NP-MRD: Showing NP-Card for LysoPA(18:0/0:0) (NP0123453)

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Record Information

Version

2.0

Created at

2022-05-12 09:28:59 UTC

Updated at

2022-05-12 09:28:59 UTC

NP-MRD ID

NP0123453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

LysoPA(18:0/0:0)

Description

LysoPA(18:0/0:0), Also known as lpa(18:0), 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. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. LysoPA(18:0/0:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa). LysoPA(18:0/0:0) Is a lysophosphatidic acid. LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233 ). LysoPA(18:0/0:0) Exists in all living species, ranging from bacteria to humans. In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. In each pathway, at least two phospholipase activities are required: Phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. Fatty acids containing 16 and 18 carbons are the most common. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410 ). It is the biosynthetic precursor of phosphatidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

LPA(18:0/0:0)
  Mrv1652304052008222D          

 29 28  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
  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
M  END

     RDKit          3D

 72 71  0  0  0  0  0  0  0  0999 V2000
   -7.1730   -0.6442   -2.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5690    0.8193   -2.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4224    1.6989   -1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9991    1.3598   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8637    2.2172    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6332    2.0746   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1167    0.6372   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    0.1872    0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2578   -1.2328    0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0343   -1.3590   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107   -2.7457   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1145   -3.4800    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9360   -3.1486    1.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9477   -2.0210    2.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256   -0.6146    2.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0606   -0.1850    1.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587    1.2855    1.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.8703    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819    1.8272   -0.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0488    2.4537    0.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449    3.0210   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6337    2.0483   -1.0858 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6042    2.7065   -1.8449 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2806    0.8766   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8193   -0.0268   -1.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5489   -1.3432   -0.6098 P   0  0  2  0  0  5  0  0  0  0  0  0
    6.7493   -1.9169    0.5450 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0908   -0.9477   -0.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7272   -2.5460   -1.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0922   -0.6908   -2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3874   -1.1075   -1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7666   -1.1596   -2.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4574    0.9545   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9043    1.1403   -3.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5767    1.4892   -2.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7511    2.7526   -1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8682    1.5116    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927    0.2931   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6465    2.0306    1.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012    3.2922    0.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500    2.7589   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8276    2.3386   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    0.6744   -1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8796   -0.0067   -1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9370    0.8475    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820    0.3065    1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504   -1.9357    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624   -1.5469    1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070   -0.5471   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4365   -1.1872   -1.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3206   -3.3501   -0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3303   -2.7985   -1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0729   -3.6075    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0287   -4.6096    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -3.2779    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0082   -4.0912    2.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759   -2.1234    3.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0290   -2.1595    3.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1080   -0.0406    3.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -0.1494    2.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424   -0.3772    1.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273   -0.7340    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622    1.7854    2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8580    1.4284    0.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8077    3.4474    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263    3.8946   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608    1.7193   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5107    2.5205   -1.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0023    1.2167    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4770    0.3141    0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6861   -1.7454   -0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4965   -2.3426   -2.4024 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 26 25  1  6
 26 28  1  0
 26 29  1  0
 26 27  2  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 15 59  1  0
 15 60  1  0
 16 61  1  0
 16 62  1  0
 17 63  1  0
 17 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  6
 23 68  1  0
 24 69  1  0
 24 70  1  0
 28 71  1  0
 29 72  1  0
M  END

LPA(18:0/0:0)
  Mrv1652304052008222D          

 29 28  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
  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
M  END
> <DATABASE_ID>
NP0123453

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H43O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h20,22H,2-19H2,1H3,(H2,24,25,26)

> <INCHI_KEY>
LAYXSTYJRSVXIH-UHFFFAOYSA-N

> <FORMULA>
C21H43O7P

> <MOLECULAR_WEIGHT>
438.542

> <EXACT_MASS>
438.274640723

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.46415817744267

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-hydroxy-3-(octadecanoyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.847611178333334

> <ALOGPS_LOGS>
-5.48

> <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>
114.18239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-(octadecanoyloxy)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LPA(18:0/0:0)                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-APR-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
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                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

View in JSmol

Synonyms

Value	Source
Lysophosphatidic acid(18:0/0:0)	HMDB
Lysophosphatidic acid(18:0)	HMDB
LPA(18:0)	HMDB
LPA(18:0/0:0)	HMDB
1-Stearoyl-glycero-3-phosphate	HMDB
1-Octadecanoyl-glycero-3-phosphate	HMDB
1-Octadecanoyl-phosphatidic acid	HMDB

Chemical Formula

C₂₁H₄₃O₇P

Average Mass

438.5420 Da

Monoisotopic Mass

438.27464 Da

IUPAC Name

[2-hydroxy-3-(octadecanoyloxy)propoxy]phosphonic acid

Traditional Name

2-hydroxy-3-(octadecanoyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

InChI Identifier

InChI=1S/C21H43O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h20,22H,2-19H2,1H3,(H2,24,25,26)

InChI Key

LAYXSTYJRSVXIH-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	5.01	ALOGPS
logP	5.85	ChemAxon
logS	-5.5	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	22	ChemAxon
Refractivity	114.18 m³·mol⁻¹	ChemAxon
Polarizability	51.46 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

HMDB0007854

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

89567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for LysoPA(18:0/0:0) (NP0123453)

MOL for NP0123453 (LysoPA(18:0/0:0))

3D MOL for NP0123453 (LysoPA(18:0/0:0))

3D SDF for NP0123453 (LysoPA(18:0/0:0))

3D-SDF for NP0123453 (LysoPA(18:0/0:0))

PDB for NP0123453 (LysoPA(18:0/0:0))

3D PDB for NP0123453 (LysoPA(18:0/0:0))

SMILES for NP0123453 (LysoPA(18:0/0:0))

INCHI for NP0123453 (LysoPA(18:0/0:0))

Structure for NP0123453 (LysoPA(18:0/0:0))

3D Structure for NP0123453 (LysoPA(18:0/0:0))