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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:21:09 UTC

Update Date

2021-09-14 15:00:46 UTC

HMDB ID

HMDB0012215

Secondary Accession Numbers

HMDB12215

Metabolite Identification

Common Name

Dihydrozeatin

Description

Dihydrozeatin (CAS: 23599-75-9) belongs to the class of organic compounds known as 6-alkylaminopurines. 6-Alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Dihydrozeatin is an intermediate in zeatin biosynthesis. It is converted from dihydrozeatin riboside and is then converted into dihydrozeatin-O-glucoside via glycosyltransferases (EC 2.4.1.- ). Dihydrozeatin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0012215
     RDKit          3D
Dihydrozeatin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.3686    1.3662    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0876   -0.0928    0.2067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1485   -0.8666   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881   -0.3993   -1.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601   -0.4997   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5935    0.1072    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440   -0.3471   -0.1835 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213    0.0758    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467    0.9160    1.3361 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    1.3644    1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653    0.9294    1.3034 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2711    0.0799    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -0.4698   -0.4319 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208   -1.2432   -1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -1.1882   -1.2714 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0749   -0.3660   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.5324   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325    1.9542   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845    1.7996    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -0.4467    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464   -0.7716   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -1.9253   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.4899   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6794   -0.2071   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977   -1.6060   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6051    1.1932    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5985   -0.2748    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -1.0085   -0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    2.0446    2.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781   -0.3078   -0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -1.8322   -2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  8  1  0
 16 12  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
M  END


  Mrv1652309272007332D          

 16 17  0  0  0  0            999 V2000
 9995.8930 9998.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1786 9998.5232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1786 9997.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8930 9997.2856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6074 9997.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6074 9998.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3920 9997.4431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8770 9998.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3921 9998.7780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8930 9999.7607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.177610000.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4619 9999.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.746710000.1716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.0313 9999.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.315710000.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.746710000.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  8  9  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  5  7  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  6  0  0  0
 14 15  1  0  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012215

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](CO)CCNC1=NC=NC2=C1N=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h5-7,16H,2-4H2,1H3,(H2,11,12,13,14,15)/t7-/m1/s1

> <INCHI_KEY>
XXFACTAYGKKOQB-SSDOTTSWSA-N

> <FORMULA>
C10H15N5O

> <MOLECULAR_WEIGHT>
221.259

> <EXACT_MASS>
221.127660127

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.566260444919735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-methyl-4-[(9H-purin-6-yl)amino]butan-1-ol

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.022884575666666813

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.478057088834127

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.869743789288108

> <JCHEM_PKA_STRONGEST_BASIC>
4.070395689508308

> <JCHEM_POLAR_SURFACE_AREA>
86.72

> <JCHEM_REFRACTIVITY>
62.366600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-methyl-4-(9H-purin-6-ylamino)butan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012215
     RDKit          3D
Dihydrozeatin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.3686    1.3662    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0876   -0.0928    0.2067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1485   -0.8666   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881   -0.3993   -1.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601   -0.4997   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5935    0.1072    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440   -0.3471   -0.1835 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213    0.0758    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467    0.9160    1.3361 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    1.3644    1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653    0.9294    1.3034 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2711    0.0799    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -0.4698   -0.4319 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208   -1.2432   -1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -1.1882   -1.2714 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0749   -0.3660   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.5324   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325    1.9542   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845    1.7996    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -0.4467    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464   -0.7716   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -1.9253   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.4899   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6794   -0.2071   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977   -1.6060   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6051    1.1932    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5985   -0.2748    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -1.0085   -0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    2.0446    2.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781   -0.3078   -0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -1.8322   -2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  8  1  0
 16 12  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8659.0008664.680   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8657.6678663.910   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8657.6678662.370   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8659.0008661.600   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8660.3348662.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8660.3348663.910   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8661.7988661.894   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8662.7048663.140   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8661.7998664.386   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0    8659.0008666.220   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8657.6658666.987   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8656.3298666.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8654.9948666.987   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8653.6588666.220   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8652.3238666.987   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8654.9948668.532   0.000  0.00  0.00           C+0
CONECT    1    6    2   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    6    4    7                                                  
CONECT    6    5    1    9                                                  
CONECT    7    8    5                                                       
CONECT    8    9    7                                                       
CONECT    9    8    6                                                       
CONECT   10   11    1                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0012215
HETATM    1  C1  UNL     1      -3.369   1.366   0.158  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.088  -0.093   0.207  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.149  -0.867  -0.576  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.088  -0.399  -1.891  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.760  -0.500  -0.320  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.594   0.107   0.399  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.644  -0.347  -0.183  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.921   0.076   0.307  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.947   0.916   1.336  1.00  0.00           N  
HETATM   10  C7  UNL     1       3.122   1.364   1.860  1.00  0.00           C  
HETATM   11  N3  UNL     1       4.265   0.929   1.303  1.00  0.00           N  
HETATM   12  C8  UNL     1       4.271   0.080   0.263  1.00  0.00           C  
HETATM   13  N4  UNL     1       5.271  -0.470  -0.432  1.00  0.00           N  
HETATM   14  C9  UNL     1       4.721  -1.243  -1.368  1.00  0.00           C  
HETATM   15  N5  UNL     1       3.363  -1.188  -1.271  1.00  0.00           N  
HETATM   16  C10 UNL     1       3.075  -0.366  -0.258  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.355   1.532  -0.335  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.632   1.954  -0.413  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.485   1.800   1.194  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.184  -0.447   1.259  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.146  -0.772  -0.132  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.806  -1.925  -0.587  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.650   0.490  -1.955  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.679  -0.207  -1.404  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.698  -1.606  -0.293  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.605   1.193   0.439  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.599  -0.275   1.457  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.615  -1.008  -0.993  1.00  0.00           H  
HETATM   29  H13 UNL     1       3.131   2.045   2.694  1.00  0.00           H  
HETATM   30  H14 UNL     1       6.278  -0.308  -0.255  1.00  0.00           H  
HETATM   31  H15 UNL     1       5.261  -1.832  -2.101  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    5   20
CONECT    3    4   21   22
CONECT    4   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8   28
CONECT    8    9    9   16
CONECT    9   10
CONECT   10   11   11   29
CONECT   11   12
CONECT   12   13   16   16
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16
END

HMDB0012215
     RDKit          3D
Dihydrozeatin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.3686    1.3662    0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0876   -0.0928    0.2067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1485   -0.8666   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0881   -0.3993   -1.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601   -0.4997   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5935    0.1072    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440   -0.3471   -0.1835 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213    0.0758    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467    0.9160    1.3361 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    1.3644    1.8604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653    0.9294    1.3034 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2711    0.0799    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -0.4698   -0.4319 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208   -1.2432   -1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -1.1882   -1.2714 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0749   -0.3660   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3546    1.5324   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325    1.9542   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845    1.7996    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835   -0.4467    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464   -0.7716   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -1.9253   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6501    0.4899   -1.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6794   -0.2071   -1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977   -1.6060   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6051    1.1932    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5985   -0.2748    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -1.0085   -0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    2.0446    2.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781   -0.3078   -0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -1.8322   -2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  8  1  0
 16 12  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methyl-4-(1H-purin-6-ylamino)butan-1-ol	ChEBI
2-Methyl-4-(9H-purin-6-ylamino)butan-1-ol	ChEBI
N6-(4-Hydroxyisopentanyl)adenine	ChEBI
N(6)-(4-Hydroxyisopentanyl)adenine	ChEBI
R-(+)-Dihydrozeatin	HMDB
2-Methyl-4-(1H-purin-6-ylamino)-1-butanol	HMDB
2-Methyl-4-(purin-6-ylamino)-1-butanol	HMDB
2-Methyl-4-(9H-purin-6-ylamino)-1-butanol	HMDB
(±)-6-(4-hydroxy-3-methylbutylamino)purine	HMDB
(±)-dihydrozeatin	HMDB
6-(4-Hydroxy-3-methylbutylamino)purine	HMDB
dhZ	HMDB

Chemical Formula

C₁₀H₁₅N₅O

Average Molecular Weight

221.259

Monoisotopic Molecular Weight

221.127660127

IUPAC Name

(2R)-2-methyl-4-[(9H-purin-6-yl)amino]butan-1-ol

Traditional Name

(2R)-2-methyl-4-(9H-purin-6-ylamino)butan-1-ol

CAS Registry Number

37789-32-5

SMILES

C[C@@H](CO)CCNC1=NC=NC2=C1N=CN2

InChI Identifier

InChI=1S/C10H15N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h5-7,16H,2-4H2,1H3,(H2,11,12,13,14,15)/t7-/m1/s1

InChI Key

XXFACTAYGKKOQB-SSDOTTSWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-alkylaminopurines. 6-Alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-alkylaminopurines

Alternative Parents

Substituents

6-alkylaminopurine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Secondary amine
Azacycle
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

6-alkylaminopurine (CHEBI:17874 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	0.87	ALOGPS
logP	0.023	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	4.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.37 m³·mol⁻¹	ChemAxon
Polarizability	23.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	148.076	30932474
DeepCCS	[M-H]-	145.691	30932474
DeepCCS	[M-2H]-	179.622	30932474
DeepCCS	[M+Na]+	154.228	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.95 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2845 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.88 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	107.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	904.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	216.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	63.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	293.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	281.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	294.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	602.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	182.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	778.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	174.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	215.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	100.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrozeatin	C[C@@H](CO)CCNC1=NC=NC2=C1N=CN2	2797.1	Standard polar	33892256
Dihydrozeatin	C[C@@H](CO)CCNC1=NC=NC2=C1N=CN2	2318.1	Standard non polar	33892256
Dihydrozeatin	C[C@@H](CO)CCNC1=NC=NC2=C1N=CN2	2520.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrozeatin,1TMS,isomer #1	C[C@H](CCNC1=NC=NC2=C1N=C[NH]2)CO[Si](C)(C)C	2354.5	Semi standard non polar	33892256
Dihydrozeatin,1TMS,isomer #2	C[C@@H](CO)CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C	2301.9	Semi standard non polar	33892256
Dihydrozeatin,1TMS,isomer #3	C[C@@H](CO)CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C	2343.1	Semi standard non polar	33892256
Dihydrozeatin,2TMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C)CO[Si](C)(C)C	2288.2	Semi standard non polar	33892256
Dihydrozeatin,2TMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C)CO[Si](C)(C)C	2334.0	Standard non polar	33892256
Dihydrozeatin,2TMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C)CO[Si](C)(C)C	3111.0	Standard polar	33892256
Dihydrozeatin,2TMS,isomer #2	C[C@H](CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C)CO[Si](C)(C)C	2327.4	Semi standard non polar	33892256
Dihydrozeatin,2TMS,isomer #2	C[C@H](CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C)CO[Si](C)(C)C	2321.8	Standard non polar	33892256
Dihydrozeatin,2TMS,isomer #2	C[C@H](CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C)CO[Si](C)(C)C	3386.0	Standard polar	33892256
Dihydrozeatin,2TMS,isomer #3	C[C@@H](CO)CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C)[Si](C)(C)C	2336.7	Semi standard non polar	33892256
Dihydrozeatin,2TMS,isomer #3	C[C@@H](CO)CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C)[Si](C)(C)C	2395.8	Standard non polar	33892256
Dihydrozeatin,2TMS,isomer #3	C[C@@H](CO)CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C)[Si](C)(C)C	3210.4	Standard polar	33892256
Dihydrozeatin,3TMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C	2352.7	Semi standard non polar	33892256
Dihydrozeatin,3TMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C	2358.9	Standard non polar	33892256
Dihydrozeatin,3TMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C	2876.8	Standard polar	33892256
Dihydrozeatin,1TBDMS,isomer #1	C[C@H](CCNC1=NC=NC2=C1N=C[NH]2)CO[Si](C)(C)C(C)(C)C	2580.0	Semi standard non polar	33892256
Dihydrozeatin,1TBDMS,isomer #2	C[C@@H](CO)CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C(C)(C)C	2512.3	Semi standard non polar	33892256
Dihydrozeatin,1TBDMS,isomer #3	C[C@@H](CO)CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C	2544.7	Semi standard non polar	33892256
Dihydrozeatin,2TBDMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	2681.9	Semi standard non polar	33892256
Dihydrozeatin,2TBDMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	2771.1	Standard non polar	33892256
Dihydrozeatin,2TBDMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=C[NH]2)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	3208.7	Standard polar	33892256
Dihydrozeatin,2TBDMS,isomer #2	C[C@H](CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	2708.2	Semi standard non polar	33892256
Dihydrozeatin,2TBDMS,isomer #2	C[C@H](CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	2747.5	Standard non polar	33892256
Dihydrozeatin,2TBDMS,isomer #2	C[C@H](CCNC1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	3439.0	Standard polar	33892256
Dihydrozeatin,2TBDMS,isomer #3	C[C@@H](CO)CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2703.0	Semi standard non polar	33892256
Dihydrozeatin,2TBDMS,isomer #3	C[C@@H](CO)CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2773.8	Standard non polar	33892256
Dihydrozeatin,2TBDMS,isomer #3	C[C@@H](CO)CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3241.3	Standard polar	33892256
Dihydrozeatin,3TBDMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	2892.1	Semi standard non polar	33892256
Dihydrozeatin,3TBDMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	2986.8	Standard non polar	33892256
Dihydrozeatin,3TBDMS,isomer #1	C[C@H](CCN(C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	3059.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrozeatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-006y-4910000000-64e07d4d0ad79ac1f160	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrozeatin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 10V, Positive-QTOF	splash10-0fk9-1190000000-eeed45e6f34029f4f288	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 20V, Positive-QTOF	splash10-0fri-5940000000-20ce0273455d75e25277	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 40V, Positive-QTOF	splash10-0a4r-9300000000-722b9fb7a98ff5ce3305	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 10V, Negative-QTOF	splash10-00di-0490000000-c80669658787bc48e39a	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 20V, Negative-QTOF	splash10-008c-1940000000-97f5feb5ab1aa84752c8	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 40V, Negative-QTOF	splash10-0a59-1900000000-6c5349b3ee02af070ccc	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 10V, Positive-QTOF	splash10-00di-0090000000-0b3ddc08e2bd1f21331e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 20V, Positive-QTOF	splash10-0079-0790000000-dda44e87b7e9cc931c4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 40V, Positive-QTOF	splash10-066u-5900000000-a0a55ed77aada87563e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 10V, Negative-QTOF	splash10-00di-0090000000-6bb36ac7b8bd1dcfd7ec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 20V, Negative-QTOF	splash10-0ul0-0690000000-39d021b0aa264bbb635b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrozeatin 40V, Negative-QTOF	splash10-05o3-5900000000-26fafdca8800a4115e9e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000093

Chemspider ID

26329318

KEGG Compound ID

Not Available

BioCyc ID

CPD-332

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

688447

PDB ID

Not Available

ChEBI ID

17874

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Dihydrozeatin (HMDB0012215)

MOL for HMDB0012215 (Dihydrozeatin)

3D MOL for HMDB0012215 (Dihydrozeatin)

3D SDF for HMDB0012215 (Dihydrozeatin)

3D-SDF for HMDB0012215 (Dihydrozeatin)

PDB for HMDB0012215 (Dihydrozeatin)

3D PDB for HMDB0012215 (Dihydrozeatin)

SMILES for HMDB0012215 (Dihydrozeatin)

INCHI for HMDB0012215 (Dihydrozeatin)

Structure for HMDB0012215 (Dihydrozeatin)

3D Structure for HMDB0012215 (Dihydrozeatin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra