NP-MRD: Showing NP-Card for ADP-ribose 1''-2'' cyclic phosphate (NP0091544)

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Record Information

Version

1.0

Created at

2022-05-11 18:40:54 UTC

Updated at

2022-05-11 18:40:54 UTC

NP-MRD ID

NP0091544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ADP-ribose 1''-2'' cyclic phosphate

Description

PC(16:1(9Z)/22:0) Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. A third route to PC synthesis involves the conversion of either PS or PE to PC. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. PC(16:1(9Z)/22:0) Is an extremely weak basic (essentially neutral) compound (based on its pKa). PC(16:1(9Z)/22:0) Is a phosphatidylcholine (PC or GPCho). Within humans, PC(16:1(9Z)/22:0) Participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and PC(16:1(9Z)/22:0) Can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/22:0) Through the action of the enzyme phosphatidylethanolamine N-methyltransferase. In addition, cytidine monophosphate and PC(16:1(9Z)/22:0) Can be biosynthesized from CDP-choline and DG(16:1(9Z)/22:0/0:0) Through its interaction with the enzyme choline/ethanolaminephosphotransferase. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the behenic acid moiety is derived from groundnut oil. In humans, PC(16:1(9Z)/22:0) Is involved in phosphatidylcholine biosynthesis. Outside of the human body, PC(16:1(9Z)/22:0) Has been detected, but not quantified in, several different foods, such as cow milks, cow milks, cow milks, and cow milks. This could make PC(16:1(9Z)/22:0) A potential biomarker for the consumption of these foods. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Fatty acids containing 16, 18 and 20 carbons are the most common. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PC(16:1(9Z)/22:0), In particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of behenic acid at the C-2 position. 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. It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PCs can be synthesized via three different routes.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241201502D          

 39 43  0  0  1  0            999 V2000
   12.0302   -4.8503    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.5134   -4.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6927   -4.0976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6447   -5.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3246   -9.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7742  -10.1956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -10.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8385  -11.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3890  -10.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1320   -9.7506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1964  -10.7040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9268  -11.9692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1740  -12.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6204  -11.6951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7954  -11.6972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3122  -12.3659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5270  -12.1129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5249  -11.2879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3088  -11.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8562  -10.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1033  -11.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4347  -10.6590    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.9179   -9.9903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9515  -11.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7660  -10.1758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8502   -9.3551    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6708   -9.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0294   -9.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9343   -8.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6871   -8.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712   -7.3762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1567   -6.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4904   -6.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3110   -6.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4846   -6.9619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3167   -5.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3502   -6.9993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8608  -12.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5691  -13.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 16 39  1  6  0  0  0
 17 18  1  0  0  0  0
 17 38  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 31 35  1  0  0  0  0
 32 33  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 33 36  1  0  0  0  0
 34 35  1  0  0  0  0
  1 36  1  0  0  0  0
  4 34  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
  -10.3952   -0.5118    0.0596 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0898   -1.0974    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8775   -2.3407    0.5340 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6574   -2.8672    0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6109   -2.0625    0.5324 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7787   -0.7982    0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0363   -0.2546   -0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8499    0.9886   -0.5510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5365    1.2545   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8890    0.1483   -0.1778 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5020    0.0453    0.0519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8632    1.2990   -0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    0.9511   -0.0251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6236    1.9765   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526    1.1039   -0.9462 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5083    2.3759    0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9519    1.1411    1.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9536    0.2760   -0.6026 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6565    1.4750   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8539    1.1655    0.4425 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8738   -0.2239    0.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3838   -0.7848   -0.5365 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9536   -1.9865   -0.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5741   -1.8863   -0.5791 P   0  0  2  0  0  5  0  0  0  0  0  0
    8.8957   -2.8497   -1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4954   -2.1376    0.8017 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6132   -0.2710   -1.0772 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3437    0.1799   -1.0586 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1795    1.4189   -0.1655 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1527    1.4033    0.8457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2862   -0.4596   -0.3467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9668   -1.1960    0.8092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7074   -0.9190   -0.7523 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8928   -2.2426   -0.3387 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6979   -0.0885    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9513   -0.5011   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5383   -3.9035    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0688    2.1707   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839   -0.2068    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283    1.0454    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    2.3843   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    2.7388    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716    0.4523    2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2906    2.0053    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1233    1.6365   -1.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6069   -1.0353   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
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 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  6
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 16 17  2  0
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 20 19  1  6
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 20 21  2  0
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 23 24  1  0
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 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 31  1  1
 29 30  2  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 13 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
  7  2  1  0
 38 11  1  0
 10  6  1  0
 34 25  1  0
 33 27  1  0
  1 40  1  0
  1 41  1  0
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  9 43  1  0
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 27 53  1  6
 31 54  1  0
 33 55  1  6
 34 56  1  6
 35 57  1  0
 36 58  1  6
 37 59  1  0
 38 60  1  6
 39 61  1  0
M  END


  Mrv0541 02241201502D          

 39 43  0  0  1  0            999 V2000
   12.0302   -4.8503    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.5134   -4.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6927   -4.0976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6447   -5.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3246   -9.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7742  -10.1956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -10.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8385  -11.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3890  -10.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1320   -9.7506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1964  -10.7040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9268  -11.9692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1740  -12.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6204  -11.6951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7954  -11.6972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3122  -12.3659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5270  -12.1129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5249  -11.2879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3088  -11.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8562  -10.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1033  -11.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4347  -10.6590    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.9179   -9.9903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9515  -11.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7660  -10.1758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8502   -9.3551    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6708   -9.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0294   -9.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9343   -8.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6871   -8.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7712   -7.3762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1567   -6.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4904   -6.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3110   -6.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4846   -6.9619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3167   -5.2647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3502   -6.9993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8608  -12.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5691  -13.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 14  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 16 39  1  6  0  0  0
 17 18  1  0  0  0  0
 17 38  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 31 35  1  0  0  0  0
 32 33  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 33 36  1  0  0  0  0
 34 35  1  0  0  0  0
  1 36  1  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2OC3OP(O)(=O)OC3C2O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N5O16P3/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-37(24,25)36-38(26,27)31-2-6-9(22)11-15(33-6)35-39(28,29)34-11/h3-6,8-11,14-15,21-23H,1-2H2,(H,24,25)(H,26,27)(H,28,29)(H2,16,17,18)/t5-,6-,8-,9?,10-,11?,14-,15?/m1/s1

> <INCHI_KEY>
NPSPRYXPOGPCPM-PNUFQSOHSA-N

> <FORMULA>
C15H22N5O16P3

> <MOLECULAR_WEIGHT>
621.2804

> <EXACT_MASS>
621.027439217

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
49.45665077153953

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2H-2λ⁵-furo[2,3-d][1,3,2]dioxaphosphol-5-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid

> <ALOGPS_LOGP>
-1.28

> <JCHEM_LOGP>
-6.324328954886622

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
1.9415909556394526

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.350523039338686

> <JCHEM_PKA_STRONGEST_BASIC>
4.996835503117071

> <JCHEM_POLAR_SURFACE_AREA>
306.82

> <JCHEM_REFRACTIVITY>
118.21719999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2λ⁵-furo[2,3-d][1,3,2]dioxaphosphol-5-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic 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  P   UNK     0      22.456  -9.054   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      23.358  -7.806   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      21.826  -7.649   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      23.603 -10.081   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      30.473 -17.885   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      29.445 -19.032   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      29.925 -20.495   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.432 -20.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.459 -19.664   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      31.980 -18.201   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      33.967 -19.981   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      31.597 -22.343   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      30.191 -22.973   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      29.158 -21.831   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      27.618 -21.835   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.716 -23.083   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.250 -22.611   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.246 -21.071   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      26.710 -20.591   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      23.998 -20.169   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      22.593 -20.799   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      21.345 -19.897   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      22.247 -18.649   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.443 -21.145   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      20.097 -18.995   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0      20.254 -17.463   0.000  0.00  0.00           P+0
HETATM   27  O   UNK     0      21.785 -17.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      18.722 -17.306   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      20.411 -15.931   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      21.816 -15.301   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.973 -13.769   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.826 -12.741   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.449 -11.333   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.981 -11.490   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      23.305 -12.996   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      21.125  -9.827   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      19.320 -13.065   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      24.007 -23.519   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      27.196 -24.546   0.000  0.00  0.00           O+0
CONECT    1    2    3    4   36                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1   34                                                       
CONECT    5    6   10                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14    7   13   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   39                                                  
CONECT   17   16   18   38                                                  
CONECT   18   17   19   20                                                  
CONECT   19   15   18                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35    4                                                  
CONECT   35   31   34                                                       
CONECT   36   33    1                                                       
CONECT   37   32                                                            
CONECT   38   17                                                            
CONECT   39   16                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Adenosine diphosphate ribose 1"-2" cyclic phosphate	HMDB
ADP Ribose 1'',2''-phosphate	HMDB
ADP-Ribose 1 ,2 -cyclic phosphate	HMDB
ADP-Ribose 1' ,2' -cyclic phosphate	HMDB
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2H-2λ⁵-furo[2,3-D][1,3,2]dioxaphosphol-5-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinate	Generator
ADP-Ribose 1"-2" cyclic phosphoric acid	Generator

Chemical Formula

C₁₅H₂₂N₅O₁₆P₃

Average Mass

621.2804 Da

Monoisotopic Mass

621.02744 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2H-2λ⁵-furo[2,3-d][1,3,2]dioxaphosphol-5-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(5R)-2,6-dihydroxy-2-oxo-tetrahydro-2λ⁵-furo[2,3-d][1,3,2]dioxaphosphol-5-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2OC3OP(O)(=O)OC3C2O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C15H22N5O16P3/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-37(24,25)36-38(26,27)31-2-6-9(22)11-15(33-6)35-39(28,29)34-11/h3-6,8-11,14-15,21-23H,1-2H2,(H,24,25)(H,26,27)(H,28,29)(H2,16,17,18)/t5-,6-,8-,9?,10-,11?,14-,15?/m1/s1

InChI Key

NPSPRYXPOGPCPM-PNUFQSOHSA-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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
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	-1.3	ALOGPS
logP	-6.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	306.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.22 m³·mol⁻¹	ChemAxon
Polarizability	49.46 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025209

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for ADP-ribose 1''-2'' cyclic phosphate (NP0091544)

MOL for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

3D MOL for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

3D SDF for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

3D-SDF for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

PDB for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

3D PDB for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

SMILES for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

INCHI for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

Structure for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)

3D Structure for NP0091544 (ADP-ribose 1''-2'' cyclic phosphate)