Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:37:15 UTC

Update Date

2022-03-07 02:56:07 UTC

HMDB ID

HMDB0039238

Secondary Accession Numbers

HMDB39238

Metabolite Identification

Common Name

6-Benzylaminopurine

Description

6-Benzylaminopurine (6-BAP), also known as N6-benzyladenine or cytokinin B, 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. 6-Benzylaminopurine is a very strong basic compound (based on its pKa). Outside of the human body, 6-benzylaminopurine has been detected, but not quantified in, garden tomato (var.) and wild celeries. This could make 6-benzylaminopurine a potential biomarker for the consumption of these foods. 6-Benzylaminopurine is a synthetic cytokinin applied externally postharvest to maintain the quality, delay senescence, and improve the nutritional value of green vegetables (PMID: 22148319 ).

Structure

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

HMDB0039238
     RDKit          3D
6-Benzylaminopurine
 28 30  0  0  0  0  0  0  0  0999 V2000
    4.6949   -0.7441   -0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217   -0.3691   -1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706    0.2043   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    0.4322   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938    1.0514   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2553    0.0642   -0.2384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5971    0.5153   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    1.8324   -0.1646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982    2.2373   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1558    1.2981   -0.2878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.0145   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6410   -1.1445   -0.4918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602   -2.2244   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818   -1.7670   -0.4636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051   -0.4267   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343    0.0483    1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9907   -0.5295    1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6737   -1.1973   -0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6800   -0.5384   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030    0.5064   -2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675    1.7660   -0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    1.6220    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091   -0.9250   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458    3.3043   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6749   -1.1381   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1060   -3.2741   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614    0.2268    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4195   -0.8162    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  4 16  1  0
 16 17  2  0
 17  1  1  0
 15  7  1  0
 15 11  2  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
M  END

  Mrv0541 02241216342D          

 17 19  0  0  0  0            999 V2000
    2.8189    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0884    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6035    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5333    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5333    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1044    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  2  0  0  0  0
  7 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 12 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039238

> <DATABASE_NAME>
hmdb

> <SMILES>
C(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H11N5/c1-2-4-9(5-3-1)6-13-11-10-12(15-7-14-10)17-8-16-11/h1-5,7-8H,6H2,(H2,13,14,15,16,17)

> <INCHI_KEY>
NWBJYWHLCVSVIJ-UHFFFAOYSA-N

> <FORMULA>
C12H11N5

> <MOLECULAR_WEIGHT>
225.2492

> <EXACT_MASS>
225.101445377

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.61969310088466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-benzyl-9H-purin-6-amine

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.4951644686666667

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.28321024022187

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.867655926014256

> <JCHEM_PKA_STRONGEST_BASIC>
5.055377673202723

> <JCHEM_POLAR_SURFACE_AREA>
66.49000000000001

> <JCHEM_REFRACTIVITY>
66.70530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyladenine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039238
     RDKit          3D
6-Benzylaminopurine
 28 30  0  0  0  0  0  0  0  0999 V2000
    4.6949   -0.7441   -0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217   -0.3691   -1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706    0.2043   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    0.4322   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938    1.0514   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2553    0.0642   -0.2384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5971    0.5153   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    1.8324   -0.1646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982    2.2373   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1558    1.2981   -0.2878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.0145   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6410   -1.1445   -0.4918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602   -2.2244   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818   -1.7670   -0.4636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051   -0.4267   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343    0.0483    1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9907   -0.5295    1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6737   -1.1973   -0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6800   -0.5384   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030    0.5064   -2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675    1.7660   -0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    1.6220    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091   -0.9250   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458    3.3043   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6749   -1.1381   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1060   -3.2741   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614    0.2268    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4195   -0.8162    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  4 16  1  0
 16 17  2  0
 17  1  1  0
 15  7  1  0
 15 11  2  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
M  END

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       5.262   4.620   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.928   3.850   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.928   2.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.594   1.540   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.594   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.928  -0.770   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.262   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.727  -0.476   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.632   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       6.727   2.016   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.262   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.262   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.595   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.595   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.262   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.928   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.928   6.930   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3    7                                                  
CONECT   12    1   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0039238
HETATM    1  C1  UNL     1       4.695  -0.744  -0.074  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.122  -0.369  -1.276  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.871   0.204  -1.267  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.142   0.432  -0.122  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.794   1.051  -0.125  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.255   0.064  -0.238  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.597   0.515  -0.253  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.914   1.832  -0.165  1.00  0.00           N  
HETATM    9  C7  UNL     1      -3.198   2.237  -0.181  1.00  0.00           C  
HETATM   10  N3  UNL     1      -4.156   1.298  -0.288  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.910  -0.015  -0.379  1.00  0.00           C  
HETATM   12  N4  UNL     1      -4.641  -1.145  -0.492  1.00  0.00           N  
HETATM   13  C9  UNL     1      -3.860  -2.224  -0.545  1.00  0.00           C  
HETATM   14  N5  UNL     1      -2.582  -1.767  -0.464  1.00  0.00           N  
HETATM   15  C10 UNL     1      -2.605  -0.427  -0.362  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.734   0.048   1.083  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.991  -0.530   1.095  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.674  -1.197  -0.032  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.680  -0.538  -2.211  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.403   0.506  -2.207  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.668   1.766  -0.964  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.601   1.622   0.810  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.009  -0.925  -0.305  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.446   3.304  -0.109  1.00  0.00           H  
HETATM   25  H8  UNL     1      -5.675  -1.138  -0.529  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.106  -3.274  -0.635  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.161   0.227   1.990  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.419  -0.816   2.060  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    4   20
CONECT    4    5   16
CONECT    5    6   21   22
CONECT    6    7   23
CONECT    7    8    8   15
CONECT    8    9
CONECT    9   10   10   24
CONECT   10   11
CONECT   11   12   15   15
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15
CONECT   16   17   17   27
CONECT   17   28
END

HMDB0039238
     RDKit          3D
6-Benzylaminopurine
 28 30  0  0  0  0  0  0  0  0999 V2000
    4.6949   -0.7441   -0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217   -0.3691   -1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706    0.2043   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    0.4322   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938    1.0514   -0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2553    0.0642   -0.2384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5971    0.5153   -0.2534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    1.8324   -0.1646 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982    2.2373   -0.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1558    1.2981   -0.2878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9098   -0.0145   -0.3788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6410   -1.1445   -0.4918 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602   -2.2244   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818   -1.7670   -0.4636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051   -0.4267   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343    0.0483    1.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9907   -0.5295    1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6737   -1.1973   -0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6800   -0.5384   -2.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030    0.5064   -2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6675    1.7660   -0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    1.6220    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091   -0.9250   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458    3.3043   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6749   -1.1381   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1060   -3.2741   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1614    0.2268    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4195   -0.8162    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  4 16  1  0
 16 17  2  0
 17  1  1  0
 15  7  1  0
 15 11  2  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 16 27  1  0
 17 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-(Benzylamino)purine	ChEBI
6-[(Phenylmethyl)amino]-9H-purine	ChEBI
6-BAP	ChEBI
BAP	ChEBI
Benzyladenine	ChEBI
Cytokinin b	ChEBI
N-BENZYL-9H-purin-6-amine	ChEBI
N(6)-(Benzylamino)purine	ChEBI
N6-Benzyladenine	ChEBI
N-Benzyladenine	Kegg
6-Benzylaminopurine	ChEBI
6-(N-Benzylamino)purine	HMDB, MeSH
6-Benzyl adenine	HMDB
6-Benzyladenine	HMDB, MeSH
Aminopurine, 6-benzyl	HMDB
Benzyl(purin-6-yl)amine	HMDB
Benzylaminopurine	HMDB, MeSH
N(6)-Benzylaminopurine	HMDB
N-(Phenylmethyl)-1H-purin-6-amine	HMDB
N-(Phenylmethyl)-9H-purin-6-amine	HMDB
N-6-Benzyladenine	HMDB
N-Benzyl-1H-purin-6-amine	HMDB
N-Benzyl-adenine	HMDB
N(6)-Benzyladenine	MeSH, HMDB
6-BA CPD	MeSH, HMDB
6-Benzylaminopurin	MeSH, HMDB
6-BA	HMDB
6-Benzylaminoadenine	HMDB
BA	HMDB
N6-(Benzylamino)purine	HMDB
N6-Benzylaminopurine	HMDB

Chemical Formula

C₁₂H₁₁N₅

Average Molecular Weight

225.2492

Monoisotopic Molecular Weight

225.101445377

IUPAC Name

N-benzyl-9H-purin-6-amine

Traditional Name

benzyladenine

CAS Registry Number

1214-39-7

SMILES

C(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H11N5/c1-2-4-9(5-3-1)6-13-11-10-12(15-7-14-10)17-8-16-11/h1-5,7-8H,6H2,(H2,13,14,15,16,17)

InChI Key

NWBJYWHLCVSVIJ-UHFFFAOYSA-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
Benzylamine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Imidolactam
Imidazole
Heteroaromatic compound
Azole
Secondary amine
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

6-aminopurines (CHEBI:29022 )
Cytokinins (C11263 )
a small molecule (CPD-4604 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039238)
Cytoplasm (HMDB: HMDB0039238)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039238)

Source

Exogenous

Exogenous (HMDB: HMDB0039238)

Food

Food (HMDB: HMDB0039238)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Vegetable

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Endogenous

Plant

Plant (HMDB: HMDB0039238)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039238)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	229 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.06 mg/mL at 20 °C	Not Available
LogP	1.57	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.5	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	5.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.71 m³·mol⁻¹	ChemAxon
Polarizability	23.62 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	151.921	31661259
DarkChem	[M-H]-	152.084	31661259
DeepCCS	[M+H]+	146.812	30932474
DeepCCS	[M-H]-	144.417	30932474
DeepCCS	[M-2H]-	177.75	30932474
DeepCCS	[M+Na]+	152.725	30932474
AllCCS	[M+H]+	152.6	32859911
AllCCS	[M+H-H2O]+	148.5	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.5	32859911
AllCCS	[M-H]-	154.1	32859911
AllCCS	[M+Na-2H]-	153.7	32859911
AllCCS	[M+HCOO]-	153.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Benzylaminopurine	C(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C1	3091.3	Standard polar	33892256
6-Benzylaminopurine	C(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C1	2299.6	Standard non polar	33892256
6-Benzylaminopurine	C(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C1	2569.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Benzylaminopurine,1TMS,isomer #1	C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]2	2300.5	Semi standard non polar	33892256
6-Benzylaminopurine,1TMS,isomer #1	C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]2	2328.6	Standard non polar	33892256
6-Benzylaminopurine,1TMS,isomer #2	C[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C21	2356.0	Semi standard non polar	33892256
6-Benzylaminopurine,1TMS,isomer #2	C[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C21	2351.8	Standard non polar	33892256
6-Benzylaminopurine,2TMS,isomer #1	C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C	2331.2	Semi standard non polar	33892256
6-Benzylaminopurine,2TMS,isomer #1	C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C	2399.5	Standard non polar	33892256
6-Benzylaminopurine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]2	2515.7	Semi standard non polar	33892256
6-Benzylaminopurine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]2	2536.2	Standard non polar	33892256
6-Benzylaminopurine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C21	2544.5	Semi standard non polar	33892256
6-Benzylaminopurine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C21	2535.6	Standard non polar	33892256
6-Benzylaminopurine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C	2707.7	Semi standard non polar	33892256
6-Benzylaminopurine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C	2758.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 6-Benzylaminopurine GC-MS (2 TMS)	splash10-00kg-8897000000-b735bd69f4d3c66c6866	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 6-Benzylaminopurine GC-MS (1 TMS)	splash10-052g-5950000000-3a3ea3a0f6612856b943	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 6-Benzylaminopurine GC-MS (Non-derivatized)	splash10-00kg-8897000000-b735bd69f4d3c66c6866	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 6-Benzylaminopurine GC-MS (Non-derivatized)	splash10-052g-5950000000-3a3ea3a0f6612856b943	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Benzylaminopurine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-6950000000-ee50c643ac085461c8d4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Benzylaminopurine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine DI-ESI-qTof , Positive-QTOF	splash10-0002-0900000000-6df717266d1bfff2a278	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-qTof , Positive-QTOF	splash10-0006-9321100001-76476c391804e93ba174	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOF	splash10-00di-0090000000-187dcd7d2b7e6ad10113	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOF	splash10-00di-0290000000-db56ee844739463558d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOF	splash10-001i-0900000000-25690980dd53487d74c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOF	splash10-001i-0900000000-8a68b4bbc9e5d341c542	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOF	splash10-001i-1900000000-3cd72cd7d4abfc7f4c2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOF	splash10-004i-0090000000-0fd45fd2505a135cfdc9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOF	splash10-004i-2090000000-820b2c69e4f3d818f46f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-f523baaa0e67f3b2d3ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-56177b73949cf0e41d53	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-abe81a4ac3253400d818	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-IT , positive-QTOF	splash10-0006-9100000000-d1e59ff4c955cf6f217f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine , positive-QTOF	splash10-0006-9321100001-76476c391804e93ba174	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine 30V, Positive-QTOF	splash10-00e9-0690000000-53e234ca2a60bc40569c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine 75V, Negative-QTOF	splash10-001i-0900000000-3c22bc94ac89f78700e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine 60V, Positive-QTOF	splash10-0006-9000000000-87d1e238eb0f41136496	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine 45V, Positive-QTOF	splash10-0006-9010000000-59735dfe8428c40f98c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 6-Benzylaminopurine 15V, Positive-QTOF	splash10-004i-0090000000-088e97a7b53ae27bbcd5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Benzylaminopurine 10V, Positive-QTOF	splash10-004i-3290000000-520ea084b21e6473325c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Benzylaminopurine 20V, Positive-QTOF	splash10-0006-9530000000-60cd2a57975649d890d4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Benzylaminopurine 40V, Positive-QTOF	splash10-0006-9300000000-f295aa371b019646c4a5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Benzylaminopurine 10V, Negative-QTOF	splash10-00di-0490000000-d90701b935a56d70f2fd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Benzylaminopurine 20V, Negative-QTOF	splash10-05gi-1940000000-3e59c6e16e278e5e7a9d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Benzylaminopurine 40V, Negative-QTOF	splash10-0api-4900000000-511da7d1749324bac7e5	2015-04-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

6-Benzylaminopurine

METLIN ID

Not Available

PubChem Compound

62389

PDB ID

EMU

ChEBI ID

29022

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1212511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Xu F, Yang Z, Chen X, Jin P, Wang X, Zheng Y: 6-Benzylaminopurine delays senescence and enhances health-promoting compounds of harvested broccoli. J Agric Food Chem. 2012 Jan 11;60(1):234-40. doi: 10.1021/jf2040884. Epub 2011 Dec 23. [PubMed:22148319 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 6-Benzylaminopurine (HMDB0039238)

MOL for HMDB0039238 (6-Benzylaminopurine)

3D MOL for HMDB0039238 (6-Benzylaminopurine)

3D SDF for HMDB0039238 (6-Benzylaminopurine)

3D-SDF for HMDB0039238 (6-Benzylaminopurine)

PDB for HMDB0039238 (6-Benzylaminopurine)

3D PDB for HMDB0039238 (6-Benzylaminopurine)

SMILES for HMDB0039238 (6-Benzylaminopurine)

INCHI for HMDB0039238 (6-Benzylaminopurine)

Structure for HMDB0039238 (6-Benzylaminopurine)

3D Structure for HMDB0039238 (6-Benzylaminopurine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra