NP-MRD: Showing NP-Card for 2'-O-Acetyl-ADP-ribose (NP0055005)

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Record Information

Version

2.0

Created at

2022-04-28 01:10:56 UTC

Updated at

2022-04-28 01:10:56 UTC

NP-MRD ID

NP0055005

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-O-Acetyl-ADP-ribose

Description

[({[(2R,3S,4S,5R)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. 2'-O-Acetyl-ADP-ribose is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on [({[(2R,3S,4S,5R)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203102D          

 39 42  0  0  1  0            999 V2000
    0.0865   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -1.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635   -4.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184   -5.2257    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
    0.1338   -5.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1733   -6.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803   -6.1818    0.0000 P   0  0  2  0  0  0  0  0  0  0  0  0
    1.8088   -6.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873   -6.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422   -7.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8492   -7.3095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4623   -6.7574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1768   -7.1699    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0052   -7.9769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1848   -8.0632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7723   -8.7776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5573   -8.5900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3023   -9.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8544   -9.9877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4954   -9.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9304   -6.8344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1518   -5.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030   -4.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  7 14  2  0  0  0  0
 11 15  1  0  0  0  0
  4 16  1  6  0  0  0
  3 17  1  6  0  0  0
  2 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  1  0  0  0
 30 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 29 37  1  1  0  0  0
 23 38  1  6  0  0  0
 20 39  1  1  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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    9.9686    0.5567   -0.8450 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3265   -0.6225    0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3038    0.2761   -0.2091 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2266   -0.3715   -1.0223 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3761   -1.7454   -1.1397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649   -0.0184   -0.2882 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9033   -1.0937   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8520   -0.7609    0.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834   -1.8750    0.2912 P   0  0  2  0  0  5  0  0  0  0  0  0
    1.6398   -2.8510    1.4430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -2.7261   -1.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1367   -1.0007    0.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4123    0.4792    1.0401 P   0  0  1  0  0  5  0  0  0  0  0  0
    0.9982    0.2238    2.4099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5233    1.4215    0.1823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0675    1.2927    1.1254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    0.7826    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    1.5717    0.3827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2760    1.1465   -0.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6703    2.0869   -1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6546    1.2436   -1.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2489   -0.0157   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8668   -1.2314   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1786   -1.3685   -1.8819 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1715   -2.3341   -1.0246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9143   -2.2334   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3155   -1.0455   -0.3229 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9716    0.0921   -0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3163    1.9114    1.4647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2920    1.0720    1.9977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082    1.3656    1.7354 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0178    0.0214    2.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3844    0.0356    1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5497    0.8142    0.9836 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2588    0.7372    2.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4009   -1.5909   -0.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2371   -2.4234    0.4861 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2929   -1.0578    1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7428    1.0989   -0.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1416    0.0439   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7633   -1.9597   -2.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5388    0.9396   -0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3070   -2.0854   -0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6017   -1.2061   -1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633   -3.5792   -1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0844    2.1642   -0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405   -0.2773    0.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6443    0.9343   -0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0758    2.6381    0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7493    3.1720   -1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3422   -2.0461   -2.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0026   -0.8222   -1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4233   -3.1670   -0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0240   -0.5467    1.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2082    1.8438    0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7169    1.5997    2.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5 38  1  0
 38 39  1  0
 38 37  1  0
 37  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  1
 11 13  1  0
 11 12  2  0
 11 14  1  0
 15 14  1  6
 15 17  1  0
 15 16  2  0
 15 18  1  0
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 20 21  1  0
 21 22  1  0
 22 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 22 23  1  0
 23 24  1  0
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 25 26  1  0
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 27 29  1  0
 29 30  2  0
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 31 32  2  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
 35 20  1  0
 32 23  1  0
 32 26  1  0
  1 40  1  0
  1 41  1  0
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  5 43  1  6
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  8 46  1  6
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 17 50  1  0
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 35 61  1  1
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 24 55  1  0
 28 56  1  0
 28 57  1  0
 30 58  1  0
  6 44  1  6
  7 45  1  0
M  END


  Mrv1652304282203102D          

 39 42  0  0  1  0            999 V2000
    0.0865   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3556    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7723   -8.7776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5573   -8.5900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7030   -4.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
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  8 11  2  0  0  0  0
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  7 14  2  0  0  0  0
 11 15  1  0  0  0  0
  4 16  1  6  0  0  0
  3 17  1  6  0  0  0
  2 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  1  0  0  0
 30 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 29 37  1  1  0  0  0
 23 38  1  6  0  0  0
 20 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0055005

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@H](O)O[C@H](CO[P@@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@@H](O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H25N5O15P2/c1-6(23)34-13-11(25)8(36-17(13)27)3-33-39(30,31)37-38(28,29)32-2-7-10(24)12(26)16(35-7)22-5-21-9-14(18)19-4-20-15(9)22/h4-5,7-8,10-13,16-17,24-27H,2-3H2,1H3,(H,28,29)(H,30,31)(H2,18,19,20)/t7-,8-,10+,11+,12+,13+,16-,17-/m1/s1

> <INCHI_KEY>
BFNOPXRXIQJDHO-PVHUSWGDSA-N

> <FORMULA>
C17H25N5O15P2

> <MOLECULAR_WEIGHT>
601.355

> <EXACT_MASS>
601.082239121

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.398633935419845

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3S,4S,5R)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid

> <ALOGPS_LOGP>
-1.67

> <JCHEM_LOGP>
-5.625594063836669

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.18736701428328

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8536387682877145

> <JCHEM_PKA_STRONGEST_BASIC>
4.009033539754207

> <JCHEM_POLAR_SURFACE_AREA>
297.59

> <JCHEM_REFRACTIVITY>
120.27479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2R,3S,4S,5R)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       0.161  -5.259   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.744  -6.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.208  -6.029   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.208  -4.489   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       2.530   1.777   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -3.454  -3.584   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.454  -6.934   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.268  -7.970   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.238  -8.290   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       1.714  -9.755   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0       0.250 -10.230   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.190 -11.219   0.000  0.00  0.00           O+0
HETATM   23  P   UNK     0       3.697 -11.539   0.000  0.00  0.00           P+0
HETATM   24  O   UNK     0       3.376 -13.046   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.203 -11.860   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.679 -13.324   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.185 -13.644   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.330 -12.614   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.663 -13.384   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.343 -14.890   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.812 -15.051   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.042 -16.385   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.374 -16.035   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.898 -17.499   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.928 -18.644   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.391 -17.819   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.070 -12.758   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.017 -10.033   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       3.179  -9.279   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    8   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   11                                                            
CONECT   16    4                                                            
CONECT   17    3                                                            
CONECT   18    2   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   39                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25   38                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31   33                                                  
CONECT   31   30   27   32                                                  
CONECT   32   31                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   29                                                            
CONECT   38   23                                                            
CONECT   39   20                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
[({[(2R,3S,4S,5R)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinate	Generator

Chemical Formula

C₁₇H₂₅N₅O₁₅P₂

Average Mass

601.3550 Da

Monoisotopic Mass

601.08224 Da

IUPAC Name

[({[(2R,3S,4S,5R)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid

Traditional Name

{[(2R,3S,4S,5R)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@H](O)O[C@H](CO[P@@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@@H](O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H]1O

InChI Identifier

InChI=1S/C17H25N5O15P2/c1-6(23)34-13-11(25)8(36-17(13)27)3-33-39(30,31)37-38(28,29)32-2-7-10(24)12(26)16(35-7)22-5-21-9-14(18)19-4-20-15(9)22/h4-5,7-8,10-13,16-17,24-27H,2-3H2,1H3,(H,28,29)(H,30,31)(H2,18,19,20)/t7-,8-,10+,11+,12+,13+,16-,17-/m1/s1

InChI Key

BFNOPXRXIQJDHO-PVHUSWGDSA-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
Arabidopsis thaliana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-1.7	ALOGPS
logP	-5.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	297.59 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.27 m³·mol⁻¹	ChemAxon
Polarizability	48.4 Å³	ChemAxon
Number of Rings	4	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

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

162988858

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2'-O-Acetyl-ADP-ribose (NP0055005)

MOL for NP0055005 (2'-O-Acetyl-ADP-ribose)

3D MOL for NP0055005 (2'-O-Acetyl-ADP-ribose)

3D SDF for NP0055005 (2'-O-Acetyl-ADP-ribose)

3D-SDF for NP0055005 (2'-O-Acetyl-ADP-ribose)

PDB for NP0055005 (2'-O-Acetyl-ADP-ribose)

3D PDB for NP0055005 (2'-O-Acetyl-ADP-ribose)

SMILES for NP0055005 (2'-O-Acetyl-ADP-ribose)

INCHI for NP0055005 (2'-O-Acetyl-ADP-ribose)

Structure for NP0055005 (2'-O-Acetyl-ADP-ribose)

3D Structure for NP0055005 (2'-O-Acetyl-ADP-ribose)