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

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00nb-5900000000-90ab9a21246ad658bda0	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-2900000000-6683cd8579813b4f1ebb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00nb-5900000000-90ab9a21246ad658bda0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00nb-5900000000-90ab9a21246ad658bda0	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8910000000-20fcd1fc2d9e095b2c24	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9630000000-7eda678c0ecd65b2e479	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0090000000-993c95f96e1ca69a41c0	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0090000000-e72ac58f23bacbf37344	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0090000000-d1585cc46cbce84a0506	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0091000000-fd89101236e85a2d9154	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-35027c88ff732ff74b4c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-3cac469ac1efde0a3543	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-e5833c7aa4795570bdc4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-9090000000-909ebad9120d01bf8e79	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-9000000000-fb5a2e21c48a7d72aac8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0udi-0090000000-09c91b61deabc72625f3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0udi-0090000000-993c95f96e1ca69a41c0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0udi-0090000000-e72ac58f23bacbf37344	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 17V, positive	splash10-000i-0490000000-472e6cf8ba7a80f708b8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0a4i-0090000000-3c6c13dcd5649fd90845	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0a4i-0090000000-e5cccbc8340bb0dce9d3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0a4i-2490000000-1dbd141e66d6e7a165ae	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0090000000-202819132f83589a248b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-749f09fec19d95c21683	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-5005f244d7d1c3502c3e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zg0-1090000000-cac7fce9a75b0f1abd63	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-2e782c63ccf72afe9be9	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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	Data Source	Reference
MMDBr0002880	Cholest-5-En-3Beta-Yl (9Z-Hexadecenoate)	Cholesterol	carboxyl ester lipase	VMH	11230747 8112342
MMDBr0002896	Palmitoleic acid	(2E)-Hexadecenoyl-CoA	Not Available	VMH	8584017
MMDBr0002897	Palmitoleic acid	(2E)-Hexadecenoyl-CoA	Not Available	VMH	8584017
MMDBr0002980	Palmitoleic acid	Palmitoleyl-CoA	Not Available	VMH	8584017
MMDBr0004398	Palmitoleic acid	Palmitoleyl-CoA	Not Available	VMH	10479480 9784915
MMDBr0004399	Palmitoleic acid	Palmitoleyl-CoA	Not Available	VMH	10479480 9784915
MMDBr0007082	1-Hexadec-9-enoyl-sn-glycerol 3-phosphate	Glycerol 3-phosphate	Not Available	VMH	30371894
MMDBr0007089	1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1)	sn-glycero-3-phosphoethanolamine	Not Available	VMH	30371894
MMDBr0007096	1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1)	Glycerophosphoglycerol	Not Available	VMH	30371894
MMDBr0007103	2-hexadec-9-enoyl-sn-glycerol 3-phosphate	Glycerol 3-phosphate	Not Available	VMH	30371894
MMDBr0007110	2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:1)	sn-glycero-3-phosphoethanolamine	Not Available	VMH	30371894
MMDBr0007116	2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1)	Glycerophosphoglycerol	Not Available	VMH	30371894
MMDBr0007804	Palmitoleic acid	Palmitoleyl-CoA	Not Available	VMH	30371894
MMDBr0009187	Palmitoleyl-CoA	Palmitoleic acid	acyl-CoA thioesterase 1	VMH	30371894
MMDBr0010205	Cholest-5-En-3Beta-Yl (9Z-Hexadecenoate)	Cholesterol	carboxyl ester lipase	VMH; KEGG	30371894

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	Firmicutes	344	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	Actinobacteria	124	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	Proteobacteria	180	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	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	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	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Seed	Carica papaya	FooDB	31437929
Plant	Seed	Sesamum orientale	FooDB	31437929
Plant	Pollen or spore	Taraxacum officinale	FooDB	31437929
Plant	Seed oil	Juglans nigra	FooDB	31437929
Plant	Leaves	Petroselinum crispum	FooDB	31437929
Plant	Seed	Cucumis melo	FooDB	31437929
Plant	Plant	Arachis hypogaea	FooDB	31437929

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:0x0000559d036413b0>

3D MOL for #<Metabolite:0x0000559d036413b0>

3D SDF for #<Metabolite:0x0000559d036413b0>

3D-SDF for #<Metabolite:0x0000559d036413b0>

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Structure for #<Metabolite:0x0000559d036413b0>

3D Structure for #<Metabolite:0x0000559d036413b0>