NP-MRD: Showing NP-Card for (2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid (NP0305302)

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Record Information

Version

1.0

Created at

2022-09-10 21:01:25 UTC

Updated at

2022-09-10 21:01:25 UTC

NP-MRD ID

NP0305302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid

Description

PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as GPG(18:2/22:6) Or GPG(40:8), Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Thus, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphoglycerol lipid molecule. PG also serves as a precursor for the synthesis of cardiolipin. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions. In particular, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from PGP(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1. In addition, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and CDP-DG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and cytidine monophosphate; which is catalyzed by the enzyme cardiolipin synthase. In humans, PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in cardiolipin biosynthesis. The linoleic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. (2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid is found in Trypanosoma brucei. It was first documented in 1995 (PMID: 7834746). PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position (PMID: 11413487) (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241201132D          

 59 58  0  0  1  0            999 V2000
   20.7801  -10.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1051  -10.4912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4298  -10.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4554  -10.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7547  -10.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5782  -11.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1305  -10.1015    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.7407   -9.4262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5204  -10.7766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8057   -9.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4808  -10.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1560   -9.7116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.8312  -10.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6928  -11.3005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.4691   -9.6749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7324   -9.0267    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.5440   -9.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8931  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6077  -10.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3222  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0367  -10.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7513  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4658  -10.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1804  -10.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8949  -10.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6094  -10.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3239  -10.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0385  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7529  -10.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4676  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1820  -10.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8966  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6111  -10.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3256  -10.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0401  -10.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0401   -9.2536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8586  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5731  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0021  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4312  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1457  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8603  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5748  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2894  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0039  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7184  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4329  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1475  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8619  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5765  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2910  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0055  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7200  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4346  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1492  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8637  -11.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8637  -12.5084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 13 15  1  0  0  0  0
 12 16  1  6  0  0  0
 12 17  1  1  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  2  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  2  0  0  0  0
 28 27  1  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  2  0  0  0  0
  5 35  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  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  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58  6  1  0  0  0  0
 58 59  2  0  0  0  0
M  END

     RDKit          3D

132131  0  0  0  0  0  0  0  0999 V2000
    0.9858   -1.3219    9.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0056   -2.3455    7.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -2.0282    6.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7406   -1.7810    5.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -1.8011    5.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972   -0.4460    4.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2252   -0.2499    3.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3872   -1.3356    2.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5442   -1.1530    1.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148   -1.0048    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.9998   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5120   -2.1035   -1.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9742   -1.9436   -2.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.6473   -2.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8268   -0.6230   -3.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7612    0.1666   -2.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4712    1.0995   -1.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383    2.5301   -2.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8349    3.2498   -3.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1991    2.8303   -4.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2135    3.2774   -5.4113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882    4.7515   -5.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6585    5.5980   -5.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9270    5.1181   -4.5623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526    6.2918   -4.2004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9793    6.4026   -4.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    5.2334   -4.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    5.0180   -4.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304    5.9863   -5.6198 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430    3.8074   -4.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    3.4429   -3.3210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211    2.1356   -3.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2588    1.6023   -2.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.2921   -2.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3649   -0.3130   -0.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -1.6205   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4905   -2.3008    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0904   -3.5339    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2606   -4.3820   -0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0120   -5.6087   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -6.8069   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964   -7.1411    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4521   -7.9744   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1409   -8.3721   -0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -9.2108    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9588  -10.4927    0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    6.5387   -2.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    5.5622   -2.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4725    5.8255   -0.3945 P   0  0  2  0  0  5  0  0  0  0  0  0
   -1.7874    7.2826   -0.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0754    5.4941    0.2010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6301    4.8763    0.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9873    5.3098    1.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0383    4.3221    2.1435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1409    4.3099    1.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719    2.9164    2.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612    2.0446    2.5663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -1.0278    9.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -0.5202    8.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -1.8443   10.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -3.2793    8.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0326   -2.6743    7.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0832   -2.0072    7.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261   -1.5528    5.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205   -1.8963    6.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2825   -2.6352    4.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2034    0.4128    5.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    0.8013    3.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -1.3313    2.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1898   -2.3553    2.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6063   -1.1461    1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7892   -0.8702   -0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0428   -1.1510    0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4705    0.0130   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335   -3.1012   -0.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0843   -2.8138   -3.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -0.6038   -4.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0305302

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C46H75O10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(50)56-44(42-55-57(51,52)54-40-43(48)39-47)41-53-45(49)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26,28,32,34,43-44,47-48H,3-4,6,8-10,15-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,51,52)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-,44+/m0/s1

> <INCHI_KEY>
GMXYXYLCBAOPHA-KNVYJNGISA-N

> <FORMULA>
C46H75O10P

> <MOLECULAR_WEIGHT>
819.0555

> <EXACT_MASS>
818.509785132

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
93.19972951736227

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
7.72

> <JCHEM_LOGP>
11.598227586

> <ALOGPS_LOGS>
-6.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.641245576372423

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8907737771412285

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9689647678483633

> <JCHEM_POLAR_SURFACE_AREA>
148.82000000000002

> <JCHEM_REFRACTIVITY>
241.0497000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
40

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.72e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      38.790 -18.856   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      37.530 -19.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.269 -18.856   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      40.050 -19.584   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      35.009 -19.584   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      36.546 -21.039   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      41.310 -18.856   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      40.583 -17.596   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      42.038 -20.116   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      42.571 -18.128   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      43.831 -18.856   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.091 -18.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      46.352 -18.856   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      38.627 -21.094   0.000  0.00  0.00           H+0
HETATM   15  O   UNK     0      47.542 -18.060   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0      46.167 -16.850   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      43.949 -16.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.001 -19.584   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.334 -18.813   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.668 -19.584   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.002 -18.814   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.336 -19.584   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.670 -18.814   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.003 -18.813   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.337 -19.584   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.671 -18.813   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.005 -18.814   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.338 -19.584   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.672 -18.814   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.006 -19.584   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      28.340 -18.814   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.674 -19.584   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.007 -18.814   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      32.341 -19.584   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      33.675 -18.814   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      33.675 -17.273   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.203 -21.039   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.537 -21.809   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.870 -21.039   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.204 -21.039   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.538 -21.809   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.871 -21.039   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.205 -21.039   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      16.539 -21.809   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      17.873 -21.039   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      19.207 -21.039   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      20.541 -21.809   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      21.874 -21.039   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      23.208 -21.039   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      24.542 -21.809   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      25.876 -21.039   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      27.209 -21.039   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      28.543 -21.809   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      29.877 -21.039   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      31.211 -21.039   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      32.545 -21.809   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      33.878 -21.039   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      35.212 -21.809   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      35.212 -23.349   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   14                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   35                                                       
CONECT    6    2   58                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16   17                                             
CONECT   13   12   15                                                       
CONECT   14    2                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18   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   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36    5                                                  
CONECT   36   35                                                            
CONECT   37   38                                                            
CONECT   38   37   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   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57    6   59                                                  
CONECT   59   58                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  116    0
END

View in JSmol

Synonyms

Value	Source
1-(9Z,12Z-Octadecadienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1'-glycerol)	HMDB
1-Linoleoyl-2-docosahexaenoyl-sn-glycero-3-phosphoglycerol	HMDB
GPG(18:2/22:6)	HMDB
GPG(18:2N6/22:6N3)	HMDB
GPG(18:2W6/22:6W3)	HMDB
GPG(40:8)	HMDB
PG(18:2/22:6)	HMDB
PG(18:2N6/22:6N3)	HMDB
PG(18:2W6/22:6W3)	HMDB
PG(40:8)	HMDB
Phosphatidylglycerol(18:2/22:6)	HMDB
Phosphatidylglycerol(18:2n6/22:6n3)	HMDB
Phosphatidylglycerol(18:2W6/22:6W3)	HMDB
Phosphatidylglycerol(40:8)	HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoglycerol	HMDB
PG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))	Lipid Annotator

Chemical Formula

C₄₆H₇₅O₁₀P

Average Mass

819.0555 Da

Monoisotopic Mass

818.50979 Da

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C46H75O10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(50)56-44(42-55-57(51,52)54-40-43(48)39-47)41-53-45(49)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26,28,32,34,43-44,47-48H,3-4,6,8-10,15-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,51,52)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t43-,44+/m0/s1

InChI Key

GMXYXYLCBAOPHA-KNVYJNGISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols 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

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoglycerols (LMGP04010045 )

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	7.72	ALOGPS
logP	11.6	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	241.05 m³·mol⁻¹	ChemAxon
Polarizability	93.2 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

External Links

HMDB ID

HMDB0010659

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027809

KNApSAcK ID

Not Available

Chemspider ID

24768158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52926310

PDB ID

Not Available

ChEBI ID

89365

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 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid (NP0305302)

MOL for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D MOL for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D SDF for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D-SDF for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

PDB for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D PDB for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

SMILES for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

INCHI for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

Structure for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)

3D Structure for NP0305302 ((2s)-2,3-dihydroxypropoxy((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propoxy)phosphinic acid)