NP-MRD: Showing NP-Card for Dothistromin (NP0051608)

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Record Information

Version

2.0

Created at

2022-04-27 22:54:34 UTC

Updated at

2022-04-27 22:54:34 UTC

NP-MRD ID

NP0051608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dothistromin

Description

Dothistromin belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Dothistromin is found in Cercospora spp., Dothistroma pini and Pinus radiata. Dothistromin was first documented in 2019 (PMID: 31590374). Based on a literature review a small amount of articles have been published on Dothistromin (PMID: 35448744) (PMID: 35241965) (PMID: 34616379) (PMID: 31053329).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200542D          

 27 31  0  0  1  0            999 V2000
    8.1499    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2578    1.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6034    1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8412    1.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7332    2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3876    2.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2797    3.6206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710    2.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8630    3.4337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3166    2.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4245    1.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868    0.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2947    0.1621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701    0.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0078    1.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999    1.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5543    2.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    3.2468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0887    2.0766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6952    1.3515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2633    0.7532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8840    1.5016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761    2.3195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5206    2.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0510    2.7129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    2.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7114    0.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 15 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 19 26  1  6  0  0  0
  3 27  1  0  0  0  0
M  END

     RDKit          3D

 39 43  0  0  0  0  0  0  0  0999 V2000
    2.1750   -0.5619   -2.8672 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -0.1527   -1.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -0.0478   -1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -0.4011   -1.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6572   -0.2998   -1.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8492    0.1328   -0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7745    0.4905    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741    0.9026    1.9335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    0.3869    0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6770    0.7412    0.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4710    1.1340    2.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089    0.6287    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1338    0.9556    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0229    1.3923    2.4422 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244    0.8363    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5364    0.4004   -0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4552    0.0637   -1.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5496   -0.3831   -2.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2102    0.1938   -0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2858    0.1431    0.1349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8378    1.4093    0.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -0.7367    1.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668   -1.5986    0.6696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9894   -2.7519    1.3921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1897   -1.8737   -0.5869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765   -0.6130   -1.0351 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8923   -0.5859   -2.0379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963   -0.7350   -2.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5349    1.1903    2.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2862    1.5458    3.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2534    1.1063    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5231    0.3014   -1.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4272   -0.4919   -3.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1803    2.1397    0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0868   -0.1890    2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300   -1.4122    1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6722   -0.9643    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8852   -2.6625    1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7895   -0.1131   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  1
 20 26  1  0
 26 25  1  0
 26 27  1  0
 27  5  1  0
  5  4  2  0
  4  3  1  0
  3  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19  2  1  0
  2  1  2  0
 25 23  1  0
  6  5  1  0
 19 12  1  0
  6 20  1  0
  2  3  1  0
 24 38  1  0
 23 37  1  6
 22 35  1  0
 22 36  1  0
 21 34  1  0
 26 39  1  6
  4 28  1  0
  8 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
M  END


  Mrv1652304282200542D          

 27 31  0  0  1  0            999 V2000
    8.1499    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2578    1.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6034    1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8412    1.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7332    2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3876    2.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2797    3.6206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710    2.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8630    3.4337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3166    2.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4245    1.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1868    0.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2947    0.1621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701    0.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0078    1.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8999    1.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5543    2.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    3.2468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0887    2.0766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6952    1.3515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2633    0.7532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8840    1.5016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761    2.3195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5206    2.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0510    2.7129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    2.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7114    0.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 15 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 19 26  1  6  0  0  0
  3 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C[C@]2(O)[C@H](O1)OC1=CC3=C(C(O)=C21)C(=O)C1=C(O)C=CC(O)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O9/c19-6-1-2-7(20)12-11(6)14(22)5-3-8-13(16(24)10(5)15(12)23)18(25)4-9(21)27-17(18)26-8/h1-3,9,17,19-21,24-25H,4H2/t9-,17+,18-/m1/s1

> <INCHI_KEY>
FBPGRTYADYGYRG-AHBCHLHISA-N

> <FORMULA>
C18H12O9

> <MOLECULAR_WEIGHT>
372.285

> <EXACT_MASS>
372.048131966

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
34.05212656727893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,6R,8S)-2,4,6,15,18-pentahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaene-13,20-dione

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.858456715

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.731240050243118

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.09903289940111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9837976643333066

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
87.25740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,6R,8S)-2,4,6,15,18-pentahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaene-13,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      15.213   4.643   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.415   3.116   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.193   2.178   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.770   2.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.569   4.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.790   5.232   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.589   6.758   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.146   4.883   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.944   6.410   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.924   3.945   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.126   2.418   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.549   1.829   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.750   0.303   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.904   1.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.481   2.069   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.280   3.596   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.501   4.534   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.300   6.061   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.766   3.876   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.031   2.523   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.091   1.406   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.517   2.803   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.315   4.330   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.705   4.993   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.962   5.064   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.500   5.230   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      14.395   0.651   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   24   26                                             
CONECT   20   19   21   22                                                  
CONECT   21   20   15                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   19                                                            
CONECT   27    3                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₂O₉

Average Mass

372.2850 Da

Monoisotopic Mass

372.04813 Da

IUPAC Name

(4R,6R,8S)-2,4,6,15,18-pentahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaene-13,20-dione

Traditional Name

(4R,6R,8S)-2,4,6,15,18-pentahydroxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1(12),2,10,14,16,18-hexaene-13,20-dione

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@]2(O)[C@H](O1)OC1=CC3=C(C(O)=C21)C(=O)C1=C(O)C=CC(O)=C1C3=O

InChI Identifier

InChI=1S/C18H12O9/c19-6-1-2-7(20)12-11(6)14(22)5-3-8-13(16(24)10(5)15(12)23)18(25)4-9(21)27-17(18)26-8/h1-3,9,17,19-21,24-25H,4H2/t9-,17+,18-/m1/s1

InChI Key

FBPGRTYADYGYRG-AHBCHLHISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cercospora spp.	-	KNApSAcK
Dothistroma pini	-	KNApSAcK
Pinus radiata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Naphthofuran
Coumaran
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Tertiary alcohol
Tetrahydrofuran
Vinylogous acid
Hemiacetal
Ketone
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthraquinone (CHEBI:4704 )
Anthraquinone type (C10334 )

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	1.86	ALOGPS
logP	2.86	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.26 m³·mol⁻¹	ChemAxon
Polarizability	34.05 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002817

Chemspider ID

97126

KEGG Compound ID

C10334

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108014

PDB ID

Not Available

ChEBI ID

4704

Good Scents ID

Not Available

References

General References

McCarthy HM, Tarallo M, Mesarich CH, McDougal RL, Bradshaw RE: Targeted Gene Mutations in the Forest Pathogen Dothistroma septosporum Using CRISPR/Cas9. Plants (Basel). 2022 Apr 8;11(8). pii: plants11081016. doi: 10.3390/plants11081016. [PubMed:35448744 ]
Shahid F, Alghamdi YS, Mashraqi M, Khurshid M, Ashfaq UA: Proteome based mapping and molecular docking revealed DnaA as a potential drug target against Shigella sonnei. Saudi J Biol Sci. 2022 Feb;29(2):1147-1159. doi: 10.1016/j.sjbs.2021.09.051. Epub 2021 Oct 1. [PubMed:35241965 ]
Huang K, Tang J, Zou Y, Sun X, Lan J, Wang W, Xu P, Wu X, Ma R, Wang Q, Wang Z, Liu J: Whole Genome Sequence of Alternaria alternata, the Causal Agent of Black Spot of Kiwifruit. Front Microbiol. 2021 Sep 20;12:713462. doi: 10.3389/fmicb.2021.713462. eCollection 2021. [PubMed:34616379 ]
Bradshaw RE, Ormond S, Dupont PY, Chettri P, Ozturk IK, McDougal RL, Bulman LS, Cox MP: Reduced Virulence of an Introduced Forest Pathogen over 50 Years. Microorganisms. 2019 Oct 5;7(10). pii: microorganisms7100420. doi: 10.3390/microorganisms7100420. [PubMed:31590374 ]
Ozturk IK, Dupont PY, Chettri P, McDougal R, Bohl OJ, Cox RJ, Bradshaw RE: Evolutionary relics dominate the small number of secondary metabolism genes in the hemibiotrophic fungus Dothistroma septosporum. Fungal Biol. 2019 May;123(5):397-407. doi: 10.1016/j.funbio.2019.02.006. Epub 2019 Feb 27. [PubMed:31053329 ]

Showing NP-Card for Dothistromin (NP0051608)

MOL for NP0051608 (Dothistromin)

3D MOL for NP0051608 (Dothistromin)

3D SDF for NP0051608 (Dothistromin)

3D-SDF for NP0051608 (Dothistromin)

PDB for NP0051608 (Dothistromin)

3D PDB for NP0051608 (Dothistromin)

SMILES for NP0051608 (Dothistromin)

INCHI for NP0051608 (Dothistromin)

Structure for NP0051608 (Dothistromin)

3D Structure for NP0051608 (Dothistromin)