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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (41) Show 41 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-06-16 18:12:22 UTC

Update Date

2022-11-30 19:04:10 UTC

HMDB ID

HMDB0012408

Secondary Accession Numbers

HMDB12408

Metabolite Identification

Common Name

PS(18:3(9Z,12Z,15Z)/14:1(9Z))

Description

PS(18:3(9Z,12Z,15Z)/14:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines 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. PS(18:3(9Z,12Z,15Z)/14:1(9Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the myristoleic acid moiety is derived from milk fats. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.

Structure

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


  Mrv0541 02241204012D          

 52 51  0  0  1  0            999 V2000
   24.4273   -4.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.6851   -5.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0100   -6.2918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.3349   -5.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3602   -6.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6597   -6.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4832   -7.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0353   -5.9021    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.6456   -5.2269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4251   -6.5772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7105   -5.5123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3855   -5.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0607   -5.5123    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.5978   -7.1011    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.7515   -4.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3997   -5.2800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7515   -3.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9022   -5.9961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7992   -5.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5136   -6.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2281   -5.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9426   -5.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6571   -6.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3716   -5.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0861   -5.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8005   -6.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5150   -5.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2295   -5.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9439   -6.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6584   -5.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3729   -6.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0874   -5.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8019   -6.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5163   -5.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2308   -6.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9453   -5.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9453   -5.0543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4805   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1950   -7.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9094   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6239   -7.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3384   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0529   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7674   -7.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4819   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1963   -7.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9108   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6253   -7.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3397   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0543   -7.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7687   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7687   -8.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  3  7  1  6  0  0  0
  8  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  3 14  1  1  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 13  1  1  6  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  2  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  2  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  2  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34 33  1  0  0  0  0
 35 34  1  0  0  0  0
 36 35  1  0  0  0  0
 37 36  2  0  0  0  0
  6 36  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  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
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51  7  1  0  0  0  0
 51 52  2  0  0  0  0
M  END

HMDB0012408
     RDKit          3D
PS(18:3(9Z,12Z,15Z)/14:1(9Z))
116115  0  0  0  0  0  0  0  0999 V2000
    3.5368   -5.4329   -3.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0869   -4.3191   -2.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9992   -3.9581   -1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -4.0720   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -4.5455    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265   -5.0828    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5024   -4.5788    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.3767    1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4020   -2.3790    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9240   -1.2017    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -0.7492    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9131    0.4883    1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113    1.0916    2.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6535    1.5801    1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    2.6469    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1485    3.1689   -0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703    3.7524   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305    4.3215   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9680    5.5776   -1.1516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1155    3.6204   -1.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0532    4.3090   -2.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040    3.4336   -2.8789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9129    2.7005   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885    3.5798   -0.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3447    2.6556    0.1950 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.7803    1.3886   -0.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    2.3951    1.5452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7472    3.4472    0.7544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5799    2.4363    1.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8694    2.9575    1.7798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6478    3.6668    0.7857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7233    3.7348    3.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2409    4.8776    3.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0133    3.2430    4.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824    2.4529   -3.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9704    2.4135   -5.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    3.2811   -5.4447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4163    1.3913   -5.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    0.3829   -5.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2389   -0.4494   -4.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -1.4440   -3.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874   -2.3047   -2.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5274   -1.4404   -1.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029   -2.2995   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021   -3.2550    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086   -3.3035    1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5846   -2.3615    2.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792   -3.1341    3.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786   -2.2048    4.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7654   -2.9387    5.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067   -5.5627   -4.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -6.3693   -2.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6264   -5.0623   -3.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426   -4.5869   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070   -3.4545   -3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0599   -3.5566   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -3.7296    0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -3.7587    1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -5.3532    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752   -6.0418   -0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4112   -5.0684    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9508   -3.0085    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5414   -3.7106    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3804   -2.6387   -0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5130   -0.5305   -0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0258   -1.4989    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308   -0.3821   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742    1.1790    0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6091    0.1568    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239    0.2975    2.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943    1.8887    2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    0.7181    0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656    2.0512    1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5686    3.4697    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    2.2834   -0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    2.3843   -1.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6380    3.9940   -1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004    4.5426    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    2.9653    0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    5.0575   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4956    4.8811   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8029    4.0682   -3.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    1.9855   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678    2.0896   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    3.2479    2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0193    1.9517    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7850    1.6568    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4896    2.0555    2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1912    3.7168   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6487    3.3268    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1174    2.7897    3.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939    1.9596   -6.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299    0.9475   -6.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -0.3485   -6.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923    0.8452   -4.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7838    0.1718   -3.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292   -1.0309   -4.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.1351   -4.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241204012D          

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  3  2  1  0  0  0  0
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  6  4  1  0  0  0  0
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  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
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 37 36  2  0  0  0  0
  6 36  1  0  0  0  0
 38 39  1  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
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 51 52  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012408

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C38H66NO10P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-19-14-12-10-8-6-4-2/h5,7,10-13,16-17,34-35H,3-4,6,8-9,14-15,18-33,39H2,1-2H3,(H,42,43)(H,44,45)/b7-5-,12-10-,13-11-,17-16-/t34-,35+/m1/s1

> <INCHI_KEY>
FMGPGIMIGMLEBQ-JHJZYHDZSA-N

> <FORMULA>
C38H66NO10P

> <MOLECULAR_WEIGHT>
727.9051

> <EXACT_MASS>
727.442433849

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
82.19656139542735

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-({hydroxy[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
8.045820138899273

> <ALOGPS_LOGS>
-6.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.178396015655446

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4680339991787528

> <JCHEM_PKA_STRONGEST_BASIC>
9.376604467850061

> <JCHEM_POLAR_SURFACE_AREA>
171.68

> <JCHEM_REFRACTIVITY>
201.30020000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{[hydroxy(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxyphosphoryl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012408
     RDKit          3D
PS(18:3(9Z,12Z,15Z)/14:1(9Z))
116115  0  0  0  0  0  0  0  0999 V2000
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    7.4020   -2.3790    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6167   -0.7492    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1040    3.4336   -2.8789 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.0426   -4.5869   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070   -3.4545   -3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0599   -3.5566   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -3.7296    0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -3.7587    1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -5.3532    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752   -6.0418   -0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4112   -5.0684    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9508   -3.0085    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5414   -3.7106    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3804   -2.6387   -0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5130   -0.5305   -0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0258   -1.4989    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308   -0.3821   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742    1.1790    0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6091    0.1568    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239    0.2975    2.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943    1.8887    2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    0.7181    0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656    2.0512    1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5686    3.4697    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    2.2834   -0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    2.3843   -1.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6380    3.9940   -1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004    4.5426    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    2.9653    0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    5.0575   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4956    4.8811   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8029    4.0682   -3.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    1.9855   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678    2.0896   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    3.2479    2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0193    1.9517    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7850    1.6568    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4896    2.0555    2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1912    3.7168   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6487    3.3268    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1174    2.7897    3.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939    1.9596   -6.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299    0.9475   -6.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -0.3485   -6.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923    0.8452   -4.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7838    0.1718   -3.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292   -1.0309   -4.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.1351   -4.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -0.9216   -3.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -3.1065   -2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9040   -2.7564   -3.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -0.8036   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -0.8668   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0074   -2.8512   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -1.6176    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260   -4.0073   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -4.0636    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -1.8781    2.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -1.5950    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940   -3.7122    2.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -3.8422    3.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647   -1.5560    4.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.5430    3.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0998   -3.6481    6.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1376   -2.1828    6.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -3.4392    5.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
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M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  H   UNK     0      45.598  -8.950   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      40.479 -11.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.219 -11.745   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      37.958 -11.017   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      41.739 -11.745   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      36.698 -11.745   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      38.235 -13.200   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0      42.999 -11.017   0.000  0.00  0.00           P+0
HETATM    9  O   UNK     0      42.272  -9.757   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      43.727 -12.277   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      44.260 -10.290   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      45.520 -11.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      46.780 -10.290   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      40.316 -13.255   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      48.069  -8.994   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      49.279  -9.856   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      48.069  -7.436   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      48.351 -11.193   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      12.692 -10.975   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.025 -11.745   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.359 -10.975   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.693 -10.975   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.027 -11.745   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.360 -10.975   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.694 -10.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.028 -11.745   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.361 -10.975   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.695 -10.975   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.029 -11.745   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.362 -10.975   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      28.696 -11.745   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.030 -10.975   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.364 -11.745   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      32.697 -10.975   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      34.031 -11.745   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      35.365 -10.975   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      35.365  -9.435   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.564 -13.970   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.897 -13.200   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      22.231 -13.970   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      23.565 -13.200   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      24.898 -13.970   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      26.232 -13.970   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      27.566 -13.200   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      28.900 -13.970   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      30.233 -13.200   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      31.567 -13.970   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      32.901 -13.200   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      34.234 -13.970   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      35.568 -13.200   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      36.902 -13.970   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      36.902 -15.510   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    3    5                                                       
CONECT    3    2    4    7   14                                             
CONECT    4    3    6                                                       
CONECT    5    2    8                                                       
CONECT    6    4   36                                                       
CONECT    7    3   51                                                       
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   15   18    1                                             
CONECT   14    3                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19   20                                                            
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37    6                                                  
CONECT   37   36                                                            
CONECT   38   39                                                            
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50    7   52                                                  
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  102    0
END

COMPND    HMDB0012408
HETATM    1  C1  UNL     1       3.537  -5.433  -3.364  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.087  -4.319  -2.456  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.999  -3.958  -1.537  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.057  -4.072  -0.256  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.082  -4.545   0.654  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.327  -5.083   0.182  1.00  0.00           C  
HETATM    7  C7  UNL     1       6.502  -4.579   0.418  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.736  -3.377   1.209  1.00  0.00           C  
HETATM    9  C9  UNL     1       7.402  -2.379   0.341  1.00  0.00           C  
HETATM   10  C10 UNL     1       6.924  -1.202   0.048  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.617  -0.749   0.581  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.913   0.488   1.419  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.711   1.092   2.050  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.653   1.580   1.101  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.183   2.647   0.200  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.148   3.169  -0.748  1.00  0.00           C  
HETATM   17  C17 UNL     1       1.970   3.752  -0.043  1.00  0.00           C  
HETATM   18  C18 UNL     1       0.930   4.322  -0.903  1.00  0.00           C  
HETATM   19  O1  UNL     1       0.968   5.578  -1.152  1.00  0.00           O  
HETATM   20  O2  UNL     1      -0.115   3.620  -1.486  1.00  0.00           O  
HETATM   21  C19 UNL     1      -1.053   4.309  -2.284  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.104   3.434  -2.879  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.913   2.700  -1.832  1.00  0.00           C  
HETATM   24  O3  UNL     1      -3.489   3.580  -0.900  1.00  0.00           O  
HETATM   25  P1  UNL     1      -4.345   2.656   0.195  1.00  0.00           P  
HETATM   26  O4  UNL     1      -4.780   1.389  -0.456  1.00  0.00           O  
HETATM   27  O5  UNL     1      -3.366   2.395   1.545  1.00  0.00           O  
HETATM   28  O6  UNL     1      -5.747   3.447   0.754  1.00  0.00           O  
HETATM   29  C22 UNL     1      -6.580   2.436   1.243  1.00  0.00           C  
HETATM   30  C23 UNL     1      -7.869   2.957   1.780  1.00  0.00           C  
HETATM   31  N1  UNL     1      -8.648   3.667   0.786  1.00  0.00           N  
HETATM   32  C24 UNL     1      -7.723   3.735   3.028  1.00  0.00           C  
HETATM   33  O7  UNL     1      -8.241   4.878   3.152  1.00  0.00           O  
HETATM   34  O8  UNL     1      -7.013   3.243   4.113  1.00  0.00           O  
HETATM   35  O9  UNL     1      -1.582   2.453  -3.751  1.00  0.00           O  
HETATM   36  C25 UNL     1      -1.970   2.414  -5.074  1.00  0.00           C  
HETATM   37  O10 UNL     1      -2.800   3.281  -5.445  1.00  0.00           O  
HETATM   38  C26 UNL     1      -1.416   1.391  -5.979  1.00  0.00           C  
HETATM   39  C27 UNL     1      -0.534   0.383  -5.345  1.00  0.00           C  
HETATM   40  C28 UNL     1      -1.239  -0.449  -4.288  1.00  0.00           C  
HETATM   41  C29 UNL     1      -0.318  -1.444  -3.673  1.00  0.00           C  
HETATM   42  C30 UNL     1      -0.987  -2.305  -2.646  1.00  0.00           C  
HETATM   43  C31 UNL     1      -1.527  -1.440  -1.536  1.00  0.00           C  
HETATM   44  C32 UNL     1      -2.203  -2.299  -0.464  1.00  0.00           C  
HETATM   45  C33 UNL     1      -1.302  -3.255   0.142  1.00  0.00           C  
HETATM   46  C34 UNL     1      -1.009  -3.303   1.413  1.00  0.00           C  
HETATM   47  C35 UNL     1      -1.585  -2.361   2.386  1.00  0.00           C  
HETATM   48  C36 UNL     1      -2.379  -3.134   3.452  1.00  0.00           C  
HETATM   49  C37 UNL     1      -2.979  -2.205   4.457  1.00  0.00           C  
HETATM   50  C38 UNL     1      -3.765  -2.939   5.522  1.00  0.00           C  
HETATM   51  H1  UNL     1       4.307  -5.563  -4.163  1.00  0.00           H  
HETATM   52  H2  UNL     1       3.410  -6.369  -2.783  1.00  0.00           H  
HETATM   53  H3  UNL     1       2.626  -5.062  -3.833  1.00  0.00           H  
HETATM   54  H4  UNL     1       5.043  -4.587  -2.077  1.00  0.00           H  
HETATM   55  H5  UNL     1       4.207  -3.455  -3.228  1.00  0.00           H  
HETATM   56  H6  UNL     1       2.060  -3.557  -1.990  1.00  0.00           H  
HETATM   57  H7  UNL     1       2.102  -3.730   0.269  1.00  0.00           H  
HETATM   58  H8  UNL     1       4.252  -3.759   1.465  1.00  0.00           H  
HETATM   59  H9  UNL     1       3.550  -5.353   1.306  1.00  0.00           H  
HETATM   60  H10 UNL     1       5.275  -6.042  -0.410  1.00  0.00           H  
HETATM   61  H11 UNL     1       7.411  -5.068   0.007  1.00  0.00           H  
HETATM   62  H12 UNL     1       5.951  -3.008   1.848  1.00  0.00           H  
HETATM   63  H13 UNL     1       7.541  -3.711   1.986  1.00  0.00           H  
HETATM   64  H14 UNL     1       8.380  -2.639  -0.097  1.00  0.00           H  
HETATM   65  H15 UNL     1       7.513  -0.530  -0.616  1.00  0.00           H  
HETATM   66  H16 UNL     1       5.026  -1.499   1.096  1.00  0.00           H  
HETATM   67  H17 UNL     1       5.031  -0.382  -0.326  1.00  0.00           H  
HETATM   68  H18 UNL     1       6.474   1.179   0.763  1.00  0.00           H  
HETATM   69  H19 UNL     1       6.609   0.157   2.217  1.00  0.00           H  
HETATM   70  H20 UNL     1       4.224   0.297   2.680  1.00  0.00           H  
HETATM   71  H21 UNL     1       4.994   1.889   2.776  1.00  0.00           H  
HETATM   72  H22 UNL     1       3.215   0.718   0.589  1.00  0.00           H  
HETATM   73  H23 UNL     1       2.866   2.051   1.761  1.00  0.00           H  
HETATM   74  H24 UNL     1       4.569   3.470   0.860  1.00  0.00           H  
HETATM   75  H25 UNL     1       5.099   2.283  -0.338  1.00  0.00           H  
HETATM   76  H26 UNL     1       2.887   2.384  -1.475  1.00  0.00           H  
HETATM   77  H27 UNL     1       3.638   3.994  -1.341  1.00  0.00           H  
HETATM   78  H28 UNL     1       2.300   4.543   0.663  1.00  0.00           H  
HETATM   79  H29 UNL     1       1.505   2.965   0.604  1.00  0.00           H  
HETATM   80  H30 UNL     1      -1.540   5.057  -1.641  1.00  0.00           H  
HETATM   81  H31 UNL     1      -0.496   4.881  -3.052  1.00  0.00           H  
HETATM   82  H32 UNL     1      -2.803   4.068  -3.452  1.00  0.00           H  
HETATM   83  H33 UNL     1      -2.209   1.986  -1.333  1.00  0.00           H  
HETATM   84  H34 UNL     1      -3.668   2.090  -2.351  1.00  0.00           H  
HETATM   85  H35 UNL     1      -3.315   3.248   2.030  1.00  0.00           H  
HETATM   86  H36 UNL     1      -6.019   1.952   2.066  1.00  0.00           H  
HETATM   87  H37 UNL     1      -6.785   1.657   0.484  1.00  0.00           H  
HETATM   88  H38 UNL     1      -8.490   2.056   2.050  1.00  0.00           H  
HETATM   89  H39 UNL     1      -8.191   3.717  -0.135  1.00  0.00           H  
HETATM   90  H40 UNL     1      -9.649   3.327   0.727  1.00  0.00           H  
HETATM   91  H41 UNL     1      -6.117   2.790   3.980  1.00  0.00           H  
HETATM   92  H42 UNL     1      -0.794   1.960  -6.733  1.00  0.00           H  
HETATM   93  H43 UNL     1      -2.230   0.947  -6.595  1.00  0.00           H  
HETATM   94  H44 UNL     1      -0.193  -0.349  -6.117  1.00  0.00           H  
HETATM   95  H45 UNL     1       0.392   0.845  -4.948  1.00  0.00           H  
HETATM   96  H46 UNL     1      -1.784   0.172  -3.567  1.00  0.00           H  
HETATM   97  H47 UNL     1      -2.029  -1.031  -4.845  1.00  0.00           H  
HETATM   98  H48 UNL     1       0.112  -2.135  -4.446  1.00  0.00           H  
HETATM   99  H49 UNL     1       0.541  -0.922  -3.160  1.00  0.00           H  
HETATM  100  H50 UNL     1      -0.318  -3.106  -2.268  1.00  0.00           H  
HETATM  101  H51 UNL     1      -1.904  -2.756  -3.133  1.00  0.00           H  
HETATM  102  H52 UNL     1      -0.791  -0.804  -1.050  1.00  0.00           H  
HETATM  103  H53 UNL     1      -2.391  -0.867  -1.985  1.00  0.00           H  
HETATM  104  H54 UNL     1      -3.007  -2.851  -1.053  1.00  0.00           H  
HETATM  105  H55 UNL     1      -2.754  -1.618   0.172  1.00  0.00           H  
HETATM  106  H56 UNL     1      -0.826  -4.007  -0.529  1.00  0.00           H  
HETATM  107  H57 UNL     1      -0.305  -4.064   1.821  1.00  0.00           H  
HETATM  108  H58 UNL     1      -0.717  -1.878   2.901  1.00  0.00           H  
HETATM  109  H59 UNL     1      -2.243  -1.595   2.023  1.00  0.00           H  
HETATM  110  H60 UNL     1      -3.194  -3.712   2.985  1.00  0.00           H  
HETATM  111  H61 UNL     1      -1.724  -3.842   3.990  1.00  0.00           H  
HETATM  112  H62 UNL     1      -2.265  -1.556   4.971  1.00  0.00           H  
HETATM  113  H63 UNL     1      -3.698  -1.543   3.930  1.00  0.00           H  
HETATM  114  H64 UNL     1      -3.100  -3.648   6.029  1.00  0.00           H  
HETATM  115  H65 UNL     1      -4.138  -2.183   6.224  1.00  0.00           H  
HETATM  116  H66 UNL     1      -4.663  -3.439   5.079  1.00  0.00           H  
CONECT    1    2   51   52   53
CONECT    2    3   54   55
CONECT    3    4    4   56
CONECT    4    5   57
CONECT    5    6   58   59
CONECT    6    7    7   60
CONECT    7    8   61
CONECT    8    9   62   63
CONECT    9   10   10   64
CONECT   10   11   65
CONECT   11   12   66   67
CONECT   12   13   68   69
CONECT   13   14   70   71
CONECT   14   15   72   73
CONECT   15   16   74   75
CONECT   16   17   76   77
CONECT   17   18   78   79
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   80   81
CONECT   22   23   35   82
CONECT   23   24   83   84
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   85
CONECT   28   29
CONECT   29   30   86   87
CONECT   30   31   32   88
CONECT   31   89   90
CONECT   32   33   33   34
CONECT   34   91
CONECT   35   36
CONECT   36   37   37   38
CONECT   38   39   92   93
CONECT   39   40   94   95
CONECT   40   41   96   97
CONECT   41   42   98   99
CONECT   42   43  100  101
CONECT   43   44  102  103
CONECT   44   45  104  105
CONECT   45   46   46  106
CONECT   46   47  107
CONECT   47   48  108  109
CONECT   48   49  110  111
CONECT   49   50  112  113
CONECT   50  114  115  116
END

HMDB0012408
     RDKit          3D
PS(18:3(9Z,12Z,15Z)/14:1(9Z))
116115  0  0  0  0  0  0  0  0999 V2000
    3.5368   -5.4329   -3.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0869   -4.3191   -2.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9992   -3.9581   -1.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -4.0720   -0.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -4.5455    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265   -5.0828    0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5024   -4.5788    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.3767    1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4020   -2.3790    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9240   -1.2017    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -0.7492    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9131    0.4883    1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113    1.0916    2.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6535    1.5801    1.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    2.6469    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1485    3.1689   -0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703    3.7524   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305    4.3215   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9680    5.5776   -1.1516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1155    3.6204   -1.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0532    4.3090   -2.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040    3.4336   -2.8789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9129    2.7005   -1.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4885    3.5798   -0.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3447    2.6556    0.1950 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.7803    1.3886   -0.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3662    2.3951    1.5452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7472    3.4472    0.7544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5799    2.4363    1.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8694    2.9575    1.7798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6478    3.6668    0.7857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7233    3.7348    3.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2409    4.8776    3.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0133    3.2430    4.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824    2.4529   -3.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9704    2.4135   -5.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    3.2811   -5.4447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4163    1.3913   -5.9792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    0.3829   -5.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2389   -0.4494   -4.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177   -1.4440   -3.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9874   -2.3047   -2.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5274   -1.4404   -1.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029   -2.2995   -0.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021   -3.2550    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0086   -3.3035    1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5846   -2.3615    2.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792   -3.1341    3.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786   -2.2048    4.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7654   -2.9387    5.5216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067   -5.5627   -4.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4103   -6.3693   -2.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6264   -5.0623   -3.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426   -4.5869   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2070   -3.4545   -3.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0599   -3.5566   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -3.7296    0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -3.7587    1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -5.3532    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752   -6.0418   -0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4112   -5.0684    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9508   -3.0085    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5414   -3.7106    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3804   -2.6387   -0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5130   -0.5305   -0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0258   -1.4989    1.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308   -0.3821   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742    1.1790    0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6091    0.1568    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239    0.2975    2.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943    1.8887    2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    0.7181    0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656    2.0512    1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5686    3.4697    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    2.2834   -0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873    2.3843   -1.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6380    3.9940   -1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004    4.5426    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    2.9653    0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401    5.0575   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4956    4.8811   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8029    4.0682   -3.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089    1.9855   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678    2.0896   -2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    3.2479    2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0193    1.9517    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7850    1.6568    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4896    2.0555    2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1912    3.7168   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6487    3.3268    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1174    2.7897    3.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7939    1.9596   -6.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299    0.9475   -6.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -0.3485   -6.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3923    0.8452   -4.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7838    0.1718   -3.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292   -1.0309   -4.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -2.1351   -4.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -0.9216   -3.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184   -3.1065   -2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9040   -2.7564   -3.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914   -0.8036   -1.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -0.8668   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0074   -2.8512   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536   -1.6176    0.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260   -4.0073   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -4.0636    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -1.8781    2.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432   -1.5950    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1940   -3.7122    2.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -3.8422    3.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647   -1.5560    4.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6978   -1.5430    3.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0998   -3.6481    6.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1376   -2.1828    6.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -3.4392    5.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 32 34  1  0
 22 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  2  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
  1 51  1  0
  1 52  1  0
  1 53  1  0
  2 54  1  0
  2 55  1  0
  3 56  1  0
  4 57  1  0
  5 58  1  0
  5 59  1  0
  6 60  1  0
  7 61  1  0
  8 62  1  0
  8 63  1  0
  9 64  1  0
 10 65  1  0
 11 66  1  0
 11 67  1  0
 12 68  1  0
 12 69  1  0
 13 70  1  0
 13 71  1  0
 14 72  1  0
 14 73  1  0
 15 74  1  0
 15 75  1  0
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 16 77  1  0
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 21 80  1  0
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 22 82  1  6
 23 83  1  0
 23 84  1  0
 27 85  1  0
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 29 87  1  0
 30 88  1  1
 31 89  1  0
 31 90  1  0
 34 91  1  0
 38 92  1  0
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 41 99  1  0
 42100  1  0
 42101  1  0
 43102  1  0
 43103  1  0
 44104  1  0
 44105  1  0
 45106  1  0
 46107  1  0
 47108  1  0
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 48110  1  0
 48111  1  0
 49112  1  0
 49113  1  0
 50114  1  0
 50115  1  0
 50116  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-a-Linolenoyl-2-myristoleoyl-sn-glycero-3-phosphoserine	HMDB
1-alpha-Linolenoyl-2-myristoleoyl-sn-glycero-3-phosphoserine	HMDB
Phosphatidylserine(18:3/14:1)	HMDB
Phosphatidylserine(18:3n3/14:1n5)	HMDB
Phosphatidylserine(18:3W3/14:1W5)	HMDB
Phosphatidylserine(32:4)	HMDB
PS(18:3/14:1)	HMDB
PS(18:3N3/14:1N5)	HMDB
PS(18:3W3/14:1W5)	HMDB
PS(32:4)	HMDB
pSer(18:3/14:1)	HMDB
pSer(18:3n3/14:1n5)	HMDB
pSer(18:3W3/14:1W5)	HMDB
pSer(32:4)	HMDB
1-(9Z,12Z,15Z-Octadeatrienoyl)-2-(9Z-tetradecenoyl)-sn-glycero-3-phosphoserine	HMDB
PS(18:3(9Z,12Z,15Z)/14:1(9Z))	Lipid Annotator

Chemical Formula

C₃₈H₆₆NO₁₀P

Average Molecular Weight

727.9051

Monoisotopic Molecular Weight

727.442433849

IUPAC Name

(2S)-2-amino-3-({hydroxy[(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxy]phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[hydroxy(2R)-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]-2-[(9Z)-tetradec-9-enoyloxy]propoxyphosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O

InChI Identifier

InChI=1S/C38H66NO10P/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-19-14-12-10-8-6-4-2/h5,7,10-13,16-17,34-35H,3-4,6,8-9,14-15,18-33,39H2,1-2H3,(H,42,43)(H,44,45)/b7-5-,12-10-,13-11-,17-16-/t34-,35+/m1/s1

InChI Key

FMGPGIMIGMLEBQ-JHJZYHDZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoserines

Direct Parent

Phosphatidylserines

Alternative Parents

Substituents

Diacyl-glycerol-3-phosphoserine
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Tricarboxylic acid or derivatives
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
Primary amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoserines (LMGP03010400 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

endoplasmic reticulum (HMDB: HMDB0012408)

golgi apparatus membrane (HMDB: HMDB0012408)
cell membrane (HMDB: HMDB0012408)
Membrane (HMDB: HMDB0012408)
Extracellular (HMDB: HMDB0012408)

Cell

All cells and tissues (HMDB: HMDB0012408)

Tissue

All Tissues (HMDB: HMDB0012408)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

phosphatidylserine biosynthesis (HMDB: HMDB0012408)
Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/14:1(9Z)) (PathBank: SMP0014506)
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/14:1(9Z)) (PathBank: SMP0015346)

Role

Biological role

Nutrient

Nutrient (PMID: 15979148)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00017 g/L	ALOGPS
logP	4.09	ALOGPS
logP	8.05	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	171.68 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	201.3 m³·mol⁻¹	ChemAxon
Polarizability	82.2 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]+	279.697	31661259
DarkChem	[M-H]-	270.302	31661259
DeepCCS	[M+H]+	279.348	30932474
DeepCCS	[M-H]-	277.452	30932474
DeepCCS	[M-2H]-	310.695	30932474
DeepCCS	[M+Na]+	285.127	30932474
AllCCS	[M+H]+	273.6	32859911
AllCCS	[M+H-H2O]+	273.3	32859911
AllCCS	[M+NH4]+	273.8	32859911
AllCCS	[M+Na]+	273.9	32859911
AllCCS	[M-H]-	260.6	32859911
AllCCS	[M+Na-2H]-	267.0	32859911
AllCCS	[M+HCOO]-	274.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PS(18:3(9Z,12Z,15Z)/14:1(9Z))	[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O	5216.8	Standard polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z))	[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O	4566.5	Standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z))	[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCC)C(O)=O	5102.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	5044.1	Semi standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	4148.4	Standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	6575.8	Standard polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	5113.1	Semi standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	4472.6	Standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	6276.2	Standard polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #3	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	5165.2	Semi standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #3	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	4463.1	Standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #3	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](N[Si](C)(C)C)C(=O)O)O[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	5895.8	Standard polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #4	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	5299.2	Semi standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #4	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	4565.7	Standard non polar	33892256
PS(18:3(9Z,12Z,15Z)/14:1(9Z)),2TMS,isomer #4	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)OC(=O)CCCCCCC/C=C\CCCC	6479.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	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 - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 10V, Positive-QTOF	splash10-001q-0000099900-9e6c17982fdc56ae95aa	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 20V, Positive-QTOF	splash10-000y-0900099900-9299a72e76027c634b6b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 40V, Positive-QTOF	splash10-000y-0900099900-9299a72e76027c634b6b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 10V, Positive-QTOF	splash10-004i-0000010900-493f985a37752f287013	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 20V, Positive-QTOF	splash10-002f-0011291400-634c65e493fd1880dc96	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 40V, Positive-QTOF	splash10-0006-0011291100-7c41102f37878514a2c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 10V, Negative-QTOF	splash10-004i-0000000900-d749c423e348de08a1c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 20V, Negative-QTOF	splash10-004i-0000001900-916d75e720d968676f93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 40V, Negative-QTOF	splash10-01t9-0195506400-ce2c3932ceff062849d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 10V, Positive-QTOF	splash10-0w29-0000016900-1f49f2701902cb8f4836	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 20V, Positive-QTOF	splash10-0udi-0000002900-0b50db78a93d891fe455	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PS(18:3(9Z,12Z,15Z)/14:1(9Z)) 40V, Positive-QTOF	splash10-0a4i-0090033100-6a94b8c704edb16eb4a5	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

All Tissues
Brain
Heart
Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/14:1(9Z))		Not Available
Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/14:1(9Z))		Not Available

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

FDB029024

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

52925510

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

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 ]
van Engeland M, Nieland LJ, Ramaekers FC, Schutte B, Reutelingsperger CP: Annexin V-affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry. 1998 Jan 1;31(1):1-9. [PubMed:9450519 ]
Vance JE, Tasseva G: Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells. Biochim Biophys Acta. 2013 Mar;1831(3):543-54. doi: 10.1016/j.bbalip.2012.08.016. Epub 2012 Aug 29. [PubMed:22960354 ]
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.
Jean E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. The Journal of Lipid Research, 49, 1377-1387..

Only showing the first 10 proteins. There are 41 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Group 10 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:: PLA2G10
Uniprot ID:: O15496
Molecular weight:: 18153.04

Enzyme Details

2. Diacylglycerol kinase gamma

General function:: Involved in diacylglycerol kinase activity
Specific function:: Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:: DGKG
Uniprot ID:: P49619
Molecular weight:: 89095.3

Enzyme Details

3. Diacylglycerol kinase alpha

General function:: Involved in diacylglycerol kinase activity
Specific function:: Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:: DGKA
Uniprot ID:: P23743
Molecular weight:: 82629.5

Enzyme Details

4. Diacylglycerol kinase delta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:: DGKD
Uniprot ID:: Q16760
Molecular weight:: 134524.2

Enzyme Details

5. Diacylglycerol kinase beta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:: DGKB
Uniprot ID:: Q9Y6T7
Molecular weight:: 90594.7

Enzyme Details

6. Protein kinase C alpha type

General function:: Involved in protein serine/threonine kinase activity
Specific function:: PKC is activated by diacylglycerol which in turn phosphorylates a range of cellular proteins. PKC also serves as the receptor for phorbol esters, a class of tumor promoters
Gene Name:: PRKCA
Uniprot ID:: P17252
Molecular weight:: 76763.5

Enzyme Details

7. Probable phospholipid-transporting ATPase IA

General function:: Involved in ATP binding
Specific function:: May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids, mainly in secretory vesicles
Gene Name:: ATP8A1
Uniprot ID:: Q9Y2Q0
Molecular weight:: 131368.2

Enzyme Details

8. Phospholipid scramblase 1

General function:: Involved in calcium ion binding
Specific function:: May play a role in the antiviral response of interferon (IFN) by amplifying and enhancing the IFN response through increased expression of select subset of potent antiviral genes. May contribute to cytokine-regulated cell proliferation and differentiation
Gene Name:: PLSCR1
Uniprot ID:: O15162
Molecular weight:: 35048.8

Enzyme Details

9. Phosphatidylserine synthase 1

General function:: Involved in phosphatidylserine biosynthetic process
Specific function:: Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine.
Gene Name:: PTDSS1
Uniprot ID:: P48651
Molecular weight:: 55527.18

Enzyme Details

10. 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

Only showing the first 10 proteins. There are 41 proteins in total.

Show all enzymes and transporters

Showing metabocard for PS(18:3(9Z,12Z,15Z)/14:1(9Z)) (HMDB0012408)

MOL for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

3D MOL for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

3D SDF for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

3D-SDF for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

PDB for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

3D PDB for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

SMILES for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

INCHI for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

Structure for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

3D Structure for HMDB0012408 (PS(18:3(9Z,12Z,15Z)/14:1(9Z)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes