NP-MRD: Showing NP-Card for streptonigrin, rufocromomycin (NP0023989)

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Record Information

Version

1.0

Created at

2021-06-19 15:47:27 UTC

Updated at

2021-06-19 15:47:27 UTC

NP-MRD ID

NP0023989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

streptonigrin, rufocromomycin

Provided By

JEOL Database JEOL Logo

Description

Streptonigrin, also known as rufocromomycin or brunemycin, belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other. streptonigrin, rufocromomycin is found in Streptomyces flocculus. It was first documented in 1989 (PMID: 2738877). Based on a literature review a significant number of articles have been published on streptonigrin (PMID: 10328288) (PMID: 10465544) (PMID: 1905760) (PMID: 34326026).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192117473D          

 59 62  0  0  0  0            999 V2000
   -4.0548   -5.4583    3.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -5.0645    1.7100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557   -4.0548    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2310   -4.1946   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5078   -5.2924   -0.8922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059   -3.1253   -0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613   -3.2380   -1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -1.9401    0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343   -1.0198   -0.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.1138    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8728    0.9603   -2.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6687    0.3183   -3.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3461    0.3253    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  2  0  0  0  0
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  9 10  2  0  0  0  0
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 31 19  1  0  0  0  0
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 29 20  1  0  0  0  0
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 11 31  2  0  0  0  0
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 17 18  1  0  0  0  0
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  1 38  1  0  0  0  0
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M  CHG  2  12   1  16  -1
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
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   -3.2310   -4.1946   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5078   -5.2924   -0.8922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059   -3.1253   -0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613   -3.2380   -1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2  12   1  16  -1
M  END


  Mrv1652306192117473D          

 59 62  0  0  0  0            999 V2000
   -4.0548   -5.4583    3.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -5.0645    1.7100 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7761    6.6731   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708    7.1761    0.9717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2321    8.2927    0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6891    5.2706   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916    4.5578    0.8756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203    2.4354   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    3.1677    0.0798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    0.3253    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501   -0.6356    2.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -1.7929    1.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3518   -2.8164    1.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7807   -2.6216    3.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -6.4872    3.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5490   -4.8339    3.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -5.4402    3.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537   -5.3025   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -6.0406   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -0.6517   -1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557    4.0779   -2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137    2.5656   -2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    2.8921   -3.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412    4.8474   -3.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    7.2718   -3.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8842   10.6149   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    9.3619   -3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    9.3842   -2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    9.2280    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590    8.2415   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884    8.2795    1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    5.2329    1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061    2.7902    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    4.1765    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    1.2096    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4893   -0.4804    3.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0  0  0  0
 10 11  1  0  0  0  0
 17 13  1  0  0  0  0
 19 20  1  0  0  0  0
  9 10  2  0  0  0  0
 20 21  2  0  0  0  0
 31 19  1  0  0  0  0
 21 22  1  0  0  0  0
 10 33  1  0  0  0  0
 22 23  2  0  0  0  0
 13 12  2  0  0  0  0
 23 26  1  0  0  0  0
 33 34  2  0  0  0  0
 26 29  2  0  0  0  0
 29 20  1  0  0  0  0
 34 35  1  0  0  0  0
 13 14  1  0  0  0  0
 12 11  1  0  0  0  0
 14 15  2  0  0  0  0
 11 31  2  0  0  0  0
 14 16  1  0  0  0  0
 36  3  1  0  0  0  0
 17 18  1  0  0  0  0
 19 17  2  0  0  0  0
 23 24  1  0  0  0  0
  3  4  2  0  0  0  0
 26 27  1  0  0  0  0
 35  8  2  0  0  0  0
  3  2  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6  8  1  0  0  0  0
 29 30  1  0  0  0  0
 35 36  1  0  0  0  0
 31 32  1  0  0  0  0
  2  1  1  0  0  0  0
 36 37  2  0  0  0  0
 27 28  1  0  0  0  0
  8  9  1  0  0  0  0
 24 25  1  0  0  0  0
 12 43  1  0  0  0  0
 33 58  1  0  0  0  0
 34 59  1  0  0  0  0
 21 47  1  0  0  0  0
 22 48  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
 30 55  1  0  0  0  0
 32 56  1  0  0  0  0
 32 57  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
 28 52  1  0  0  0  0
 28 53  1  0  0  0  0
 28 54  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 25 51  1  0  0  0  0
M  CHG  2  12   1  16  -1
M  END
> <DATABASE_ID>
NP0023989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C([H])C([H])=C1C1=C(C(=[N+]([H])C(C2=NC3=C(C([H])=C2[H])C(=O)C(OC([H])([H])[H])=C(N([H])[H])C3=O)=C1N([H])[H])C([O-])=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)

> <INCHI_KEY>
PVYJZLYGTZKPJE-UHFFFAOYSA-N

> <FORMULA>
C25H22N4O8

> <MOLECULAR_WEIGHT>
506.471

> <EXACT_MASS>
506.143763684

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
51.94356590525889

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridin-1-ium-2-carboxylate

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.2591930479604969

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.222329623398704

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1695214876170485

> <JCHEM_PKA_STRONGEST_BASIC>
4.648701618441994

> <JCHEM_POLAR_SURFACE_AREA>
201.26

> <JCHEM_REFRACTIVITY>
145.49719999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridin-1-ium-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -4.0548   -5.4583    3.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -5.0645    1.7100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557   -4.0548    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2310   -4.1946   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5078   -5.2924   -0.8922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059   -3.1253   -0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613   -3.2380   -1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -1.9401    0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343   -1.0198   -0.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.1138    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301    1.0282   -0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8678    0.3836   -1.3787 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.8728    0.9603   -2.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7397   -0.0479   -2.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    0.3183   -3.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733   -1.2282   -2.4396 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0090    2.3556   -2.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674    3.0081   -2.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377    3.1058   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1126    4.5817   -1.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    5.3428   -2.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496    6.7432   -2.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    7.4240   -1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    8.7879   -1.1074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    9.5584   -2.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761    6.6731   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708    7.1761    0.9717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2321    8.2927    0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6891    5.2706   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916    4.5578    0.8756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203    2.4354   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    3.1677    0.0798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    0.3253    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501   -0.6356    2.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -1.7929    1.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3518   -2.8164    1.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7807   -2.6216    3.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -6.4872    3.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5490   -4.8339    3.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -5.4402    3.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537   -5.3025   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -6.0406   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -0.6517   -1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557    4.0779   -2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137    2.5656   -2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    2.8921   -3.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412    4.8474   -3.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    7.2718   -3.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8842   10.6149   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    9.3619   -3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    9.3842   -2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    9.2280    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590    8.2415   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884    8.2795    1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    5.2329    1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061    2.7902    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    4.1765    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    1.2096    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4893   -0.4804    3.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
 10 11  1  0
 17 13  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
 31 19  1  0
 21 22  1  0
 10 33  1  0
 22 23  2  0
 13 12  2  0
 23 26  1  0
 33 34  2  0
 26 29  2  0
 29 20  1  0
 34 35  1  0
 13 14  1  0
 12 11  1  0
 14 15  2  0
 11 31  2  0
 14 16  1  0
 36  3  1  0
 17 18  1  0
 19 17  2  0
 23 24  1  0
  3  4  2  0
 26 27  1  0
 35  8  2  0
  3  2  1  0
  4  6  1  0
  4  5  1  0
  6  8  1  0
 29 30  1  0
 35 36  1  0
 31 32  1  0
  2  1  1  0
 36 37  2  0
 27 28  1  0
  8  9  1  0
 24 25  1  0
 12 43  1  0
 33 58  1  0
 34 59  1  0
 21 47  1  0
 22 48  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
  5 41  1  0
  5 42  1  0
 30 55  1  0
 32 56  1  0
 32 57  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  CHG  2  12   1  16  -1
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.055  -5.458   3.024  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.444  -5.064   1.710  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.656  -4.055   1.159  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.231  -4.195  -0.110  0.00  0.00           C+0
HETATM    5  N   UNK     0      -3.508  -5.292  -0.892  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.406  -3.125  -0.768  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.061  -3.238  -1.942  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.036  -1.940   0.032  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.234  -1.020  -0.584  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.913   0.114   0.089  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.030   1.028  -0.638  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.868   0.384  -1.379  0.00  0.00           N+1
HETATM   13  C   UNK     0       1.873   0.960  -2.056  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.740  -0.048  -2.743  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.669   0.318  -3.507  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.373  -1.228  -2.440  0.00  0.00           O-1
HETATM   17  C   UNK     0       2.009   2.356  -2.015  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.167   3.008  -2.729  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.038   3.106  -1.297  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.113   4.582  -1.262  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.596   5.343  -2.319  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.650   6.743  -2.295  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.230   7.424  -1.217  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.267   8.788  -1.107  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.746   9.558  -2.183  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.776   6.673  -0.164  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.371   7.176   0.972  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.232   8.293   0.759  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.689   5.271  -0.188  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.192   4.558   0.876  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.020   2.435  -0.616  0.00  0.00           C+0
HETATM   32  N   UNK     0      -0.990   3.168   0.080  0.00  0.00           N+0
HETATM   33  C   UNK     0      -1.346   0.325   1.396  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.150  -0.636   2.013  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.506  -1.793   1.317  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.352  -2.816   1.939  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.781  -2.622   3.071  0.00  0.00           O+0
HETATM   38  H   UNK     0      -4.395  -6.487   3.176  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.549  -4.834   3.773  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.967  -5.440   3.154  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.154  -5.303  -1.847  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.088  -6.041  -0.532  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.863  -0.652  -1.472  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.256   4.078  -2.525  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.114   2.566  -2.401  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.055   2.892  -3.812  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.141   4.847  -3.176  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.219   7.272  -3.140  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.884  10.615  -1.934  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.294   9.362  -3.111  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.327   9.384  -2.310  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.674   9.228   0.857  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.759   8.242  -0.200  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.988   8.280   1.550  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.551   5.233   1.485  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.906   2.790   0.283  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.889   4.176   0.150  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.047   1.210   1.955  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.489  -0.480   3.037  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    3    1                                                       
CONECT    3   36    4    2                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   41   42                                                  
CONECT    6    7    4    8                                                  
CONECT    7    6                                                            
CONECT    8   35    6    9                                                  
CONECT    9   10    8                                                       
CONECT   10   11    9   33                                                  
CONECT   11   10   12   31                                                  
CONECT   12   13   11   43                                                  
CONECT   13   17   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   19                                                  
CONECT   18   17   44   45   46                                             
CONECT   19   20   31   17                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22   47                                                  
CONECT   22   21   23   48                                                  
CONECT   23   22   26   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   49   50   51                                             
CONECT   26   23   29   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   52   53   54                                             
CONECT   29   26   20   30                                                  
CONECT   30   29   55                                                       
CONECT   31   19   11   32                                                  
CONECT   32   31   56   57                                                  
CONECT   33   10   34   58                                                  
CONECT   34   33   35   59                                                  
CONECT   35   34    8   36                                                  
CONECT   36    3   35   37                                                  
CONECT   37   36                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43   12                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   25                                                            
CONECT   50   25                                                            
CONECT   51   25                                                            
CONECT   52   28                                                            
CONECT   53   28                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   32                                                            
CONECT   57   32                                                            
CONECT   58   33                                                            
CONECT   59   34                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  124    0
END

RDKit          3D

59 62  0  0  0  0  0  0  0  0999 V2000
   -4.0548   -5.4583    3.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4435   -5.0645    1.7100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557   -4.0548    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2310   -4.1946   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5078   -5.2924   -0.8922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4059   -3.1253   -0.7680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613   -3.2380   -1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -1.9401    0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2343   -1.0198   -0.5841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131    0.1138    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301    1.0282   -0.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8678    0.3836   -1.3787 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.8728    0.9603   -2.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7397   -0.0479   -2.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    0.3183   -3.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733   -1.2282   -2.4396 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0090    2.3556   -2.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674    3.0081   -2.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377    3.1058   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1126    4.5817   -1.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    5.3428   -2.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496    6.7432   -2.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    7.4240   -1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667    8.7879   -1.1074 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    9.5584   -2.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7761    6.6731   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3708    7.1761    0.9717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2321    8.2927    0.7590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6891    5.2706   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916    4.5578    0.8756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0203    2.4354   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    3.1677    0.0798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    0.3253    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501   -0.6356    2.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -1.7929    1.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3518   -2.8164    1.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7807   -2.6216    3.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -6.4872    3.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5490   -4.8339    3.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -5.4402    3.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537   -5.3025   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -6.0406   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -0.6517   -1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557    4.0779   -2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1137    2.5656   -2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    2.8921   -3.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412    4.8474   -3.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    7.2718   -3.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8842   10.6149   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935    9.3619   -3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    9.3842   -2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    9.2280    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7590    8.2415   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884    8.2795    1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5515    5.2329    1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061    2.7902    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886    4.1765    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    1.2096    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4893   -0.4804    3.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
 10 11  1  0
 17 13  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
 31 19  1  0
 21 22  1  0
 10 33  1  0
 22 23  2  0
 13 12  2  0
 23 26  1  0
 33 34  2  0
 26 29  2  0
 29 20  1  0
 34 35  1  0
 13 14  1  0
 12 11  1  0
 14 15  2  0
 11 31  2  0
 14 16  1  0
 36  3  1  0
 17 18  1  0
 19 17  2  0
 23 24  1  0
  3  4  2  0
 26 27  1  0
 35  8  2  0
  3  2  1  0
  4  6  1  0
  4  5  1  0
  6  8  1  0
 29 30  1  0
 35 36  1  0
 31 32  1  0
  2  1  1  0
 36 37  2  0
 27 28  1  0
  8  9  1  0
 24 25  1  0
 12 43  1  0
 33 58  1  0
 34 59  1  0
 21 47  1  0
 22 48  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
  5 41  1  0
  5 42  1  0
 30 55  1  0
 32 56  1  0
 32 57  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
M  CHG  2  12   1  16  -1
M  END

View in JSmol

Synonyms

Value	Source
5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid	ChEBI
Rufocromomicina	ChEBI
Rufocromomycin	ChEBI
Rufocromomycine	ChEBI
Rufocromomycinum	ChEBI
Streptonigran	ChEBI
Nigrin	Kegg
5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinate	Generator
Brunemycin	HMDB
Bruneomycin	HMDB

Chemical Formula

C₂₅H₂₂N₄O₈

Average Mass

506.4710 Da

Monoisotopic Mass

506.14376 Da

IUPAC Name

5-amino-6-(7-amino-6-methoxy-5,8-dioxo-5,8-dihydroquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridin-1-ium-2-carboxylate

Traditional Name

5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridin-1-ium-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C([H])C([H])=C1C1=C(C(=[N+]([H])C(C2=NC3=C(C([H])=C2[H])C(=O)C(OC([H])([H])[H])=C(N([H])[H])C3=O)=C1N([H])[H])C([O-])=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)

InChI Key

PVYJZLYGTZKPJE-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, THF-d8, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, THF-d8, 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
Streptomyces albus	JEOL database	Anderberg, P. I., et al, Magn. Reson. Chem. 40, 313 (2002)

Species Where Detected

Species Name	Source	Reference
Micromonospora sp. IM 2670	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Bipyridines and oligopyridines

Direct Parent

Bipyridines and oligopyridines

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.67	ALOGPS
logP	0.26	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	1.17	ChemAxon
pKa (Strongest Basic)	4.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	201.26 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.5 m³·mol⁻¹	ChemAxon
Polarizability	51.94 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

HMDB0258512

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Streptonigrin

METLIN ID

Not Available

PubChem Compound

5298

PDB ID

Not Available

ChEBI ID

9287

Good Scents ID

Not Available

References

General References

Ryu CK, Lee IK, Jung SH, Lee CO: Synthesis and cytotoxic activities of 6-chloro-7-arylamino-5,8-isoquinolinediones. Bioorg Med Chem Lett. 1999 Apr 19;9(8):1075-80. doi: 10.1016/s0960-894x(99)00152-3. [PubMed:10328288 ]
Fryatt T, Goroski DT, Nilson ZD, Moody CJ, Beall HD: Novel quinolinequinone antitumor agents: structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1). Bioorg Med Chem Lett. 1999 Aug 2;9(15):2195-8. doi: 10.1016/s0960-894x(99)00369-8. [PubMed:10465544 ]
Rao KV, Beach JW: Streptonigrin and related compounds. 5. Synthesis and evaluation of some isoquinoline analogues. J Med Chem. 1991 Jun;34(6):1871-9. doi: 10.1021/jm00110a018. [PubMed:1905760 ]
Moustatih A, Garnier-Suillerot A: Bifunctional antitumor compounds: synthesis and characterization of a Au(III)-streptonigrin complex with thiol-modulating properties. J Med Chem. 1989 Jul;32(7):1426-31. doi: 10.1021/jm00127a004. [PubMed:2738877 ]
Lin TH, Wu CC, Tseng CY, Fang JH, Lin CT: Effects of gallic acid on capsular polysaccharide biosynthesis in Klebsiella pneumoniae. J Microbiol Immunol Infect. 2021 Jul 22. pii: S1684-1182(21)00141-9. doi: 10.1016/j.jmii.2021.07.002. [PubMed:34326026 ]
Anderberg, P. I., et al. (2002). Anderberg, P. I., et al, Magn. Reson. Chem. 40, 313 (2002). Mag. Reson. Chem..

Showing NP-Card for streptonigrin, rufocromomycin (NP0023989)

MOL for NP0023989 (streptonigrin, rufocromomycin)

3D MOL for NP0023989 (streptonigrin, rufocromomycin)

3D SDF for NP0023989 (streptonigrin, rufocromomycin)

3D-SDF for NP0023989 (streptonigrin, rufocromomycin)

PDB for NP0023989 (streptonigrin, rufocromomycin)

3D PDB for NP0023989 (streptonigrin, rufocromomycin)

SMILES for NP0023989 (streptonigrin, rufocromomycin)

INCHI for NP0023989 (streptonigrin, rufocromomycin)

Structure for NP0023989 (streptonigrin, rufocromomycin)

3D Structure for NP0023989 (streptonigrin, rufocromomycin)