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Showing NP-Card for 6-Ethylmercaptopurine (NP0002881)

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Record Information
Version2.0
Created at2020-11-23 19:42:42 UTC
Updated at2021-08-12 19:52:24 UTC
NP-MRD IDNP0002881
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Ethylmercaptopurine
Provided ByBMRBBMRB logo
Description6-(Ethylsulfanyl)-9H-purine, also known as 6-ethylmercaptopurine, belongs to the class of organic compounds known as 6-thiopurines. 6-Thiopurines are compounds containing a purine that carries a thiol group at the 6-position. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Based on a literature review very few articles have been published on 6-(ethylsulfanyl)-9H-purine.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002881 (6-Ethylmercaptopurine)


     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -3.7643   -0.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230   -0.9981    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117    1.5492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6793    2.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    2.3800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296    0.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0068    0.3642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8669   -1.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033   -1.4577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6386   -0.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    1.0630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596   -1.8783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2350   -0.1125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889   -2.1735    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985    0.7678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996    4.0964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929   -2.1202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8088   -2.8349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  1
  1 14  1  0
  1 15  1  0
  2 16  1  1
  2 17  1  0
  6 18  1  0
 10 19  1  0
 11 20  1  0
M  END
Download

3D MOL for NP0002881 (6-Ethylmercaptopurine)

NP0002881
     RDKit          3D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -3.7104    0.6923    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212    0.3363    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -0.5734    1.1652 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -0.9348    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -2.0690   -0.5195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -2.3209   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4749   -1.4781   -1.2473 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.3335   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2397    0.7062   -0.3277 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373    1.5810    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    1.1086    0.8150 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639   -0.0814    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    1.2148    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.2379    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4918    1.3525    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6530   -0.3069   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845    1.2758   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -3.2339   -1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827    0.7883   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    2.5140    0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  1  0
 10 11  2  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
  2 16  1  0
  2 17  1  0
  6 18  1  0
  9 19  1  0
 10 20  1  0
M  END
Download

3D SDF for NP0002881 (6-Ethylmercaptopurine)


     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -3.7643   -0.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8230   -0.9981    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680    0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117    1.5492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6793    2.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    2.3800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296    0.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0068    0.3642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8669   -1.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033   -1.4577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6386   -0.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    1.0630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596   -1.8783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2350   -0.1125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889   -2.1735    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985    0.7678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996    4.0964    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929   -2.1202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8088   -2.8349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  1
  1 14  1  0
  1 15  1  0
  2 16  1  1
  2 17  1  0
  6 18  1  0
 10 19  1  0
 11 20  1  0
M  END
> <DATABASE_ID>
NP0002881

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCSC1=NC=NC2=C1N=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C7H8N4S/c1-2-12-7-5-6(9-3-8-5)10-4-11-7/h3-4H,2H2,1H3,(H,8,9,10,11)

> <INCHI_KEY>
XTJLAIOQORFEOI-UHFFFAOYSA-N

> <FORMULA>
C7H8N4S

> <MOLECULAR_WEIGHT>
180.23

> <EXACT_MASS>
180.046967448

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
18.123259913772905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(ethylsulfanyl)-9H-purine

> <JCHEM_LOGP>
1.1791603526666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.919279560816868

> <JCHEM_PKA_STRONGEST_BASIC>
2.601659889375831

> <JCHEM_POLAR_SURFACE_AREA>
54.46

> <JCHEM_REFRACTIVITY>
49.4556

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-Ethyl-MP

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002881 (6-Ethylmercaptopurine)

NP0002881
     RDKit          3D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -3.7104    0.6923    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212    0.3363    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889   -0.5734    1.1652 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -0.9348    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065   -2.0690   -0.5195 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4253   -2.3209   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4749   -1.4781   -1.2473 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -0.3335   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2397    0.7062   -0.3277 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373    1.5810    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254    1.1086    0.8150 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639   -0.0814    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3446    1.2148    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570   -0.2379    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4918    1.3525    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6530   -0.3069   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845    1.2758   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4892   -3.2339   -1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827    0.7883   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    2.5140    0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  1  0
 10 11  2  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
  2 16  1  0
  2 17  1  0
  6 18  1  0
  9 19  1  0
 10 20  1  0
M  END
Download

PDB for NP0002881 (6-Ethylmercaptopurine)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   12  S   UNK     0       6.121  -2.310   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1   12                                                       
CONECT    3    8    9                                                       
CONECT    4   10   11                                                       
CONECT    5    6    7    8                                                  
CONECT    6    5    9   10                                                  
CONECT    7    5   11   12                                                  
CONECT    8    3    5                                                       
CONECT    9    3    6                                                       
CONECT   10    4    6                                                       
CONECT   11    4    7                                                       
CONECT   12    2    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for NP0002881 (6-Ethylmercaptopurine)

COMPND    NP0002881
HETATM    1  C1  UNL     1      -3.710   0.692   0.812  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.421   0.336   0.095  1.00  0.00           C  
HETATM    3  S1  UNL     1      -1.289  -0.573   1.165  1.00  0.00           S  
HETATM    4  C3  UNL     1       0.184  -0.935   0.217  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.306  -2.069  -0.520  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.425  -2.321  -1.226  1.00  0.00           C  
HETATM    7  N2  UNL     1       2.475  -1.478  -1.247  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.412  -0.333  -0.535  1.00  0.00           C  
HETATM    9  N3  UNL     1       3.240   0.706  -0.328  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.637   1.581   0.493  1.00  0.00           C  
HETATM   11  N4  UNL     1       1.425   1.109   0.815  1.00  0.00           N  
HETATM   12  C7  UNL     1       1.264  -0.081   0.187  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.345   1.215   0.045  1.00  0.00           H  
HETATM   14  H2  UNL     1      -4.257  -0.238   1.095  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.492   1.353   1.654  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.653  -0.307  -0.779  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.985   1.276  -0.297  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.489  -3.234  -1.802  1.00  0.00           H  
HETATM   19  H7  UNL     1       4.183   0.788  -0.748  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.110   2.514   0.813  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4
CONECT    4    5    5   12
CONECT    5    6
CONECT    6    7    7   18
CONECT    7    8
CONECT    8    9   12   12
CONECT    9   10   19
CONECT   10   11   11   20
CONECT   11   12
END
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SMILES for NP0002881 (6-Ethylmercaptopurine)

CCSC1=NC=NC2=C1N=CN2
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INCHI for NP0002881 (6-Ethylmercaptopurine)

InChI=1S/C7H8N4S/c1-2-12-7-5-6(9-3-8-5)10-4-11-7/h3-4H,2H2,1H3,(H,8,9,10,11)
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View in JSmol
Synonyms
ValueSource
6-EthylmercaptopurineKegg
6-(Ethylsulphanyl)-9H-purineGenerator
6-EthylthiopurineMeSH
Chemical FormulaC7H8N4S
Average Mass180.2300 Da
Monoisotopic Mass180.04697 Da
IUPAC Name6-(ethylsulfanyl)-9H-purine
Traditional Name6-Ethyl-MP
CAS Registry NumberNot Available
SMILES
CCSC1=NC=NC2=C1N=CN2
InChI Identifier
InChI=1S/C7H8N4S/c1-2-12-7-5-6(9-3-8-5)10-4-11-7/h3-4H,2H2,1H3,(H,8,9,10,11)
InChI KeyXTJLAIOQORFEOI-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, methanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-thiopurines. 6-Thiopurines are compounds containing a purine that carries a thiol group at the 6-position. 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-thiopurines
Alternative Parents
Substituents
  • 6-thiopurine
  • Aryl thioether
  • Alkylarylthioether
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Azacycle
  • Sulfenyl compound
  • Thioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.18ChemAxon
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.46 m³·mol⁻¹ChemAxon
Polarizability18.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID85692
KEGG Compound IDC14623
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References