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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

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

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 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.	10.29 minutes	32390414
Predicted by Siyang on May 30, 2022	22.3118 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2923.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	614.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	242.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	370.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	566.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	977.2 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	777.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2081.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	613.7 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	1782.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	760.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	480.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	648.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	589.7 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	8.0 seconds	40023050

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

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 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	244.4 +/- 108.9 uM	Adult (>18 years old)	Not Specified	Normal	27329611	details
Blood	Detected and Quantified	250 +/- 70 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected and Quantified	240 +/- 100 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	19.0639 +/- 11.674 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	34 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	27 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	18 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	12 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 but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected and Quantified	31.0 (5.0-85.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected and Quantified	4.5 +/- 2.8 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	6.390 +/- 4.279 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	14.7 +/- 0.169 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	9.66 +/- 6.8 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	7 uM	Adult (>18 years old)	Both	Normal	2000815	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2 uM	Children (1-13 years old)	Both	Normal	8412012	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	2.0 +/- 2.0 uM	Adult (>18 years old)	Both	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	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	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	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
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	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 Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes