MiMeDB: Showing metabocard for Palmitoleic acid (MMDBc0000599)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:49 UTC

Update Date

2024-09-29 08:22:08 UTC

Metabolite ID

MMDBc0000599

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>
MMDBc0000599

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₆H₃₀O₂

Average Mass

254.4082

Monoisotopic Mass

254.224580204

IUPAC Name

(9Z)-hexadec-9-enoic acid

Traditional Name

palmitoleic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Cerebrospinal Fluid (CSF)
Feces
Placenta
Prostate
Saliva
Skeletal Muscle
Urine

Tissue Locations

Adipose Tissue
Placenta
Prostate
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0196664	S-acyl fatty acid synthase thioesterase, medium chain	Enzyme	Q9NV23	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018177	Water	Palmitoleic acid	Thioesterase 1/protease 1/lysophospholipase L1	Lipid (ester bond) hydrolysis	PathBank	31602464
MMDBr0036304	PC(18:0/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036305	PC(18:1(11Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036306	PC(18:1(9Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036307	PC(18:2(9Z,12Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036308	PC(18:3(6Z,9Z,12Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036309	PC(18:3(9Z,12Z,15Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036310	PC(20:0/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036311	PC(20:1(11Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036312	PC(20:2(11Z,14Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036313	PC(20:3(5Z,8Z,11Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036314	PC(20:3(8Z,11Z,14Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036315	PC(20:4(5Z,8Z,11Z,14Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036316	PC(20:4(8Z,11Z,14Z,17Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036317	PC(20:5(5Z,8Z,11Z,14Z,17Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036318	PC(22:2(13Z,16Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0036319	PC(24:1(15Z)/16:1(9Z))	Palmitoleic acid	Lipid droplet phospholipase 1	Hydrolysis	RHEA	34755880
MMDBr0038706	Palmitoleic acid	Palmitoleyl-CoA	Long-chain-fatty-acid--CoA ligase 1	Hydrolysis; Ligation	RHEA	34755880
MMDBr0038957	Palmitoleic acid	N-[(Z)-Hexadec-9-enoyl]-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880
MMDBr0038997	Palmitoleic acid	palmitoyl-CoA	Medium/long-chain-fatty-acid--CoA/3-oxocholest-4-en-26-oate--CoA ligase (FACL) (EC 6.2.1.2) (EC 6.2.1.3) (EC 6.2.1.42) (Acyl-CoA synthetase) (FACL19) (Steroid-CoA ligase) (Steroid-coenzyme A ligase)	Hydrolysis; Ligation	RHEA	34755880
MMDBr0039464	DG(16:1(9Z)/0:0/19:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039465	DG(16:1(9Z)/10:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039466	DG(16:1(9Z)/12:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039467	DG(16:1(9Z)/14:0(3-OH)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039468	DG(16:1(9Z)/14:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039469	DG(16:1(9Z)/15:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039470	DG(16:1(9Z)/16:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039471	DG(16:1(9Z)/16:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039472	DG(16:1(9Z)/16:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039473	DG(16:1(9Z)/17:0cycw7/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039474	DG(16:1(9Z)/17:0cycw7c/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039475	DG(16:1(9Z)/18:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039476	DG(16:1(9Z)/18:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039477	DG(16:1(9Z)/18:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039478	DG(16:1(9Z)/19:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039479	DG(16:1(9Z)/19:0cycv8c/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039480	DG(16:1(9Z)/19:0cycw8c/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039481	DG(16:1(9Z)/19:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039482	DG(16:1(9Z)/20:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039483	DG(16:1(9Z)/20:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039484	DG(16:1(9Z)/20:1(13Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039485	DG(16:1(9Z)/22:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039486	DG(16:1(9Z)/22:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039487	DG(16:1(9Z)/22:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039488	DG(16:1(9Z)/23:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039489	DG(16:1(9Z)/23:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039490	DG(16:1(9Z)/24:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039491	DG(16:1(9Z)/24:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039492	DG(16:1(9Z)/24:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039493	DG(16:1(9Z)/25:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039494	DG(16:1(9Z)/25:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039495	DG(16:1(9Z)/25:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039496	DG(16:1(9Z)/26:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039497	DG(16:1(9Z)/26:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039498	DG(16:1(9Z)/26:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039499	DG(16:1(9Z)/27:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039500	DG(16:1(9Z)/27:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039501	DG(16:1(9Z)/27:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039502	DG(16:1(9Z)/28:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039503	DG(16:1(9Z)/28:1(11Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039504	DG(16:1(9Z)/28:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039505	DG(16:1(9Z)/29:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039506	DG(16:1(9Z)/30:0/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039507	DG(16:1n7/0:0/18:1n9)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039508	DG(15:0cyclo/16:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039509	DG(17:0cycw7c/16:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880
MMDBr0039510	DG(19:0cycv8c/16:1(9Z)/0:0)	Palmitoleic acid	Carboxylesterase Culp1	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Isovaleric acidemia	Slight Decrease	Association	Human Blood	HMDB	27329611

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	316	Human feces; Human stool; Human ; Human supragingival plaque; Human saliva; Human mucosa; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human urine; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	109	Human ; Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	173	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	15	Human ; Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	28	Human feces; Human stool; Human ; Human supragingival plaque; Human saliva; Human mucosa; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human urine; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	7	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
General Exposome	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	206.0	92.7			uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	HMDB	27329611
Human Cerebrospinal fluid (csf)	Detected and Quantified	2				uM	Children (1-13 years old)	Both	Normal	HMDB	8412012
Human Blood	Detected and Quantified	7				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	8				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	12				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	13				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	15				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	18				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	21				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	27				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	28				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	34				uM	Adult (>18 years old)	Both	Normal	HMDB	2000815
Human Blood	Detected and Quantified	14.7	0.169			uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	19.0639	11.674			uM	Adult (>18 years old)	Female	Normal	HMDB	9368807
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.0	2.0			uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Urine	Detected and Quantified	2.8		0.7	6.6	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	2702744
Human Blood	Detected and Quantified	240	100			uM	Adult (>18 years old)	Female	Normal	HMDB	14608088
Human Blood	Detected and Quantified	244.4	108.9			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	27329611
Human Blood	Detected and Quantified	250	70			uM	Adult (>18 years old)	Male	Normal	HMDB	14608088
Human Blood	Detected and Quantified	31.0		5.0	85.0	uM	Adult (>18 years old)	Both	Normal	HMDB	8412012
Human Blood	Detected and Quantified	6.390	4.279			uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	6.390	4.279			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	9.66	6.8			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Urine	Detected and Quantified	0.03	0.02			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified			1.9	6.3	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	4.5	2.8			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20809147
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23384618
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24740205
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0003229

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

References

Synthesis Reference

Not Available

General References

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 ]
Prandota J: Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. Drugs. 1988 May;35(5):542-78. doi: 10.2165/00003495-198835050-00004. [PubMed:3293970 ]
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. doi: 10.1177/000456329803500213. [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. doi: 10.1016/s0953-6205(01)00119-4. [PubMed:11297913 ]
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. doi: 10.1152/ajpendo.00105.2002. [PubMed:12217898 ]
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. doi: 10.1111/j.0022-202X.2005.23682.x. [PubMed:15854043 ]
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 ]
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 ]

Showing metabocard for Palmitoleic acid (MMDBc0000599)

MOL for #<Metabolite:0x00007f92048df318>

3D MOL for #<Metabolite:0x00007f92048df318>

3D SDF for #<Metabolite:0x00007f92048df318>

3D-SDF for #<Metabolite:0x00007f92048df318>

PDB for #<Metabolite:0x00007f92048df318>

3D PDB for #<Metabolite:0x00007f92048df318>

SMILES for #<Metabolite:0x00007f92048df318>

INCHI for #<Metabolite:0x00007f92048df318>

Structure for #<Metabolite:0x00007f92048df318>

3D Structure for #<Metabolite:0x00007f92048df318>