NP-MRD: Showing NP-Card for {[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid (NP0267982)

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Record Information

Version

2.0

Created at

2022-09-08 12:57:07 UTC

Updated at

2022-09-08 12:57:07 UTC

NP-MRD ID

NP0267982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid

Description

9-Ribosyl-trans-zeatin 5'-diphosphate, also known as trans-zeatin riboside diphosphate or TZRDP, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. 9-Ribosyl-trans-zeatin 5'-diphosphate is possibly neutral. {[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid is found in Apis cerana. A purine ribonucleoside 5'-diphosphate that is ADP substituted at position N-6 by a (2E)-4-hydroxy-3-methylbut-2-en-1-yl group.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308202020492D          

 33 35  0  0  1  0            999 V2000
    2.9699   -0.4391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2169   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517   -1.6105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4719    0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2169    0.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5058   -0.6065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823   -1.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -2.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9699    0.8575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5058    1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130   -1.6105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4640   -2.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8026   -3.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    0.6065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4640    1.8195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183   -0.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039   -3.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    2.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673   -1.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0835    1.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621   -1.4849    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274    2.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7987   -1.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621   -2.2797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621   -0.6901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385    1.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274    3.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -1.4849    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -0.6483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -1.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    2.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 27 33  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -6.6430    0.2023   -2.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2217    0.4095   -1.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6081   -0.0379   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3324   -0.7580   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2567   -0.1079    0.5458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572   -0.6655    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499   -1.8116   -0.0904 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025   -2.3149   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3926   -1.7182    0.5943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416   -0.5722    1.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9274   -0.0473    1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619    1.0778    1.9621 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6022    1.2267    2.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    0.2225    1.9825 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673    0.0387    2.2526 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3775    0.1129    1.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -0.6734    1.4287 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2979   -0.9651    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6990    0.2487   -0.3597 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5986    0.0535   -1.7752 P   0  0  1  0  0  5  0  0  0  0  0  0
    6.9727   -0.5137   -1.4664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340   -0.9684   -2.8770 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8507    1.5876   -2.4538 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4804    1.9731   -2.5646 P   0  0  0  0  0  5  0  0  0  0  0  0
    8.3315    0.7391   -2.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7412    2.8844   -3.9682 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9873    2.9452   -1.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290   -1.9146    1.9681 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7247   -2.7633    2.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -1.2807    2.9315 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5494   -1.0629    4.1373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5140    1.1363   -0.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4060    2.4157   -1.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3187    0.6343   -3.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    0.7183   -2.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5711   -0.8832   -2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0851    0.1478    0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0706   -0.9073   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4098   -1.7921    0.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4243    0.7758    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1674   -3.2516   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    2.0740    3.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9162    0.8757    2.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.1960    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5871   -1.4234   -0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1195   -1.6530    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2965   -1.8428   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7348    3.0046   -4.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9394    2.7857   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481   -2.4240    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524   -3.5408    1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9456   -1.8869    3.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5931   -0.0764    4.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8352    1.1484    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3242    0.6135   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0809    2.6059   -2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 32  1  0
 32 33  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  1
 20 22  1  0
 20 21  2  0
 20 23  1  0
 23 24  1  0
 24 26  1  0
 24 27  1  0
 24 25  2  0
 17 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 11  6  1  0
 30 15  1  0
 14 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 32 54  1  0
 32 55  1  0
 33 56  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  8 41  1  0
 13 42  1  0
 15 43  1  1
 17 44  1  1
 18 45  1  0
 18 46  1  0
 22 47  1  0
 26 48  1  0
 27 49  1  0
 28 50  1  6
 29 51  1  0
 30 52  1  1
 31 53  1  0
M  END


  Mrv1652308202020492D          

 33 35  0  0  1  0            999 V2000
    2.9699   -0.4391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2169   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517   -1.6105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4719    0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2169    0.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5058   -0.6065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823   -1.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006   -2.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9699    0.8575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5058    1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947   -0.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2130   -1.6105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4640   -2.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8026   -3.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    0.6065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4640    1.8195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183   -0.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0039   -3.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    2.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673   -1.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0835    1.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621   -1.4849    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274    2.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7987   -1.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621   -2.2797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621   -0.6901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385    1.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6274    3.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -1.4849    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -0.6483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4719   -1.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0648    2.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 27 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO)=C/CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H23N5O11P2/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(30-15)5-29-33(27,28)31-32(24,25)26/h2,6-7,9,11-12,15,21-23H,3-5H2,1H3,(H,27,28)(H,16,17,18)(H2,24,25,26)/b8-2+/t9-,11-,12-,15-/m1/s1

> <INCHI_KEY>
MXFPFNSSZYNJGX-HNNGNKQASA-N

> <FORMULA>
C15H23N5O11P2

> <MOLECULAR_WEIGHT>
511.321

> <EXACT_MASS>
511.086930577

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.13767784456799

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

> <ALOGPS_LOGP>
-0.56

> <JCHEM_LOGP>
-4.207250007622994

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.09400239172889

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7667247100920163

> <JCHEM_PKA_STRONGEST_BASIC>
3.822943815788348

> <JCHEM_POLAR_SURFACE_AREA>
238.83999999999997

> <JCHEM_REFRACTIVITY>
111.3277

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-20         0                                  
HETATM    1  N   UNK     0       5.544  -0.820   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.138  -0.429   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.763  -3.006   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.481   0.351   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.138   1.132   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.811  -1.132   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       3.514  -2.069   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.295  -4.412   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.544   1.601   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.811   1.913   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.483  -0.429   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.264  -3.006   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.733  -4.412   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.232  -5.661   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       1.483   1.132   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       2.733   3.396   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.781  -1.679   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.874  -5.661   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.483   4.177   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.312  -2.772   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.156   3.396   0.000  0.00  0.00           C+0
HETATM   22  P   UNK     0      -1.796  -2.772   0.000  0.00  0.00           P+0
HETATM   23  C   UNK     0      -1.171   4.177   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.358  -2.772   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.796  -4.255   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.796  -1.288   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.499   3.396   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.171   5.661   0.000  0.00  0.00           C+0
HETATM   29  P   UNK     0      -4.919  -2.772   0.000  0.00  0.00           P+0
HETATM   30  O   UNK     0      -4.919  -1.210   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.919  -4.333   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.481  -2.772   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -3.854   4.165   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13   14                                                  
CONECT    9    4    5                                                       
CONECT   10    5   15   16                                                  
CONECT   11    6   15                                                       
CONECT   12    7   17   13                                                  
CONECT   13    8   18   12                                                  
CONECT   14    8                                                            
CONECT   15   10   11                                                       
CONECT   16   10   19                                                       
CONECT   17   12   20                                                       
CONECT   18   13                                                            
CONECT   19   16   21                                                       
CONECT   20   17   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24   25   26                                             
CONECT   23   21   27   28                                                  
CONECT   24   22   29                                                       
CONECT   25   22                                                            
CONECT   26   22                                                            
CONECT   27   23   33                                                       
CONECT   28   23                                                            
CONECT   29   24   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   27                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
9-beta-D-Ribofuranosyl-trans-zeatin 5'-diphosphate	ChEBI
9-beta-D-Ribosyl-trans-zeatin 5'-diphosphate	ChEBI
trans-Zeatin 9-beta-D-ribofuranoside 5'-diphosphate	ChEBI
trans-Zeatin riboside diphosphate	ChEBI
TZRDP	ChEBI
9-b-D-Ribofuranosyl-trans-zeatin 5'-diphosphate	Generator
9-b-D-Ribofuranosyl-trans-zeatin 5'-diphosphoric acid	Generator
9-beta-D-Ribofuranosyl-trans-zeatin 5'-diphosphoric acid	Generator
9-Β-D-ribofuranosyl-trans-zeatin 5'-diphosphate	Generator
9-Β-D-ribofuranosyl-trans-zeatin 5'-diphosphoric acid	Generator
9-b-D-Ribosyl-trans-zeatin 5'-diphosphate	Generator
9-b-D-Ribosyl-trans-zeatin 5'-diphosphoric acid	Generator
9-beta-D-Ribosyl-trans-zeatin 5'-diphosphoric acid	Generator
9-Β-D-ribosyl-trans-zeatin 5'-diphosphate	Generator
9-Β-D-ribosyl-trans-zeatin 5'-diphosphoric acid	Generator
trans-Zeatin 9-b-D-ribofuranoside 5'-diphosphate	Generator
trans-Zeatin 9-b-D-ribofuranoside 5'-diphosphoric acid	Generator
trans-Zeatin 9-beta-D-ribofuranoside 5'-diphosphoric acid	Generator
trans-Zeatin 9-β-D-ribofuranoside 5'-diphosphate	Generator
trans-Zeatin 9-β-D-ribofuranoside 5'-diphosphoric acid	Generator
trans-Zeatin riboside diphosphoric acid	Generator
9-Ribosyl-trans-zeatin 5'-diphosphoric acid	Generator

Chemical Formula

C₁₅H₂₃N₅O₁₁P₂

Average Mass

511.3210 Da

Monoisotopic Mass

511.08693 Da

IUPAC Name

[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional Name

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

C\C(CO)=C/CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C15H23N5O11P2/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(30-15)5-29-33(27,28)31-32(24,25)26/h2,6-7,9,11-12,15,21-23H,3-5H2,1H3,(H,27,28)(H,16,17,18)(H2,24,25,26)/b8-2+/t9-,11-,12-,15-/m1/s1

InChI Key

MXFPFNSSZYNJGX-HNNGNKQASA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside diphosphates

Alternative Parents

Substituents

Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-alkylaminopurine
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Secondary aliphatic/aromatic amine
Alkyl phosphate
Imidolactam
Monosaccharide
Pyrimidine
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Azacycle
Secondary amine
Oxacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine ribonucleoside 5'-diphosphate (CHEBI:71875 )
adenosine 5'-phosphate (CHEBI:71875 )
N-glycosylzeatin (CHEBI:71875 )

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	-0.56	ALOGPS
logP	-4.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	3.82	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	238.84 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	111.33 m³·mol⁻¹	ChemAxon
Polarizability	45.14 Å³	ChemAxon
Number of Rings	3	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

28533720

KEGG Compound ID

Not Available

BioCyc ID

CPD-4204

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24892783

PDB ID

Not Available

ChEBI ID

71875

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid (NP0267982)

MOL for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

3D MOL for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

3D SDF for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

3D-SDF for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

PDB for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

3D PDB for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

SMILES for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

INCHI for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

Structure for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)

3D Structure for NP0267982 ({[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-{[(2e)-4-hydroxy-3-methylbut-2-en-1-yl]amino}purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid)