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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:43 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003229

Secondary Accession Numbers

HMDB0060082
HMDB03229
HMDB60082

Metabolite Identification

Common Name

Palmitoleic acid

Description

Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40% respectively. Palmitoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.

Structure

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

HMDB0003229
     RDKit          3D
Palmitoleic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -3.4781   -3.5522    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159   -2.0825    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1546   -1.3995    1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6006    0.0160    1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870    0.8765    2.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972    1.1041    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    1.7653    1.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2729    1.2627    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541   -0.0451    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126   -0.9045   -0.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -0.5297   -1.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001   -0.6231   -2.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764    0.1117   -1.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    1.5980   -1.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1446    2.1472   -0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4256    1.7712   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6078    1.1658   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5999    2.1261   -0.7720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3422   -3.9621    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -3.6700   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914   -4.0771   -0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6929   -1.6250   -0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068   -2.0215    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -1.5915    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4842   -1.9757    2.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7075   -0.0156    1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.5218    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750    0.5631    3.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4551    1.9001    2.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043    0.2772    2.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3195    1.9106    3.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    2.7783    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369    1.8178   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495   -0.6162    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611    0.0934    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555   -0.8963   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -1.9714   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    0.4741   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627   -1.2307   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -0.3611   -3.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -1.7202   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248   -0.1785   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2678   -0.2263   -0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1609    1.8993   -2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    2.0806   -1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734    1.6859    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0531    3.2495   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    1.6416   -0.9298 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
M  END

  Mrv1652309272007472D          

 18 17  0  0  0  0            999 V2000
 9999.736810000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.451910001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.166810000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.882010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.707010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.422610000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.136310001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.852010000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.567710001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.281310000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.997010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.022010001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.307110000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.592210001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.877110000.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.162410001.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.447510000.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.162410001.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003229

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC\C=C/CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-

> <INCHI_KEY>
SECPZKHBENQXJG-FPLPWBNLSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.4082

> <EXACT_MASS>
254.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.8701849596776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z)-hexadec-9-enoic acid

> <ALOGPS_LOGP>
6.71

> <JCHEM_LOGP>
5.894661121

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.20019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitoleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003229
     RDKit          3D
Palmitoleic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -3.4781   -3.5522    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159   -2.0825    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1546   -1.3995    1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6006    0.0160    1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870    0.8765    2.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972    1.1041    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    1.7653    1.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2729    1.2627    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541   -0.0451    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126   -0.9045   -0.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -0.5297   -1.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001   -0.6231   -2.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764    0.1117   -1.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    1.5980   -1.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1446    2.1472   -0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4256    1.7712   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6078    1.1658   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5999    2.1261   -0.7720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3422   -3.9621    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -3.6700   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914   -4.0771   -0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6929   -1.6250   -0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068   -2.0215    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -1.5915    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4842   -1.9757    2.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7075   -0.0156    1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.5218    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750    0.5631    3.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4551    1.9001    2.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043    0.2772    2.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3195    1.9106    3.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    2.7783    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369    1.8178   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495   -0.6162    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611    0.0934    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555   -0.8963   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -1.9714   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    0.4741   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627   -1.2307   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -0.3611   -3.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -1.7202   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248   -0.1785   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2678   -0.2263   -0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1609    1.8993   -2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    2.0806   -1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734    1.6859    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0531    3.2495   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    1.6416   -0.9298 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.1758667.784   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.5108668.552   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.8458667.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8670.1808668.552   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8671.7208668.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8673.0568667.784   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8674.3888668.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.7248667.784   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8677.0608668.552   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8678.3928667.784   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8679.7288668.552   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.8418668.552   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.5078667.784   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.1728668.552   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.8378667.784   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8659.5038668.552   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8658.1698667.784   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8659.5038670.094   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0003229
HETATM    1  C1  UNL     1      -3.478  -3.552   0.298  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.916  -2.083   0.392  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.155  -1.400   1.532  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.601   0.016   1.599  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.987   0.877   2.621  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.497   1.104   2.524  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.102   1.765   1.288  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.273   1.263   0.411  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.354  -0.045   0.589  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.013  -0.905  -0.587  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.484  -0.530  -1.924  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.900  -0.623  -2.260  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.976   0.112  -1.595  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.964   1.598  -1.641  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.145   2.147  -0.884  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.426   1.771  -1.479  1.00  0.00           C  
HETATM   17  O1  UNL     1       5.608   1.166  -2.553  1.00  0.00           O  
HETATM   18  O2  UNL     1       6.600   2.126  -0.772  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.342  -3.962   1.319  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.559  -3.670  -0.289  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.291  -4.077  -0.238  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.693  -1.625  -0.591  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.007  -2.022   0.544  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.092  -1.592   1.460  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.484  -1.976   2.454  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.708  -0.016   1.831  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.566   0.522   0.592  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.275   0.563   3.665  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.455   1.900   2.513  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.904   0.277   2.890  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.319   1.911   3.328  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.550   2.778   1.091  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.037   1.818  -0.514  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.050  -0.616   1.487  1.00  0.00           H  
HETATM   35  H17 UNL     1       1.461   0.093   0.719  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.155  -0.896  -0.592  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.223  -1.971  -0.324  1.00  0.00           H  
HETATM   38  H20 UNL     1       0.083   0.474  -2.253  1.00  0.00           H  
HETATM   39  H21 UNL     1      -0.063  -1.231  -2.652  1.00  0.00           H  
HETATM   40  H22 UNL     1       2.008  -0.361  -3.385  1.00  0.00           H  
HETATM   41  H23 UNL     1       2.258  -1.720  -2.296  1.00  0.00           H  
HETATM   42  H24 UNL     1       3.925  -0.179  -2.200  1.00  0.00           H  
HETATM   43  H25 UNL     1       3.268  -0.226  -0.573  1.00  0.00           H  
HETATM   44  H26 UNL     1       3.161   1.899  -2.716  1.00  0.00           H  
HETATM   45  H27 UNL     1       2.040   2.081  -1.325  1.00  0.00           H  
HETATM   46  H28 UNL     1       4.073   1.686   0.147  1.00  0.00           H  
HETATM   47  H29 UNL     1       4.053   3.249  -0.721  1.00  0.00           H  
HETATM   48  H30 UNL     1       7.463   1.642  -0.930  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8    8   32
CONECT    8    9   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   17   18
CONECT   18   48
END

HMDB0003229
     RDKit          3D
Palmitoleic acid
 48 47  0  0  0  0  0  0  0  0999 V2000
   -3.4781   -3.5522    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159   -2.0825    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1546   -1.3995    1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6006    0.0160    1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870    0.8765    2.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972    1.1041    2.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1017    1.7653    1.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2729    1.2627    0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541   -0.0451    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126   -0.9045   -0.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -0.5297   -1.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001   -0.6231   -2.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764    0.1117   -1.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    1.5980   -1.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1446    2.1472   -0.8840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4256    1.7712   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6078    1.1658   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5999    2.1261   -0.7720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3422   -3.9621    1.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -3.6700   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914   -4.0771   -0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6929   -1.6250   -0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068   -2.0215    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -1.5915    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4842   -1.9757    2.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7075   -0.0156    1.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5659    0.5218    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750    0.5631    3.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4551    1.9001    2.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9043    0.2772    2.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3195    1.9106    3.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5498    2.7783    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369    1.8178   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0495   -0.6162    1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4611    0.0934    0.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555   -0.8963   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -1.9714   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0826    0.4741   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627   -1.2307   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -0.3611   -3.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -1.7202   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248   -0.1785   -2.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2678   -0.2263   -0.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1609    1.8993   -2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    2.0806   -1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734    1.6859    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0531    3.2495   -0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    1.6416   -0.9298 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 18 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z)-Hexadecenoic acid	ChEBI
(Z)-9-Hexadecenoic acid	ChEBI
(Z)-Hexadec-9-enoic acid	ChEBI
16:1DElta9	ChEBI
9-cis-Hexadecenoic acid	ChEBI
cis-9-Hexadecenoic acid	ChEBI
cis-9-Palmitoleic acid	ChEBI
cis-delta-9-Hexadecenoic acid	ChEBI
cis-Delta(9)-Hexadecenoic acid	ChEBI
cis-Palmitoleic acid	ChEBI
Oleopalmitic acid	ChEBI
Palmitolinoleic acid	ChEBI
Zoomaric acid	ChEBI
Zoomeric acid	ChEBI
(9Z)-Hexadec-9-enoate	Kegg
(9Z)-Hexadecenoate	Generator
(Z)-9-Hexadecenoate	Generator
(Z)-Hexadec-9-enoate	Generator
9-cis-Hexadecenoate	Generator
cis-9-Hexadecenoate	Generator
cis-9-Palmitoleate	Generator
cis-delta-9-Hexadecenoate	Generator
cis-Δ-9-hexadecenoate	Generator
cis-Δ-9-hexadecenoic acid	Generator
cis-delta(9)-Hexadecenoate	Generator
cis-Δ(9)-hexadecenoate	Generator
cis-Δ(9)-hexadecenoic acid	Generator
cis-Palmitoleate	Generator
Oleopalmitate	Generator
Palmitolinoleate	Generator
Zoomarate	Generator
Zoomerate	Generator
(9Z)-Hexadec-9-enoic acid	Generator
Palmitoleate	Generator
9-Hexadecenoate	HMDB
9-Hexadecenoic acid	HMDB
Hexadecenoate	HMDB
Hexadecenoate (N-C16:1)	HMDB
Hexadecenoic acid	HMDB
Palmitoleic acid, (Z)-isomer	HMDB
Palmitoleic acid, (e)-isomer	HMDB
C16:1 trans-9	HMDB
Palmitelaidic acid	HMDB
(9Z)-9-Hexadecenoic acid	HMDB
9Z-Hexadecenoic acid	HMDB
C16:1	HMDB
FA(16:1(9Z))	HMDB
FA(16:1n7)	HMDB
cis-delta9-Hexadecenoic acid	HMDB
cis-Δ9-hexadecenoic acid	HMDB
Palmitoleic acid	HMDB

Chemical Formula

C₁₆H₃₀O₂

Average Molecular Weight

254.4082

Monoisotopic Molecular Weight

254.224580204

IUPAC Name

(9Z)-hexadec-9-enoic acid

Traditional Name

palmitoleic acid

CAS Registry Number

373-49-9

SMILES

CCCCCC\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-

InChI Key

SECPZKHBENQXJG-FPLPWBNLSA-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
Unsaturated 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

hexadec-9-enoic acid (CHEBI:28716 )
Unsaturated fatty acids (C08362 )
Monounsaturated fatty acids (C08362 )
Unsaturated fatty acids (LMFA01030056 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0003229)

Muscle tissue

Skeletal muscle (HMDB: HMDB0003229)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 8412012)
Cerebrospinal Fluid (CSF) (PMID: 8412012)
Saliva (PMID: 20809147)

Organ

Prostate (HMDB: HMDB0003229)
Placenta (HMDB: HMDB0003229)

Excreta

Biofluid or Excreta

Urine (PMID: 2702744)
Feces (PMID: 22411374)

Cellular substructure

Membrane (HMDB: HMDB0003229)
Extracellular (HMDB: HMDB0003229)

Source

Exogenous

Exogenous (HMDB: HMDB0003229)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Oilseed crop

Other seed

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Aquatic origin

Fish

Anchovy (FooDB: FOOD00566)
Blue whiting (FooDB: FOOD00567)
Carp bream (FooDB: FOOD00568)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Burbot (FooDB: FOOD00313)
Sturgeon (FooDB: FOOD00570)
Charr (FooDB: FOOD00571)
Gadus (Common cod) (FooDB: FOOD00515)
Common dab (FooDB: FOOD00574)
Spiny dogfish (FooDB: FOOD00575)
Anguilliformes (FooDB: FOOD00577)
Flatfish (FooDB: FOOD00535)
Garfish (FooDB: FOOD00579)
Haddock (FooDB: FOOD00374)
Gadiformes (FooDB: FOOD00580)
Atlantic halibut (FooDB: FOOD00516)
Greenland halibut/turbot (FooDB: FOOD00370)
Lake trout (FooDB: FOOD00582)
Lemon sole (FooDB: FOOD00583)
Common ling (FooDB: FOOD00397)
Lumpsucker (FooDB: FOOD00585)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Norway haddock (FooDB: FOOD00588)
Norway pout (FooDB: FOOD00590)
Perciformes (FooDB: FOOD00527)
Northern pike (FooDB: FOOD00431)
Pikeperch (FooDB: FOOD00595)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Pollock (FooDB: FOOD00513)
Rainbow trout (FooDB: FOOD00444)
Pacific ocean perch (FooDB: FOOD00598)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
True sole (FooDB: FOOD00604)
Catfish (FooDB: FOOD00605)
Thunnus (FooDB: FOOD00607)
Turbot (FooDB: FOOD00364)
Whitefish (FooDB: FOOD00503)
Whiting (FooDB: FOOD00504)
Atlantic wolffish (FooDB: FOOD00296)
American butterfish (FooDB: FOOD00315)
Atlantic herring (FooDB: FOOD00292)
Devilfish (FooDB: FOOD00349)
Fishes (FooDB: FOOD00865)

Crustacean

Fish product

Other fish product (FooDB: FOOD00665)

Amphibian

True frog (FooDB: FOOD00578)

Mollusk

Pinniped

True seal (FooDB: FOOD00600)

Seaweed

Cetacean

Cetacea (Dolphin, Porpoise, Whale) (FooDB: FOOD00609)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Fruit product

Other fruit product (FooDB: FOOD00765)
Fruit preserve (FooDB: FOOD00660)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Beverage

Distilled beverage

Spirit (FooDB: FOOD00276)
Gin (FooDB: FOOD00625)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Vodka (FooDB: FOOD00622)
Whisky (FooDB: FOOD00623)

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Other beverage

Fortified wines

Water

Water (FooDB: FOOD00664)

Alcoholic beverage

Other alcoholic beverage (FooDB: FOOD00278)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Baby food

Baby food (FooDB: FOOD00668)

Animal origin

Swine

Domestic pig (FooDB: FOOD00536)

Bovine

Cattle (Beef, Veal) (FooDB: FOOD00495)

Poultry

Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Turkey (FooDB: FOOD00494)
Chicken (FooDB: FOOD00329)

Lagomorph

Mountain hare (FooDB: FOOD00581)
Rabbit (FooDB: FOOD00528)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Leavened bread

Wheat bread (FooDB: FOOD00808)
Rye bread (FooDB: FOOD00809)

Cereal

Cereal product

Bread products

Other bread product (FooDB: FOOD00805)

Flat bread

Crisp bread (FooDB: FOOD00640)

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Baking good

Sugar

Sugar (FooDB: FOOD00651)

Dressing

Salad dressing (FooDB: FOOD00645)

Condiment

Substitute

Sugar substitute (FooDB: FOOD00656)

Seasoning

Salt (FooDB: FOOD00647)
Vinegar (FooDB: FOOD00628)

Sauce

Sauce (FooDB: FOOD00646)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Dish

Ground meat

Sausage (FooDB: FOOD00652)
Meatball (FooDB: FOOD00653)
Pate (FooDB: FOOD00655)
Cold cut (FooDB: FOOD00770)

Other dish

Dumpling (FooDB: FOOD00669)
Other dish (FooDB: FOOD00836)
Pizza (FooDB: FOOD00637)
Soup (FooDB: FOOD00670)

Fat and oil

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)

Animal fat

Fish oil (FooDB: FOOD00990)

Milk and milk product

Other milk product

Butter (FooDB: FOOD00648)
Casein (FooDB: FOOD00659)
Whey (FooDB: FOOD00658)
Cream (FooDB: FOOD00650)
Dried milk (FooDB: FOOD00689)

Fermented milk product

Cheese (FooDB: FOOD00617)
Yogurt (FooDB: FOOD00620)
Ymer (FooDB: FOOD00638)

Unfermented milk

Fermented milk

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Confectionery

Candy

Dessert

Pastry (FooDB: FOOD00641)
Gelatin dessert (FooDB: FOOD00725)

Other confectionery

Honey (FooDB: FOOD00626)
Marzipan (FooDB: FOOD00644)
Toffee (FooDB: FOOD00635)
Meringue (FooDB: FOOD00680)

Frozen dessert

Ice cream (FooDB: FOOD00624)
Other frozen dessert (FooDB: FOOD00729)

Spread

Chocolate spread (FooDB: FOOD00676)

Cocoa and cocoa product

Cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Coffee and coffee product

Coffee

Snack

Cracker (FooDB: FOOD00787)
Other snack food (FooDB: FOOD00639)

Egg

Eggs (FooDB: FOOD00619)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Synthetic

Personal care products

Soap (HMDB: HMDB0003229)

Endogenous

Endogenous (HMDB: HMDB0003229)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (PathBank: SMP0121278)
Inner Membrane Transport (PathBank: SMP0121270)

5alpha-reductase inhibitor (HMDB: HMDB0003229)

EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor (HMDB: HMDB0003229)

Industrial application

Pharmaceutical industry

Biomarker

Isovaleric acidemia (MarkerDB: MDB00030007)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-0.1 °C	Not Available
Boiling Point	363.00 to 364.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.13 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.402 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	167.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002150

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00045 g/L	ALOGPS
logP	6.71	ALOGPS
logP	5.89	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.99	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	13	ChemAxon
Refractivity	78.2 m³·mol⁻¹	ChemAxon
Polarizability	32.87 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]+	168.78	31661259
DarkChem	[M-H]-	170.5	31661259
DeepCCS	[M+H]+	171.995	30932474
DeepCCS	[M-H]-	167.975	30932474
DeepCCS	[M-2H]-	205.412	30932474
DeepCCS	[M+Na]+	181.21	30932474
AllCCS	[M+H]+	170.1	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	174.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Palmitoleic acid	CCCCCC\C=C/CCCCCCCC(O)=O	2908.9	Standard polar	33892256
Palmitoleic acid	CCCCCC\C=C/CCCCCCCC(O)=O	1900.8	Standard non polar	33892256
Palmitoleic acid	CCCCCC\C=C/CCCCCCCC(O)=O	1956.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Palmitoleic acid,1TMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C	2021.5	Semi standard non polar	33892256
Palmitoleic acid,1TBDMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2269.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Palmitoleic acid GC-MS (1 TMS)	splash10-00nb-5900000000-90ab9a21246ad658bda0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Palmitoleic acid GC-EI-TOF (Non-derivatized)	splash10-00mk-2900000000-6683cd8579813b4f1ebb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Palmitoleic acid GC-MS (Non-derivatized)	splash10-00nb-5900000000-90ab9a21246ad658bda0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Palmitoleic acid GC-MS (Non-derivatized)	splash10-00nb-5900000000-90ab9a21246ad658bda0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8910000000-20fcd1fc2d9e095b2c24	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9630000000-7eda678c0ecd65b2e479	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid ESI-TOF 20V, Negative-QTOF	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid ESI-TOF , Negative-QTOF	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid ESI-TOF 10V, Negative-QTOF	splash10-0udi-0090000000-993c95f96e1ca69a41c0	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid ESI-TOF 20V, Negative-QTOF	splash10-0udi-0090000000-e72ac58f23bacbf37344	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid ESI-TOF 10V, Negative-QTOF	splash10-0udi-0090000000-d1585cc46cbce84a0506	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid ESI-TOF , Negative-QTOF	splash10-0udi-0091000000-fd89101236e85a2d9154	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0090000000-35027c88ff732ff74b4c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0090000000-3cac469ac1efde0a3543	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-QQ , negative-QTOF	splash10-0udi-0090000000-e5833c7aa4795570bdc4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-QQ , negative-QTOF	splash10-0udi-9090000000-909ebad9120d01bf8e79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-QQ , negative-QTOF	splash10-004j-9000000000-fb5a2e21c48a7d72aac8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-IT , negative-QTOF	splash10-0udi-0090000000-09c91b61deabc72625f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-TOF , negative-QTOF	splash10-0udi-0090000000-993c95f96e1ca69a41c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid LC-ESI-TOF , negative-QTOF	splash10-0udi-0090000000-e72ac58f23bacbf37344	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid n/a 17V, positive-QTOF	splash10-000i-0490000000-472e6cf8ba7a80f708b8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid Orbitrap 1V, positive-QTOF	splash10-0a4i-0090000000-3c6c13dcd5649fd90845	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid Orbitrap 2V, positive-QTOF	splash10-0a4i-0090000000-e5cccbc8340bb0dce9d3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleic acid Orbitrap 3V, positive-QTOF	splash10-0a4i-2490000000-1dbd141e66d6e7a165ae	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleic acid 10V, Positive-QTOF	splash10-052r-0090000000-202819132f83589a248b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleic acid 20V, Positive-QTOF	splash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleic acid 40V, Positive-QTOF	splash10-052f-9600000000-749f09fec19d95c21683	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleic acid 10V, Negative-QTOF	splash10-0udi-0090000000-5005f244d7d1c3502c3e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleic acid 20V, Negative-QTOF	splash10-0zg0-1090000000-cac7fce9a75b0f1abd63	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleic acid 40V, Negative-QTOF	splash10-0a4l-9320000000-2e782c63ccf72afe9be9	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Adipose Tissue
Placenta
Prostate
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	13 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	15 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	18 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	21 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	27 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	28 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	34 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	19.0639 +/- 11.674 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	240 +/- 100 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	250 +/- 70 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected and Quantified	31.0 (5.0-85.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected and Quantified	9.66 +/- 6.8 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected and Quantified	6.390 +/- 4.279 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	4.5 +/- 2.8 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	1.9-6.3 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	14.7 +/- 0.169 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	244.4 +/- 108.9 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected and Quantified	7 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	8 uM	Adult (>18 years old)	Both	Normal	2000815	details
Blood	Detected and Quantified	12 uM	Adult (>18 years old)	Both	Normal	2000815	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.0 +/- 2.0 uM	Adult (>18 years old)	Both	Normal	8412012	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2 uM	Children (1-13 years old)	Both	Normal	8412012	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	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	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)	Both	Normal	20809147	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	2.8 (0.7-6.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	0.03 +/- 0.02 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	206.0 +/- 92.7 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	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	liver cirrhosis	23384618	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Cirrhosis
Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Colorectal cancer
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 ] 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 ] 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 ]

Associated OMIM IDs

243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB04257

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

28716

Food Biomarker Ontology

Not Available

VMH ID

HDCEA

MarkerDB ID

MDB00030007

Good Scents ID

rw1271951

References

Synthesis Reference

Xu, Huashun; Luo, Yuping; Li, Siguang. Palmitoleic acid production by fermentation with yeast. Zhongguo Youzhi (1999), 24(6), 53-55.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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 ]
Rossner S, Walldius G, Bjorvell H: Fatty acid composition in serum lipids and adipose tissue in severe obesity before and after six weeks of weight loss. Int J Obes. 1989;13(5):603-12. [PubMed:2583914 ]
Ho RC, Davy KP, Hickey MS, Summers SA, Melby CL: Behavioral, metabolic, and molecular correlates of lower insulin sensitivity in Mexican-Americans. Am J Physiol Endocrinol Metab. 2002 Oct;283(4):E799-808. [PubMed:12217898 ]
Hori Y, Nakamura K, Yamamoto M, Shimada K, Nakadaira H, Shibuya N, Endoh K, Ogoshi K: Determination of free fatty acids in human bile by high-performance liquid chromatography. Ann Clin Biochem. 1998 Mar;35 ( Pt 2):279-82. [PubMed:9547901 ]
Yli-Jama P, Haugen TS, Rebnord HM, Ringstad J, Pedersen JI: Selective mobilisation of fatty acids from human adipose tissue. Eur J Intern Med. 2001 Apr;12(2):107-115. [PubMed:11297913 ]
Prandota J: Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. Drugs. 1988 May;35(5):542-78. [PubMed:3293970 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
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 ]

Enzymes

Enzyme Details

1. S-acyl fatty acid synthase thioesterase, medium chain

General function:: Involved in biosynthetic process
Specific function:: In fatty acid biosynthesis chain termination and release of the free fatty acid product is achieved by hydrolysis of the thio ester by a thioesterase I, a component of the fatty acid synthetase complex. The chain length of the released fatty acid is usually C16. However, in the mammary glands of non-ruminant mammals, and in the uropygial gland of certain waterfowl there exists a second thioesterase which releases medium-chain length fatty acids (C8 to C2) (By similarity).
Gene Name:: OLAH
Uniprot ID:: Q9NV23
Molecular weight:: 29930.82

Showing metabocard for Palmitoleic acid (HMDB0003229)

MOL for HMDB0003229 (Palmitoleic acid)

3D MOL for HMDB0003229 (Palmitoleic acid)

3D SDF for HMDB0003229 (Palmitoleic acid)

3D-SDF for HMDB0003229 (Palmitoleic acid)

PDB for HMDB0003229 (Palmitoleic acid)

3D PDB for HMDB0003229 (Palmitoleic acid)

SMILES for HMDB0003229 (Palmitoleic acid)

INCHI for HMDB0003229 (Palmitoleic acid)

Structure for HMDB0003229 (Palmitoleic acid)

3D Structure for HMDB0003229 (Palmitoleic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes