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Showing NP-Card for Dihydrozeatin-7-N-dihydrozeatin (NP0334807)

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Record Information
Version2.0
Created at2024-09-10 20:02:55 UTC
Updated at2024-09-10 20:02:55 UTC
NP-MRD IDNP0334807
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrozeatin-7-N-dihydrozeatin
DescriptionDihydrozeatin-7-N-dihydrozeatin belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Dihydrozeatin-7-N-dihydrozeatin is involved in the cytokinin 7-N glucoside biosynthesis in plants, as a product of the N-glucosylation of dihydrozeatin by UDP-glucose. Dihydrozeatin-7-N-dihydrozeatin is a very strong basic compound (based on its pKa). The addition at the N position decreases the physiological activity of the cytokine. N-glucosylation is common in radish. This leads to believe that the N-glucosylation may be a strategy of detoxification for plants. When plants are exposed to a high concentration of cytokinins, the latter become mostly conjugated into 7-N glucosides.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)


  Mrv0541 02241203502D          

 27 29  0  0  1  0            999 V2000
    9.8040   -9.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8040  -10.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891   -9.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891  -10.8539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741   -9.6165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741  -10.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5848   -9.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0688  -10.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5848  -10.6943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891   -8.3789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3747   -7.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6598   -8.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9565   -7.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9567   -7.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -8.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5272   -7.9655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8379   -8.5770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6463   -8.4065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2878   -7.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8993   -7.6256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5408   -7.1856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3494   -7.0152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1963   -9.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7079   -7.4551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6023   -6.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9909   -6.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2439   -5.7888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  2  1  2  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  2  0  0  0  0
 10  3  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 17  7  1  6  0  0  0
 18 23  1  1  0  0  0
 20 24  1  6  0  0  0
 22 25  1  1  0  0  0
 21 26  1  6  0  0  0
 27 26  1  0  0  0  0
M  END
Download

3D MOL for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)

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3D SDF for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)

  Mrv0541 02241203502D          

 27 29  0  0  1  0            999 V2000
    9.8040   -9.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8040  -10.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891   -9.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891  -10.8539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741   -9.6165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741  -10.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5848   -9.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0688  -10.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5848  -10.6943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891   -8.3789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3747   -7.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6598   -8.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9565   -7.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9567   -7.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -8.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5272   -7.9655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8379   -8.5770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6463   -8.4065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2878   -7.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8993   -7.6256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5408   -7.1856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3494   -7.0152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1963   -9.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7079   -7.4551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6023   -6.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9909   -6.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2439   -5.7888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  2  1  2  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  2  0  0  0  0
 10  3  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 17  7  1  6  0  0  0
 18 23  1  1  0  0  0
 20 24  1  6  0  0  0
 22 25  1  1  0  0  0
 21 26  1  6  0  0  0
 27 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334807

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)CCNC1=NC=NC2=C1N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O6/c1-8(4-22)2-3-17-14-10-15(19-6-18-14)20-7-21(10)16-13(26)12(25)11(24)9(5-23)27-16/h6-9,11-13,16,22-26H,2-5H2,1H3,(H,17,18,19)/t8?,9-,11-,12+,13-,16-/m1/s1

> <INCHI_KEY>
WSELIHNWDGFXRQ-UFZVAZPKSA-N

> <FORMULA>
C16H25N5O6

> <MOLECULAR_WEIGHT>
383.3996

> <EXACT_MASS>
383.180483557

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
38.64201900169878

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{6-[(4-hydroxy-3-methylbutyl)amino]-7H-purin-7-yl}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.72

> <JCHEM_LOGP>
-2.209859008666666

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.27037016236536

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.35881218007312

> <JCHEM_PKA_STRONGEST_BASIC>
5.129656612981334

> <JCHEM_POLAR_SURFACE_AREA>
166.01

> <JCHEM_REFRACTIVITY>
96.54559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{6-[(4-hydroxy-3-methylbutyl)amino]purin-7-yl}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)
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PDB for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      18.301 -17.951   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.301 -19.491   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.966 -17.180   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      16.966 -20.261   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      15.632 -17.951   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      15.632 -19.491   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      19.758 -17.478   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      20.662 -18.721   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      19.758 -19.963   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      16.966 -15.641   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      15.633 -14.871   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.298 -15.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.985 -14.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.986 -13.341   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.651 -15.639   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.317 -14.869   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.231 -16.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.740 -15.692   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      19.204 -14.881   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      22.212 -14.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.676 -13.413   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.186 -13.095   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.766 -16.832   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      23.721 -13.916   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      21.658 -11.627   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      18.650 -12.263   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      19.122 -10.806   0.000  0.00  0.00           O+0
CONECT    1    3    7    2                                                  
CONECT    2    4    1    9                                                  
CONECT    3    1    5   10                                                  
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    1    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    2    8                                                       
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   18   19    7                                                  
CONECT   18   17   20   23                                                  
CONECT   19   17   21                                                       
CONECT   20   18   22   24                                                  
CONECT   21   19   22   26                                                  
CONECT   22   20   21   25                                                  
CONECT   23   18                                                            
CONECT   24   20                                                            
CONECT   25   22                                                            
CONECT   26   21   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

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3D PDB for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)
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SMILES for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)
CC(CO)CCNC1=NC=NC2=C1N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Download
INCHI for NP0334807 (Dihydrozeatin-7-N-dihydrozeatin)
InChI=1S/C16H25N5O6/c1-8(4-22)2-3-17-14-10-15(19-6-18-14)20-7-21(10)16-13(26)12(25)11(24)9(5-23)27-16/h6-9,11-13,16,22-26H,2-5H2,1H3,(H,17,18,19)/t8?,9-,11-,12+,13-,16-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC16H25N5O6
Average Mass383.3996 Da
Monoisotopic Mass383.18048 Da
IUPAC Name(2R,3R,4S,5S,6R)-2-{6-[(4-hydroxy-3-methylbutyl)amino]-7H-purin-7-yl}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,3R,4S,5S,6R)-2-{6-[(4-hydroxy-3-methylbutyl)amino]purin-7-yl}-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
CC(CO)CCNC1=NC=NC2=C1N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C16H25N5O6/c1-8(4-22)2-3-17-14-10-15(19-6-18-14)20-7-21(10)16-13(26)12(25)11(24)9(5-23)27-16/h6-9,11-13,16,22-26H,2-5H2,1H3,(H,17,18,19)/t8?,9-,11-,12+,13-,16-/m1/s1
InChI KeyWSELIHNWDGFXRQ-UFZVAZPKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentGlycosylamines  
Alternative Parents
Substituents
  • Hexose monosaccharide
    • 

  • N-glycosyl compound
    • 

  • 6-alkylaminopurine
    • 

  • 6-aminopurine
    • 

  • Imidazopyrimidine
    • 

  • Purine
    • 

  • Aminopyrimidine
    • 

  • Secondary aliphatic/aromatic amine
    • 

  • Monosaccharide
    • 

  • N-substituted imidazole
    • 

  • Oxane
    • 

  • Pyrimidine
    • 

  • Imidolactam
    • 

  • Azole
    • 

  • Heteroaromatic compound
    • 

  • Imidazole
    • 

  • Secondary alcohol
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Polyol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Primary alcohol
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organopnictogen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.72ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.01 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity96.55 m³·mol⁻¹ChemAxon
Polarizability38.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0012211  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028856  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-4615  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481388  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available