NP-MRD: Showing NP-Card for Scytonine (NP0005249)

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Record Information

Version

2.0

Created at

2020-12-09 02:32:52 UTC

Updated at

2021-07-15 16:51:27 UTC

NP-MRD ID

NP0005249

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scytonine

Provided By

NPAtlas

Description

Scytonine is found in Cyanobacterium. Scytonine was first documented in 2004 (PMID: 15104503). Based on a literature review very few articles have been published on methyl 2-{2-[(1E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indol-3-yl}-3-oxo-3H,4H-cyclopenta[b]indole-1-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121113D          

 61 66  0  0  0  0            999 V2000
    1.6565    3.6026    1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474    2.4643    0.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778    1.2843    0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    1.2271    1.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7311    0.0765   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0578   -1.0588   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1999   -1.4006    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9914    0.1614   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0169    0.8947   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8478    2.0810   -2.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6482    1.7326   -1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666    0.4861   -1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169   -0.1255   -1.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
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M  END

     RDKit          3D

 61 66  0  0  0  0  0  0  0  0999 V2000
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    2.0474    2.4643    0.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242121113D          

 61 66  0  0  0  0            999 V2000
    1.6565    3.6026    1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474    2.4643    0.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7827   -3.4606    2.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8456   -4.3607    3.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361   -4.3050    2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -3.3461    1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -2.4590    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7515   -2.0460   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -3.2326   -1.5291 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -1.3816   -1.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415   -1.5357   -2.5330 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7676   -0.4049   -2.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9554   -0.0555   -3.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    1.1906   -2.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8478    2.0810   -2.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6482    1.7326   -1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666    0.4861   -1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169   -0.1255   -1.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085    4.1528    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    4.3093    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315    3.3217    2.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    1.6260   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    0.5539   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9218    0.6755    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4208    1.9999    4.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233    1.3668    4.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6434    0.5531   -4.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3986    1.5933   -4.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7838   -3.4841    3.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -5.1206    3.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -5.0164    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7228   -3.2884    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2540   -2.4242   -3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4739   -0.7643   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4569    1.4451   -3.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613    3.0644   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1549    2.4686   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  6 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39  5  1  0  0  0  0
 28  7  1  0  0  0  0
 39 31  2  0  0  0  0
 17 11  1  0  0  0  0
 28 23  1  0  0  0  0
 38 33  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
 10 43  1  0  0  0  0
 12 44  1  0  0  0  0
 13 45  1  0  0  0  0
 15 46  1  0  0  0  0
 16 47  1  0  0  0  0
 17 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 22 52  1  0  0  0  0
 24 53  1  0  0  0  0
 25 54  1  0  0  0  0
 26 55  1  0  0  0  0
 27 56  1  0  0  0  0
 32 57  1  0  0  0  0
 34 58  1  0  0  0  0
 35 59  1  0  0  0  0
 36 60  1  0  0  0  0
 37 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(\C(=O)OC([H])([H])[H])C2=C(C3=C([H])C([H])=C([H])C([H])=C3N2[H])C2=C(C(=O)OC([H])([H])[H])C3=C(N([H])C4=C([H])C([H])=C([H])C([H])=C34)C2=O)C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C31H22N2O6/c1-38-30(36)20(15-16-11-13-17(34)14-12-16)27-23(18-7-3-5-9-21(18)32-27)25-26(31(37)39-2)24-19-8-4-6-10-22(19)33-28(24)29(25)35/h3-15,32-34H,1-2H3/b20-15+

> <INCHI_KEY>
RBULROHCVWCNGA-HMMYKYKNSA-N

> <FORMULA>
C31H22N2O6

> <MOLECULAR_WEIGHT>
518.525

> <EXACT_MASS>
518.147786436

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
55.70365006817879

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-{2-[(1E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indol-3-yl}-3-oxo-3H,4H-cyclopenta[b]indole-1-carboxylate

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
5.399598422

> <ALOGPS_LOGS>
-6.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.80962029676564

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.305780638090248

> <JCHEM_PKA_STRONGEST_BASIC>
-5.960368972024374

> <JCHEM_POLAR_SURFACE_AREA>
121.47999999999999

> <JCHEM_REFRACTIVITY>
146.17140000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.04e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{2-[(1E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indol-3-yl}-3-oxo-4H-cyclopenta[b]indole-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 66  0  0  0  0  0  0  0  0999 V2000
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   -0.5197   -0.3093   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.2992   -2.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    1.4656   -4.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884   -1.5474    1.1131 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772   -2.5049    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827   -3.4606    2.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8456   -4.3607    3.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361   -4.3050    2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -3.3461    1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -2.4590    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7515   -2.0460   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -3.2326   -1.5291 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -1.3816   -1.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415   -1.5357   -2.5330 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7676   -0.4049   -2.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9554   -0.0555   -3.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    1.1906   -2.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8478    2.0810   -2.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6482    1.7326   -1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666    0.4861   -1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169   -0.1255   -1.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085    4.1528    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    4.3093    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315    3.3217    2.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    1.6260   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    0.5539   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9218    0.6755    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4208    1.9999    4.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233    1.3668    4.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700    1.2537    2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434    0.5531   -4.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9831    2.3066   -4.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3986    1.5933   -4.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080   -1.3932    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7838   -3.4841    3.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1729   -5.0164    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7228   -3.2884    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2540   -2.4242   -3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4739   -0.7643   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4569    1.4451   -3.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613    3.0644   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1549    2.4686   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  8 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  6 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39  5  1  0
 28  7  1  0
 39 31  2  0
 17 11  1  0
 28 23  1  0
 38 33  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
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 21 50  1  0
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 24 53  1  0
 25 54  1  0
 26 55  1  0
 27 56  1  0
 32 57  1  0
 34 58  1  0
 35 59  1  0
 36 60  1  0
 37 61  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  C   UNK     0       1.657   3.603   1.132  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.047   2.464   0.386  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.378   1.284   0.364  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.330   1.227   1.073  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.731   0.077  -0.385  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.058  -1.059  -0.422  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.200  -1.401   0.259  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.438  -0.834   0.209  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.991   0.161  -0.675  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.017   0.895  -0.289  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.739   0.897   0.946  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.119   0.734   0.876  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.850   0.802   2.023  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.265   1.030   3.271  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.042   1.095   4.423  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.900   1.187   3.309  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.123   1.122   2.149  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.454   0.336  -2.043  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.520  -0.309  -2.516  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.021   1.299  -2.903  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.496   1.466  -4.230  0.00  0.00           C+0
HETATM   22  N   UNK     0      -2.188  -1.547   1.113  0.00  0.00           N+0
HETATM   23  C   UNK     0      -1.477  -2.505   1.701  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.783  -3.461   2.659  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.846  -4.361   3.112  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.436  -4.305   2.594  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.747  -3.346   1.631  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.214  -2.459   1.198  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.752  -2.046  -1.273  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.391  -3.233  -1.529  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.942  -1.382  -1.763  0.00  0.00           C+0
HETATM   32  N   UNK     0       4.042  -1.536  -2.533  0.00  0.00           N+0
HETATM   33  C   UNK     0       4.768  -0.405  -2.534  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.955  -0.056  -3.152  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.510   1.191  -2.993  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.848   2.081  -2.200  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.648   1.733  -1.574  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.067   0.486  -1.716  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.917  -0.126  -1.230  0.00  0.00           C+0
HETATM   40  H   UNK     0       2.608   4.153   1.379  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.040   4.309   0.568  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.232   3.322   2.125  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.352   1.626  -1.081  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.626   0.554  -0.061  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.922   0.676   1.964  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.421   2.000   4.725  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.423   1.367   4.279  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.070   1.254   2.249  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.643   0.553  -4.835  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.983   2.307  -4.740  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.399   1.593  -4.108  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.208  -1.393   1.293  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.784  -3.484   3.048  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.085  -5.121   3.872  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.173  -5.016   2.954  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.723  -3.288   1.223  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.254  -2.424  -3.036  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.474  -0.764  -3.778  0.00  0.00           H+0
HETATM   59  H   UNK     0       7.457   1.445  -3.498  0.00  0.00           H+0
HETATM   60  H   UNK     0       6.261   3.064  -2.059  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.155   2.469  -0.953  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   39                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   44                                                  
CONECT   13   12   14   45                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   46                                                       
CONECT   16   14   17   47                                                  
CONECT   17   16   11   48                                                  
CONECT   18    9   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   49   50   51                                             
CONECT   22    8   23   52                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   53                                                  
CONECT   25   24   26   54                                                  
CONECT   26   25   27   55                                                  
CONECT   27   26   28   56                                                  
CONECT   28   27    7   23                                                  
CONECT   29    6   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   39                                                  
CONECT   32   31   33   57                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   58                                                  
CONECT   35   34   36   59                                                  
CONECT   36   35   37   60                                                  
CONECT   37   36   38   61                                                  
CONECT   38   37   39   33                                                  
CONECT   39   38    5   31                                                  
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43   10                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   32                                                            
CONECT   58   34                                                            
CONECT   59   35                                                            
CONECT   60   36                                                            
CONECT   61   37                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  132    0
END

RDKit          3D

61 66  0  0  0  0  0  0  0  0999 V2000
    1.6565    3.6026    1.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474    2.4643    0.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778    1.2843    0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    1.2271    1.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7311    0.0765   -0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0578   -1.0588   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1999   -1.4006    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4376   -0.8344    0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9914    0.1614   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0169    0.8947   -0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7386    0.8965    0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1190    0.7336    0.8761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8503    0.8021    2.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2654    1.0304    3.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0417    1.0950    4.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    1.1873    3.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1229    1.1221    2.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543    0.3364   -2.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197   -0.3093   -2.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.2992   -2.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    1.4656   -4.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884   -1.5474    1.1131 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772   -2.5049    1.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827   -3.4606    2.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8456   -4.3607    3.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361   -4.3050    2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471   -3.3461    1.6314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -2.4590    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7515   -2.0460   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -3.2326   -1.5291 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -1.3816   -1.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0415   -1.5357   -2.5330 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7676   -0.4049   -2.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9554   -0.0555   -3.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    1.1906   -2.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8478    2.0810   -2.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6482    1.7326   -1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666    0.4861   -1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169   -0.1255   -1.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085    4.1528    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    4.3093    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2315    3.3217    2.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    1.6260   -1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    0.5539   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9218    0.6755    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4208    1.9999    4.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233    1.3668    4.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700    1.2537    2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6434    0.5531   -4.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9831    2.3066   -4.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3986    1.5933   -4.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080   -1.3932    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7838   -3.4841    3.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0845   -5.1206    3.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -5.0164    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7228   -3.2884    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2540   -2.4242   -3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4739   -0.7643   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4569    1.4451   -3.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613    3.0644   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1549    2.4686   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
  8 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  6 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39  5  1  0
 28  7  1  0
 39 31  2  0
 17 11  1  0
 28 23  1  0
 38 33  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
 27 56  1  0
 32 57  1  0
 34 58  1  0
 35 59  1  0
 36 60  1  0
 37 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 2-{2-[(1E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indol-3-yl}-3-oxo-3H,4H-cyclopenta[b]indole-1-carboxylic acid	Generator

Chemical Formula

C₃₁H₂₂N₂O₆

Average Mass

518.5250 Da

Monoisotopic Mass

518.14779 Da

IUPAC Name

methyl 2-{2-[(1E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indol-3-yl}-3-oxo-3H,4H-cyclopenta[b]indole-1-carboxylate

Traditional Name

methyl 2-{2-[(1E)-1-(4-hydroxyphenyl)-3-methoxy-3-oxoprop-1-en-2-yl]-1H-indol-3-yl}-3-oxo-4H-cyclopenta[b]indole-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C\C1=CC=C(O)C=C1)\C1=C(C2=CC=CC=C2N1)C1=C(C(=O)OC)C2=C(NC3=CC=CC=C23)C1=O

InChI Identifier

InChI=1S/C31H22N2O6/c1-38-30(36)20(15-16-11-13-17(34)14-12-16)27-23(18-7-3-5-9-21(18)32-27)25-26(31(37)39-2)24-19-8-4-6-10-22(19)33-28(24)29(25)35/h3-15,32-34H,1-2H3/b20-15+

InChI Key

RBULROHCVWCNGA-HMMYKYKNSA-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
Cyanobacterium	NPAtlas	15104503

Species Where Detected

Species Name	Source	Reference
Scytonema sp.	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	4.87	ALOGPS
logP	5.4	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.48 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.17 m³·mol⁻¹	ChemAxon
Polarizability	55.7 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA001113

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026696

Chemspider ID

8431535

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10256051

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bultel-Ponce V, Felix-Theodose F, Sarthou C, Ponge JF, Bodo B: New pigments from the terrestrial cyanobacterium Scytonema sp. collected on the Mitaraka inselberg, French Guyana. J Nat Prod. 2004 Apr;67(4):678-81. doi: 10.1021/np034031u. [PubMed:15104503 ]

Showing NP-Card for Scytonine (NP0005249)

MOL for NP0005249 (Scytonine)

3D MOL for NP0005249 (Scytonine)

3D SDF for NP0005249 (Scytonine)

3D-SDF for NP0005249 (Scytonine)

PDB for NP0005249 (Scytonine)

3D PDB for NP0005249 (Scytonine)

SMILES for NP0005249 (Scytonine)

INCHI for NP0005249 (Scytonine)

Structure for NP0005249 (Scytonine)

3D Structure for NP0005249 (Scytonine)