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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:37:15 UTC
Update Date2022-03-07 02:56:07 UTC
HMDB IDHMDB0039238
Secondary Accession Numbers
  • HMDB39238
Metabolite Identification
Common Name6-Benzylaminopurine
Description6-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
Data?1587136609
Synonyms
ValueSource
6-(Benzylamino)purineChEBI
6-[(Phenylmethyl)amino]-9H-purineChEBI
6-BAPChEBI
BAPChEBI
BenzyladenineChEBI
Cytokinin bChEBI
N-BENZYL-9H-purin-6-amineChEBI
N(6)-(Benzylamino)purineChEBI
N6-BenzyladenineChEBI
N-BenzyladenineKegg
6-BenzylaminopurineChEBI
6-(N-Benzylamino)purineHMDB, MeSH
6-Benzyl adenineHMDB
6-BenzyladenineHMDB, MeSH
Aminopurine, 6-benzylHMDB
Benzyl(purin-6-yl)amineHMDB
BenzylaminopurineHMDB, MeSH
N(6)-BenzylaminopurineHMDB
N-(Phenylmethyl)-1H-purin-6-amineHMDB
N-(Phenylmethyl)-9H-purin-6-amineHMDB
N-6-BenzyladenineHMDB
N-Benzyl-1H-purin-6-amineHMDB
N-Benzyl-adenineHMDB
N(6)-BenzyladenineMeSH, HMDB
6-BA CPDMeSH, HMDB
6-BenzylaminopurinMeSH, HMDB
6-BAHMDB
6-BenzylaminoadenineHMDB
BAHMDB
N6-(Benzylamino)purineHMDB
N6-BenzylaminopurineHMDB
Chemical FormulaC12H11N5
Average Molecular Weight225.2492
Monoisotopic Molecular Weight225.101445377
IUPAC NameN-benzyl-9H-purin-6-amine
Traditional Namebenzyladenine
CAS Registry Number1214-39-7
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 KeyNWBJYWHLCVSVIJ-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point229 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.06 mg/mL at 20 °CNot Available
LogP1.57Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP1.79ALOGPS
logP1.5ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)5.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.71 m³·mol⁻¹ChemAxon
Polarizability23.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.92131661259
DarkChem[M-H]-152.08431661259
DeepCCS[M+H]+146.81230932474
DeepCCS[M-H]-144.41730932474
DeepCCS[M-2H]-177.7530932474
DeepCCS[M+Na]+152.72530932474
AllCCS[M+H]+152.632859911
AllCCS[M+H-H2O]+148.532859911
AllCCS[M+NH4]+156.432859911
AllCCS[M+Na]+157.532859911
AllCCS[M-H]-154.132859911
AllCCS[M+Na-2H]-153.732859911
AllCCS[M+HCOO]-153.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-BenzylaminopurineC(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C13091.3Standard polar33892256
6-BenzylaminopurineC(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C12299.6Standard non polar33892256
6-BenzylaminopurineC(NC1=C2N=CNC2=NC=N1)C1=CC=CC=C12569.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Benzylaminopurine,1TMS,isomer #1C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]22300.5Semi standard non polar33892256
6-Benzylaminopurine,1TMS,isomer #1C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]22328.6Standard non polar33892256
6-Benzylaminopurine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C212356.0Semi standard non polar33892256
6-Benzylaminopurine,1TMS,isomer #2C[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C212351.8Standard non polar33892256
6-Benzylaminopurine,2TMS,isomer #1C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C2331.2Semi standard non polar33892256
6-Benzylaminopurine,2TMS,isomer #1C[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C2399.5Standard non polar33892256
6-Benzylaminopurine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]22515.7Semi standard non polar33892256
6-Benzylaminopurine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=C[NH]22536.2Standard non polar33892256
6-Benzylaminopurine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C212544.5Semi standard non polar33892256
6-Benzylaminopurine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=NC2=C(NCC3=CC=CC=C3)N=CN=C212535.6Standard non polar33892256
6-Benzylaminopurine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C2707.7Semi standard non polar33892256
6-Benzylaminopurine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CC1=CC=CC=C1)C1=NC=NC2=C1N=CN2[Si](C)(C)C(C)(C)C2758.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 6-Benzylaminopurine GC-MS (2 TMS)splash10-00kg-8897000000-b735bd69f4d3c66c68662014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 6-Benzylaminopurine GC-MS (1 TMS)splash10-052g-5950000000-3a3ea3a0f6612856b9432014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 6-Benzylaminopurine GC-MS (Non-derivatized)splash10-00kg-8897000000-b735bd69f4d3c66c68662017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 6-Benzylaminopurine GC-MS (Non-derivatized)splash10-052g-5950000000-3a3ea3a0f6612856b9432017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Benzylaminopurine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6950000000-ee50c643ac085461c8d42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Benzylaminopurine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine DI-ESI-qTof , Positive-QTOFsplash10-0002-0900000000-6df717266d1bfff2a2782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-qTof , Positive-QTOFsplash10-0006-9321100001-76476c391804e93ba1742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOFsplash10-00di-0090000000-187dcd7d2b7e6ad101132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOFsplash10-00di-0290000000-db56ee844739463558d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-25690980dd53487d74c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-8a68b4bbc9e5d341c5422017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , negative-QTOFsplash10-001i-1900000000-3cd72cd7d4abfc7f4c2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOFsplash10-004i-0090000000-0fd45fd2505a135cfdc92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOFsplash10-004i-2090000000-820b2c69e4f3d818f46f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-f523baaa0e67f3b2d3ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-56177b73949cf0e41d532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-QQ , positive-QTOFsplash10-0006-9000000000-abe81a4ac3253400d8182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine LC-ESI-IT , positive-QTOFsplash10-0006-9100000000-d1e59ff4c955cf6f217f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine , positive-QTOFsplash10-0006-9321100001-76476c391804e93ba1742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine 30V, Positive-QTOFsplash10-00e9-0690000000-53e234ca2a60bc40569c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine 75V, Negative-QTOFsplash10-001i-0900000000-3c22bc94ac89f78700e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine 60V, Positive-QTOFsplash10-0006-9000000000-87d1e238eb0f411364962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine 45V, Positive-QTOFsplash10-0006-9010000000-59735dfe8428c40f98c62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Benzylaminopurine 15V, Positive-QTOFsplash10-004i-0090000000-088e97a7b53ae27bbcd52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Benzylaminopurine 10V, Positive-QTOFsplash10-004i-3290000000-520ea084b21e6473325c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Benzylaminopurine 20V, Positive-QTOFsplash10-0006-9530000000-60cd2a57975649d890d42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Benzylaminopurine 40V, Positive-QTOFsplash10-0006-9300000000-f295aa371b019646c4a52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Benzylaminopurine 10V, Negative-QTOFsplash10-00di-0490000000-d90701b935a56d70f2fd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Benzylaminopurine 20V, Negative-QTOFsplash10-05gi-1940000000-3e59c6e16e278e5e7a9d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Benzylaminopurine 40V, Negative-QTOFsplash10-0api-4900000000-511da7d1749324bac7e52015-04-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018775
KNApSAcK IDC00000092
Chemspider ID56177
KEGG Compound IDC11263
BioCyc IDCPD-4604
BiGG IDNot Available
Wikipedia Link6-Benzylaminopurine
METLIN IDNot Available
PubChem Compound62389
PDB IDEMU
ChEBI ID29022
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1212511
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .