NP-MRD: Showing NP-Card for Zeatin riboside (NP0021801)

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Record Information

Version

2.0

Created at

2021-01-06 07:03:55 UTC

Updated at

2021-07-15 17:37:19 UTC

NP-MRD ID

NP0021801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Zeatin riboside

Provided By

NPAtlas

Description

Trans-zeatin riboside belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Zeatin riboside is found in Agrobacterium tumefaciens, Brassica napus, Brassica campestris , Vinca rosea , Datura innoxia , Ecklonia maxima, Euglena gracilis, Dolichos lablab , Mercurialis ambigua, Plasmodiophora brassicae, Pseudomonas syringae, Rhizopogon roseolus, Corynebacterium fascians, Solanum tuberosum , Phaseolus mungo and Zea mays . Zeatin riboside was first documented in 1967 (PMID: 6036233). Based on a literature review a small amount of articles have been published on trans-zeatin riboside (PMID: 12379786) (PMID: 20488581) (PMID: 21790030) (PMID: 21867755).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 46 48  0  0  0  0            999 V2000
    5.0160   -1.5061   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351   -0.0840   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    0.2861    0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0313   -0.6409    1.8728 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6626   -0.2791    2.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428   -0.2418    1.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436   -0.5349   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607   -0.4927   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848   -0.1448   -0.6665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703    0.1592    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.1098    1.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    0.4575    2.6864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.7079    2.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1297    0.7154    0.6365 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.0684   -1.8941   -0.8133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0549   -1.7544   -1.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3571    0.4387   -1.3608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3799    1.3039   -1.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    1.1891   -0.7598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4890    2.5693   -0.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795    0.8988   -1.2888 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5296    2.2022   -0.8101 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 23 43  1  0  0  0  0
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 25 46  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    5.0160   -1.5061   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351   -0.0840   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242105183D          

 46 48  0  0  0  0            999 V2000
    5.0160   -1.5061   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351   -0.0840   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1253    2.2776   -0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
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 15 35  1  1  0  0  0
 17 36  1  1  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  0  0  0  0
 20 40  1  6  0  0  0
 21 41  1  0  0  0  0
 22 42  1  6  0  0  0
 23 43  1  0  0  0  0
 24 44  1  0  0  0  0
 24 45  1  0  0  0  0
 25 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(=C(/[H])C([H])([H])N([H])C1=NC([H])=NC2=C1N=C([H])N2[C@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@@]1([H])O[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N5O5/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(24)11(23)9(5-22)25-15/h2,6-7,9,11-12,15,21-24H,3-5H2,1H3,(H,16,17,18)/b8-2+/t9-,11-,12-,15-/m1/s1

> <INCHI_KEY>
GOSWTRUMMSCNCW-HNNGNKQASA-N

> <FORMULA>
C15H21N5O5

> <MOLECULAR_WEIGHT>
351.3577

> <EXACT_MASS>
351.154268807

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.133938729084804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R)-2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

> <ALOGPS_LOGP>
-0.39

> <JCHEM_LOGP>
-1.708784857333333

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.868550575327028

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.453119668971691

> <JCHEM_PKA_STRONGEST_BASIC>
3.7015539782741884

> <JCHEM_POLAR_SURFACE_AREA>
145.78

> <JCHEM_REFRACTIVITY>
89.58189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-zeatin riboside

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    5.0160   -1.5061   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351   -0.0840   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    0.2861    0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0313   -0.6409    1.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -0.2791    2.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428   -0.2418    1.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436   -0.5349   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607   -0.4927   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848   -0.1448   -0.6665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703    0.1592    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.1098    1.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    0.4575    2.6864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.7079    2.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8187    0.5278    1.1811 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1297    0.7154    0.6365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8099   -0.5075    0.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7667   -0.5035   -0.2791 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0684   -1.8941   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0549   -1.7544   -1.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3571    0.4387   -1.3608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3799    1.3039   -1.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    1.1891   -0.7598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4890    2.5693   -0.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795    0.8988   -1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5296    2.2022   -0.8101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7714   -1.6575   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4306   -2.1221    0.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0838   -1.9030   -1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6039    1.3455    1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -1.6964    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253   -0.6335    2.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4047   -0.0329    3.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768   -0.7421   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1915    1.0130    3.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7486    1.4255    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7308   -0.1340    0.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557   -2.3181   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -2.5194    0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0246   -2.5467   -2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -0.1618   -2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5411    2.0138   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3195    1.0338   -1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8426    2.8451    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6425    0.6584   -1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170    0.8728   -2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1253    2.2776   -0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  2 24  1  0
 24 25  1  0
 11  6  1  0
 22 15  1  0
 14 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
 13 34  1  0
 15 35  1  1
 17 36  1  1
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  6
 21 41  1  0
 22 42  1  6
 23 43  1  0
 24 44  1  0
 24 45  1  0
 25 46  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.016  -1.506  -0.655  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.035  -0.084  -0.297  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.572   0.286   0.882  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.031  -0.641   1.873  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.663  -0.279   2.167  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.643  -0.242   1.182  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.844  -0.535  -0.115  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.861  -0.493  -1.037  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.385  -0.145  -0.667  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.670   0.159   0.590  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.351   0.110   1.517  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.207   0.458   2.686  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.512   0.708   2.479  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.819   0.528   1.181  0.00  0.00           N+0
HETATM   15  C   UNK     0      -3.130   0.715   0.637  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.810  -0.507   0.700  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.767  -0.503  -0.279  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.068  -1.894  -0.813  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.055  -1.754  -1.801  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.357   0.439  -1.361  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.380   1.304  -1.745  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.191   1.189  -0.760  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.489   2.569  -0.820  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.580   0.899  -1.289  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.530   2.202  -0.810  0.00  0.00           O+0
HETATM   26  H   UNK     0       5.771  -1.658  -1.483  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.431  -2.122   0.180  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.084  -1.903  -1.048  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.604   1.345   1.111  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.999  -1.696   1.546  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.625  -0.634   2.810  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.405  -0.033   3.144  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.077  -0.742  -2.088  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.192   1.013   3.283  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.749   1.426   1.261  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.731  -0.134   0.154  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.156  -2.318  -1.295  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.454  -2.519   0.011  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.025  -2.547  -2.409  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.058  -0.162  -2.247  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.541   2.014  -1.075  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.320   1.034  -1.385  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.843   2.845   0.074  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.643   0.658  -1.483  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.017   0.873  -2.242  0.00  0.00           H+0
HETATM   46  H   UNK     0       6.125   2.278  -0.001  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3   24                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5   30   31                                             
CONECT    5    4    6   32                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15   10                                                  
CONECT   15   14   16   22   35                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   20   36                                             
CONECT   18   17   19   37   38                                             
CONECT   19   18   39                                                       
CONECT   20   17   21   22   40                                             
CONECT   21   20   41                                                       
CONECT   22   20   23   15   42                                             
CONECT   23   22   43                                                       
CONECT   24    2   25   44   45                                             
CONECT   25   24   46                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    8                                                            
CONECT   34   13                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
CONECT   45   24                                                            
CONECT   46   25                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   96    0
END

RDKit          3D

46 48  0  0  0  0  0  0  0  0999 V2000
    5.0160   -1.5061   -0.6550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351   -0.0840   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    0.2861    0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0313   -0.6409    1.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626   -0.2791    2.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428   -0.2418    1.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436   -0.5349   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607   -0.4927   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848   -0.1448   -0.6665 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6703    0.1592    0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.1098    1.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    0.4575    2.6864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5116    0.7079    2.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8187    0.5278    1.1811 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1297    0.7154    0.6365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8099   -0.5075    0.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7667   -0.5035   -0.2791 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0684   -1.8941   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0549   -1.7544   -1.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3571    0.4387   -1.3608 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3799    1.3039   -1.7446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    1.1891   -0.7598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4890    2.5693   -0.8198 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795    0.8988   -1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5296    2.2022   -0.8101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7714   -1.6575   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4306   -2.1221    0.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0838   -1.9030   -1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6039    1.3455    1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -1.6964    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253   -0.6335    2.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4047   -0.0329    3.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0768   -0.7421   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1915    1.0130    3.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7486    1.4255    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7308   -0.1340    0.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557   -2.3181   -1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -2.5194    0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0246   -2.5467   -2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -0.1618   -2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5411    2.0138   -1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3195    1.0338   -1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8426    2.8451    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6425    0.6584   -1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170    0.8728   -2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1253    2.2776   -0.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  2 24  1  0
 24 25  1  0
 11  6  1  0
 22 15  1  0
 14 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
 13 34  1  0
 15 35  1  1
 17 36  1  1
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  6
 21 41  1  0
 22 42  1  6
 23 43  1  0
 24 44  1  0
 24 45  1  0
 25 46  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(e)-N-(4-Hydroxy-3-methyl-2-butenyl)adenosine	ChEBI
9-beta-D-Ribofuranosyl-trans-zeatin	ChEBI
9-beta-D-Ribosyl-trans-zeatin	ChEBI
trans-Zeatin 9-beta-D-ribofuranoside	ChEBI
Zeatin riboside	ChEBI
9-b-D-Ribofuranosyl-trans-zeatin	Generator
9-Β-D-ribofuranosyl-trans-zeatin	Generator
9-b-D-Ribosyl-trans-zeatin	Generator
9-Β-D-ribosyl-trans-zeatin	Generator
trans-Zeatin 9-b-D-ribofuranoside	Generator
trans-Zeatin 9-β-D-ribofuranoside	Generator
Ribosylzeatin	MeSH
Zeatin riboside, (e)-isomer	MeSH
N-(4-Hydroxy-3-methyl-2-butenyl)adenosine	MeSH
Zeatin riboside, (cis-(Z))-isomer	MeSH
N-[(2E)-4-Hydroxy-3-methyl-2-buten-1-yl]adenosine	PhytoBank
6-(4-Hydroxy-3-methyl-trans-2-butenylamino)-9-beta-D-ribofuranosylpurine	PhytoBank
6-(4-Hydroxy-3-methyl-trans-2-butenylamino)-9-β-D-ribofuranosylpurine	PhytoBank
9-Ribosyl-trans-zeatin	PhytoBank
9-beta-D-Ribofuranosylzeatin	PhytoBank
9-β-D-Ribofuranosylzeatin	PhytoBank
N6-(4-Hydroxy-3-methylbut-2-trans-enyl)adenosine	PhytoBank
N6-(trans-4-Hydroxy-3-methylbut-2-enyl)adenosine	PhytoBank
Ribosyl-trans-zeatin	PhytoBank
Zeatin ribonucleoside	PhytoBank
Zeatin 9-riboside	PhytoBank
Zeatin 9-beta-ribonucleoside	PhytoBank
Zeatin 9-β-ribonucleoside	PhytoBank
Zeatin-9-beta-D-ribofuranoside	PhytoBank
Zeatin-9-β-D-ribofuranoside	PhytoBank
trans-Zeatin 9-riboside	PhytoBank
trans-Zeatin riboside	PhytoBank

Chemical Formula

C₁₅H₂₁N₅O₅

Average Mass

351.3577 Da

Monoisotopic Mass

351.15427 Da

IUPAC Name

(2R,3R,4S,5R)-2-(6-{[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Traditional Name

trans-zeatin riboside

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H21N5O5/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(24)11(23)9(5-22)25-15/h2,6-7,9,11-12,15,21-24H,3-5H2,1H3,(H,16,17,18)/b8-2+/t9-,11-,12-,15-/m1/s1

InChI Key

GOSWTRUMMSCNCW-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, 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
Abies balsamea	KNApSAcK Database	22123792
Acer pseudoplatanus	KNApSAcK Database	22123792
Actinidia chinensis	KNApSAcK Database	22123792
Agrobacterium tumefaciens	Bacteria	KNApSAcK
Arabidopsis thaliana	KNApSAcK Database	22123792
Beta vulgaris	KNApSAcK Database	22123792
Brassica campestris	KNApSAcK Database	22123792
Brassica napus	LOTUS Database	35616633
Brassica oleracea	KNApSAcK Database	22123792
Brassica rapa subsp. oleifera	Plant	KNApSAcK
Castanea spp.	KNApSAcK Database	22123792
Catharanthus roseus	Plant	KNApSAcK
Cichorium intybus	KNApSAcK Database	22123792
Cocos nucifera	KNApSAcK Database	22123792
Datura innoxia	KNApSAcK Database	22123792
Datura inoxia	Plant	KNApSAcK
Daucus carota	KNApSAcK Database	22123792
Dolichos lablab	KNApSAcK Database	22123792
Ecklonia maxima	Chromalveolata	KNApSAcK
Euglena gracilis	Excavata	KNApSAcK
Glycine max	KNApSAcK Database	22123792
Gossypium hirsutum	KNApSAcK Database	22123792
Humulus lupulus	KNApSAcK Database	22123792
Ipomoea batatas	KNApSAcK Database	22123792
Lablab purpureus	Plant	KNApSAcK
Lupinus luteus	KNApSAcK Database	22123792
Mangifera indica	KNApSAcK Database	22123792
Medicago sativa	KNApSAcK Database	22123792
Mercurialis ambigua	Plant	KNApSAcK
Mercurialis annua	KNApSAcK Database	22123792
Nicotiana tabacum	KNApSAcK Database	22123792
Oryza sativa	KNApSAcK Database	22123792
Phaseolus mungo	KNApSAcK Database	22123792
Phaseolus vulgaris	KNApSAcK Database	22123792
Picea sitchensis	KNApSAcK Database	22123792
Pinus radiata	KNApSAcK Database	22123792
Pisum sativum	KNApSAcK Database	22123792
Plasmodiophora brassicae	-	KNApSAcK
Prunus cerasus	KNApSAcK Database	22123792
Pseudomonas syringae	LOTUS Database	35616633
Pseudotsuga menziesii	KNApSAcK Database	22123792
Pyrus communis	KNApSAcK Database	22123792
Rhizopogon roseolus	NPAtlas	6036233
Rhodococcus fascians	Bacteria	KNApSAcK
Sechium edule	KNApSAcK Database	22123792
Solanum lycopersicum	KNApSAcK Database	22123792
Solanum tuberosum	Plant	KNApSAcK
Triticum aestivum	KNApSAcK Database	22123792
Vigna mungo	Plant	KNApSAcK
Vinca rosea	KNApSAcK Database	22123792
Zea mays	KNApSAcK Database	22123792
Zea mays L.	Plant	KNApSAcK

Species Where Detected

Species Name	Source	Reference
Bradyrhizobium japonicum	KNApSAcK Database	22123792
Corynebacterium fascians	KNApSAcK Database	22123792
Rhizopogon ochraceorubens	KNApSAcK Database	22123792
Saccharomyces cerevisiae	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-alkylaminopurine
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Secondary amine
Oxacycle
Amine
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleoside analogue (CHEBI:71693 )
9-ribosylzeatin (CHEBI:71693 )

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	-0.39	ALOGPS
logP	-1.7	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.58 m³·mol⁻¹	ChemAxon
Polarizability	36.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA009273

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440982

PDB ID

Not Available

ChEBI ID

71693

Good Scents ID

Not Available

References

General References

Miller CO: Zeatin and zeatin riboside from a mycorrhizal fungus. Science. 1967 Sep 1;157(3792):1055-7. doi: 10.1126/science.157.3792.1055. [PubMed:6036233 ]
Kuroha T, Kato H, Asami T, Yoshida S, Kamada H, Satoh S: A trans-zeatin riboside in root xylem sap negatively regulates adventitious root formation on cucumber hypocotyls. J Exp Bot. 2002 Nov;53(378):2193-200. doi: 10.1093/jxb/erf077. [PubMed:12379786 ]
Abul Y, Menendez V, Gomez-Campo C, Revilla MA, Lafont F, Fernandez H: Occurrence of plant growth regulators in Psilotum nudum. J Plant Physiol. 2010 Sep 15;167(14):1211-3. doi: 10.1016/j.jplph.2010.03.015. Epub 2010 May 21. [PubMed:20488581 ]
Sokolova MG, Akimova GP, Vaishlia OB: [Effect of phytohormones synthesized by rhizosphere bacteria on plants]. Prikl Biokhim Mikrobiol. 2011 May-Jun;47(3):302-7. [PubMed:21790030 ]
Liang Y, Zhu X, Zhao M, Liu H: Sensitive quantification of isoprenoid cytokinins in plants by selective immunoaffinity purification and high performance liquid chromatography-quadrupole-time of flight mass spectrometry. Methods. 2012 Feb;56(2):174-9. doi: 10.1016/j.ymeth.2011.08.006. Epub 2011 Aug 16. [PubMed:21867755 ]

Showing NP-Card for Zeatin riboside (NP0021801)

MOL for NP0021801 (Zeatin riboside)

3D MOL for NP0021801 (Zeatin riboside)

3D SDF for NP0021801 (Zeatin riboside)

3D-SDF for NP0021801 (Zeatin riboside)

PDB for NP0021801 (Zeatin riboside)

3D PDB for NP0021801 (Zeatin riboside)

SMILES for NP0021801 (Zeatin riboside)

INCHI for NP0021801 (Zeatin riboside)

Structure for NP0021801 (Zeatin riboside)

3D Structure for NP0021801 (Zeatin riboside)