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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:43 UTC
HMDB IDHMDB00473
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-Dimethylaminopurine
Description6-Dimethylaminopurine is a serine threonine protein kinase inhibitor. It inhibits the germinal vesicle breakdown and the meiotic maturation of oocytes. (PMID 2540051 ). 6-Dimethylaminopurine can be used to rtificially lengthen the pre-maturation period of oocyte growth, in vitro, by inhibiting germinal vesicle breakdown in mouse and human oocytes. (PMID: 10655310 ).
Structure
Thumb
Synonyms
ValueSource
6-(dimethylamino)PurineChEBI
6-DimethyladenineChEBI
6-DimethylaminopurineChEBI
N,N-Dimethyl-1H-purin-6-amineChEBI
N,N-Dimethyl-6-aminopurineChEBI
N,N-DimethyladenineChEBI
N(6)-DimethyladenineChEBI
6,6-DimethyladenineHMDB
6-(dimethylamino)-PurineHMDB
6-Dimethylamine purineHMDB
DimethyladenineHMDB
DMAPHMDB
N,N-Dimethyl-adenineHMDB
N6,N6-Dimethyl-adenineHMDB
N6,N6-DimethyladenineHMDB
Chemical FormulaC7H9N5
Average Molecular Weight163.1799
Monoisotopic Molecular Weight163.085795313
IUPAC NameN,N-dimethyl-7H-purin-6-amine
Traditional Name6-(dimethylamino)-purine
CAS Registry Number938-55-6
SMILES
CN(C)C1=NC=NC2=C1NC=N2
InChI Identifier
InChI=1S/C7H9N5/c1-12(2)7-5-6(9-3-8-5)10-4-11-7/h3-4H,1-2H3,(H,8,9,10,11)
InChI KeyInChIKey=BVIAOQMSVZHOJM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 6-alkylaminopurines. These 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
  • Dialkylarylamine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.07 mg/mLALOGPS
logP0.53ALOGPS
logP0.36ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)10.19ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.7 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.95 m3·mol-1ChemAxon
Polarizability16.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0300-2900000000-3190d18e3cc2e66cc97dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-aab2d716306424dc0765View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9500000000-91620b9504a7308b12e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-93fb9b2f222378a415d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-c6797046cc77d63cba06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-55b592d8f334e4afae80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-266255a5066deb62d134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-716bd3f65c301c7559b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-e5e0a5fa678fabe408c6View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022062
KNApSAcK IDNot Available
Chemspider ID3022
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDMAP
NuGOwiki LinkHMDB00473
Metagene LinkHMDB00473
METLIN ID5460
PubChem Compound3134
PDB ID42C
ChEBI ID60281
References
Synthesis ReferenceBaker, B. R.; Joseph, Joseph P.; Schaub, Robert E. Puromycin. Synthetic studies. I. Synthesis of 6-dimethylaminopurine, a hydrolytic fragment. Journal of Organic Chemistry (1954), 19 631-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rime H, Neant I, Guerrier P, Ozon R: 6-Dimethylaminopurine (6-DMAP), a reversible inhibitor of the transition to metaphase during the first meiotic cell division of the mouse oocyte. Dev Biol. 1989 May;133(1):169-79. [2540051 ]
  2. Anderiesz C, Fong CY, Bongso A, Trounson AO: Regulation of human and mouse oocyte maturation in vitro with 6-dimethylaminopurine. Hum Reprod. 2000 Feb;15(2):379-88. [10655310 ]