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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-16 03:42:25 UTC

Update Date

2022-03-07 03:17:52 UTC

HMDB ID

HMDB0062305

Secondary Accession Numbers

HMDB62305

Metabolite Identification

Common Name

1-(11Z-eicosenoyl)-glycero-3-phosphate

Description

PA(20:1(11z)/0:0)is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(20:1(11z)/0:0), in particular, consists of two 11Z-eicosenoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.

Structure

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


  Mrv1652303161704422D          

 34 33  0  0  1  0            999 V2000
    5.9961    5.9368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    7.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    8.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    9.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    9.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   10.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2842    3.8743    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421    4.6993    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565    5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5546    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7296    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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
  2 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  2  0  0  0  0
M  END

HMDB0062305
     RDKit          3D
1-(11Z-eicosenoyl)-glycero-3-phosphate
 76 75  0  0  0  0  0  0  0  0999 V2000
   -7.0775    0.5273   -3.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4331    0.7665   -3.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0463   -0.4292   -2.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2296   -0.9733   -1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0299    0.0217   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2218   -0.5696    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8466   -1.0299    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0761    0.1625   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7282   -0.1832   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323    0.3386   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    1.3439    1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456    0.8596    2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    0.5835    1.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957    0.1133    3.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7200   -0.1745    2.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3731    1.0523    2.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7984    0.7754    1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094    0.3087    2.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0602    0.0331    2.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2477   -1.0333    1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450   -1.6145    1.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4975   -1.3541    1.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8344   -2.3042    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3657   -1.9306   -1.1788 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9999   -1.8211   -1.2245 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0134   -0.5650   -1.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6217   -0.1436   -2.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023    1.3502   -3.1373 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.2799    2.1505   -3.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7084    2.2140   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6480    1.1458   -4.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1191    0.3625   -4.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4420    1.4242   -3.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5567   -0.3292   -3.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4374    1.6690   -2.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1105    1.0311   -4.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0822   -0.2284   -2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0647   -1.2453   -3.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2956   -1.3876   -1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8220   -1.8212   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0057    0.3327    0.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5560    0.9645   -0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0551    0.2622    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7772   -1.3433    1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9390   -1.8481   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455   -1.4675    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6449    0.4267   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240    1.0121    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801   -0.9390   -1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.0288   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    2.2610    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    1.7276    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0060    1.6881    3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4497   -0.0282    2.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372    1.5191    1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -0.2624    1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1905   -0.7608    3.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    0.9749    3.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394   -0.8996    1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851   -0.6609    3.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668    1.8968    2.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    1.4888    1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154    1.7516    1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    0.0938    0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5197    1.0372    3.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184   -0.6782    3.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4836    1.0048    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6401   -0.2107    3.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3934   -3.3163    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9683   -2.4185    0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7309   -2.6674   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705   -1.3670   -2.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1096   -0.6270   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289    0.1451   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938    2.1450   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290    0.2333   -4.0067 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  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
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 18 66  1  0
 19 67  1  0
 19 68  1  0
 23 69  1  0
 23 70  1  0
 24 71  1  6
 25 72  1  0
 26 73  1  0
 26 74  1  0
 30 75  1  0
 31 76  1  0
M  END


  Mrv1652303161704422D          

 34 33  0  0  1  0            999 V2000
    5.9961    5.9368    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    5.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    7.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    7.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    8.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    9.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    9.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   10.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    4.2868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9974    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4263    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1408    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552    5.5243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2842    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2842    3.8743    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987    3.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4276    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1421    4.6993    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565    5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5546    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7296    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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
  2 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062305

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H45O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28/h9-10,22,24H,2-8,11-21H2,1H3,(H2,26,27,28)/b10-9-/t22-/m1/s1

> <INCHI_KEY>
OAYFHKCHTMNTLM-MZMPXXGTSA-N

> <FORMULA>
C23H45O7P

> <MOLECULAR_WEIGHT>
464.58

> <EXACT_MASS>
464.290290787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.05168118322928

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propoxy]phosphonic acid

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
6.374826851666667

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.531115837556447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.505317785248875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4039997949880556

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
124.50099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062305
     RDKit          3D
1-(11Z-eicosenoyl)-glycero-3-phosphate
 76 75  0  0  0  0  0  0  0  0999 V2000
   -7.0775    0.5273   -3.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4331    0.7665   -3.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0463   -0.4292   -2.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2296   -0.9733   -1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0299    0.0217   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2218   -0.5696    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8466   -1.0299    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0761    0.1625   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7282   -0.1832   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323    0.3386   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    1.3439    1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456    0.8596    2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    0.5835    1.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2957    0.1133    3.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7200   -0.1745    2.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3731    1.0523    2.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7984    0.7754    1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6094    0.3087    2.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0602    0.0331    2.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2477   -1.0333    1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450   -1.6145    1.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4975   -1.3541    1.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8344   -2.3042    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3657   -1.9306   -1.1788 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9999   -1.8211   -1.2245 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0134   -0.5650   -1.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6217   -0.1436   -2.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023    1.3502   -3.1373 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.2799    2.1505   -3.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7084    2.2140   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6480    1.1458   -4.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1191    0.3625   -4.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4420    1.4242   -3.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5567   -0.3292   -3.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4374    1.6690   -2.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1105    1.0311   -4.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0822   -0.2284   -2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0647   -1.2453   -3.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2956   -1.3876   -1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8220   -1.8212   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0057    0.3327    0.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5560    0.9645   -0.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0551    0.2622    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7772   -1.3433    1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9390   -1.8481   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455   -1.4675    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6449    0.4267   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240    1.0121    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801   -0.9390   -1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.0288   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    2.2610    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    1.7276    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0060    1.6881    3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4497   -0.0282    2.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372    1.5191    1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -0.2624    1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1905   -0.7608    3.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    0.9749    3.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394   -0.8996    1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851   -0.6609    3.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668    1.8968    2.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    1.4888    1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154    1.7516    1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    0.0938    0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5197    1.0372    3.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184   -0.6782    3.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4836    1.0048    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6401   -0.2107    3.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3934   -3.3163    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9683   -2.4185    0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7309   -2.6674   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705   -1.3670   -2.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1096   -0.6270   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289    0.1451   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938    2.1450   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290    0.2333   -4.0067 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  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 15 60  1  0
 16 61  1  0
 16 62  1  0
 17 63  1  0
 17 64  1  0
 18 65  1  0
 18 66  1  0
 19 67  1  0
 19 68  1  0
 23 69  1  0
 23 70  1  0
 24 71  1  6
 25 72  1  0
 26 73  1  0
 26 74  1  0
 30 75  1  0
 31 76  1  0
M  END

HEADER    PROTEIN                                 16-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAR-17         0                                  
HETATM    1  H   UNK     0      11.193  11.082   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      12.526  10.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.860  11.082   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860  12.622   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.194  13.392   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.194  14.932   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.527  15.702   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.527  17.242   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.861  18.012   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.861  19.552   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.526   8.772   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      11.193   8.002   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      13.860   8.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.194   8.772   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.527   8.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.861   8.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.195   8.002   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.528   8.772   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.862   8.002   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.196   8.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.529   8.002   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.863   8.772   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.863  10.312   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      27.197   8.002   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      28.530   8.772   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.864   8.002   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      28.530   7.232   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0      29.864   6.462   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      31.198   8.772   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      32.532   8.002   0.000  0.00  0.00           O+0
HETATM   31  P   UNK     0      33.865   8.772   0.000  0.00  0.00           P+0
HETATM   32  O   UNK     0      35.199   9.542   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      34.635   7.438   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      33.095  10.106   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
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                                                            
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   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   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

COMPND    HMDB0062305
HETATM    1  C1  UNL     1      -7.077   0.527  -3.757  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.433   0.767  -3.176  1.00  0.00           C  
HETATM    3  C3  UNL     1      -9.046  -0.429  -2.524  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.230  -0.973  -1.374  1.00  0.00           C  
HETATM    5  C5  UNL     1      -8.030   0.022  -0.282  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.222  -0.570   0.831  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.847  -1.030   0.419  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.076   0.163  -0.125  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.728  -0.183  -0.550  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.632   0.339  -0.041  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.664   1.344   1.032  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.946   0.860   2.297  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.503   0.584   1.914  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.296   0.113   3.095  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.720  -0.175   2.688  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.373   1.052   2.158  1.00  0.00           C  
HETATM   17  C17 UNL     1       3.798   0.775   1.743  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.609   0.309   2.892  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.060   0.033   2.564  1.00  0.00           C  
HETATM   20  C20 UNL     1       6.248  -1.033   1.549  1.00  0.00           C  
HETATM   21  O1  UNL     1       5.245  -1.614   1.096  1.00  0.00           O  
HETATM   22  O2  UNL     1       7.498  -1.354   1.136  1.00  0.00           O  
HETATM   23  C21 UNL     1       7.834  -2.304   0.196  1.00  0.00           C  
HETATM   24  C22 UNL     1       7.366  -1.931  -1.179  1.00  0.00           C  
HETATM   25  O3  UNL     1       6.000  -1.821  -1.224  1.00  0.00           O  
HETATM   26  C23 UNL     1       8.013  -0.565  -1.478  1.00  0.00           C  
HETATM   27  O4  UNL     1       7.622  -0.144  -2.756  1.00  0.00           O  
HETATM   28  P1  UNL     1       8.302   1.350  -3.137  1.00  0.00           P  
HETATM   29  O5  UNL     1       7.280   2.151  -3.908  1.00  0.00           O  
HETATM   30  O6  UNL     1       8.708   2.214  -1.730  1.00  0.00           O  
HETATM   31  O7  UNL     1       9.648   1.146  -4.139  1.00  0.00           O  
HETATM   32  H1  UNL     1      -7.119   0.362  -4.855  1.00  0.00           H  
HETATM   33  H2  UNL     1      -6.442   1.424  -3.537  1.00  0.00           H  
HETATM   34  H3  UNL     1      -6.557  -0.329  -3.326  1.00  0.00           H  
HETATM   35  H4  UNL     1      -8.437   1.669  -2.532  1.00  0.00           H  
HETATM   36  H5  UNL     1      -9.110   1.031  -4.039  1.00  0.00           H  
HETATM   37  H6  UNL     1     -10.082  -0.228  -2.259  1.00  0.00           H  
HETATM   38  H7  UNL     1      -9.065  -1.245  -3.298  1.00  0.00           H  
HETATM   39  H8  UNL     1      -7.296  -1.388  -1.750  1.00  0.00           H  
HETATM   40  H9  UNL     1      -8.822  -1.821  -0.944  1.00  0.00           H  
HETATM   41  H10 UNL     1      -9.006   0.333   0.168  1.00  0.00           H  
HETATM   42  H11 UNL     1      -7.556   0.964  -0.622  1.00  0.00           H  
HETATM   43  H12 UNL     1      -7.055   0.262   1.575  1.00  0.00           H  
HETATM   44  H13 UNL     1      -7.777  -1.343   1.393  1.00  0.00           H  
HETATM   45  H14 UNL     1      -5.939  -1.848  -0.320  1.00  0.00           H  
HETATM   46  H15 UNL     1      -5.345  -1.468   1.306  1.00  0.00           H  
HETATM   47  H16 UNL     1      -5.645   0.427  -1.081  1.00  0.00           H  
HETATM   48  H17 UNL     1      -5.224   1.012   0.522  1.00  0.00           H  
HETATM   49  H18 UNL     1      -3.580  -0.939  -1.362  1.00  0.00           H  
HETATM   50  H19 UNL     1      -1.634   0.029  -0.424  1.00  0.00           H  
HETATM   51  H20 UNL     1      -2.054   2.261   0.727  1.00  0.00           H  
HETATM   52  H21 UNL     1      -3.642   1.728   1.288  1.00  0.00           H  
HETATM   53  H22 UNL     1      -2.006   1.688   3.031  1.00  0.00           H  
HETATM   54  H23 UNL     1      -2.450  -0.028   2.687  1.00  0.00           H  
HETATM   55  H24 UNL     1      -0.137   1.519   1.451  1.00  0.00           H  
HETATM   56  H25 UNL     1      -0.503  -0.262   1.187  1.00  0.00           H  
HETATM   57  H26 UNL     1      -0.190  -0.761   3.555  1.00  0.00           H  
HETATM   58  H27 UNL     1       0.316   0.975   3.824  1.00  0.00           H  
HETATM   59  H28 UNL     1       1.639  -0.900   1.824  1.00  0.00           H  
HETATM   60  H29 UNL     1       2.285  -0.661   3.509  1.00  0.00           H  
HETATM   61  H30 UNL     1       2.367   1.897   2.910  1.00  0.00           H  
HETATM   62  H31 UNL     1       1.826   1.489   1.279  1.00  0.00           H  
HETATM   63  H32 UNL     1       4.215   1.752   1.396  1.00  0.00           H  
HETATM   64  H33 UNL     1       3.753   0.094   0.870  1.00  0.00           H  
HETATM   65  H34 UNL     1       4.520   1.037   3.718  1.00  0.00           H  
HETATM   66  H35 UNL     1       4.218  -0.678   3.276  1.00  0.00           H  
HETATM   67  H36 UNL     1       6.484   1.005   2.184  1.00  0.00           H  
HETATM   68  H37 UNL     1       6.640  -0.211   3.474  1.00  0.00           H  
HETATM   69  H38 UNL     1       7.393  -3.316   0.421  1.00  0.00           H  
HETATM   70  H39 UNL     1       8.968  -2.418   0.194  1.00  0.00           H  
HETATM   71  H40 UNL     1       7.731  -2.667  -1.951  1.00  0.00           H  
HETATM   72  H41 UNL     1       5.670  -1.367  -2.039  1.00  0.00           H  
HETATM   73  H42 UNL     1       9.110  -0.627  -1.363  1.00  0.00           H  
HETATM   74  H43 UNL     1       7.629   0.145  -0.727  1.00  0.00           H  
HETATM   75  H44 UNL     1       9.694   2.145  -1.561  1.00  0.00           H  
HETATM   76  H45 UNL     1      10.029   0.233  -4.007  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6   41   42
CONECT    6    7   43   44
CONECT    7    8   45   46
CONECT    8    9   47   48
CONECT    9   10   10   49
CONECT   10   11   50
CONECT   11   12   51   52
CONECT   12   13   53   54
CONECT   13   14   55   56
CONECT   14   15   57   58
CONECT   15   16   59   60
CONECT   16   17   61   62
CONECT   17   18   63   64
CONECT   18   19   65   66
CONECT   19   20   67   68
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   69   70
CONECT   24   25   26   71
CONECT   25   72
CONECT   26   27   73   74
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   30   75
CONECT   31   76
END

HMDB0062305
     RDKit          3D
1-(11Z-eicosenoyl)-glycero-3-phosphate
 76 75  0  0  0  0  0  0  0  0999 V2000
   -7.0775    0.5273   -3.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4331    0.7665   -3.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0463   -0.4292   -2.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2296   -0.9733   -1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0299    0.0217   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2218   -0.5696    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7282   -0.1832   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323    0.3386   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    1.3439    1.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456    0.8596    2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    0.5835    1.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7200   -0.1745    2.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3731    1.0523    2.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6094    0.3087    2.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0602    0.0331    2.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5567   -0.3292   -3.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1105    1.0311   -4.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0822   -0.2284   -2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2956   -1.3876   -1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7772   -1.3433    1.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9390   -1.8481   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3455   -1.4675    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6449    0.4267   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2240    1.0121    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5801   -0.9390   -1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.0288   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    2.2610    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    1.7276    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0060    1.6881    3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4497   -0.0282    2.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1372    1.5191    1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5033   -0.2624    1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1905   -0.7608    3.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    0.9749    3.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6394   -0.8996    1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851   -0.6609    3.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668    1.8968    2.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8257    1.4888    1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2154    1.7516    1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    0.0938    0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5197    1.0372    3.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2184   -0.6782    3.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4836    1.0048    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6401   -0.2107    3.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3934   -3.3163    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9683   -2.4185    0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7309   -2.6674   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705   -1.3670   -2.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1096   -0.6270   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289    0.1451   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6938    2.1450   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0290    0.2333   -4.0067 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
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  1 32  1  0
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 30 75  1  0
 31 76  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(11Z-Eicosenoyl)-glycero-3-phosphoric acid	Generator

Chemical Formula

C₂₃H₄₅O₇P

Average Molecular Weight

464.58

Monoisotopic Molecular Weight

464.290290787

IUPAC Name

[(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propoxy]phosphonic acid

Traditional Name

(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C23H45O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28/h9-10,22,24H,2-8,11-21H2,1H3,(H2,26,27,28)/b10-9-/t22-/m1/s1

InChI Key

OAYFHKCHTMNTLM-MZMPXXGTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Monoacylglycerophosphates (LMGP10050026 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062305)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.001 g/l	ALOGPS
LogP	5.56	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.56	ALOGPS
logP	6.37	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	124.5 m³·mol⁻¹	ChemAxon
Polarizability	54.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	220.674	31661259
DarkChem	[M-H]-	216.597	31661259
DeepCCS	[M+H]+	224.809	30932474
DeepCCS	[M-H]-	221.166	30932474
DeepCCS	[M-2H]-	257.333	30932474
DeepCCS	[M+Na]+	233.624	30932474
AllCCS	[M+H]+	220.4	32859911
AllCCS	[M+H-H2O]+	218.6	32859911
AllCCS	[M+NH4]+	222.0	32859911
AllCCS	[M+Na]+	222.5	32859911
AllCCS	[M-H]-	214.2	32859911
AllCCS	[M+Na-2H]-	217.4	32859911
AllCCS	[M+HCOO]-	221.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	11.01 minutes	32390414
Predicted by Siyang on May 30, 2022	16.5617 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.56 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3016.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	220.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	586.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	812.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	746.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	420.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1684.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	663.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1489.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	639.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	450.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	325.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	311.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(11Z-eicosenoyl)-glycero-3-phosphate	[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	3907.2	Standard polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate	[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	3055.6	Standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate	[H]\C(CCCCCCCC)=C(/[H])CCCCCCCCCC(=O)OC[C@@]([H])(O)COP(O)(O)=O	3479.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(11Z-eicosenoyl)-glycero-3-phosphate,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C	3495.4	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,1TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C	3488.7	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3463.3	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	3223.4	Standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C	4091.2	Standard polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3457.9	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3236.4	Standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3779.3	Standard polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,3TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3433.9	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,3TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3238.2	Standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,3TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	3522.5	Standard polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3741.4	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,1TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C	3710.9	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3935.9	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3504.9	Standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4108.2	Standard polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3913.9	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3493.9	Standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,2TBDMS,isomer #2	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3901.4	Standard polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4130.1	Semi standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3608.8	Standard non polar	33892256
1-(11Z-eicosenoyl)-glycero-3-phosphate,3TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3698.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(11Z-eicosenoyl)-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positive	splash10-01ot-9440000000-99f9c894e994426b2d91	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(11Z-eicosenoyl)-glycero-3-phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 1-(11Z-eicosenoyl)-glycero-3-phosphate 10V, Positive-QTOF	splash10-014i-0000900000-17a74e4b2e0746fe7dfd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(11Z-eicosenoyl)-glycero-3-phosphate 20V, Positive-QTOF	splash10-014i-0000900000-17a74e4b2e0746fe7dfd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(11Z-eicosenoyl)-glycero-3-phosphate 40V, Positive-QTOF	splash10-00dm-0950700000-41c485b930c1d100558a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(11Z-eicosenoyl)-glycero-3-phosphate 10V, Negative-QTOF	splash10-03di-0000900000-8d11c97e9d5aad9f979a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(11Z-eicosenoyl)-glycero-3-phosphate 20V, Negative-QTOF	splash10-03di-0000900000-8d11c97e9d5aad9f979a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(11Z-eicosenoyl)-glycero-3-phosphate 40V, Negative-QTOF	splash10-114i-2905600000-cc5a89d7cb5d196f3588	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52929759

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
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 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. [PubMed:3748188 ]
Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 1-(11Z-eicosenoyl)-glycero-3-phosphate (HMDB0062305)

MOL for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

3D MOL for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

3D SDF for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

3D-SDF for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

PDB for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

3D PDB for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

SMILES for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

INCHI for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

Structure for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

3D Structure for HMDB0062305 (1-(11Z-eicosenoyl)-glycero-3-phosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra