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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:21:19 UTC

Update Date

2022-11-30 19:24:23 UTC

HMDB ID

HMDB0112106

Secondary Accession Numbers

None

Metabolite Identification

Common Name

FAHFA(16:0/9-O-18:0)

Description

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are endogenous lipids found in adipose tissue and serum that correlate with insulin sensitivity and are reduced in insulin-resistant humans. Structurally, they are characterized by a branched ester linkage between a fatty acid and a hydroxy-fatty acid. Different positions of the branched ester on the hydroxy fatty acid results in different isomers. FAHFA(16:0/9-O-18:0), in particular, is formed from the condensation of the carboxy group of palmitic acid with the hydroxy group of 9-hydroxyoctadecanoic acid. It is alternatively named 9-PAHSA since it is the 9-hydroxy isomer of the PAHSA (palmitic acid-hydroxystearic acid) family.↵↵↵

Structure

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


  Mrv1652309081718212D          

 38 37  0  0  0  0            999 V2000
    8.6774   -4.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2303    1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6902    0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0276   -4.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8800    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8377   -4.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3400    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3778   -3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5298    0.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1879   -4.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7280   -3.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5382   -3.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0783   -2.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8884   -3.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4285   -2.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9897   -0.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2386   -2.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4496   -3.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1796   -0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6395   -2.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7197   -3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7787   -2.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6395   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3695   -2.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5298   -4.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5888   -2.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8294   -0.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5593   -2.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7999   -4.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1289   -1.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2893   -1.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6100   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9391   -1.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1501   -4.3777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8800   -5.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2091   -2.5067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4792   -1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 19  1  0  0  0  0
 22 19  1  0  0  0  0
 23 18  1  0  0  0  0
 24 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 26  1  0  0  0  0
 31 27  1  0  0  0  0
 32 28  1  0  0  0  0
 32 29  1  0  0  0  0
 33 30  1  0  0  0  0
 34 31  1  0  0  0  0
 35 33  2  0  0  0  0
 36 33  1  0  0  0  0
 37 34  2  0  0  0  0
 38 32  1  0  0  0  0
 38 34  1  0  0  0  0
M  END

HMDB0112106
     RDKit          3D
FAHFA(16:0/9-O-18:0)
104103  0  0  0  0  0  0  0  0999 V2000
   11.2340    0.0057    2.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4336    1.0741    1.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1706    0.5308    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6131   -0.4834   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4444   -1.0918   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4899   -1.8095    0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3654   -2.3686   -0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6137   -1.2921   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890   -0.2891   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520    0.7956   -1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1485    0.2196   -2.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3828    1.2723   -2.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7564    2.2967   -1.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644    1.7739   -0.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4261    1.1091   -1.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.6397   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463    0.7594    0.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    0.0720   -0.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4343   -0.3835    0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171    0.4595    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5516    0.7052   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6483    1.6537   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0831    2.9734    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3561    3.7408   -0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6862    4.9935   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4086    6.1112    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561    5.9871    1.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6871    7.3744    1.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603   -1.8761    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0417   -2.4818   -1.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1166   -3.9592   -0.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0736   -4.6221   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0246   -4.4964    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7219   -4.9451    2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4484   -6.4091    1.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1674   -6.8137    2.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202   -5.9575    3.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6586   -8.0806    2.2610 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8129   -0.5920    1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9638    0.4984    3.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6324   -0.6671    2.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0717    1.5436    0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
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 38104  1  0
M  END


  Mrv1652309081718212D          

 38 37  0  0  0  0            999 V2000
    8.6774   -4.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2303    1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 38 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112106

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H66O4/c1-3-5-7-9-11-12-13-14-15-16-18-23-27-31-34(37)38-32(28-24-20-17-10-8-6-4-2)29-25-21-19-22-26-30-33(35)36/h32H,3-31H2,1-2H3,(H,35,36)

> <INCHI_KEY>
MHQWHZLXDBVXML-UHFFFAOYSA-N

> <FORMULA>
C34H66O4

> <MOLECULAR_WEIGHT>
538.898

> <EXACT_MASS>
538.496110605

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
72.87027947752182

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(hexadecanoyloxy)octadecanoic acid

> <ALOGPS_LOGP>
9.99

> <JCHEM_LOGP>
12.680055482999999

> <ALOGPS_LOGS>
-7.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6153253511662795

> <JCHEM_PKA_STRONGEST_BASIC>
-7.041497883564826

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
161.54650000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
32

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.78e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(hexadecanoyloxy)octadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112106
     RDKit          3D
FAHFA(16:0/9-O-18:0)
104103  0  0  0  0  0  0  0  0999 V2000
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 34101  1  0
 35102  1  0
 35103  1  0
 38104  1  0
M  END

HEADER    PROTEIN                                 08-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-17         0                                  
HETATM    1  C   UNK     0      16.198  -9.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      48.963   2.306   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.710  -9.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      47.955   1.141   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.718  -8.172   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.443   1.432   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.230  -8.463   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.435   0.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.239  -7.299   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      43.922   0.559   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.751  -7.590   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.759  -6.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.271  -6.716   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.279  -5.552   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.792  -5.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.800  -4.679   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.914  -0.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.312  -4.970   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.906  -5.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.402  -0.314   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.394  -5.552   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.410  -7.299   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.320  -3.806   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.394  -1.478   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      39.890  -4.097   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      43.922  -7.590   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.832  -4.097   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      38.881  -1.187   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.377  -3.806   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      44.426  -9.045   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      33.841  -2.933   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      37.873  -2.351   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      45.939  -9.336   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      35.353  -3.224   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      46.947  -8.172   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      46.443 -10.791   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      35.857  -4.679   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      36.361  -2.060   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   17                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   18                                                       
CONECT   17   10   20                                                       
CONECT   18   16   23                                                       
CONECT   19   21   22                                                       
CONECT   20   17   24                                                       
CONECT   21   19   25                                                       
CONECT   22   19   26                                                       
CONECT   23   18   27                                                       
CONECT   24   20   28                                                       
CONECT   25   21   29                                                       
CONECT   26   22   30                                                       
CONECT   27   23   31                                                       
CONECT   28   24   32                                                       
CONECT   29   25   32                                                       
CONECT   30   26   33                                                       
CONECT   31   27   34                                                       
CONECT   32   28   29   38                                                  
CONECT   33   30   35   36                                                  
CONECT   34   31   37   38                                                  
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   34                                                            
CONECT   38   32   34                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   74    0
END

COMPND    HMDB0112106
HETATM    1  C1  UNL     1      11.234   0.006   2.351  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.434   1.074   1.686  1.00  0.00           C  
HETATM    3  C3  UNL     1       9.171   0.531   1.033  1.00  0.00           C  
HETATM    4  C4  UNL     1       9.613  -0.483  -0.001  1.00  0.00           C  
HETATM    5  C5  UNL     1       8.444  -1.092  -0.727  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.490  -1.810   0.176  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.365  -2.369  -0.678  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.614  -1.292  -1.430  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.989  -0.289  -0.506  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.252   0.796  -1.248  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.148   0.220  -2.067  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.383   1.272  -2.841  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.756   2.297  -1.955  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.764   1.774  -0.975  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.426   1.109  -1.610  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.323   0.640  -0.532  1.00  0.00           C  
HETATM   17  O1  UNL     1      -0.946   0.759   0.658  1.00  0.00           O  
HETATM   18  O2  UNL     1      -2.564   0.072  -0.739  1.00  0.00           O  
HETATM   19  C17 UNL     1      -3.434  -0.384   0.254  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.617   0.459   0.420  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.552   0.705  -0.689  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.648   1.654  -0.177  1.00  0.00           C  
HETATM   23  C21 UNL     1      -6.083   2.973   0.334  1.00  0.00           C  
HETATM   24  C22 UNL     1      -5.356   3.741  -0.707  1.00  0.00           C  
HETATM   25  C23 UNL     1      -4.686   4.993  -0.300  1.00  0.00           C  
HETATM   26  C24 UNL     1      -5.409   6.111   0.286  1.00  0.00           C  
HETATM   27  C25 UNL     1      -6.056   5.987   1.604  1.00  0.00           C  
HETATM   28  C26 UNL     1      -6.687   7.374   1.924  1.00  0.00           C  
HETATM   29  C27 UNL     1      -3.560  -1.876   0.244  1.00  0.00           C  
HETATM   30  C28 UNL     1      -4.042  -2.482  -1.022  1.00  0.00           C  
HETATM   31  C29 UNL     1      -4.117  -3.959  -0.990  1.00  0.00           C  
HETATM   32  C30 UNL     1      -5.074  -4.622  -0.097  1.00  0.00           C  
HETATM   33  C31 UNL     1      -5.025  -4.496   1.364  1.00  0.00           C  
HETATM   34  C32 UNL     1      -3.722  -4.945   2.007  1.00  0.00           C  
HETATM   35  C33 UNL     1      -3.448  -6.409   1.711  1.00  0.00           C  
HETATM   36  C34 UNL     1      -2.167  -6.814   2.356  1.00  0.00           C  
HETATM   37  O3  UNL     1      -1.520  -5.958   3.019  1.00  0.00           O  
HETATM   38  O4  UNL     1      -1.659  -8.081   2.261  1.00  0.00           O  
HETATM   39  H1  UNL     1      11.813  -0.592   1.611  1.00  0.00           H  
HETATM   40  H2  UNL     1      11.964   0.498   3.048  1.00  0.00           H  
HETATM   41  H3  UNL     1      10.632  -0.667   2.991  1.00  0.00           H  
HETATM   42  H4  UNL     1      10.138   1.827   2.433  1.00  0.00           H  
HETATM   43  H5  UNL     1      11.072   1.544   0.892  1.00  0.00           H  
HETATM   44  H6  UNL     1       8.559   0.090   1.837  1.00  0.00           H  
HETATM   45  H7  UNL     1       8.605   1.360   0.589  1.00  0.00           H  
HETATM   46  H8  UNL     1      10.223  -1.279   0.471  1.00  0.00           H  
HETATM   47  H9  UNL     1      10.265   0.049  -0.722  1.00  0.00           H  
HETATM   48  H10 UNL     1       7.918  -0.234  -1.235  1.00  0.00           H  
HETATM   49  H11 UNL     1       8.827  -1.825  -1.463  1.00  0.00           H  
HETATM   50  H12 UNL     1       8.009  -2.708   0.586  1.00  0.00           H  
HETATM   51  H13 UNL     1       7.086  -1.161   0.952  1.00  0.00           H  
HETATM   52  H14 UNL     1       5.653  -2.857   0.016  1.00  0.00           H  
HETATM   53  H15 UNL     1       6.804  -3.075  -1.398  1.00  0.00           H  
HETATM   54  H16 UNL     1       6.226  -0.810  -2.213  1.00  0.00           H  
HETATM   55  H17 UNL     1       4.810  -1.851  -1.995  1.00  0.00           H  
HETATM   56  H18 UNL     1       4.244  -0.824   0.154  1.00  0.00           H  
HETATM   57  H19 UNL     1       5.731   0.133   0.203  1.00  0.00           H  
HETATM   58  H20 UNL     1       4.988   1.310  -1.934  1.00  0.00           H  
HETATM   59  H21 UNL     1       3.931   1.586  -0.546  1.00  0.00           H  
HETATM   60  H22 UNL     1       3.556  -0.490  -2.808  1.00  0.00           H  
HETATM   61  H23 UNL     1       2.426  -0.349  -1.451  1.00  0.00           H  
HETATM   62  H24 UNL     1       1.595   0.723  -3.417  1.00  0.00           H  
HETATM   63  H25 UNL     1       3.098   1.734  -3.552  1.00  0.00           H  
HETATM   64  H26 UNL     1       2.566   2.805  -1.376  1.00  0.00           H  
HETATM   65  H27 UNL     1       1.268   3.116  -2.531  1.00  0.00           H  
HETATM   66  H28 UNL     1       1.205   1.060  -0.239  1.00  0.00           H  
HETATM   67  H29 UNL     1       0.364   2.670  -0.420  1.00  0.00           H  
HETATM   68  H30 UNL     1      -0.929   1.908  -2.231  1.00  0.00           H  
HETATM   69  H31 UNL     1      -0.143   0.295  -2.309  1.00  0.00           H  
HETATM   70  H32 UNL     1      -2.878  -0.217   1.291  1.00  0.00           H  
HETATM   71  H33 UNL     1      -4.269   1.490   0.771  1.00  0.00           H  
HETATM   72  H34 UNL     1      -5.262   0.137   1.310  1.00  0.00           H  
HETATM   73  H35 UNL     1      -5.109   1.188  -1.572  1.00  0.00           H  
HETATM   74  H36 UNL     1      -6.166  -0.195  -0.982  1.00  0.00           H  
HETATM   75  H37 UNL     1      -7.294   1.908  -1.043  1.00  0.00           H  
HETATM   76  H38 UNL     1      -7.202   1.176   0.643  1.00  0.00           H  
HETATM   77  H39 UNL     1      -7.063   3.559   0.498  1.00  0.00           H  
HETATM   78  H40 UNL     1      -5.627   2.913   1.320  1.00  0.00           H  
HETATM   79  H41 UNL     1      -6.140   3.978  -1.511  1.00  0.00           H  
HETATM   80  H42 UNL     1      -4.612   3.026  -1.180  1.00  0.00           H  
HETATM   81  H43 UNL     1      -4.162   5.387  -1.239  1.00  0.00           H  
HETATM   82  H44 UNL     1      -3.787   4.724   0.389  1.00  0.00           H  
HETATM   83  H45 UNL     1      -4.718   7.013   0.315  1.00  0.00           H  
HETATM   84  H46 UNL     1      -6.200   6.466  -0.448  1.00  0.00           H  
HETATM   85  H47 UNL     1      -5.282   5.862   2.407  1.00  0.00           H  
HETATM   86  H48 UNL     1      -6.861   5.278   1.690  1.00  0.00           H  
HETATM   87  H49 UNL     1      -7.538   7.241   2.615  1.00  0.00           H  
HETATM   88  H50 UNL     1      -5.943   8.013   2.412  1.00  0.00           H  
HETATM   89  H51 UNL     1      -6.997   7.801   0.950  1.00  0.00           H  
HETATM   90  H52 UNL     1      -3.989  -2.258   1.171  1.00  0.00           H  
HETATM   91  H53 UNL     1      -2.465  -2.232   0.324  1.00  0.00           H  
HETATM   92  H54 UNL     1      -5.066  -2.132  -1.318  1.00  0.00           H  
HETATM   93  H55 UNL     1      -3.383  -2.111  -1.860  1.00  0.00           H  
HETATM   94  H56 UNL     1      -3.068  -4.305  -0.697  1.00  0.00           H  
HETATM   95  H57 UNL     1      -4.251  -4.375  -2.053  1.00  0.00           H  
HETATM   96  H58 UNL     1      -5.130  -5.743  -0.325  1.00  0.00           H  
HETATM   97  H59 UNL     1      -6.149  -4.319  -0.402  1.00  0.00           H  
HETATM   98  H60 UNL     1      -5.760  -5.339   1.750  1.00  0.00           H  
HETATM   99  H61 UNL     1      -5.492  -3.625   1.840  1.00  0.00           H  
HETATM  100  H62 UNL     1      -2.891  -4.327   1.621  1.00  0.00           H  
HETATM  101  H63 UNL     1      -3.797  -4.858   3.109  1.00  0.00           H  
HETATM  102  H64 UNL     1      -4.226  -7.068   2.095  1.00  0.00           H  
HETATM  103  H65 UNL     1      -3.343  -6.537   0.619  1.00  0.00           H  
HETATM  104  H66 UNL     1      -1.920  -8.692   1.493  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3   42   43
CONECT    3    4   44   45
CONECT    4    5   46   47
CONECT    5    6   48   49
CONECT    6    7   50   51
CONECT    7    8   52   53
CONECT    8    9   54   55
CONECT    9   10   56   57
CONECT   10   11   58   59
CONECT   11   12   60   61
CONECT   12   13   62   63
CONECT   13   14   64   65
CONECT   14   15   66   67
CONECT   15   16   68   69
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   29   70
CONECT   20   21   71   72
CONECT   21   22   73   74
CONECT   22   23   75   76
CONECT   23   24   77   78
CONECT   24   25   79   80
CONECT   25   26   81   82
CONECT   26   27   83   84
CONECT   27   28   85   86
CONECT   28   87   88   89
CONECT   29   30   90   91
CONECT   30   31   92   93
CONECT   31   32   94   95
CONECT   32   33   96   97
CONECT   33   34   98   99
CONECT   34   35  100  101
CONECT   35   36  102  103
CONECT   36   37   37   38
CONECT   38  104
END

HMDB0112106
     RDKit          3D
FAHFA(16:0/9-O-18:0)
104103  0  0  0  0  0  0  0  0999 V2000
   11.2340    0.0057    2.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4336    1.0741    1.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1706    0.5308    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6131   -0.4834   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4444   -1.0918   -0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4899   -1.8095    0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3654   -2.3686   -0.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6137   -1.2921   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890   -0.2891   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520    0.7956   -1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1485    0.2196   -2.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3828    1.2723   -2.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7564    2.2967   -1.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644    1.7739   -0.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4261    1.1091   -1.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230    0.6397   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463    0.7594    0.6584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5640    0.0720   -0.7388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4343   -0.3835    0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171    0.4595    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5516    0.7052   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6483    1.6537   -0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0831    2.9734    0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3561    3.7408   -0.7074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6862    4.9935   -0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4086    6.1112    0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0561    5.9871    1.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6871    7.3744    1.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603   -1.8761    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0417   -2.4818   -1.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1166   -3.9592   -0.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0736   -4.6221   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0246   -4.4964    1.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7219   -4.9451    2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4484   -6.4091    1.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1674   -6.8137    2.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5202   -5.9575    3.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6586   -8.0806    2.2610 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8129   -0.5920    1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9638    0.4984    3.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6324   -0.6671    2.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1381    1.8273    2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0717    1.5436    0.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5592    0.0898    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6048    1.3604    0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2226   -1.2786    0.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2648    0.0486   -0.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9179   -0.2338   -1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8273   -1.8251   -1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0094   -2.7075    0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0855   -1.1610    0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6533   -2.8573    0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -3.0754   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2263   -0.8101   -2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8097   -1.8507   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437   -0.8243    0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7310    0.1334    0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9884    1.3100   -1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306    1.5862   -0.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562   -0.4899   -2.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4260   -0.3486   -1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5951    0.7229   -3.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978    1.7342   -3.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5657    2.8054   -1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676    3.1165   -2.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    1.0597   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644    2.6701   -0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295    1.9078   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426    0.2949   -2.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778   -0.2172    1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2691    1.4896    0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2625    0.1368    1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1092    1.1877   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1662   -0.1953   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2940    1.9084   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2018    1.1762    0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0633    3.5585    0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6266    2.9129    1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    3.9777   -1.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119    3.0258   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    5.3868   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7874    4.7235    0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7179    7.0127    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2002    6.4655   -0.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2820    5.8618    2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8606    5.2783    1.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5379    7.2407    2.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9427    8.0128    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9968    7.8011    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891   -2.2577    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4653   -2.2318    0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0662   -2.1318   -1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -2.1113   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679   -4.3050   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510   -4.3754   -2.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1302   -5.7429   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1491   -4.3195   -0.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7599   -5.3385    1.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4918   -3.6247    1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909   -4.3266    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973   -4.8577    3.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2255   -7.0684    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3430   -6.5374    0.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9195   -8.6917    1.4931 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 19 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  4 47  1  0
  5 48  1  0
  5 49  1  0
  6 50  1  0
  6 51  1  0
  7 52  1  0
  7 53  1  0
  8 54  1  0
  8 55  1  0
  9 56  1  0
  9 57  1  0
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 10 59  1  0
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 15 69  1  0
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 33 98  1  0
 33 99  1  0
 34100  1  0
 34101  1  0
 35102  1  0
 35103  1  0
 38104  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-(Palmitoyloxy)octadecanoic acid	ChEBI
9-(Palmitoyloxy)stearic acid	ChEBI
Palmitic acid-9-hydroxystearic acid	ChEBI
9-(Palmitoyloxy)octadecanoate	Generator
9-(Palmitoyloxy)stearate	Generator
Palmitate-9-hydroxystearate	Generator
9-PAHSA	HMDB
9-[(1-oxohexadecyl)oxy]-octadecanoic acid	HMDB
Palmitic-acid-9-hydroxy-stearic acid	HMDB
9-Palmitic acid hydroxy stearic acid	HMDB
FAHFA(16:0/9-O-18:0)	SMPDB

Chemical Formula

C₃₄H₆₆O₄

Average Molecular Weight

538.898

Monoisotopic Molecular Weight

538.496110605

IUPAC Name

9-(hexadecanoyloxy)octadecanoic acid

Traditional Name

9-(hexadecanoyloxy)octadecanoic acid

CAS Registry Number

1481636-31-0

SMILES

CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C34H66O4/c1-3-5-7-9-11-12-13-14-15-16-18-23-27-31-34(37)38-32(28-24-20-17-10-8-6-4-2)29-25-21-19-22-26-30-33(35)36/h32H,3-31H2,1-2H3,(H,35,36)

InChI Key

MHQWHZLXDBVXML-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
Fatty acid ester
Dicarboxylic acid or derivatives
Carboxylic acid ester
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:84425 )
FAHFA (CHEBI:84425 )

Ontology

Not Available

Endogenous (HMDB: HMDB0112106)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	9.99	ALOGPS
logP	12.68	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	161.55 m³·mol⁻¹	ChemAxon
Polarizability	72.87 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]+	239.285	31661259
DarkChem	[M-H]-	236.557	31661259
DeepCCS	[M+H]+	241.574	30932474
DeepCCS	[M-H]-	239.024	30932474
DeepCCS	[M-2H]-	272.902	30932474
DeepCCS	[M+Na]+	248.253	30932474
AllCCS	[M+H]+	258.4	32859911
AllCCS	[M+H-H2O]+	257.5	32859911
AllCCS	[M+NH4]+	259.2	32859911
AllCCS	[M+Na]+	259.4	32859911
AllCCS	[M-H]-	238.1	32859911
AllCCS	[M+Na-2H]-	241.4	32859911
AllCCS	[M+HCOO]-	245.1	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.	10.27 minutes	32390414
Predicted by Siyang on May 30, 2022	40.7408 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5182.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	1107.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	439.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	529.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	970.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1825.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1613.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3835.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1022.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	3308.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1410.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	799.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	1067.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	981.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
FAHFA(16:0/9-O-18:0)	CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O	4861.3	Standard polar	33892256
FAHFA(16:0/9-O-18:0)	CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O	3658.6	Standard non polar	33892256
FAHFA(16:0/9-O-18:0)	CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O	3804.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
FAHFA(16:0/9-O-18:0),1TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(=O)O[Si](C)(C)C	3777.5	Semi standard non polar	33892256
FAHFA(16:0/9-O-18:0),1TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	4117.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - FAHFA(16:0/9-O-18:0) GC-MS (1 TMS) - 70eV, Positive	splash10-06y9-8474190000-91fd219d021806c4fdf3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - FAHFA(16:0/9-O-18:0) GC-MS (Non-derivatized) - 70eV, Positive	splash10-01px-8981810000-5085fea57d916f0930c2	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - FAHFA(16:0/9-O-18:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - FAHFA(16:0/9-O-18:0) GC-MS ("FAHFA(16:0/9-O-18:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 10V, Positive-QTOF	splash10-00dr-0050190000-5633492761d952d13984	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 20V, Positive-QTOF	splash10-0080-1291110000-7f435a45569407cb8635	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 40V, Positive-QTOF	splash10-0006-9880300000-dc79101b90189aafc2a1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 10V, Negative-QTOF	splash10-000i-0050190000-9bb2a355a74fc7705b65	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 20V, Negative-QTOF	splash10-052s-0090120000-329d52cfba11df3030c3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 40V, Negative-QTOF	splash10-0a5c-4290000000-28b82f0aceb34026f53f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 10V, Negative-QTOF	splash10-000i-0000090000-c5fba0b4937b1521a8a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 20V, Negative-QTOF	splash10-000i-0000090000-c5fba0b4937b1521a8a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - FAHFA(16:0/9-O-18:0) 40V, Negative-QTOF	splash10-052k-0490040000-2cca4feda1b7e425b796	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34449000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72189985

PDB ID

Not Available

ChEBI ID

84425

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for FAHFA(16:0/9-O-18:0) (HMDB0112106)

MOL for HMDB0112106 (FAHFA(16:0/9-O-18:0))

3D MOL for HMDB0112106 (FAHFA(16:0/9-O-18:0))

3D SDF for HMDB0112106 (FAHFA(16:0/9-O-18:0))

3D-SDF for HMDB0112106 (FAHFA(16:0/9-O-18:0))

PDB for HMDB0112106 (FAHFA(16:0/9-O-18:0))

3D PDB for HMDB0112106 (FAHFA(16:0/9-O-18:0))

SMILES for HMDB0112106 (FAHFA(16:0/9-O-18:0))

INCHI for HMDB0112106 (FAHFA(16:0/9-O-18:0))

Structure for HMDB0112106 (FAHFA(16:0/9-O-18:0))

3D Structure for HMDB0112106 (FAHFA(16:0/9-O-18:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra