NP-MRD: Showing NP-Card for Palmitoleic acid (NP0001123)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:43 UTC

Updated at

2024-09-17 15:44:03 UTC

NP-MRD ID

NP0001123

Secondary Accession Numbers

None

Natural Product 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>
NP0001123

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
SECPZKHBENQXJG-FPLPWBNLSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.4082

> <EXACT_MASS>
254.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
32.8701849596776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.71

> <JCHEM_LOGP>
5.894661121

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
78.20019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitoleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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

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

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

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

View in JSmol View NMR Assignments

Synonyms

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

Chemical Formula

C₁₆H₃₀O₂

Average Mass

254.4082 Da

Monoisotopic Mass

254.22458 Da

IUPAC Name

(9Z)-hexadec-9-enoic acid

Traditional Name

palmitoleic acid

CAS Registry Number

373-49-9

SMILES

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

InChI Identifier

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

InChI Key

SECPZKHBENQXJG-FPLPWBNLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	LOTUS Database	35616633
Abies pinsapo	LOTUS Database	35616633
Abutilon ramosum	LOTUS Database	35616633
Acorus calamus	LOTUS Database	35616633
Aesculus hippocastanum	LOTUS Database	35616633
Agaricus blazei	LOTUS Database	35616633
Agave decipiens	LOTUS Database	35616633
Agelas conifera	LOTUS Database	35616633
Agrimonia pilosa	LOTUS Database	35616633
Alchemilla pentaphyllea	LOTUS Database	35616633
Allamanda cathartica	LOTUS Database	35616633
Allium hirtifolium	Plant	KNApSAcK
Aloe vera var.chinensis	KNApSAcK Database	22123792
Alpinia oxyphylla	KNApSAcK Database	22123792
Amaranthus caudatus	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	LOTUS Database	35616633
Anisophyllea laurina	LOTUS Database	35616633
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
Aquilaria sinensis	LOTUS Database	35616633
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arnica montana	LOTUS Database	35616633
Asclepias syriaca	LOTUS Database	35616633
Astragalus hamosus	LOTUS Database	35616633
Bellis perennis	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica hirta	KNApSAcK Database	22123792
Bryonia alba	LOTUS Database	35616633
Bubalus bubalis	FooDB	FooDB
Cachrys sicula	LOTUS Database	35616633
Callyspongia fallax	LOTUS Database	35616633
Calophyllum inophyllum	KNApSAcK Database	22123792
Calopyllum calaba	-	KNApSAcK
Canavalia ensiformis	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Carica papaya	LOTUS Database	35616633
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cassia fistula	LOTUS Database	35616633
Cervicornia cuspidifera	LOTUS Database	35616633
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chlamydomonas reinhardtii	LOTUS Database	35616633
Citrullus colocynthis	LOTUS Database	35616633
Cleistanthus collinus	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Curcuma longa	LOTUS Database	35616633
Dermochelys coriacea	LOTUS Database	35616633
Dictamnus albus	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Dryopteris carthusiana	LOTUS Database	35616633
Echinacea purpurea	LOTUS Database	35616633
Elaeagnus angustifolia	LOTUS Database	35616633
Elaeis guineensis	KNApSAcK Database	22123792
Epilobium parviflorum	LOTUS Database	35616633
Equus caballus	FooDB	FooDB
Erigeron caucasicus	LOTUS Database	35616633
Fagopyrum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Festuca rubra	LOTUS Database	35616633
Fumaria vaillantii	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Ganoderma australe	LOTUS Database	35616633
Garcinia xanthochymus	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hibiscus cannabinus	LOTUS Database	35616633
Hippophae rhamnoides	KNApSAcK Database	22123792
Hypericum maculatum	LOTUS Database	35616633
Inula grandis	LOTUS Database	35616633
Isatis tinctoria	KNApSAcK Database	22123792
Jodina rhombifolia	LOTUS Database	35616633
Juglans nigra L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lactuca saligna L.	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Laminaria japonica	KNApSAcK Database	22123792
Lepidium meyenii	LOTUS Database	35616633
Leporidae	FooDB	FooDB
Leptolyngbya tenuis	LOTUS Database	35616633
Lepus timidus	FooDB	FooDB
Macadamia integrifolia	LOTUS Database	35616633
Macadamia ternifolia	KNApSAcK Database	22123792
Mangifera indica	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mentha spicata	LOTUS Database	35616633
Mitracarpus hirtus	LOTUS Database	35616633
Momordica charantia	LOTUS Database	35616633
Moquilea tomentosa	LOTUS Database	35616633
Mucuna puriens	Plant	KNApSAcK
Musa paradisiaca	LOTUS Database	35616633
Mycale laevis	LOTUS Database	35616633
Myrmekioderma rea	LOTUS Database	35616633
Nigella sativa	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Nymphaea alba	KNApSAcK Database	22123792
Odocoileus	FooDB	FooDB
Oecophylla smaragdina	LOTUS Database	35616633
Oenothera biennis	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Oncophorus crispifolius	LOTUS Database	35616633
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Penicillium oxalicum	LOTUS Database	35616633
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus coccineus	LOTUS Database	35616633
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pinus radiata	LOTUS Database	35616633
Pinus sibirica	Plant	KNApSAcK
Pistacia vera	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633
Proiphys amboinensis	LOTUS Database	35616633
Prunus armeniaca	KNApSAcK Database	22123792
Pseudo-nitzschia multistriata	LOTUS Database	35616633
Pterodon emarginatus	LOTUS Database	35616633
Punica granatum	KNApSAcK Database	22123792
Rehmannia glutinosa	KNApSAcK Database	22123792
Sabal minor	LOTUS Database	35616633
Saccharina japonica	Plant	KNApSAcK
Salmonella enterica	LOTUS Database	35616633
Salpa thompsoni	LOTUS Database	35616633
Scomber japonicus	LOTUS Database	35616633
Sesamum indicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sideritis taurica	LOTUS Database	35616633
Sinapis alba	Plant	KNApSAcK
Sinopodophyllum hexandrum	LOTUS Database	35616633
Smenospongia aurea	LOTUS Database	35616633
Stellaria dichotoma	LOTUS Database	35616633
Sterculia foetida	LOTUS Database	35616633
Sterculia tragacantha	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Stuckenia pectinata	LOTUS Database	35616633
Suaeda aegyptiaca	LOTUS Database	35616633
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Talaromyces flavus	LOTUS Database	35616633
Taonia atomaria	LOTUS Database	35616633
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tilia cordata	Plant	KNApSAcK
Tilia cordata Mill.	KNApSAcK Database	22123792
Treculia africana	LOTUS Database	35616633
Trichosanthes kirilowii	KNApSAcK Database	22123792
Trichosanthes rosthornii	KNApSAcK Database	22123792
Trifolium alexandrinum	LOTUS Database	35616633
Tripneustes ventricosus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633
Turnera ulmifolia	LOTUS Database	35616633
Vitex trifolia	KNApSAcK Database	22123792
Xestospongia muta	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Serum)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Liquid

Experimental Properties

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

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

External Links

HMDB ID

HMDB0003229

DrugBank ID

DB04257

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1271951

References

General References

Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. [PubMed:15854043 ]
Rossner S, Walldius G, Bjorvell H: Fatty acid composition in serum lipids and adipose tissue in severe obesity before and after six weeks of weight loss. Int J Obes. 1989;13(5):603-12. [PubMed:2583914 ]
Ho RC, Davy KP, Hickey MS, Summers SA, Melby CL: Behavioral, metabolic, and molecular correlates of lower insulin sensitivity in Mexican-Americans. Am J Physiol Endocrinol Metab. 2002 Oct;283(4):E799-808. [PubMed:12217898 ]
Yli-Jama P, Haugen TS, Rebnord HM, Ringstad J, Pedersen JI: Selective mobilisation of fatty acids from human adipose tissue. Eur J Intern Med. 2001 Apr;12(2):107-115. [PubMed:11297913 ]
Prandota J: Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. Drugs. 1988 May;35(5):542-78. [PubMed:3293970 ]

Showing NP-Card for Palmitoleic acid (NP0001123)

MOL for NP0001123 (Palmitoleic acid)

3D MOL for NP0001123 (Palmitoleic acid)

3D SDF for NP0001123 (Palmitoleic acid)

3D-SDF for NP0001123 (Palmitoleic acid)

PDB for NP0001123 (Palmitoleic acid)

3D PDB for NP0001123 (Palmitoleic acid)

SMILES for NP0001123 (Palmitoleic acid)

INCHI for NP0001123 (Palmitoleic acid)

Structure for NP0001123 (Palmitoleic acid)

3D Structure for NP0001123 (Palmitoleic acid)