NP-MRD: Showing NP-Card for Scytonemin (NP0022910)

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Record Information

Version

2.0

Created at

2021-01-06 08:03:56 UTC

Updated at

2025-04-15 20:00:15 UTC

NP-MRD ID

NP0022910

Natural Product DOI

https://doi.org/10.57994/3948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scytonemin

Provided By

NPAtlas

Description

Scytonemin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Scytonemin is found in Cyanobacterium. Scytonemin was first documented in 1993 (PMID: 8405307). Based on a literature review a small amount of articles have been published on scytonemin (PMID: 21501195) (PMID: 22688245) (PMID: 24111939) (PMID: 25056905).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105383D          

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  Mrv1652306242105383D          

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  4  5  2  0  0  0  0
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  7  8  1  0  0  0  0
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 42 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022910

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C2\C(=O)C(C3=C4C(=NC5=C([H])C([H])=C([H])C([H])=C45)\C(=C(\[H])C4=C([H])C([H])=C(O[H])C([H])=C4[H])C3=O)=C3C2=NC2=C([H])C([H])=C([H])C([H])=C32)C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C36H20N2O4/c39-21-13-9-19(10-14-21)17-25-33-29(23-5-1-3-7-27(23)37-33)31(35(25)41)32-30-24-6-2-4-8-28(24)38-34(30)26(36(32)42)18-20-11-15-22(40)16-12-20/h1-18,39-40H/b25-17+,26-18+

> <INCHI_KEY>
CGZKSPLDUIRCIO-RPCRKUJJSA-N

> <FORMULA>
C36H20N2O4

> <MOLECULAR_WEIGHT>
544.566

> <EXACT_MASS>
544.142307132

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
59.92686365158883

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-3-[(4-hydroxyphenyl)methylidene]-1-[(3E)-3-[(4-hydroxyphenyl)methylidene]-2-oxo-2H,3H-cyclopenta[b]indol-1-yl]-2H,3H-cyclopenta[b]indol-2-one

> <ALOGPS_LOGP>
5.98

> <JCHEM_LOGP>
8.121023179333333

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.248408130129775

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.646348138803525

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4567813307838096

> <JCHEM_POLAR_SURFACE_AREA>
99.32

> <JCHEM_REFRACTIVITY>
167.0632

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.25e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-3-[(4-hydroxyphenyl)methylidene]-1-[(3E)-3-[(4-hydroxyphenyl)methylidene]-2-oxocyclopenta[b]indol-1-yl]cyclopenta[b]indol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 42 62  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.801   1.670  -1.868  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.490   0.939  -1.188  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.653  -0.462  -0.456  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.582  -0.148  -1.009  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.666  -0.108  -0.141  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.878   0.186  -0.866  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.856   0.249  -0.005  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.394   0.009   1.316  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.982  -0.035   2.557  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.281  -0.293   3.710  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.923  -0.520   3.656  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.308  -0.478   2.424  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.005  -0.222   1.262  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.560   0.297  -2.280  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.384   0.491  -3.303  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.787   0.605  -3.008  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.493   1.695  -3.457  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.850   1.819  -3.188  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.514   0.853  -2.466  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.880   1.017  -2.211  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.835  -0.243  -2.010  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.486  -0.342  -2.290  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.129   0.088  -2.346  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.441   0.104  -3.400  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.778  -0.744   0.035  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.031  -0.200  -0.004  0.00  0.00           C+0
HETATM   27  N   UNK     0      -3.907  -0.876   0.681  0.00  0.00           N+0
HETATM   28  C   UNK     0      -3.258  -1.991   1.258  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.718  -3.046   2.072  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.804  -4.027   2.467  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.478  -4.024   2.112  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.040  -2.953   1.300  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.954  -2.015   0.930  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.829   0.954  -0.841  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.709   1.916  -1.200  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.065   1.732  -0.720  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.581   2.811  -0.001  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.837   2.732   0.535  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.599   1.580   0.364  0.00  0.00           C+0
HETATM   40  O   UNK     0      -8.869   1.536   0.930  0.00  0.00           O+0
HETATM   41  C   UNK     0      -7.096   0.514  -0.349  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.814   0.620  -0.885  0.00  0.00           C+0
HETATM   43  H   UNK     0       5.057   0.142   2.656  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.836  -0.322   4.656  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.411  -0.724   4.571  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.225  -0.656   2.408  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.995   0.557  -4.292  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.989   2.485  -4.026  0.00  0.00           H+0
HETATM   49  H   UNK     0       7.450   2.671  -3.530  0.00  0.00           H+0
HETATM   50  H   UNK     0       9.406   0.349  -1.690  0.00  0.00           H+0
HETATM   51  H   UNK     0       7.359  -0.993  -1.459  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.974  -1.206  -1.961  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.737  -3.080   2.364  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.153  -4.834   3.085  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.824  -4.798   2.445  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.004  -2.998   1.048  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.358   2.723  -1.792  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.970   3.720   0.123  0.00  0.00           H+0
HETATM   59  H   UNK     0      -7.260   3.555   1.094  0.00  0.00           H+0
HETATM   60  H   UNK     0      -9.193   2.336   1.454  0.00  0.00           H+0
HETATM   61  H   UNK     0      -7.691  -0.387  -0.485  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.434  -0.228  -1.466  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   43                                                  
CONECT   10    9   11   44                                                  
CONECT   11   10   12   45                                                  
CONECT   12   11   13   46                                                  
CONECT   13   12    5    8                                                  
CONECT   14    6   15   23                                                  
CONECT   15   14   16   47                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   48                                                  
CONECT   18   17   19   49                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   50                                                       
CONECT   21   19   22   51                                                  
CONECT   22   21   16   52                                                  
CONECT   23   14   24    4                                                  
CONECT   24   23                                                            
CONECT   25    3   26   33                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   53                                                  
CONECT   30   29   31   54                                                  
CONECT   31   30   32   55                                                  
CONECT   32   31   33   56                                                  
CONECT   33   32   25   28                                                  
CONECT   34   26   35    2                                                  
CONECT   35   34   36   57                                                  
CONECT   36   35   37   42                                                  
CONECT   37   36   38   58                                                  
CONECT   38   37   39   59                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39   60                                                       
CONECT   41   39   42   61                                                  
CONECT   42   41   36   62                                                  
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   15                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   29                                                            
CONECT   54   30                                                            
CONECT   55   31                                                            
CONECT   56   32                                                            
CONECT   57   35                                                            
CONECT   58   37                                                            
CONECT   59   38                                                            
CONECT   60   40                                                            
CONECT   61   41                                                            
CONECT   62   42                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  138    0
END

RDKit          3D

62 69  0  0  0  0  0  0  0  0999 V2000
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   -1.4900    0.9391   -1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6527   -0.4618   -0.4557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5818   -0.1476   -1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659   -0.1075   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785    0.1857   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    0.2491   -0.0047 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3939    0.0092    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824   -0.0348    2.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2814   -0.2931    3.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -0.5201    3.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3078   -0.4784    2.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3841    0.4914   -3.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7776   -0.7444    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0310   -0.2000   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -0.8763    0.6806 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2580   -1.9910    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7184   -3.0465    2.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043   -4.0273    2.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775   -4.0235    2.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0397   -2.9527    1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542   -2.0149    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    0.9540   -0.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7095    1.9155   -1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0653    1.7321   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814    2.8108   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8367    2.7323    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5989    1.5796    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8689    1.5357    0.9301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0963    0.5135   -0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8139    0.6195   -0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0574    0.1419    2.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359   -0.3215    4.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4108   -0.7238    4.5709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -0.6559    2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9948    0.5573   -4.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9889    2.4845   -4.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4498    2.6706   -3.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4060    0.3487   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3593   -0.9930   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739   -1.2058   -1.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -3.0799    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530   -4.8338    3.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8238   -4.7977    2.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -2.9980    1.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3580    2.7226   -1.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9703    3.7195    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2595    3.5546    1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1934    2.3357    1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6913   -0.3874   -0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4339   -0.2282   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 14 23  1  0
 23 24  2  0
  3 25  2  0
 25 26  1  0
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 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 26 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 39 41  1  0
 41 42  2  0
 34  2  1  0
 42 36  1  0
 23  4  1  0
 33 25  1  0
 13  5  1  0
 22 16  1  0
 33 28  1  0
 13  8  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 15 47  1  0
 17 48  1  0
 18 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
 32 56  1  0
 35 57  1  0
 37 58  1  0
 38 59  1  0
 40 60  1  0
 41 61  1  0
 42 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₆H₂₀N₂O₄

Average Mass

544.5660 Da

Monoisotopic Mass

544.14231 Da

IUPAC Name

(3E)-3-[(4-hydroxyphenyl)methylidene]-1-[(3E)-3-[(4-hydroxyphenyl)methylidene]-2-oxo-2H,3H-cyclopenta[b]indol-1-yl]-2H,3H-cyclopenta[b]indol-2-one

Traditional Name

(3E)-3-[(4-hydroxyphenyl)methylidene]-1-[(3E)-3-[(4-hydroxyphenyl)methylidene]-2-oxocyclopenta[b]indol-1-yl]cyclopenta[b]indol-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C2\C(=O)C(C3=C4C5=CC=CC=C5N=C4\C(=C/C4=CC=C(O)C=C4)C3=O)=C3C4=CC=CC=C4N=C23)C=C1

InChI Identifier

InChI=1S/C36H20N2O4/c39-21-13-9-19(10-14-21)17-25-33-29(23-5-1-3-7-27(23)37-33)31(35(25)41)32-30-24-6-2-4-8-28(24)38-34(30)26(36(32)42)18-20-11-15-22(40)16-12-20/h1-18,39-40H/b25-17+,26-18+

InChI Key

CGZKSPLDUIRCIO-RPCRKUJJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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
Cyanobacterium	NPAtlas	8405307
Nostoc flagelliforme		Not Available

Species Where Detected

Species Name	Source	Reference
Scytonema spp.	KNApSAcK Database	22123792

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	5.98	ALOGPS
logP	8.12	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	8.65	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	167.06 m³·mol⁻¹	ChemAxon
Polarizability	59.93 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA016943

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045068

Chemspider ID

16736974

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Scytonemin

METLIN ID

Not Available

PubChem Compound

135473381

PDB ID

Not Available

ChEBI ID

90127

Good Scents ID

Not Available

References

General References

Proteau PJ, Gerwick WH, Garcia-Pichel F, Castenholz R: The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria. Experientia. 1993 Sep 15;49(9):825-9. doi: 10.1007/BF01923559. [PubMed:8405307 ]
Balskus EP, Case RJ, Walsh CT: The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities. FEMS Microbiol Ecol. 2011 Aug;77(2):322-32. doi: 10.1111/j.1574-6941.2011.01113.x. Epub 2011 May 12. [PubMed:21501195 ]
Matsui K, Nazifi E, Hirai Y, Wada N, Matsugo S, Sakamoto T: The cyanobacterial UV-absorbing pigment scytonemin displays radical-scavenging activity. J Gen Appl Microbiol. 2012;58(2):137-44. doi: 10.2323/jgam.58.137. [PubMed:22688245 ]
Rastogi RP, Incharoensakdi A: Characterization of UV-screening compounds, mycosporine-like amino acids, and scytonemin in the cyanobacterium Lyngbya sp. CU2555. FEMS Microbiol Ecol. 2014 Jan;87(1):244-56. doi: 10.1111/1574-6941.12220. Epub 2013 Oct 15. [PubMed:24111939 ]
Vitek P, Jehlicka J, Ascaso C, Masek V, Gomez-Silva B, Olivares H, Wierzchos J: Distribution of scytonemin in endolithic microbial communities from halite crusts in the hyperarid zone of the Atacama Desert, Chile. FEMS Microbiol Ecol. 2014 Nov;90(2):351-66. doi: 10.1111/1574-6941.12387. Epub 2014 Aug 26. [PubMed:25056905 ]

Showing NP-Card for Scytonemin (NP0022910)

MOL for NP0022910 (Scytonemin)

3D MOL for NP0022910 (Scytonemin)

3D SDF for NP0022910 (Scytonemin)

3D-SDF for NP0022910 (Scytonemin)

PDB for NP0022910 (Scytonemin)

3D PDB for NP0022910 (Scytonemin)

SMILES for NP0022910 (Scytonemin)

INCHI for NP0022910 (Scytonemin)

Structure for NP0022910 (Scytonemin)

3D Structure for NP0022910 (Scytonemin)