NP-MRD: Showing NP-Card for Naphthyridinomycin (NP0022722)

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Record Information

Version

1.0

Created at

2021-01-06 07:54:16 UTC

Updated at

2021-07-15 17:39:48 UTC

NP-MRD ID

NP0022722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Naphthyridinomycin

Provided By

NPAtlas

Description

21-Hydroxy-16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]Henicosa-10(15),12-diene-11,14-dione belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton. Naphthyridinomycin is found in Streptomyces and Streptomyces lusitanus. It was first documented in 1975 (PMID: 807549). Based on a literature review very few articles have been published on 21-hydroxy-16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-5-oxa-8,17,20-triazahexacyclo[15.3.1.0³,¹⁹.0⁴,⁸.0⁹,¹⁸.0¹⁰,¹⁵]Henicosa-10(15),12-diene-11,14-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105373D          

 57 62  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242105373D          

 57 62  0  0  0  0            999 V2000
    5.8952   -0.9768   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8085   -1.6037    1.4385 N   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0327   -1.6790    2.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4389   -1.9572   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455   -0.9537    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8927   -0.9237   -0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5457    1.3783    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    2.5053    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9759    2.8605    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2734    0.0003   -1.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333   -1.3937   -3.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -2.1188   -2.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -3.8188   -2.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -2.7476   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1798   -0.8643    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152    1.6552    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    3.1999   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456    3.2787   -1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1960    4.5427   -0.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0077    1.8644   -1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355   -1.7891    1.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -2.4767    2.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181   -0.7250    2.7747 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
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 10  3  1  0  0  0  0
 22 15  1  0  0  0  0
 28 24  1  0  0  0  0
 23  8  1  0  0  0  0
 29 18  1  0  0  0  0
 28 20  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  5 34  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
 12 37  1  6  0  0  0
 13 38  1  0  0  0  0
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 14 40  1  0  0  0  0
 16 41  1  6  0  0  0
 17 42  1  0  0  0  0
 18 43  1  1  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 20 46  1  1  0  0  0
 21 47  1  1  0  0  0
 22 48  1  1  0  0  0
 23 49  1  1  0  0  0
 25 50  1  0  0  0  0
 25 51  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 28 54  1  6  0  0  0
 30 55  1  0  0  0  0
 30 56  1  0  0  0  0
 30 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])N2[C@@]([H])(O[H])[C@@]3([H])N(C([H])([H])[H])[C@]4([H])[C@]([H])(C3([H])[H])[C@@]3([H])OC([H])([H])C([H])([H])N3[C@]([H])(C3=C1C(=O)C(OC([H])([H])[H])=C(C3=O)C([H])([H])[H])[C@]24[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H27N3O6/c1-8-17(26)13-12(18(27)19(8)29-3)11(7-25)24-16-14-9(6-10(20(24)28)22(14)2)21-23(15(13)16)4-5-30-21/h9-11,14-16,20-21,25,28H,4-7H2,1-3H3/t9-,10-,11+,14+,15+,16+,20-,21+/m0/s1

> <INCHI_KEY>
SXDWNOFDSOXRRM-UHFFFAOYSA-N

> <FORMULA>
C21H27N3O6

> <MOLECULAR_WEIGHT>
417.462

> <EXACT_MASS>
417.189985601

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.54517405479033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,4R,9R,16S,18R,19R,21S)-21-hydroxy-16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-5-oxa-8,17,20-triazahexacyclo[15.3.1.0^{3,19}.0^{4,8}.0^{9,18}.0^{10,15}]henicosa-10(15),12-diene-11,14-dione

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
-0.312235443666667

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.046838054142953

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.966638972692294

> <JCHEM_PKA_STRONGEST_BASIC>
6.583178044159624

> <JCHEM_POLAR_SURFACE_AREA>
102.78

> <JCHEM_REFRACTIVITY>
106.76249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4R,9R,16S,18R,19R,21S)-21-hydroxy-16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-5-oxa-8,17,20-triazahexacyclo[15.3.1.0^{3,19}.0^{4,8}.0^{9,18}.0^{10,15}]henicosa-10(15),12-diene-11,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
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    0.5365   -1.8739   -2.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -3.0306   -1.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3721   -0.7234   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936    0.3718    0.2911 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.8504   -0.3785    0.8484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3306    1.0398    0.5924 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0947    1.5713   -0.5011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600    2.9783   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    3.6244    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6939    2.6683    0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4948    1.6031   -0.2729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8085   -1.6037    1.4385 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327   -1.6790    2.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4389   -1.9572   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455   -0.9537    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8927   -0.9237   -0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5457    1.3783    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    2.5053    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9759    2.8605    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2734    0.0003   -1.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333   -1.3937   -3.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -2.1188   -2.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -3.8188   -2.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -2.7476   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687   -2.9324    0.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074   -2.8248   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -0.6146   -1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706   -0.8050   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697    0.6443    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3017    0.2737    2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -0.8643    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152    1.6552    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    3.1999   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456    3.2787   -1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1960    4.5427   -0.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9101   -2.4767    2.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181   -0.7250    2.7747 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21 29  1  0
 29 30  1  0
 10  3  1  0
 22 15  1  0
 28 24  1  0
 23  8  1  0
 29 18  1  0
 28 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
 12 37  1  6
 13 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  6
 17 42  1  0
 18 43  1  1
 19 44  1  0
 19 45  1  0
 20 46  1  1
 21 47  1  1
 22 48  1  1
 23 49  1  1
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 28 54  1  6
 30 55  1  0
 30 56  1  0
 30 57  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       5.895  -0.977  -0.337  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.126   0.110  -0.793  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.838   0.382  -0.426  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.571   1.308   0.494  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.677   2.056   1.135  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.154   1.550   0.843  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.917   2.418   1.708  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.083   0.808   0.207  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.340  -0.117  -0.716  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.751  -0.356  -1.059  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.024  -1.203  -1.903  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.190  -0.800  -1.317  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.537  -1.874  -2.304  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.037  -3.031  -1.807  0.00  0.00           O+0
HETATM   15  N   UNK     0      -0.774  -1.108  -0.356  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.495  -2.318  -0.395  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.060  -3.251   0.575  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.932  -1.980   0.062  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.372  -0.723  -0.701  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.094   0.372   0.291  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.257  -0.283   1.359  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.850  -0.379   0.848  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.331   1.040   0.592  0.00  0.00           C+0
HETATM   24  N   UNK     0      -1.095   1.571  -0.501  0.00  0.00           N+0
HETATM   25  C   UNK     0      -0.760   2.978  -0.661  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.750   3.624   0.302  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.694   2.668   0.604  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.495   1.603  -0.273  0.00  0.00           C+0
HETATM   29  N   UNK     0      -2.809  -1.604   1.438  0.00  0.00           N+0
HETATM   30  C   UNK     0      -4.033  -1.679   2.182  0.00  0.00           C+0
HETATM   31  H   UNK     0       5.439  -1.957  -0.587  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.045  -0.954   0.763  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.893  -0.924  -0.832  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.546   1.378   1.279  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.404   2.505   2.088  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.976   2.861   0.412  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.273   0.000  -1.992  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.133  -1.394  -3.129  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.428  -2.119  -2.850  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.741  -3.819  -2.364  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.582  -2.748  -1.379  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.169  -2.932   0.858  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.607  -2.825  -0.118  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.854  -0.615  -1.653  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.471  -0.805  -0.934  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.070   0.644   0.764  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.302   0.274   2.309  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.180  -0.864   1.601  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.415   1.655   1.514  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.287   3.200  -0.392  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.046   3.279  -1.675  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.240   3.935   1.253  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.196   4.543  -0.112  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.008   1.864  -1.220  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.936  -1.789   1.575  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.910  -2.477   2.952  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.118  -0.725   2.775  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   34   35   36                                             
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   23                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11    3                                                  
CONECT   11   10                                                            
CONECT   12    9   13   15   37                                             
CONECT   13   12   14   38   39                                             
CONECT   14   13   40                                                       
CONECT   15   12   16   22                                                  
CONECT   16   15   17   18   41                                             
CONECT   17   16   42                                                       
CONECT   18   16   19   29   43                                             
CONECT   19   18   20   44   45                                             
CONECT   20   19   21   28   46                                             
CONECT   21   20   22   29   47                                             
CONECT   22   21   23   15   48                                             
CONECT   23   22   24    8   49                                             
CONECT   24   23   25   28                                                  
CONECT   25   24   26   50   51                                             
CONECT   26   25   27   52   53                                             
CONECT   27   26   28                                                       
CONECT   28   27   24   20   54                                             
CONECT   29   21   30   18                                                  
CONECT   30   29   55   56   57                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    5                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   25                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   30                                                            
CONECT   57   30                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

RDKit          3D

57 62  0  0  0  0  0  0  0  0999 V2000
    5.8952   -0.9768   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1262    0.1097   -0.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    0.3824   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5710    1.3076    0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.0563    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    1.5496    0.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9171    2.4182    1.7075 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0825    0.8075    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401   -0.1170   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7509   -0.3561   -1.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0238   -1.2026   -1.9030 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1901   -0.7995   -1.3175 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5365   -1.8739   -2.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -3.0306   -1.8067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -1.1083   -0.3556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4953   -2.3176   -0.3954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0596   -3.2513    0.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315   -1.9801    0.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3721   -0.7234   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936    0.3718    0.2911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2571   -0.2830    1.3594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8504   -0.3785    0.8484 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3306    1.0398    0.5924 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0947    1.5713   -0.5011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7600    2.9783   -0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    3.6244    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6939    2.6683    0.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4948    1.6031   -0.2729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8085   -1.6037    1.4385 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0327   -1.6790    2.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4389   -1.9572   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455   -0.9537    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8927   -0.9237   -0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5457    1.3783    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    2.5053    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9759    2.8605    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2734    0.0003   -1.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333   -1.3937   -3.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -2.1188   -2.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -3.8188   -2.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -2.7476   -1.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687   -2.9324    0.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074   -2.8248   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -0.6146   -1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706   -0.8050   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0697    0.6443    0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3017    0.2737    2.3093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798   -0.8643    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4152    1.6552    1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    3.1999   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0456    3.2787   -1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2401    3.9350    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1960    4.5427   -0.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0077    1.8644   -1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355   -1.7891    1.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -2.4767    2.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181   -0.7250    2.7747 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
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21 29  1  0
 29 30  1  0
 10  3  1  0
 22 15  1  0
 28 24  1  0
 23  8  1  0
 29 18  1  0
 28 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
 12 37  1  6
 13 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  6
 17 42  1  0
 18 43  1  1
 19 44  1  0
 19 45  1  0
 20 46  1  1
 21 47  1  1
 22 48  1  1
 23 49  1  1
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 28 54  1  6
 30 55  1  0
 30 56  1  0
 30 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₁H₂₇N₃O₆

Average Mass

417.4620 Da

Monoisotopic Mass

417.18999 Da

IUPAC Name

(1S,3S,4R,9R,16S,18R,19R,21S)-21-hydroxy-16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-5-oxa-8,17,20-triazahexacyclo[15.3.1.0^{3,19}.0^{4,8}.0^{9,18}.0^{10,15}]henicosa-10(15),12-diene-11,14-dione

Traditional Name

(1S,3S,4R,9R,16S,18R,19R,21S)-21-hydroxy-16-(hydroxymethyl)-13-methoxy-12,20-dimethyl-5-oxa-8,17,20-triazahexacyclo[15.3.1.0^{3,19}.0^{4,8}.0^{9,18}.0^{10,15}]henicosa-10(15),12-diene-11,14-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C2=C(C(CO)N3C(O)C4CC5C6OCCN6C2C3C5N4C)C1=O

InChI Identifier

InChI=1S/C21H27N3O6/c1-8-17(26)13-12(18(27)19(8)29-3)11(7-25)24-16-14-9(6-10(20(24)28)22(14)2)21-23(15(13)16)4-5-30-21/h9-11,14-16,20-21,25,28H,4-7H2,1-3H3

InChI Key

SXDWNOFDSOXRRM-UHFFFAOYSA-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
Streptomyces	NPAtlas	807549
Streptomyces lusitanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinoline quinones. These are isoquinoline derivative with a structure containing a 5,8-dihydroisoquinoline-5,8-dione skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinoline quinones

Direct Parent

Isoquinoline quinones

Alternative Parents

Substituents

Isoquinoline quinone
Isoquinolone
Diazanaphthalene
Naphthyridine
Piperazino-3,4-b-piperidine
Azepane
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
N-alkylpyrrolidine
Piperazine
Piperidine
Vinylogous ester
Oxazolidine
Pyrrolidine
Hemiaminal
Ketone
Tertiary aliphatic amine
Tertiary amine
Azacycle
Oxacycle
Alkanolamine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.19	ALOGPS
logP	-0.31	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	6.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.78 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.76 m³·mol⁻¹	ChemAxon
Polarizability	42.55 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005217

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14053009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19029905

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kluepfel D, Baker HA, Piattoni G, Sehgal SN, Sidorowicz A, Singh K, Vezina C: Naphthyridinomycin, a new broad-spectrum antibiotic. J Antibiot (Tokyo). 1975 Jul;28(7):497-502. doi: 10.7164/antibiotics.28.497. [PubMed:807549 ]

Showing NP-Card for Naphthyridinomycin (NP0022722)

MOL for NP0022722 (Naphthyridinomycin)

3D MOL for NP0022722 (Naphthyridinomycin)

3D SDF for NP0022722 (Naphthyridinomycin)

3D-SDF for NP0022722 (Naphthyridinomycin)

PDB for NP0022722 (Naphthyridinomycin)

3D PDB for NP0022722 (Naphthyridinomycin)

SMILES for NP0022722 (Naphthyridinomycin)

INCHI for NP0022722 (Naphthyridinomycin)

Structure for NP0022722 (Naphthyridinomycin)

3D Structure for NP0022722 (Naphthyridinomycin)