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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-07-12 17:07:38 UTC

HMDB ID

HMDB0000658

Secondary Accession Numbers

HMDB0005197
HMDB0062460
HMDB00658
HMDB05197
HMDB62460

Metabolite Identification

Common Name

CE(16:1)

Description

CE(16:1(9Z)), also known as (Z)-cholesterol 9-hexadecenoate or 1-palmitoleoyl-cholesterol, is an important plasma cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Cholesteryl palmitoleate is one of the two more prevalent esters that are a component of dehydroepiandrosterone fatty acid esters (DHEA-FA). DHEA-FA is formed from DHEA by lecithin-cholesterol acyltransferase, localized on high-density lipoprotein (HDL). Once DHEA-FA is formed, it is subsequently transferred to very low-density lipoprotein (VLDL) and low-density lipoprotein (LDL), like cholesteryl esters. Cholesteryl palmitoleate constitutes 20% of the total lipoidal pregnenolone (an important precursor steroid) in follicular fluid. The fatty acid components of the resulting lipoidal pregnenolone derivatives resemble those of cholesteryl esters formed in plasma by the enzymatic activity of lecithin–cholesterol acyltransferase (LCAT) (PMID: 2770299 , 8943795 ). CE(16:1(9Z)) is considered to be practically insoluble (in water) and basic.

Structure

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


  Mrv1652307201918012D          

 49 52  0  0  0  0            999 V2000
10000.6845 9997.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8214 9998.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8214 9995.8010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5454 9994.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8318 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1180 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4035 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6894 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9754 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2612 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5472 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8331 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1169 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2924 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.5784 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.8642 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.1501 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.4359 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.7219 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.0078 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8318 9996.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1098 9997.0345    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.3961 9995.8010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9721 9996.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2580 9996.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2580 9995.3821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9721 9994.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1091 9997.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3949 9997.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3971 9996.6208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6829 9996.2085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.6829 9995.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3971 9994.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1113 9995.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1113 9996.2085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.8233 9997.4532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.8233 9996.6285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.6076 9996.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0923 9997.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6076 9997.7082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.6076 9998.5327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.3227 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0379 9998.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.7528 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.4679 9998.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.1851 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.4679 9997.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8905 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3227 9998.1194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  2  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 26  4  1  1  0  0  0
 30 31  1  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 24 31  1  0  0  0  0
 27 32  1  0  0  0  0
 29 30  1  0  0  0  0
 31  1  1  1  0  0  0
 35 22  1  1  0  0  0
 30 23  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 41  1  0  0  0  0
 40 49  1  6  0  0  0
 41 42  1  0  0  0  0
 41 48  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 40 36  1  0  0  0  0
 40 39  1  0  0  0  0
 28 36  1  0  0  0  0
 36  2  1  1  0  0  0
 37  3  1  6  0  0  0
 35 37  1  0  0  0  0
M  END

HMDB0000658
     RDKit          3D
CE(16:1(9Z))
119122  0  0  0  0  0  0  0  0999 V2000
   13.9821    1.8403   -2.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281    0.8405   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1138   -0.4288   -1.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6597   -1.4506   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875   -1.0085   -0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2603   -0.7007   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1992   -0.2945   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0436   -0.8720    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6501   -2.0732   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -3.2577    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2857   -2.9391    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0169   -2.6116    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9098   -2.3105    1.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2719   -1.1385    2.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.7971    3.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385   -0.4712    2.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0746   -1.4130    2.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213    0.7630    2.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    0.9460    1.4781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2825    2.1766    2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7474    2.0942    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9976    2.1586    0.2600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0666    3.6301   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8983    1.5712   -0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    1.3376   -1.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    1.6169   -2.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954    1.8162   -1.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2395    1.4179   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3992    1.6608    0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5562    0.7651    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9399    0.9805   -1.0296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4608    2.3879   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    0.9315   -1.9573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3155    1.1133   -3.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7112    0.5377   -3.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6616   -0.0783   -1.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8337   -0.8009   -1.3592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0893   -1.8049   -2.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1174   -0.2679   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1908    0.5084    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8613   -0.2016    1.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7243   -1.2995    2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9159   -2.5023    1.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0911   -0.7916    2.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336    1.2392   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5127    1.3003   -3.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0566    2.2951   -2.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6150    2.6088   -1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6854    1.2671   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681    0.5890   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9872   -0.8181   -2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3097   -0.2129   -2.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4676   -1.7737   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3168   -2.3475   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2019   -1.8703    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7318   -0.1445    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0361   -1.5597   -1.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5745    0.1755   -1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3961    0.5935    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3035   -0.4567    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3386   -2.3455   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7075   -1.7681   -1.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2909   -3.4725    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1074   -4.1308   -0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0745   -3.8024    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6795   -2.0969    1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6988   -3.4890   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0938   -1.6864   -0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0138   -2.0303    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268   -3.1875    2.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2330   -1.2693    2.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295   -0.2163    1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.1250    3.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -1.5820    4.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415    0.0293    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740    2.1707    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138    3.0541    1.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    1.0823    2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998    2.9070    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    4.1638    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    3.7808   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    4.0572    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615    0.9089   -2.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2516    2.5406   -3.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139    0.8127   -3.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8302    2.8990   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067    0.3290   -0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1015    1.3555    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6831    2.7302    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3084   -0.2752    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4023    1.1295    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5107    2.4089   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3764    2.9921   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8700    2.9629   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3457   -0.1261   -1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3048    2.1337   -3.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7133    0.5068   -4.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5143    1.2588   -3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8298   -0.2996   -3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8556   -0.9046   -1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5054   -1.5494   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6490   -1.2038   -3.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7411   -2.6103   -2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1424   -2.1116   -2.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8414   -1.1323   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6439    0.3169   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6045    1.4622    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2665    0.9343    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8283   -0.6614    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6630    0.5248    2.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2448   -1.6580    3.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0590   -2.7988    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0602   -3.3894    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8910   -2.5040    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9592   -0.1886    3.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6608   -1.6933    2.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6582   -0.2935    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    0.3469   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    2.0874   -0.2102 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 42 44  1  0
 24 45  1  0
 45 19  1  0
 28 22  1  0
 36 31  1  0
 33 27  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  2 49  1  0
  2 50  1  0
  3 51  1  0
  3 52  1  0
  4 53  1  0
  4 54  1  0
  5 55  1  0
  5 56  1  0
  6 57  1  0
  6 58  1  0
  7 59  1  0
  8 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  0
 11 66  1  0
 12 67  1  0
 12 68  1  0
 13 69  1  0
 13 70  1  0
 14 71  1  0
 14 72  1  0
 15 73  1  0
 15 74  1  0
 19 75  1  6
 20 76  1  0
 20 77  1  0
 21 78  1  0
 21 79  1  0
 23 80  1  0
 23 81  1  0
 23 82  1  0
 25 83  1  0
 26 84  1  0
 26 85  1  0
 27 86  1  1
 28 87  1  6
 29 88  1  0
 29 89  1  0
 30 90  1  0
 30 91  1  0
 32 92  1  0
 32 93  1  0
 32 94  1  0
 33 95  1  6
 34 96  1  0
 34 97  1  0
 35 98  1  0
 35 99  1  0
 36100  1  6
 37101  1  1
 38102  1  0
 38103  1  0
 38104  1  0
 39105  1  0
 39106  1  0
 40107  1  0
 40108  1  0
 41109  1  0
 41110  1  0
 42111  1  0
 43112  1  0
 43113  1  0
 43114  1  0
 44115  1  0
 44116  1  0
 44117  1  0
 45118  1  0
 45119  1  0
M  END


  Mrv1652307201918012D          

 49 52  0  0  0  0            999 V2000
10000.6845 9997.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8214 9998.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8214 9995.8010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5454 9994.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8318 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1180 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4035 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6894 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9754 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.2612 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.5472 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.8331 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1169 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2924 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.5784 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.8642 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.1501 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.4359 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.7219 9994.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.0078 9995.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8318 9996.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1098 9997.0345    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.3961 9995.8010    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9721 9996.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2580 9996.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2580 9995.3821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9721 9994.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1091 9997.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3949 9997.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3971 9996.6208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6829 9996.2085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.6829 9995.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3971 9994.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1113 9995.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1113 9996.2085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.8233 9997.4532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.8233 9996.6285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.6076 9996.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0923 9997.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6076 9997.7082    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.6076 9998.5327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.3227 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0379 9998.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.7528 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.4679 9998.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.1851 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.4679 9997.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8905 9998.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3227 9998.1194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  2  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
 26  4  1  1  0  0  0
 30 31  1  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 24 31  1  0  0  0  0
 27 32  1  0  0  0  0
 29 30  1  0  0  0  0
 31  1  1  1  0  0  0
 35 22  1  1  0  0  0
 30 23  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 41  1  0  0  0  0
 40 49  1  6  0  0  0
 41 42  1  0  0  0  0
 41 48  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 40 36  1  0  0  0  0
 40 39  1  0  0  0  0
 28 36  1  0  0  0  0
 36  2  1  1  0  0  0
 37  3  1  6  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000658

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36+,37+,38-,39+,40+,42+,43-/m1/s1

> <INCHI_KEY>
HODJWNWCVNUPAQ-XDOSKZMUSA-N

> <FORMULA>
C43H74O2

> <MOLECULAR_WEIGHT>
623.063

> <EXACT_MASS>
622.568881623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
82.58769645556501

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate

> <ALOGPS_LOGP>
10.44

> <JCHEM_LOGP>
13.672021276333334

> <ALOGPS_LOGS>
-8.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042198548687182

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
195.32450000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.78e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000658
     RDKit          3D
CE(16:1(9Z))
119122  0  0  0  0  0  0  0  0999 V2000
   13.9821    1.8403   -2.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281    0.8405   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1138   -0.4288   -1.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6597   -1.4506   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875   -1.0085   -0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2603   -0.7007   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1992   -0.2945   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0436   -0.8720    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6501   -2.0732   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -3.2577    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2857   -2.9391    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0169   -2.6116    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9098   -2.3105    1.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2719   -1.1385    2.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.7971    3.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385   -0.4712    2.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0746   -1.4130    2.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213    0.7630    2.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    0.9460    1.4781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2825    2.1766    2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7474    2.0942    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9976    2.1586    0.2600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0666    3.6301   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8983    1.5712   -0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    1.3376   -1.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    1.6169   -2.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954    1.8162   -1.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2395    1.4179   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3992    1.6608    0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5562    0.7651    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9399    0.9805   -1.0296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4608    2.3879   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    0.9315   -1.9573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3155    1.1133   -3.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7112    0.5377   -3.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6616   -0.0783   -1.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8337   -0.8009   -1.3592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0893   -1.8049   -2.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1174   -0.2679   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1908    0.5084    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8613   -0.2016    1.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7243   -1.2995    2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9159   -2.5023    1.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0911   -0.7916    2.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336    1.2392   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5127    1.3003   -3.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0566    2.2951   -2.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6150    2.6088   -1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6854    1.2671   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681    0.5890   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9872   -0.8181   -2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3097   -0.2129   -2.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4676   -1.7737   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3168   -2.3475   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2019   -1.8703    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7318   -0.1445    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0361   -1.5597   -1.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5745    0.1755   -1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3961    0.5935    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3035   -0.4567    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3386   -2.3455   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7075   -1.7681   -1.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2909   -3.4725    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1074   -4.1308   -0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0    8667.9448661.131   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.9338663.457   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8671.9338658.828   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8663.9528657.270   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8662.6198658.041   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8661.2878657.270   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.9538658.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8658.6208657.270   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8657.2878658.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8655.9548657.270   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8654.6218658.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8653.2888657.270   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8651.9528658.041   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8650.4138658.041   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8649.0808657.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8647.7478658.041   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8646.4148657.270   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8645.0808658.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8643.7488657.270   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8642.4158658.041   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8662.6198659.581   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0    8670.6058661.131   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0    8669.2738658.828   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0    8666.6158660.356   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8665.2828659.586   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8665.2828658.047   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8666.6158657.277   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.6048662.682   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8669.2718661.913   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8669.2758660.359   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8667.9418659.589   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8667.9418658.050   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8669.2758657.280   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8670.6088658.050   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8670.6088659.589   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8671.9378661.913   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8671.9378660.373   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0    8673.4018659.898   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8674.3068661.143   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8673.4018662.389   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8673.4018663.928   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0    8674.7368664.699   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0    8676.0718663.928   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0    8677.4058664.699   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0    8678.7408663.928   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0    8680.0798664.699   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0    8678.7408662.389   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0    8672.0628664.699   0.000  0.00  0.00           C+0
HETATM   49  H   UNK     0    8674.7368663.156   0.000  0.00  0.00           H+0
CONECT    1   31                                                            
CONECT    2   36                                                            
CONECT    3   37                                                            
CONECT    4    5   26                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    5                                                            
CONECT   22   35                                                            
CONECT   23   30                                                            
CONECT   24   25   31                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27    4                                                  
CONECT   27   26   32                                                       
CONECT   28   29   36                                                       
CONECT   29   28   30                                                       
CONECT   30   31   35   29   23                                             
CONECT   31   30   32   24    1                                             
CONECT   32   31   33   27                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   30   34   22   37                                             
CONECT   36   37   40   28    2                                             
CONECT   37   36   38    3   35                                             
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   41   49   36   39                                             
CONECT   41   40   42   48                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   41                                                            
CONECT   49   40                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  104    0
END

COMPND    HMDB0000658
HETATM    1  C1  UNL     1      13.982   1.840  -2.271  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.528   0.840  -1.209  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.114  -0.429  -1.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      12.660  -1.451  -0.971  1.00  0.00           C  
HETATM    5  C5  UNL     1      11.488  -1.008  -0.156  1.00  0.00           C  
HETATM    6  C6  UNL     1      10.260  -0.701  -1.039  1.00  0.00           C  
HETATM    7  C7  UNL     1       9.199  -0.295  -0.123  1.00  0.00           C  
HETATM    8  C8  UNL     1       8.044  -0.872   0.038  1.00  0.00           C  
HETATM    9  C9  UNL     1       7.650  -2.073  -0.732  1.00  0.00           C  
HETATM   10  C10 UNL     1       7.379  -3.258   0.154  1.00  0.00           C  
HETATM   11  C11 UNL     1       6.286  -2.939   1.129  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.017  -2.612   0.411  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.910  -2.310   1.416  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.272  -1.139   2.265  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.219  -0.797   3.258  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.938  -0.471   2.606  1.00  0.00           C  
HETATM   17  O1  UNL     1       1.075  -1.413   2.562  1.00  0.00           O  
HETATM   18  O2  UNL     1       1.621   0.763   2.053  1.00  0.00           O  
HETATM   19  C17 UNL     1       0.371   0.946   1.478  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.282   2.177   2.100  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.747   2.094   1.750  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.998   2.159   0.260  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.067   3.630  -0.110  1.00  0.00           C  
HETATM   24  C22 UNL     1      -0.898   1.571  -0.551  1.00  0.00           C  
HETATM   25  C23 UNL     1      -1.146   1.338  -1.819  1.00  0.00           C  
HETATM   26  C24 UNL     1      -2.437   1.617  -2.490  1.00  0.00           C  
HETATM   27  C25 UNL     1      -3.595   1.816  -1.575  1.00  0.00           C  
HETATM   28  C26 UNL     1      -3.240   1.418  -0.134  1.00  0.00           C  
HETATM   29  C27 UNL     1      -4.399   1.661   0.761  1.00  0.00           C  
HETATM   30  C28 UNL     1      -5.556   0.765   0.379  1.00  0.00           C  
HETATM   31  C29 UNL     1      -5.940   0.981  -1.030  1.00  0.00           C  
HETATM   32  C30 UNL     1      -6.461   2.388  -1.204  1.00  0.00           C  
HETATM   33  C31 UNL     1      -4.692   0.931  -1.957  1.00  0.00           C  
HETATM   34  C32 UNL     1      -5.316   1.113  -3.282  1.00  0.00           C  
HETATM   35  C33 UNL     1      -6.711   0.538  -3.143  1.00  0.00           C  
HETATM   36  C34 UNL     1      -6.662  -0.078  -1.727  1.00  0.00           C  
HETATM   37  C35 UNL     1      -7.834  -0.801  -1.359  1.00  0.00           C  
HETATM   38  C36 UNL     1      -8.089  -1.805  -2.537  1.00  0.00           C  
HETATM   39  C37 UNL     1      -9.117  -0.268  -0.936  1.00  0.00           C  
HETATM   40  C38 UNL     1      -9.191   0.508   0.329  1.00  0.00           C  
HETATM   41  C39 UNL     1      -8.861  -0.202   1.582  1.00  0.00           C  
HETATM   42  C40 UNL     1      -9.724  -1.300   2.060  1.00  0.00           C  
HETATM   43  C41 UNL     1      -9.916  -2.502   1.234  1.00  0.00           C  
HETATM   44  C42 UNL     1     -11.091  -0.792   2.534  1.00  0.00           C  
HETATM   45  C43 UNL     1       0.434   1.239  -0.008  1.00  0.00           C  
HETATM   46  H1  UNL     1      14.513   1.300  -3.086  1.00  0.00           H  
HETATM   47  H2  UNL     1      13.057   2.295  -2.693  1.00  0.00           H  
HETATM   48  H3  UNL     1      14.615   2.609  -1.777  1.00  0.00           H  
HETATM   49  H4  UNL     1      12.685   1.267  -0.647  1.00  0.00           H  
HETATM   50  H5  UNL     1      14.368   0.589  -0.511  1.00  0.00           H  
HETATM   51  H6  UNL     1      13.987  -0.818  -2.529  1.00  0.00           H  
HETATM   52  H7  UNL     1      12.310  -0.213  -2.672  1.00  0.00           H  
HETATM   53  H8  UNL     1      13.468  -1.774  -0.281  1.00  0.00           H  
HETATM   54  H9  UNL     1      12.317  -2.347  -1.565  1.00  0.00           H  
HETATM   55  H10 UNL     1      11.202  -1.870   0.513  1.00  0.00           H  
HETATM   56  H11 UNL     1      11.732  -0.144   0.469  1.00  0.00           H  
HETATM   57  H12 UNL     1      10.036  -1.560  -1.649  1.00  0.00           H  
HETATM   58  H13 UNL     1      10.575   0.176  -1.696  1.00  0.00           H  
HETATM   59  H14 UNL     1       9.396   0.594   0.495  1.00  0.00           H  
HETATM   60  H15 UNL     1       7.304  -0.457   0.777  1.00  0.00           H  
HETATM   61  H16 UNL     1       8.339  -2.345  -1.544  1.00  0.00           H  
HETATM   62  H17 UNL     1       6.707  -1.768  -1.282  1.00  0.00           H  
HETATM   63  H18 UNL     1       8.291  -3.472   0.756  1.00  0.00           H  
HETATM   64  H19 UNL     1       7.107  -4.131  -0.477  1.00  0.00           H  
HETATM   65  H20 UNL     1       6.074  -3.802   1.814  1.00  0.00           H  
HETATM   66  H21 UNL     1       6.679  -2.097   1.759  1.00  0.00           H  
HETATM   67  H22 UNL     1       4.699  -3.489  -0.157  1.00  0.00           H  
HETATM   68  H23 UNL     1       5.094  -1.686  -0.209  1.00  0.00           H  
HETATM   69  H24 UNL     1       3.014  -2.030   0.810  1.00  0.00           H  
HETATM   70  H25 UNL     1       3.627  -3.188   2.003  1.00  0.00           H  
HETATM   71  H26 UNL     1       5.233  -1.269   2.828  1.00  0.00           H  
HETATM   72  H27 UNL     1       4.430  -0.216   1.632  1.00  0.00           H  
HETATM   73  H28 UNL     1       3.522   0.125   3.824  1.00  0.00           H  
HETATM   74  H29 UNL     1       3.080  -1.582   4.036  1.00  0.00           H  
HETATM   75  H30 UNL     1      -0.241   0.029   1.584  1.00  0.00           H  
HETATM   76  H31 UNL     1      -0.174   2.171   3.190  1.00  0.00           H  
HETATM   77  H32 UNL     1       0.214   3.054   1.622  1.00  0.00           H  
HETATM   78  H33 UNL     1      -2.094   1.082   2.115  1.00  0.00           H  
HETATM   79  H34 UNL     1      -2.300   2.907   2.268  1.00  0.00           H  
HETATM   80  H35 UNL     1      -1.317   4.164   0.546  1.00  0.00           H  
HETATM   81  H36 UNL     1      -1.648   3.781  -1.145  1.00  0.00           H  
HETATM   82  H37 UNL     1      -3.066   4.057   0.012  1.00  0.00           H  
HETATM   83  H38 UNL     1      -0.362   0.909  -2.435  1.00  0.00           H  
HETATM   84  H39 UNL     1      -2.252   2.541  -3.113  1.00  0.00           H  
HETATM   85  H40 UNL     1      -2.614   0.813  -3.232  1.00  0.00           H  
HETATM   86  H41 UNL     1      -3.830   2.899  -1.555  1.00  0.00           H  
HETATM   87  H42 UNL     1      -3.007   0.329  -0.109  1.00  0.00           H  
HETATM   88  H43 UNL     1      -4.102   1.355   1.790  1.00  0.00           H  
HETATM   89  H44 UNL     1      -4.683   2.730   0.847  1.00  0.00           H  
HETATM   90  H45 UNL     1      -5.308  -0.275   0.635  1.00  0.00           H  
HETATM   91  H46 UNL     1      -6.402   1.130   1.026  1.00  0.00           H  
HETATM   92  H47 UNL     1      -7.511   2.409  -1.581  1.00  0.00           H  
HETATM   93  H48 UNL     1      -6.376   2.992  -0.252  1.00  0.00           H  
HETATM   94  H49 UNL     1      -5.870   2.963  -1.937  1.00  0.00           H  
HETATM   95  H50 UNL     1      -4.346  -0.126  -1.867  1.00  0.00           H  
HETATM   96  H51 UNL     1      -5.305   2.134  -3.699  1.00  0.00           H  
HETATM   97  H52 UNL     1      -4.713   0.507  -4.024  1.00  0.00           H  
HETATM   98  H53 UNL     1      -7.514   1.259  -3.260  1.00  0.00           H  
HETATM   99  H54 UNL     1      -6.830  -0.300  -3.851  1.00  0.00           H  
HETATM  100  H55 UNL     1      -5.856  -0.905  -1.904  1.00  0.00           H  
HETATM  101  H56 UNL     1      -7.505  -1.549  -0.543  1.00  0.00           H  
HETATM  102  H57 UNL     1      -8.649  -1.204  -3.279  1.00  0.00           H  
HETATM  103  H58 UNL     1      -8.741  -2.610  -2.191  1.00  0.00           H  
HETATM  104  H59 UNL     1      -7.142  -2.112  -2.977  1.00  0.00           H  
HETATM  105  H60 UNL     1      -9.841  -1.132  -0.826  1.00  0.00           H  
HETATM  106  H61 UNL     1      -9.644   0.317  -1.769  1.00  0.00           H  
HETATM  107  H62 UNL     1      -8.604   1.462   0.325  1.00  0.00           H  
HETATM  108  H63 UNL     1     -10.267   0.934   0.390  1.00  0.00           H  
HETATM  109  H64 UNL     1      -7.828  -0.661   1.442  1.00  0.00           H  
HETATM  110  H65 UNL     1      -8.663   0.525   2.433  1.00  0.00           H  
HETATM  111  H66 UNL     1      -9.245  -1.658   3.039  1.00  0.00           H  
HETATM  112  H67 UNL     1      -9.059  -2.799   0.631  1.00  0.00           H  
HETATM  113  H68 UNL     1     -10.060  -3.389   1.952  1.00  0.00           H  
HETATM  114  H69 UNL     1     -10.891  -2.504   0.691  1.00  0.00           H  
HETATM  115  H70 UNL     1     -10.959  -0.189   3.461  1.00  0.00           H  
HETATM  116  H71 UNL     1     -11.661  -1.693   2.839  1.00  0.00           H  
HETATM  117  H72 UNL     1     -11.658  -0.294   1.741  1.00  0.00           H  
HETATM  118  H73 UNL     1       0.874   0.347  -0.500  1.00  0.00           H  
HETATM  119  H74 UNL     1       1.117   2.087  -0.210  1.00  0.00           H  
CONECT    1    2   46   47   48
CONECT    2    3   49   50
CONECT    3    4   51   52
CONECT    4    5   53   54
CONECT    5    6   55   56
CONECT    6    7   57   58
CONECT    7    8    8   59
CONECT    8    9   60
CONECT    9   10   61   62
CONECT   10   11   63   64
CONECT   11   12   65   66
CONECT   12   13   67   68
CONECT   13   14   69   70
CONECT   14   15   71   72
CONECT   15   16   73   74
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   45   75
CONECT   20   21   76   77
CONECT   21   22   78   79
CONECT   22   23   24   28
CONECT   23   80   81   82
CONECT   24   25   25   45
CONECT   25   26   83
CONECT   26   27   84   85
CONECT   27   28   33   86
CONECT   28   29   87
CONECT   29   30   88   89
CONECT   30   31   90   91
CONECT   31   32   33   36
CONECT   32   92   93   94
CONECT   33   34   95
CONECT   34   35   96   97
CONECT   35   36   98   99
CONECT   36   37  100
CONECT   37   38   39  101
CONECT   38  102  103  104
CONECT   39   40  105  106
CONECT   40   41  107  108
CONECT   41   42  109  110
CONECT   42   43   44  111
CONECT   43  112  113  114
CONECT   44  115  116  117
CONECT   45  118  119
END

HMDB0000658
     RDKit          3D
CE(16:1(9Z))
119122  0  0  0  0  0  0  0  0999 V2000
   13.9821    1.8403   -2.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5281    0.8405   -1.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1138   -0.4288   -1.9554 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6597   -1.4506   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4875   -1.0085   -0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2603   -0.7007   -1.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1992   -0.2945   -0.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0436   -0.8720    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6501   -2.0732   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -3.2577    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2857   -2.9391    1.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0169   -2.6116    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9098   -2.3105    1.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2719   -1.1385    2.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.7971    3.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9385   -0.4712    2.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0746   -1.4130    2.5615 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6213    0.7630    2.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    0.9460    1.4781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2825    2.1766    2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7474    2.0942    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9976    2.1586    0.2600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0666    3.6301   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8983    1.5712   -0.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    1.3376   -1.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367    1.6169   -2.4901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5954    1.8162   -1.5751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2395    1.4179   -0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3992    1.6608    0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5562    0.7651    0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9399    0.9805   -1.0296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4608    2.3879   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    0.9315   -1.9573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3155    1.1133   -3.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7112    0.5377   -3.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6616   -0.0783   -1.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8337   -0.8009   -1.3592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0893   -1.8049   -2.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1174   -0.2679   -0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1908    0.5084    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8613   -0.2016    1.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7243   -1.2995    2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9159   -2.5023    1.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0911   -0.7916    2.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336    1.2392   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5127    1.3003   -3.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0566    2.2951   -2.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6150    2.6088   -1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6854    1.2671   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3681    0.5890   -0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9872   -0.8181   -2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3097   -0.2129   -2.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4676   -1.7737   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3168   -2.3475   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2019   -1.8703    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7318   -0.1445    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0361   -1.5597   -1.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5745    0.1755   -1.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3961    0.5935    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3035   -0.4567    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3386   -2.3455   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7075   -1.7681   -1.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2909   -3.4725    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1074   -4.1308   -0.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0745   -3.8024    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6795   -2.0969    1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6988   -3.4890   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0938   -1.6864   -0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0138   -2.0303    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268   -3.1875    2.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2330   -1.2693    2.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295   -0.2163    1.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.1250    3.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -1.5820    4.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415    0.0293    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740    2.1707    3.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138    3.0541    1.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944    1.0823    2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998    2.9070    2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    4.1638    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    3.7808   -1.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    4.0572    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615    0.9089   -2.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2516    2.5406   -3.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6139    0.8127   -3.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8302    2.8990   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067    0.3290   -0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1015    1.3555    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6831    2.7302    0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3084   -0.2752    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4023    1.1295    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5107    2.4089   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3764    2.9921   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8700    2.9629   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3457   -0.1261   -1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3048    2.1337   -3.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7133    0.5068   -4.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5143    1.2588   -3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8298   -0.2996   -3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8556   -0.9046   -1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5054   -1.5494   -0.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6490   -1.2038   -3.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7411   -2.6103   -2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1424   -2.1116   -2.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8414   -1.1323   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6439    0.3169   -1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6045    1.4622    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2665    0.9343    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8283   -0.6614    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6630    0.5248    2.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2448   -1.6580    3.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0590   -2.7988    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0602   -3.3894    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8910   -2.5040    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9592   -0.1886    3.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6608   -1.6933    2.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6582   -0.2935    1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    0.3469   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    2.0874   -0.2102 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 42 44  1  0
 24 45  1  0
 45 19  1  0
 28 22  1  0
 36 31  1  0
 33 27  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  2 49  1  0
  2 50  1  0
  3 51  1  0
  3 52  1  0
  4 53  1  0
  4 54  1  0
  5 55  1  0
  5 56  1  0
  6 57  1  0
  6 58  1  0
  7 59  1  0
  8 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  0
 11 66  1  0
 12 67  1  0
 12 68  1  0
 13 69  1  0
 13 70  1  0
 14 71  1  0
 14 72  1  0
 15 73  1  0
 15 74  1  0
 19 75  1  6
 20 76  1  0
 20 77  1  0
 21 78  1  0
 21 79  1  0
 23 80  1  0
 23 81  1  0
 23 82  1  0
 25 83  1  0
 26 84  1  0
 26 85  1  0
 27 86  1  1
 28 87  1  6
 29 88  1  0
 29 89  1  0
 30 90  1  0
 30 91  1  0
 32 92  1  0
 32 93  1  0
 32 94  1  0
 33 95  1  6
 34 96  1  0
 34 97  1  0
 35 98  1  0
 35 99  1  0
 36100  1  6
 37101  1  1
 38102  1  0
 38103  1  0
 38104  1  0
 39105  1  0
 39106  1  0
 40107  1  0
 40108  1  0
 41109  1  0
 41110  1  0
 42111  1  0
 43112  1  0
 43113  1  0
 43114  1  0
 44115  1  0
 44116  1  0
 44117  1  0
 45118  1  0
 45119  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-Cholesterol 9-hexadecenoate	ChEBI
(Z)-Cholesterol 9-hexadecenoic acid	ChEBI
1-Palmitoleoyl-cholesterol	ChEBI
16:1(9Z) Cholesterol ester	ChEBI
CE(16:1(9Z))	ChEBI
CE(16:1/0:0)	ChEBI
CE(16:1n7/0:0)	ChEBI
CE(16:1W7/0:0)	ChEBI
Cholesterol cis-9-hexadecenoate	ChEBI
Cholesteryl (9Z)-hexadecenoate	ChEBI
Cholesterol cis-9-hexadecenoic acid	Generator
Cholesteryl (9Z)-hexadecenoic acid	Generator
Cholesteryl palmitoleic acid	Generator
Cholest-5-en-3b-yl (9Z-hexadecenoate)	Generator, HMDB
Cholest-5-en-3b-yl (9Z-hexadecenoic acid)	Generator, HMDB
Cholest-5-en-3beta-yl (9Z-hexadecenoic acid)	Generator, HMDB
Cholest-5-en-3β-yl (9Z-hexadecenoate)	Generator, HMDB
Cholest-5-en-3β-yl (9Z-hexadecenoic acid)	Generator, HMDB
Cholesteryl 9-hexadecenoate	HMDB
Cholesteryl 9-palmitelaidate	HMDB
Cholesteryl 9-palmitoleate	HMDB
Cholesteryl cis-9-hexadecenoate	HMDB
Cholesterol palmitoleate	HMDB
Cholesteryl cis-hexadecenoate	HMDB
Cholesteryl palmitoleate	HMDB
Cholest-5-en-3beta-yl (9Z-hexadecenoate)	HMDB

Chemical Formula

C₄₃H₇₄O₂

Average Molecular Weight

623.063

Monoisotopic Molecular Weight

622.568881623

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate

CAS Registry Number

16711-66-3

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36+,37+,38-,39+,40+,42+,43-/m1/s1

InChI Key

HODJWNWCVNUPAQ-XDOSKZMUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Cholesteryl esters

Alternative Parents

Substituents

Cholesteryl ester
Cholesterol
Cholestane-skeleton
Delta-5-steroid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholesterol ester (CHEBI:84323 )
Steryl esters (LMST01020006 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000658)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000658)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000658)

Source

Endogenous

Endogenous (HMDB: HMDB0000658)

Animal

Animal (HMDB: HMDB0000658)

Exogenous

Food

Food (HMDB: HMDB0000658)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000658)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000658)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000658)

Lipid metabolism pathway (HMDB: HMDB0000658)

Cellular process

Cell signaling (HMDB: HMDB0000658)

Biochemical process

Lipid transport (HMDB: HMDB0000658)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000658)

Molecular messenger

Signaling molecule (HMDB: HMDB0000658)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	655.26 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3.5e-20 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	17.265 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.8e-06 g/L	ALOGPS
logP	10.44	ALOGPS
logP	13.67	ChemAxon
logS	-8	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	195.32 m³·mol⁻¹	ChemAxon
Polarizability	82.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	257.005	32859911
AllCCS	[M-H]-	210.224	32859911
DeepCCS	[M-2H]-	299.989	30932474
DeepCCS	[M+Na]+	274.004	30932474
AllCCS	[M+H]+	257.0	32859911
AllCCS	[M+H-H2O]+	256.6	32859911
AllCCS	[M+NH4]+	257.3	32859911
AllCCS	[M+Na]+	257.4	32859911
AllCCS	[M-H]-	210.2	32859911
AllCCS	[M+Na-2H]-	216.1	32859911
AllCCS	[M+HCOO]-	222.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
CE(16:1(9Z))	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C	4052.1	Standard polar	33892256
CE(16:1(9Z))	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C	4708.1	Standard non polar	33892256
CE(16:1(9Z))	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C	4588.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - CE(16:1) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-4529073000-025ba6e44b9eae49618d	2017-09-20	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 10V, Positive-QTOF	splash10-00dr-1255039000-31eda8d2e0d85c9d0306	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 20V, Positive-QTOF	splash10-05n0-5449030000-a600e4e0cfe381e9f7a7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 40V, Positive-QTOF	splash10-0a4l-5719230000-9c5803bd30c50c2ab1fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 10V, Negative-QTOF	splash10-00dr-0024009000-69f58d56b9aab51b71ea	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 20V, Negative-QTOF	splash10-000i-0049003000-e8baef11f1d1279c69ac	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 40V, Negative-QTOF	splash10-00ku-2029000000-940b494f7a9dcf0e372c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 10V, Negative-QTOF	splash10-00di-0000009000-a8b40f0a55b15e3e945a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 20V, Negative-QTOF	splash10-0079-1092007000-7d857be6d28d2fb2dee3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 40V, Negative-QTOF	splash10-014i-4920005000-4432da2eefef12b90a88	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 10V, Positive-QTOF	splash10-0600-9013026000-23fa50f7ff69b4b38710	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 20V, Positive-QTOF	splash10-0a4i-9110000000-615e076cfa8f608fe391	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CE(16:1) 40V, Positive-QTOF	splash10-0a4i-9210000000-77c635e834776fd35b8d	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	118.74 +/- 45.54 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	111 +/- 4 uM	Adult (>18 years old)	Both	Normal	20671299	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20147342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

84323

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1440091

References

Synthesis Reference

Wang, Stephen T.; Peter, Frank. Gas-liquid chromatographic determination of fatty acid composition of cholesteryl esters in human serum using silica Sep-Pak cartridges. Journal of Chromatography (1983), 276(2), 249-56.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Roy R, Belanger A: Formation of lipoidal steroids in follicular fluid. J Steroid Biochem. 1989 Aug;33(2):257-62. [PubMed:2770299 ]
Lavallee B, Provost PR, Roy R, Gauthier MC, Belanger A: Dehydroepiandrosterone-fatty acid esters in human plasma: formation, transport and delivery to steroid target tissues. J Endocrinol. 1996 Sep;150 Suppl:S119-24. [PubMed:8943795 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Phosphatidylcholine-sterol acyltransferase

General function:: Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:: Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:: LCAT
Uniprot ID:: P04180
Molecular weight:: 49577.545

Enzyme Details

2. Lysosomal acid lipase/cholesteryl ester hydrolase

General function:: Involved in lipid metabolic process
Specific function:: Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:: LIPA
Uniprot ID:: P38571
Molecular weight:: 45418.71

Enzyme Details

3. Bile salt-activated lipase

General function:: Lipid transport and metabolism
Specific function:: Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:: CEL
Uniprot ID:: P19835
Molecular weight:: 79666.385

Enzyme Details

4. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Enzyme Details

5. Sterol O-acyltransferase 2

General function:: Involved in acyl-CoA binding
Specific function:: Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
Gene Name:: SOAT2
Uniprot ID:: O75908
Molecular weight:: 59895.735

Enzyme Details

6. Sterol O-acyltransferase 1

General function:: Involved in acyl-CoA binding
Specific function:: Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:: SOAT1
Uniprot ID:: P35610
Molecular weight:: 58130.665

Enzyme Details

7. Scavenger receptor class B member 1

General function:: Involved in cell adhesion
Specific function:: Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester
Gene Name:: SCARB1
Uniprot ID:: Q8WTV0
Molecular weight:: 60877.4

Enzyme Details

8. Neutral cholesterol ester hydrolase 1

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes 2-acetyl monoalkylglycerol ether, the penultimate precursor of the pathway for de novo synthesis of platelet-activating factor. May be responsible for cholesterol ester hydrolysis in macrophages, thereby contributing to the development of atherosclerosis. Also involved in organ detoxification by hydrolyzing exogenous organophosphorus compounds. May contribute to cancer pathogenesis by promoting tumor cell migration
Gene Name:: NCEH1
Uniprot ID:: Q6PIU2
Molecular weight:: 45807.4

Showing metabocard for CE(16:1) (HMDB0000658)

MOL for HMDB0000658 (CE(16:1))

3D MOL for HMDB0000658 (CE(16:1))

3D SDF for HMDB0000658 (CE(16:1))

3D-SDF for HMDB0000658 (CE(16:1))

PDB for HMDB0000658 (CE(16:1))

3D PDB for HMDB0000658 (CE(16:1))

SMILES for HMDB0000658 (CE(16:1))

INCHI for HMDB0000658 (CE(16:1))

Structure for HMDB0000658 (CE(16:1))

3D Structure for HMDB0000658 (CE(16:1))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes