NP-MRD: Showing NP-Card for 6-Benzylaminopurine (NP0331775)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2023-08-23 16:00:57 UTC

Updated at

2024-09-03 04:16:52 UTC

NP-MRD ID

NP0331775

Natural Product DOI

https://doi.org/10.57994/0840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Benzylaminopurine

Description

Cytokinin B, also known as N6-benzyladenine or 6-BAP, 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. Cytokinin B is a very strong basic compound (based on its pKa). Outside of the human body, Cytokinin B has been detected, but not quantified in, garden tomato (var.) And wild celeries. 6-Benzylaminopurine was first documented in 2006 (PMID: 16691305). This could make cytokinin b a potential biomarker for the consumption of these foods (PMID: 23043692) (PMID: 24579378).

Structure

MOL SDF PDB SMILES InChI


  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>
NP0331775

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

Value	Source
6-(Benzylamino)purine	ChEBI
6-[(Phenylmethyl)amino]-9H-purine	ChEBI
6-BAP	ChEBI
6-Benzylaminopurine	ChEBI
BAP	ChEBI
Benzyladenine	ChEBI
N-BENZYL-9H-purin-6-amine	ChEBI
N(6)-(benzylamino)Purine	ChEBI
N6-Benzyladenine	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
N-Benzyladenine	MeSH, KEGG
6-BA CPD	MeSH, HMDB
Cytokinin B	ChEBI
6-Benzylaminopurin	MeSH
6-BA	HMDB
6-Benzylaminoadenine	HMDB
BA	HMDB
N6-(Benzylamino)purine	HMDB
N6-Benzylaminopurine	HMDB

Chemical Formula

C₁₂H₁₁N₅

Average Mass

225.2492 Da

Monoisotopic Mass

225.10145 Da

IUPAC Name

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

Traditional Name

benzyladenine

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-23	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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 )

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	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

External Links

HMDB ID

HMDB0039238

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

6-Benzylaminopurine

METLIN ID

Not Available

PubChem Compound

62389

PDB ID

EMU

ChEBI ID

29022

Good Scents ID

Not Available

References

General References

Peran R, Berjak P, Pammenter NW, Kioko JI: Cryopreservation, encapsulation and promotion of shoot production of embryonic axes of a recalcitrant species Ekebergia capensis, Sparrm. Cryo Letters. 2006 Jan-Feb;27(1):5-16. [PubMed:16691305 ]
Montalban IA, Novak O, Rolcik J, Strnad M, Moncalean P: Endogenous cytokinin and auxin profiles during in vitro organogenesis from vegetative buds of Pinus radiata adult trees. Physiol Plant. 2013 Jun;148(2):214-31. doi: 10.1111/j.1399-3054.2012.01709.x. Epub 2012 Nov 1. [PubMed:23043692 ]
Verma S, Gill KS, Pruthi V, Dhugga KS, Randhaw GS: A novel combination of plant growth regulators for in vitro regeneration of complete plantlets of guar [Cyamopsis tetragonoloba (L.) Taub]. Indian J Exp Biol. 2013 Dec;51(12):1120-4. [PubMed:24579378 ]

Showing NP-Card for 6-Benzylaminopurine (NP0331775)

MOL for NP0331775 (6-Benzylaminopurine)

3D MOL for NP0331775 (6-Benzylaminopurine)

3D SDF for NP0331775 (6-Benzylaminopurine)

3D-SDF for NP0331775 (6-Benzylaminopurine)

PDB for NP0331775 (6-Benzylaminopurine)

3D PDB for NP0331775 (6-Benzylaminopurine)

SMILES for NP0331775 (6-Benzylaminopurine)

INCHI for NP0331775 (6-Benzylaminopurine)

Structure for NP0331775 (6-Benzylaminopurine)

3D Structure for NP0331775 (6-Benzylaminopurine)