NP-MRD: Showing NP-Card for LPA(22:0/0:0) (NP0122380)

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Record Information

Version

1.0

Created at

2022-05-12 08:24:44 UTC

Updated at

2022-05-12 08:24:44 UTC

NP-MRD ID

NP0122380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

LPA(22:0/0:0)

Description

LysoPA(22:0/0:0), Also known as lpa(22:0), 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. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. LysoPA(22:0/0:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa). LysoPA(22:0/0:0), In particular, consists of one chain of behenic acid at the C-1 position. It is the biosynthetic precursor of phosphatidic acid. LysoPA(22:0/0:0) Is a lysophosphatidic acid. Lysophosphatidic acid is the simplest possible glycerophospholipid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. It was first documented in 1992 (PMID: 1313792). Fatty acids containing 16 and 18 carbons are the most common (PMID: 11413487) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI

LPA(22:0/0:0)
  Mrv1652303302022392D          

 33 32  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -3.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9025   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6166   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0449   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7590   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4731   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 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
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 84 83  0  0  0  0  0  0  0  0999 V2000
   10.4226   -1.7235   -2.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4592   -1.9616   -3.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1863   -1.1466   -3.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5172   -1.5315   -2.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2621   -0.7363   -1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470    0.7332   -1.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245    1.5896   -1.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6515    1.1858   -0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    1.3628    0.8662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0433    0.9991    2.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345    1.7360    2.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.7736    2.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0140    0.3829    1.9639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670    0.5794    1.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0607   -0.7071    1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255   -1.5096    2.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1641   -0.7732    3.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -0.3786    2.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3595   -1.5247    2.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955   -1.0241    1.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949   -0.0982    0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0051    0.3032    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1747    1.0852   -0.6570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0920   -0.1566    1.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4262    0.1667    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7757   -0.3096   -0.6618 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6203   -1.6885   -0.7940 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2115    0.0212   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4185   -0.3885   -2.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0264   -0.0290   -2.7847 P   0  0  2  0  0  5  0  0  0  0  0  0
  -12.8864   -0.3013   -1.5752 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4715   -0.9913   -4.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0890    1.6294   -3.2000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4741   -1.5754   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1490   -0.7958   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694   -2.5719   -1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2301   -3.0340   -3.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9224   -1.6109   -4.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5723   -0.0878   -3.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4963   -1.2628   -4.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3234   -2.6275   -2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1869   -1.3301   -1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6160   -0.9359   -2.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -1.1142   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3029    0.9932   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0185    1.0472   -2.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5989    1.5040   -2.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6802    2.6297   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460    1.8019   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2988    0.1295   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5192    0.7691    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8851    2.4608    0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8359   -0.1262    2.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8945    1.0438    2.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7965    1.3383    3.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2550    2.8161    2.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712    2.4623    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9200    2.2432    3.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9438   -0.1136    2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6834   -0.2119    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    1.3260    1.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8702    1.0420    0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -1.3207    0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -0.4602    0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7494   -2.4727    1.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6567   -1.7201    2.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6311    0.1481    3.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3008   -1.3694    4.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528    0.1948    3.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4058    0.3213    1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5706   -2.2524    3.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -2.0102    1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -1.8706    1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612   -0.4545    2.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1522   -0.5951   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1015    0.8630    0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6047    1.2606    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0452   -0.3913    1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1428    0.1994   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6266   -2.1701    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9039   -0.4864   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4037    1.1090   -0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6155   -0.3815   -4.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7006    1.7197   -3.9774 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 30 29  1  1
 30 32  1  0
 30 33  1  0
 30 31  2  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
  5 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
 10 53  1  0
 10 54  1  0
 11 55  1  0
 11 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 17 67  1  0
 17 68  1  0
 18 69  1  0
 18 70  1  0
 19 71  1  0
 19 72  1  0
 20 73  1  0
 20 74  1  0
 21 75  1  0
 21 76  1  0
 25 77  1  0
 25 78  1  0
 26 79  1  6
 27 80  1  0
 28 81  1  0
 28 82  1  0
 32 83  1  0
 33 84  1  0
M  END

LPA(22:0/0:0)
  Mrv1652303302022392D          

 33 32  0  0  1  0            999 V2000
    9.1943   -4.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0108   -3.6472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0277   -5.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8442   -4.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0193   -4.4722    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.3810   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6710   -4.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -4.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -4.4579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6798   -5.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5233   -3.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6178   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3319   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9025   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6166   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3308   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0449   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7590   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4731   -4.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 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
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0122380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H51O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)31-22-24(26)23-32-33(28,29)30/h24,26H,2-23H2,1H3,(H2,28,29,30)

> <INCHI_KEY>
SQNPGTTUWWZACK-UHFFFAOYSA-N

> <FORMULA>
C25H51O7P

> <MOLECULAR_WEIGHT>
494.65

> <EXACT_MASS>
494.33724098

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
60.078446328664356

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3-(docosanoyloxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
6.50

> <JCHEM_LOGP>
7.625885838333334

> <ALOGPS_LOGS>
-5.87

> <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>
132.5864

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.70e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(docosanoyloxy)-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LPA(22:0/0:0)                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-20         0                                  
HETATM    1  O   UNK     0      17.163  -8.364   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.687  -6.808   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.718  -9.888   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.243  -8.332   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      18.703  -8.348   0.000  0.00  0.00           P+0
HETATM    6  C   UNK     0      15.645  -7.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.319  -8.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.977  -7.537   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.652  -8.321   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.336  -9.833   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.310  -7.566   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.310  -6.126   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.977  -8.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.644  -7.566   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.311  -8.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.978  -7.566   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.645  -8.337   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.312  -7.566   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.979  -8.337   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.354  -7.566   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.687  -8.337   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.020  -7.566   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.353  -8.337   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.686  -7.566   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.019  -8.337   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.352  -7.566   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.685  -8.337   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -11.018  -7.566   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.351  -8.337   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.684  -7.566   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -15.017  -8.337   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -16.350  -7.566   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -17.683  -8.337   0.000  0.00  0.00           C+0
CONECT    1    6    5                                                       
CONECT    2    5                                                            
CONECT    3    5                                                            
CONECT    4    5                                                            
CONECT    5    1    2    3    4                                             
CONECT    6    1    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   11                                                       
CONECT   10    7                                                            
CONECT   11    9   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                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   64    0
END

View in JSmol

Synonyms

Value	Source
1-Behenoyl-glycero-3-phosphate	HMDB
1-Behenoyl-lysophosphatidic acid	HMDB
LPA(22:0)	HMDB
Lysophosphatidic acid(22:0/0:0)	HMDB
Lysophosphatidic acid(22:0)	HMDB
LPA(22:0/0:0)	HMDB
1-Docosanoyl-phosphatidic acid	HMDB
1-Docosanoyl-glycero-3-phosphate	HMDB
1-behenoyl-glycero-3-phosphate	SMPDB, HMDB
1-behenoyl-lysophosphatidic acid	SMPDB, HMDB
LPA(22:0)	SMPDB, HMDB
Lysophosphatidic acid(22:0/0:0)	SMPDB, HMDB

Chemical Formula

C₂₅H₅₁O₇P

Average Mass

494.6500 Da

Monoisotopic Mass

494.33724 Da

IUPAC Name

[3-(docosanoyloxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

3-(docosanoyloxy)-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C25H51O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(27)31-22-24(26)23-32-33(28,29)30/h24,26H,2-23H2,1H3,(H2,28,29,30)

InChI Key

SQNPGTTUWWZACK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	6.5	ALOGPS
logP	7.63	ChemAxon
logS	-5.9	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	26	ChemAxon
Refractivity	132.59 m³·mol⁻¹	ChemAxon
Polarizability	60.08 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0114749

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

17786745

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

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 ]
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 ]

Showing NP-Card for LPA(22:0/0:0) (NP0122380)

MOL for NP0122380 (LPA(22:0/0:0))

3D MOL for NP0122380 (LPA(22:0/0:0))

3D SDF for NP0122380 (LPA(22:0/0:0))

3D-SDF for NP0122380 (LPA(22:0/0:0))

PDB for NP0122380 (LPA(22:0/0:0))

3D PDB for NP0122380 (LPA(22:0/0:0))

SMILES for NP0122380 (LPA(22:0/0:0))

INCHI for NP0122380 (LPA(22:0/0:0))

Structure for NP0122380 (LPA(22:0/0:0))

3D Structure for NP0122380 (LPA(22:0/0:0))