CONECT   45   12                                                      
CONECT   46   13                                                      
CONECT   47   13                                                      
CONECT   48   14                                                      
CONECT   49   14                                                      
CONECT   50   15                                                      
CONECT   51   15                                                      
CONECT   52   16                                                      
CONECT   53   16                                                      
CONECT   54   17                                                      
CONECT   55   17                                                      
CONECT   56   19                                                      
MASTER        0    0    0    0    0    0    0    0   56    0   56    0
END

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCCCCCCC(O)=O/file?fo...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:55})
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    0.5377    1.0036   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4582    0.9029   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  1  0  0  0  0
  2 24  1  0  0  0  0
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 18 20  2  0  0  0  0
 19 56  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
18:0	ChEBI
Acide octadecanoique	ChEBI
Acide stearique	ChEBI
C18:0	ChEBI
CH3-[CH2]16-COOH	ChEBI
N-Octadecanoic acid	ChEBI
Octadecansaeure	ChEBI
Octadecoic acid	ChEBI
Oktadekansaeure	ChEBI
Stearinsaeure	ChEBI
Stearate	Kegg
N-Octadecanoate	Generator
Octadecoate	Generator
Octadecanoic acid	HMDB
Octadecanoate	HMDB
1-Heptadecanecarboxylate	HMDB
1-Heptadecanecarboxylic acid	HMDB
Stearex beads	HMDB
Stearic acid cherry	HMDB
Stearophanate	HMDB
Stearophanic acid	HMDB
Calcium stearate	HMDB
Aluminum tristearate	HMDB
Ammonium stearate	HMDB
Zinc stearate	HMDB
Magnesium stearate	HMDB
Sodium stearate	HMDB
Aluminum monostearate	HMDB
FA(18:0)	HMDB

Chemical Formula

C₁₈H₃₆O₂

Average Molecular Weight

284.4772

Monoisotopic Molecular Weight

284.271530396

IUPAC Name

octadecanoic acid

Traditional Name

stearic acid

CAS Registry Number

57-11-4

SMILES

CCCCCCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)

InChI Key

QIQXTHQIDYTFRH-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:28842 )
saturated fatty acid (CHEBI:28842 )
straight-chain saturated fatty acid (CHEBI:28842 )
Straight chain fatty acids (C01530 )
Saturated fatty acids (C01530 )
Straight chain fatty acids (LMFA01010018 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Cellular process:

Cell signaling

Biochemical pathway:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	68.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0006 mg/mL	Not Available
LogP	8.23	SANGSTER (1993)

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.6e-05 g/L	ALOGPS
logP	8.02	ALOGPS
logP	7.15	ChemAxon
logS	-6.6	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	16	ChemAxon
Refractivity	86.29 m³·mol⁻¹	ChemAxon
Polarizability	38.64 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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DeepCCS	[M-H]-	Experimental	MetCCS_train_neg	174.423	30932474
AllCCS	[M-H]-	Experimental	Not Available	176.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000220
DarkChem	[M+H]+	Predicted	Not Available	175.843	31661259
DarkChem	[M+H]+	Predicted	Not Available	175.843	31661259
DarkChem	[M-H]-	Predicted	Not Available	174.905	31661259
DarkChem	[M-H]-	Predicted	Not Available	174.905	31661259
AllCCS	[M+H]+	Predicted	Not Available	182.317	32859911
AllCCS	[M-H]-	Predicted	Not Available	179.017	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Stearic acid,1TMS,#1	2242.349	https://arxiv.org/abs/1905.12712
Stearic acid,1TBDMS,#1	2496.2666	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0159-1900000000-9cc966384906cd35537d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0900000000-b87a9955374d11966ba6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0100-9700000000-979da356343fa0697993	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2901000000-16194c704b7abd193647	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-06yo-9110000000-6f345827577cdc861aca	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-075c-9220000000-207b53a511763954eb66	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1900000000-9cc966384906cd35537d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0900000000-b87a9955374d11966ba6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0100-9700000000-979da356343fa0697993	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0159-2901000000-16194c704b7abd193647	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1900000000-d34fc01a79cc27a32080	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9540000000-c6c002443ac3a40dabdb	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-009l-9551000000-b9a196da32e6273fad4f	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0c03-9200000000-5dd52f837d56d80fa968	2014-09-20	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-8900000000-5b42adf83e422cffefb6	2021-09-18	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-24fa3ff739ff064312ab	2021-09-18	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-001i-0090000000-1368043827a20e28c172	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001i-0090000000-5c3fa1d38cf3d0a38d74	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004r-0791000000-10ab351997f48e512657	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-9441e6362046ae198384	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-f629b105972a0728beb6	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-fbf3f8e91badb0ec251d	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-55efcdc9c7bfd521ef5a	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00lr-0090000000-a702a9f469dbb513856a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-9441e6362046ae198384	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-fbf3f8e91badb0ec251d	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-34a309d09cb2def46a19	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4690000000-f68e827f7ebccd80d5bf	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8920000000-2e865f09d760af582c07	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-34a309d09cb2def46a19	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4690000000-f68e827f7ebccd80d5bf	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-8920000000-2e865f09d760af582c07	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-b3ce35f839a30b41c718	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-1b84b49819fa37fce1ae	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-b3ce35f839a30b41c718	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00m0-1090000000-bbb339a3dbe1b9ba0d54	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-1b84b49819fa37fce1ae	2015-05-27	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl₃, predicted)	2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Adipose Tissue
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Neuron
Placenta
Platelet
Prostate
Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Plasmalogen Synthesis		Not Available
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	85 (31-470) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected and Quantified	48.8 +/- 21 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	41.119 +/- 5.521 uM	Adult (>18 years old)	Both	Normal	21359215 18953024	details
Blood	Detected and Quantified	7.90-13.5 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	8.70-13.3 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Blood	Detected and Quantified	467.524 +/- 38.667 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	460.494 +/- 31.637 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	460.494 +/- 35.152 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	464.00907 +/- 35.152 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	57 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	60 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	73 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	78 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	232 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	261 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	707.790 +/- 164.407 uM	Adult (>18 years old)	Both	Normal	17313719	details
Blood	Detected and Quantified	585.741 +/- 101.871 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	830 +/- 160 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	770 +/- 110 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22007635	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22061338	details
Blood	Detected and Quantified	22.1 +/- 0.035 uM	Adult (>18 years old)	Both	Normal	20671299	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	10.0 +/- 10.0 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	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	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected and Quantified	71.429 +/- 129.114 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	44.995 +/- 75.226 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	6.88 +/- 1.23 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	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
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)	Both	Normal	Zerihun T. Dame, ...	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	9439441	details
Urine	Detected and Quantified	3.36 +/- 2.82 umol/mmol creatinine	Adult (>18 years old)	Both	Not Available	9439441	details
Urine	Detected and Quantified	18.703 +/- 7.698 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.32-0.82 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	2.9 (1.6-6.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	0.10 +/- 0.03 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0-4.1 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	0-6.5 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	0-6.61 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	0-9.75 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	0.35-0.50 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	3.9(2.3-7.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	22061338	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	Crohns disease	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	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	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	26.428 +/- 22.351 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	33.059 +/- 25.405 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	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 ]
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 ]
Crohn's 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 ]
Iron deficiency
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 ]
Colorectal cancer
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 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

181500 (Schizophrenia)
266600 (Crohn's disease)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB03193

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

28842

Food Biomarker Ontology

Not Available

VMH ID

OCDCA

MarkerDB ID

MDB00000263

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. [PubMed:10391868 ]
Sanjurjo P, Rodriguez-Alarcon J, Rodriguez-Soriano J: Plasma fatty acid composition during the first week of life following feeding with human milk or formula. Acta Paediatr Scand. 1988 Mar;77(2):202-6. [PubMed:3354331 ]
Neoptolemos JP, Thomas BS: Erythrocyte membrane stearic acid: oleic acid ratios in colorectal cancer using tube capillary column gas liquid chromatography. Ann Clin Biochem. 1990 Jan;27 ( Pt 1):38-43. [PubMed:2310156 ]
Turpeinen AM, Wubert J, Aro A, Lorenz R, Mutanen M: Similar effects of diets rich in stearic acid or trans-fatty acids on platelet function and endothelial prostacyclin production in humans. Arterioscler Thromb Vasc Biol. 1998 Feb;18(2):316-22. [PubMed:9484999 ]
Daubresse JC: [Atherosclerosis and nutrition]. Rev Med Brux. 2000 Sep;21(4):A359-62. [PubMed:11068494 ]
Hoppu U, Rinne M, Lampi AM, Isolauri E: Breast milk fatty acid composition is associated with development of atopic dermatitis in the infant. J Pediatr Gastroenterol Nutr. 2005 Sep;41(3):335-8. [PubMed:16131990 ]
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 ]
Musial W, Kubis A: Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum. Eur J Pharm Biopharm. 2003 Mar;55(2):237-40. [PubMed:12637103 ]
Doran TA, Ford JA, Allen LC, Wong PY, Benzie RJ: Amniotic fluid lecithin/sphingomyelin ratio, palmitic acid, palmitic acid/stearic acid ratio, total cortisol, creatinine, and percentage of lipid-positive cells in assessment of fetal maturity and fetal pulmonary maturity: a comparison. Am J Obstet Gynecol. 1979 Feb 1;133(3):302-7. [PubMed:433991 ]
Kazmierczak SC, Gurachevsky A, Matthes G, Muravsky V: Electron spin resonance spectroscopy of serum albumin: a novel new test for cancer diagnosis and monitoring. Clin Chem. 2006 Nov;52(11):2129-34. Epub 2006 Sep 21. [PubMed:16990414 ]
Kelly FD, Sinclair AJ, Mann NJ, Turner AH, Abedin L, Li D: A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males. Eur J Clin Nutr. 2001 Feb;55(2):88-96. [PubMed:11305631 ]
Diani F, Cacco M, Molinaroli A, Cerruti G, Meloncelli C, Turinetto A: [Fatty acid composition of the cervical mucus obtained during ovulation and at the term of pregnancy]. Minerva Ginecol. 1998 Oct;50(10):405-10. [PubMed:9866950 ]
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 ]
Sampath H, Ntambi JM: The fate and intermediary metabolism of stearic acid. Lipids. 2005 Dec;40(12):1187-91. doi: 10.1007/s11745-005-1484-z. [PubMed:16477801 ]

Only showing the first 10 proteins. There are 72 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

Enzyme Details

2. 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

3. 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

4. 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

5. 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

6. 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

7. 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

8. 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

9. Group XIIA 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. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:: PLA2G12A
Uniprot ID:: Q9BZM1
Molecular weight:: 21066.99

Enzyme Details

10. 85/88 kDa calcium-independent phospholipase A2

General function:: Involved in metabolic process
Specific function:: Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:: PLA2G6
Uniprot ID:: O60733
Molecular weight:: 84092.635

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 72 proteins in total.

Show all enzymes and transporters

Showing metabocard for Stearic acid (HMDB0000827)

MOL for HMDB0000827 (Stearic acid)

3D MOL for HMDB0000827 (Stearic acid)

3D SDF for HMDB0000827 (Stearic acid)

3D-SDF for HMDB0000827 (Stearic acid)

PDB for HMDB0000827 (Stearic acid)

3D PDB for HMDB0000827 (Stearic acid)

SMILES for HMDB0000827 (Stearic acid)

INCHI for HMDB0000827 (Stearic acid)

Structure for HMDB0000827 (Stearic acid)

3D Structure for HMDB0000827 (Stearic acid)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes

Transporters