NP-MRD: Showing NP-Card for (+)-(1S,2S,6S,8R,7'S)-discorhabdin H2 (NP0035559)

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Record Information

Version

1.0

Created at

2021-06-20 18:58:17 UTC

Updated at

2021-06-30 00:06:36 UTC

NP-MRD ID

NP0035559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(1S,2S,6S,8R,7'S)-discorhabdin H2

Provided By

JEOL Database JEOL Logo

Description

(+)-(1S,2S,6S,8R,7'S)-discorhabdin H2 is found in Latrunculia species. It was first documented in 2010 (Grkovic, T., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120583D          

 61 68  0  0  0  0            999 V2000
   -1.8475    1.1326   -5.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3212    0.8837   -3.8845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094    1.7434   -2.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5160    0.0362   -2.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5761    0.3118   -5.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
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 20 21  2  0  0  0  0
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  7  8  1  0  0  0  0
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 17 16  1  0  0  0  0
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  7 42  1  6  0  0  0
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  1 38  1  0  0  0  0
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  1 40  1  0  0  0  0
M  CHG  2  28   1  34   1
M  END

     RDKit          3D

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M  CHG  2  28   1  34   1
M  END


  Mrv1652306202120583D          

 61 68  0  0  0  0            999 V2000
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   -0.6163   -0.2091   -3.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2239   -1.3336   -4.8176 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2477   -1.1031   -3.7319 N   0  3  0  0  0  4  0  0  0  0  0  0
    1.3670   -0.2978   -5.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484   -0.0283   -6.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.3118   -5.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0546    1.6837    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4933   -0.7987    2.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -4.6755    2.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328   -2.8549    1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -3.3046    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9323    3.4991    1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3362   -1.8919   -3.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    0.9071   -6.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
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 33 35  1  0  0  0  0
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 16  7  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  1  0  0  0  0
 28  8  1  0  0  0  0
 17 16  1  0  0  0  0
 16 12  1  1  0  0  0
 16 15  1  0  0  0  0
 12 11  2  0  0  0  0
 15 14  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 14 19  1  0  0  0  0
 14 13  1  0  0  0  0
 27 26  1  0  0  0  0
  9 10  2  0  0  0  0
 12 13  1  0  0  0  0
 35 37  1  0  0  0  0
  8 43  1  6  0  0  0
 22 20  1  0  0  0  0
  7  6  1  0  0  0  0
  2 31  1  0  0  0  0
 27 17  1  0  0  0  0
 18 20  1  0  0  0  0
 27 28  2  0  0  0  0
 25 30  1  0  0  0  0
 31  5  2  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
  3  2  1  0  0  0  0
  5  6  1  0  0  0  0
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  2  1  1  0  0  0  0
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  7 42  1  6  0  0  0
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  3 41  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  CHG  2  28   1  34   1
M  END
> <DATABASE_ID>
NP0035559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])([N+]([H])([H])[H])C([H])([H])C1=C(S[C@]2([H])[C@]3([H])C(=O)C([H])=C4S[C@@]5([H])N([H])C6=C(C7=[N+]3C([H])([H])C([H])([H])C3=C([H])N([H])C(=C73)C6=O)[C@@]24C5([H])[H])N=C([H])N1C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H22N6O4S2/c1-30-8-28-23(11(30)4-10(26)24(34)35)37-22-19-12(32)5-13-25(22)6-14(36-13)29-18-16(25)20-15-9(2-3-31(19)20)7-27-17(15)21(18)33/h5,7-8,10,14,19,22H,2-4,6,26H2,1H3,(H2,27,29,33,34,35)/p+2/t10-,14+,19-,22+,25-/m0/s1

> <INCHI_KEY>
ARYKGGHKIXVLJL-YXIWQQKDSA-P

> <FORMULA>
C25H24N6O4S2

> <MOLECULAR_WEIGHT>
536.62

> <EXACT_MASS>
536.128948465

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
54.674873934955215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5S,10R)-4-({5-[(2S)-2-azaniumyl-2-carboxyethyl]-1-methyl-1H-imidazol-4-yl}sulfanyl)-6,13-dioxo-9-thia-11,15,20lambda5-triazaheptacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{5,20}.0^{17,21}]docosa-1(20),2(12),7,14(21),16-pentaen-20-ylium

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-5.380609251219034

> <ALOGPS_LOGS>
-4.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.659667728686095

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5699923652128507

> <JCHEM_PKA_STRONGEST_BASIC>
9.203785499260894

> <JCHEM_POLAR_SURFACE_AREA>
147.73

> <JCHEM_REFRACTIVITY>
165.04340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5S,10R)-4-({5-[(2S)-2-ammonio-2-carboxyethyl]-1-methylimidazol-4-yl}sulfanyl)-6,13-dioxo-9-thia-11,15,20lambda5-triazaheptacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{5,20}.0^{17,21}]docosa-1(20),2(12),7,14(21),16-pentaen-20-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 68  0  0  0  0  0  0  0  0999 V2000
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    1.2028    0.6729    1.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    1.5931    2.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5660   -1.6032    2.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972   -3.1692    3.2016 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8708    1.2104    5.8530 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0762    1.4654    2.2892 N   0  0  0  0  0  4  0  0  0  0  0  0
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   -0.6163   -0.2091   -3.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -1.3946   -4.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2239   -1.3336   -4.8176 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2477   -1.1031   -3.7319 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3670   -0.2978   -5.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484   -0.0283   -6.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3328   -2.8549    1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -3.3046    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0979    3.7163    2.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0435   -0.2470   -3.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629   -0.9355   -4.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -1.8919   -3.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    0.9071   -6.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 25 26  1  0
 18 17  2  0
 35 36  2  0
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 26 22  2  0
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 24 25  2  0
 33 34  1  0
 20 21  2  0
 32 31  1  0
 16  7  1  0
  7  8  1  0
 18 19  1  0
 28  8  1  0
 17 16  1  0
 16 12  1  1
 16 15  1  0
 12 11  2  0
 15 14  1  0
  8  9  1  0
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 14 19  1  0
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 27 26  1  0
  9 10  2  0
 12 13  1  0
 35 37  1  0
  8 43  1  6
 22 20  1  0
  7  6  1  0
  2 31  1  0
 27 17  1  0
 18 20  1  0
 27 28  2  0
 25 30  1  0
 31  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  5  6  1  0
 30 29  1  0
  2  1  1  0
 33 57  1  6
 34 58  1  0
 34 59  1  0
 34 60  1  0
 37 61  1  0
 32 55  1  0
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 14 45  1  6
 19 48  1  0
 30 53  1  0
 30 54  1  0
 29 51  1  0
 29 52  1  0
 23 49  1  0
 24 50  1  0
  7 42  1  6
 11 44  1  0
  3 41  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
M  CHG  2  28   1  34   1
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.847   1.133  -5.210  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.321   0.884  -3.885  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.509   1.743  -2.834  0.00  0.00           C+0
HETATM    4  N   UNK     0      -1.025   1.254  -1.717  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.516   0.036  -2.051  0.00  0.00           C+0
HETATM    6  S   UNK     0       0.174  -1.001  -0.828  0.00  0.00           S+0
HETATM    7  C   UNK     0      -0.766  -0.398   0.660  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.160   0.912   1.221  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.203   0.673   1.879  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.005   1.593   2.009  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.522  -0.667   2.453  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.566  -1.603   2.441  0.00  0.00           C+0
HETATM   13  S   UNK     0       0.697  -3.169   3.202  0.00  0.00           S+0
HETATM   14  C   UNK     0      -1.069  -3.596   2.827  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.280  -2.838   1.505  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.811  -1.402   1.837  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.687  -0.821   2.948  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.238  -1.641   3.875  0.00  0.00           C+0
HETATM   19  N   UNK     0      -1.958  -3.000   3.811  0.00  0.00           N+0
HETATM   20  C   UNK     0      -3.078  -1.085   5.038  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.578  -1.824   5.874  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.196   0.352   5.020  0.00  0.00           C+0
HETATM   23  N   UNK     0      -3.871   1.210   5.853  0.00  0.00           N+0
HETATM   24  C   UNK     0      -3.675   2.515   5.409  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.864   2.480   4.296  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.578   1.132   4.085  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.746   0.659   3.040  0.00  0.00           C+0
HETATM   28  N   UNK     0      -1.076   1.465   2.289  0.00  0.00           N+1
HETATM   29  C   UNK     0      -1.053   2.970   2.594  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.320   3.491   3.345  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.616  -0.209  -3.411  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.200  -1.395  -4.240  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.224  -1.334  -4.818  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.248  -1.103  -3.732  0.00  0.00           N+1
HETATM   35  C   UNK     0       1.367  -0.298  -5.933  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.548  -0.028  -6.790  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.576   0.312  -5.889  0.00  0.00           O+0
HETATM   38  H   UNK     0      -2.787   1.685  -5.118  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.043   0.188  -5.718  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.117   1.732  -5.757  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.016   2.697  -2.945  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.798  -0.227   0.323  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.055   1.684   0.456  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.493  -0.799   2.919  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.217  -4.676   2.738  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.333  -2.855   1.195  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.698  -3.305   0.700  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.280  -3.565   4.602  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.427   0.934   6.657  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.148   3.335   5.937  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.932   3.499   1.644  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.159   3.130   3.207  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.098   3.716   2.605  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.080   4.428   3.861  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.278  -2.293  -3.614  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.917  -1.555  -5.053  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.488  -2.303  -5.256  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.043  -0.247  -3.201  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.163  -0.936  -4.182  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.336  -1.892  -3.082  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.602   0.907  -6.680  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2   31    3    1                                                  
CONECT    3    4    2   41                                                  
CONECT    4    5    3                                                       
CONECT    5   31    4    6                                                  
CONECT    6    7    5                                                       
CONECT    7   16    8    6   42                                             
CONECT    8    7   28    9   43                                             
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11   12    9   44                                                  
CONECT   12   16   11   13                                                  
CONECT   13   14   12                                                       
CONECT   14   15   19   13   45                                             
CONECT   15   16   14   46   47                                             
CONECT   16    7   17   12   15                                             
CONECT   17   18   16   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14   48                                                  
CONECT   20   21   22   18                                                  
CONECT   21   20                                                            
CONECT   22   26   23   20                                                  
CONECT   23   22   24   49                                                  
CONECT   24   23   25   50                                                  
CONECT   25   26   24   30                                                  
CONECT   26   25   22   27                                                  
CONECT   27   26   17   28                                                  
CONECT   28   29    8   27                                                  
CONECT   29   28   30   51   52                                             
CONECT   30   25   29   53   54                                             
CONECT   31   32    2    5                                                  
CONECT   32   33   31   55   56                                             
CONECT   33   35   32   34   57                                             
CONECT   34   33   58   59   60                                             
CONECT   35   36   33   37                                                  
CONECT   36   35                                                            
CONECT   37   35   61                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    3                                                            
CONECT   42    7                                                            
CONECT   43    8                                                            
CONECT   44   11                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   19                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   29                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
CONECT   54   30                                                            
CONECT   55   32                                                            
CONECT   56   32                                                            
CONECT   57   33                                                            
CONECT   58   34                                                            
CONECT   59   34                                                            
CONECT   60   34                                                            
CONECT   61   37                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  136    0
END

RDKit          3D

61 68  0  0  0  0  0  0  0  0999 V2000
   -1.8475    1.1326   -5.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3212    0.8837   -3.8845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094    1.7434   -2.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0249    1.2541   -1.7167 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5160    0.0362   -2.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1736   -1.0014   -0.8277 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656   -0.3982    0.6600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1604    0.9116    1.2210 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2028    0.6729    1.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    1.5931    2.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218   -0.6672    2.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -1.6032    2.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6972   -3.1692    3.2016 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688   -3.5965    2.8271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2799   -2.8383    1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8112   -1.4017    1.8367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6870   -0.8207    2.9476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -1.6409    3.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9585   -2.9997    3.8114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0784   -1.0850    5.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5779   -1.8242    5.8738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957    0.3519    5.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8708    1.2104    5.8530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6753    2.5147    5.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8638    2.4799    4.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5780    1.1322    4.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458    0.6585    3.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762    1.4654    2.2892 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0530    2.9695    2.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196    3.4915    3.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163   -0.2091   -3.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -1.3946   -4.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2239   -1.3336   -4.8176 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2477   -1.1031   -3.7319 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3670   -0.2978   -5.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484   -0.0283   -6.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.3118   -5.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    1.6849   -5.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427    0.1876   -5.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1165    1.7315   -5.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0158    2.6966   -2.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7977   -0.2266    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    1.6837    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4933   -0.7987    2.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2171   -4.6755    2.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328   -2.8549    1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -3.3046    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -3.5653    4.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4270    0.9344    6.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484    3.3351    5.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9323    3.4991    1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    3.1299    3.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0979    3.7163    2.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0802    4.4279    3.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -2.2934   -3.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174   -1.5550   -5.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -2.3026   -5.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0435   -0.2470   -3.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629   -0.9355   -4.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -1.8919   -3.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019    0.9071   -6.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 25 26  1  0
 18 17  2  0
 35 36  2  0
 33 35  1  0
 33 32  1  0
 26 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 33 34  1  0
 20 21  2  0
 32 31  1  0
 16  7  1  0
  7  8  1  0
 18 19  1  0
 28  8  1  0
 17 16  1  0
 16 12  1  1
 16 15  1  0
 12 11  2  0
 15 14  1  0
  8  9  1  0
  9 11  1  0
 14 19  1  0
 14 13  1  0
 27 26  1  0
  9 10  2  0
 12 13  1  0
 35 37  1  0
  8 43  1  6
 22 20  1  0
  7  6  1  0
  2 31  1  0
 27 17  1  0
 18 20  1  0
 27 28  2  0
 25 30  1  0
 31  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  5  6  1  0
 30 29  1  0
  2  1  1  0
 33 57  1  6
 34 58  1  0
 34 59  1  0
 34 60  1  0
 37 61  1  0
 32 55  1  0
 32 56  1  0
 15 46  1  0
 15 47  1  0
 14 45  1  6
 19 48  1  0
 30 53  1  0
 30 54  1  0
 29 51  1  0
 29 52  1  0
 23 49  1  0
 24 50  1  0
  7 42  1  6
 11 44  1  0
  3 41  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
M  CHG  2  28   1  34   1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄N₆O₄S₂

Average Mass

536.6200 Da

Monoisotopic Mass

536.12895 Da

IUPAC Name

(3S,4S,5S,10R)-4-({5-[(2S)-2-azaniumyl-2-carboxyethyl]-1-methyl-1H-imidazol-4-yl}sulfanyl)-6,13-dioxo-9-thia-11,15,20lambda5-triazaheptacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{5,20}.0^{17,21}]docosa-1(20),2(12),7,14(21),16-pentaen-20-ylium

Traditional Name

(3S,4S,5S,10R)-4-({5-[(2S)-2-ammonio-2-carboxyethyl]-1-methylimidazol-4-yl}sulfanyl)-6,13-dioxo-9-thia-11,15,20lambda5-triazaheptacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{5,20}.0^{17,21}]docosa-1(20),2(12),7,14(21),16-pentaen-20-ylium

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]([H])([N+]([H])([H])[H])C([H])([H])C1=C(S[C@]2([H])[C@]3([H])C(=O)C([H])=C4S[C@@]5([H])N([H])C6=C(C7=[N+]3C([H])([H])C([H])([H])C3=C([H])N([H])C(=C73)C6=O)[C@@]24C5([H])[H])N=C([H])N1C([H])([H])[H]

InChI Identifier

InChI=1S/C25H22N6O4S2/c1-30-8-28-23(11(30)4-10(26)24(34)35)37-22-19-12(32)5-13-25(22)6-14(36-13)29-18-16(25)20-15-9(2-3-31(19)20)7-27-17(15)21(18)33/h5,7-8,10,14,19,22H,2-4,6,26H2,1H3,(H2,27,29,33,34,35)/p+2/t10-,14+,19-,22+,25-/m0/s1

InChI Key

ARYKGGHKIXVLJL-YXIWQQKDSA-P

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Latrunculia sp.	JEOL database	Grkovic, T., et al, J. Nat. Prod. 73, 1686 (2010)

Chemical Taxonomy

Classification

Not classified

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	-0.78	ALOGPS
logP	-5.4	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	1.57	ChemAxon
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	147.73 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	165.04 m³·mol⁻¹	ChemAxon
Polarizability	54.67 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Grkovic, T., et al. (2010). Grkovic, T., et al, J. Nat. Prod. 73, 1686 (2010). J. Nat. Prod..

Showing NP-Card for (+)-(1S,2S,6S,8R,7'S)-discorhabdin H2 (NP0035559)

MOL for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

3D MOL for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

3D SDF for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

3D-SDF for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

PDB for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

3D PDB for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

SMILES for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

INCHI for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

Structure for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)

3D Structure for NP0035559 ((+)-(1S,2S,6S,8R,7'S)-discorhabdin H2)