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Showing metabocard for 6-Dimethylaminopurine (HMDB0000473)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:52 UTC
HMDB IDHMDB0000473
Secondary Accession Numbers
  • HMDB00473
Metabolite Identification
Common Name6-Dimethylaminopurine
Description6-Dimethylaminopurine, also known as 6,6-dimethyladenine or 6-DMAP, 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-Dimethylaminopurine is a puromycin analog that was first identified in the spores of Streptomyces alboniger (PMID: 5019066 ). It has subsequently been identified in several algae species (PMID: 4206669 ). 6-DMAP is widely used in the lab as a cell cycle inhibitor and a cyclin dependent kinase inhibitor. It also induces cell apoptosis. 6-DMAP is widely used for oocyte activation in eukaryotic cloning experiments (PMID: 29467049 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000473 (6-Dimethylaminopurine)

6-Dimethylaminopurine.mol
  Mrv1652305271900002D          

 12 13  0  0  0  0            999 V2000
    0.8643    0.0487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643   -1.2862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  4  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for HMDB0000473 (6-Dimethylaminopurine)

HMDB0000473
     RDKit          3D
6-Dimethylaminopurine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.9879    0.1943   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    0.0353    0.3297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0049    0.5185    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -0.5604    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389   -1.6744    1.1192 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -2.2457    1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4663   -1.6706    0.5283 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.5494   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0775    0.2283   -0.9609 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    1.2520   -1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    1.1305   -1.0661 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    0.0367   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -0.1700   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583    1.2394   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -0.4377   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.5042    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    0.6422    2.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -0.1323    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.1506    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7155    2.0531   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854    1.7567   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  4  1  0
 12  8  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  6 19  1  0
 10 20  1  0
 11 21  1  0
M  END
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3D SDF for HMDB0000473 (6-Dimethylaminopurine)

6-Dimethylaminopurine.mol
  Mrv1652305271900002D          

 12 13  0  0  0  0            999 V2000
    0.8643    0.0487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643   -1.2862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    1.0312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  4  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000473

> <DATABASE_NAME>
hmdb

> <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_KEY>
BVIAOQMSVZHOJM-UHFFFAOYSA-N

> <FORMULA>
C7H9N5

> <MOLECULAR_WEIGHT>
163.1799

> <EXACT_MASS>
163.085795313

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.31681816805774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-dimethyl-7H-purin-6-amine

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.3634995819999999

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.185405008874447

> <JCHEM_PKA_STRONGEST_BASIC>
3.352502039178554

> <JCHEM_POLAR_SURFACE_AREA>
57.7

> <JCHEM_REFRACTIVITY>
47.9477

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(dimethylamino)-purine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000473 (6-Dimethylaminopurine)

HMDB0000473
     RDKit          3D
6-Dimethylaminopurine
 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.9879    0.1943   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982    0.0353    0.3297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0049    0.5185    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0075   -0.5604    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389   -1.6744    1.1192 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -2.2457    1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4663   -1.6706    0.5283 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.5494   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0775    0.2283   -0.9609 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    1.2520   -1.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871    1.1305   -1.0661 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264    0.0367   -0.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0506   -0.1700   -0.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583    1.2394   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -0.4377   -1.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.5042    1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    0.6422    2.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772   -0.1323    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -3.1506    1.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7155    2.0531   -2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854    1.7567   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  4  1  0
 12  8  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  6 19  1  0
 10 20  1  0
 11 21  1  0
M  END
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PDB for HMDB0000473 (6-Dimethylaminopurine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6-Dimethylaminopurine.mol                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       1.613   0.091   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.519  -1.155   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.613  -2.401   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.149  -1.925   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.185  -2.695   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.519  -1.925   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.519  -0.385   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.185   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.149  -0.385   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.185   1.925   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.519   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.149   2.695   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    1    4                                                  
CONECT   10   11   12    8                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for HMDB0000473 (6-Dimethylaminopurine)

COMPND    HMDB0000473
HETATM    1  C1  UNL     1      -1.988   0.194  -0.945  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.298   0.035   0.330  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.005   0.518   1.506  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.008  -0.560   0.405  1.00  0.00           C  
HETATM    5  N2  UNL     1       0.239  -1.674   1.119  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.454  -2.246   1.198  1.00  0.00           C  
HETATM    7  N3  UNL     1       2.466  -1.671   0.528  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.277  -0.549  -0.206  1.00  0.00           C  
HETATM    9  N4  UNL     1       3.077   0.228  -0.961  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.379   1.252  -1.492  1.00  0.00           C  
HETATM   11  N5  UNL     1       1.087   1.130  -1.066  1.00  0.00           N  
HETATM   12  C7  UNL     1       1.026   0.037  -0.285  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.051  -0.170  -0.837  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.058   1.239  -1.265  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.528  -0.438  -1.730  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.456   1.504   1.200  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.317   0.642   2.379  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.877  -0.132   1.757  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.578  -3.151   1.798  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.715   2.053  -2.141  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.285   1.757  -1.292  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4
CONECT    3   16   17   18
CONECT    4    5    5   12
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8
CONECT    8    9   12   12
CONECT    9   10   10
CONECT   10   11   20
CONECT   11   12   21
END
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SMILES for HMDB0000473 (6-Dimethylaminopurine)

CN(C)C1=NC=NC2=C1NC=N2
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INCHI for HMDB0000473 (6-Dimethylaminopurine)

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)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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 KeyBVIAOQMSVZHOJM-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
  • Dialkylarylamine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022062
KNApSAcK IDC00032053
Chemspider ID3022
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5460
PubChem Compound3134
PDB IDNot Available
ChEBI ID60281
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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)Not Available
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. [PubMed: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. [PubMed:10655310 ]
  3. Sarngadharan MG, Pogell BM, Kariya M: Occurrence of new metabolites containing N 6 ,N 6 -dimethyladenine in spores of Streptomyces alboniger. Biochim Biophys Acta. 1972 Apr 12;262(4):405-9. doi: 10.1016/0005-2787(72)90483-2. [PubMed:5019066 ]
  4. Pakhomova MV: [N6-dimethylaminopurine in DNA of algae species]. Dokl Akad Nauk SSSR. 1974 Feb 11;214(5):1202-5. [PubMed:4206669 ]
  5. Kochan J, Nowak A, Nizanski W, Prochowska S, Migdal A, Mlodawska W, Partyka A, Witkowski M: Developmental competence of cat (Felis domesticus) oocytes and embryos after parthenogenetic stimulation using different methods. Zygote. 2018 Feb 22:1-8. doi: 10.1017/S0967199418000011. [PubMed:29467049 ]