NP-MRD: Showing NP-Card for γ-iso-Rubromycin (NP0014024)

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Record Information

Version

1.0

Created at

2021-01-05 23:17:09 UTC

Updated at

2021-07-15 17:16:09 UTC

NP-MRD ID

NP0014024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

γ-iso-Rubromycin

Provided By

NPAtlas

Description

2-[2-(3-Acetyl-7,8-dihydroxy-1-oxo-1H-isochromen-6-yl)ethyl]-4H,9H-naphtho[2,3-b]furan-4,9-dione belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. γ-iso-Rubromycin is found in Streptomyces collinus. It was first documented in 2015 (PMID: 25855820). Based on a literature review very few articles have been published on 2-[2-(3-acetyl-7,8-dihydroxy-1-oxo-1H-isochromen-6-yl)ethyl]-4H,9H-naphtho[2,3-b]furan-4,9-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119523D          

 49 53  0  0  0  0            999 V2000
   -8.7386    1.0227   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3154    1.2014   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8917    2.0175   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3169    0.4166   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0140   -0.2001   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6627   -0.0695   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242119523D          

 49 53  0  0  0  0            999 V2000
   -8.7386    1.0227   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3154    1.2014   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  8 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33  4  1  0  0  0  0
 30  6  1  0  0  0  0
 15 11  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  5 37  1  0  0  0  0
  7 38  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 12 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 21 46  1  0  0  0  0
 22 47  1  0  0  0  0
 27 48  1  0  0  0  0
 29 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C([H])=C2C([H])=C(OC(=O)C2=C1O[H])C(=O)C([H])([H])[H])C([H])([H])C([H])([H])C1=C([H])C2=C(O1)C(=O)C1=C([H])C([H])=C([H])C([H])=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H16O8/c1-11(26)18-9-13-8-12(20(27)23(30)19(13)25(31)33-18)6-7-14-10-17-21(28)15-4-2-3-5-16(15)22(29)24(17)32-14/h2-5,8-10,27,30H,6-7H2,1H3

> <INCHI_KEY>
CNCUCHMIDJODTO-UHFFFAOYSA-N

> <FORMULA>
C25H16O8

> <MOLECULAR_WEIGHT>
444.395

> <EXACT_MASS>
444.084517475

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
45.887421091792596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(3-acetyl-7,8-dihydroxy-1-oxo-1H-isochromen-6-yl)ethyl]-4H,9H-naphtho[2,3-b]furan-4,9-dione

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
4.359674967999998

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.753452047788866

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.449838029705215

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0903854562785225

> <JCHEM_POLAR_SURFACE_AREA>
131.10999999999999

> <JCHEM_REFRACTIVITY>
118.15779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[2-(3-acetyl-7,8-dihydroxy-1-oxoisochromen-6-yl)ethyl]naphtho[2,3-b]furan-4,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -8.7386    1.0227   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3154    1.2014   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8917    2.0175   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3169    0.4166   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9605    0.5410   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0140   -0.2001   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6627   -0.0695   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -0.8268    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2914   -0.6576    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    0.1629    1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386    0.2686    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8676   -0.5717    1.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0307   -0.1060    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6581    1.0170   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699    1.1869   -0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    1.7717   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829    2.7849   -1.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763    1.3162   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216    2.0340   -1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3162    1.6168   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7028    0.4962   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7430   -0.2122   -0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4353    0.1930   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4162   -0.5680    0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7506   -1.5975    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903   -1.7199    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324   -2.4836    1.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5365   -1.8436    1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0014   -2.7395    2.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861   -1.0939    0.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8386   -1.1966    1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2335   -2.0270    1.9221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6851   -0.4523    0.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1753    0.1307   -1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2654    1.9478   -1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8251    0.9201    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6406    1.2532   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    0.6545   -1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -1.6276   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1850   -0.1286   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -0.2740    2.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221    1.1863    1.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619   -1.4360    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6919    2.9208   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0583    2.1893   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7366    0.1628   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0027   -1.0823    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543   -3.1596    2.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4342   -3.3386    3.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  8 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33  4  1  0
 30  6  1  0
 15 11  1  0
 23 18  1  0
 24 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 27 48  1  0
 29 49  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      -8.739   1.023  -0.931  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.315   1.201  -1.242  0.00  0.00           C+0
HETATM    3  O   UNK     0      -6.892   2.018  -2.108  0.00  0.00           O+0
HETATM    4  C   UNK     0      -6.317   0.417  -0.536  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.960   0.541  -0.776  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.014  -0.200  -0.109  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.663  -0.070  -0.348  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.744  -0.827   0.346  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.291  -0.658   0.077  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.388   0.163   1.136  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.839   0.269   0.751  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.868  -0.572   1.119  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.031  -0.106   0.543  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.658   1.017  -0.164  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.370   1.187  -0.006  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.669   1.772  -0.910  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.383   2.785  -1.559  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.076   1.316  -0.894  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.022   2.034  -1.601  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.316   1.617  -1.588  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.703   0.496  -0.886  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.743  -0.212  -0.182  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.435   0.193  -0.184  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.416  -0.568   0.568  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.751  -1.597   1.218  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.190  -1.720   1.286  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.232  -2.484   1.982  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.537  -1.844   1.517  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001  -2.740   2.461  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.486  -1.094   0.833  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.839  -1.197   1.051  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.234  -2.027   1.922  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.685  -0.452   0.372  0.00  0.00           O+0
HETATM   34  H   UNK     0      -9.175   0.131  -1.423  0.00  0.00           H+0
HETATM   35  H   UNK     0      -9.265   1.948  -1.227  0.00  0.00           H+0
HETATM   36  H   UNK     0      -8.825   0.920   0.177  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.641   1.253  -1.523  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.340   0.655  -1.107  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.222  -1.628  -0.017  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.185  -0.129  -0.891  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.342  -0.274   2.133  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.022   1.186   1.180  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.762  -1.436   1.747  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.692   2.921  -2.152  0.00  0.00           H+0
HETATM   45  H   UNK     0       9.058   2.189  -2.151  0.00  0.00           H+0
HETATM   46  H   UNK     0       9.737   0.163  -0.876  0.00  0.00           H+0
HETATM   47  H   UNK     0       8.003  -1.082   0.372  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.454  -3.160   2.682  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.434  -3.339   3.022  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6   37                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8   38                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   39   40                                             
CONECT   10    9   11   41   42                                             
CONECT   11   10   12   15                                                  
CONECT   12   11   13   43                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   11                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20   44                                                  
CONECT   20   19   21   45                                                  
CONECT   21   20   22   46                                                  
CONECT   22   21   23   47                                                  
CONECT   23   22   24   18                                                  
CONECT   24   23   25   13                                                  
CONECT   25   24                                                            
CONECT   26    8   27   28                                                  
CONECT   27   26   48                                                       
CONECT   28   26   29   30                                                  
CONECT   29   28   49                                                       
CONECT   30   28   31    6                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    4                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    5                                                            
CONECT   38    7                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   27                                                            
CONECT   49   29                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

RDKit          3D

49 53  0  0  0  0  0  0  0  0999 V2000
   -8.7386    1.0227   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3154    1.2014   -1.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8917    2.0175   -2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3169    0.4166   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9605    0.5410   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0140   -0.2001   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6627   -0.0695   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -0.8268    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2914   -0.6576    0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    0.1629    1.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386    0.2686    0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8676   -0.5717    1.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0307   -0.1060    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6581    1.0170   -0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699    1.1869   -0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    1.7717   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829    2.7849   -1.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0763    1.3162   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0216    2.0340   -1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3162    1.6168   -1.5883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7028    0.4962   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7430   -0.2122   -0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4353    0.1930   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4162   -0.5680    0.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7506   -1.5975    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903   -1.7199    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324   -2.4836    1.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5365   -1.8436    1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0014   -2.7395    2.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861   -1.0939    0.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8386   -1.1966    1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2335   -2.0270    1.9221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6851   -0.4523    0.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1753    0.1307   -1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2654    1.9478   -1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8251    0.9201    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6406    1.2532   -1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    0.6545   -1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -1.6276   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1850   -0.1286   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -0.2740    2.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0221    1.1863    1.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619   -1.4360    1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6919    2.9208   -2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0583    2.1893   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7366    0.1628   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0027   -1.0823    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543   -3.1596    2.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4342   -3.3386    3.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  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
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
  8 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33  4  1  0
 30  6  1  0
 15 11  1  0
 23 18  1  0
 24 13  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 27 48  1  0
 29 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
g-Iso-rubromycin	Generator
Γ-iso-rubromycin	Generator

Chemical Formula

C₂₅H₁₆O₈

Average Mass

444.3950 Da

Monoisotopic Mass

444.08452 Da

IUPAC Name

2-[2-(3-acetyl-7,8-dihydroxy-1-oxo-1H-isochromen-6-yl)ethyl]-4H,9H-naphtho[2,3-b]furan-4,9-dione

Traditional Name

2-[2-(3-acetyl-7,8-dihydroxy-1-oxoisochromen-6-yl)ethyl]naphtho[2,3-b]furan-4,9-dione

CAS Registry Number

Not Available

SMILES

CC(=O)C1=CC2=CC(CCC3=CC4=C(O3)C(=O)C3=CC=CC=C3C4=O)=C(O)C(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C25H16O8/c1-11(26)18-9-13-8-12(20(27)23(30)19(13)25(31)33-18)6-7-14-10-17-21(28)15-4-2-3-5-16(15)22(29)24(17)32-14/h2-5,8-10,27,30H,6-7H2,1H3

InChI Key

CNCUCHMIDJODTO-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 collinus	NPAtlas	25855820

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Isocoumarin
Furanoid fatty acid
2-benzopyran
Naphthalene
Benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Hydroxy fatty acid
Fatty acyl
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Furan
Lactone
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

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	3.92	ALOGPS
logP	4.36	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.45	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.16 m³·mol⁻¹	ChemAxon
Polarizability	45.89 Å³	ChemAxon
Number of Rings	5	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

NPA020514

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588852

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Erratum: Borderud SP, Li Y, Burkhalter JE, Sheffer CE and Ostroff JS. Electronic cigarette use among patients with cancer: Characteristics of electronic cigarette users and their smoking cessation outcomes. Cancer. doi: 10.1002/ cncr.28811. Cancer. 2015 Mar 1;121(5):800. doi: 10.1002/cncr.29118. [PubMed:25855820 ]

Showing NP-Card for γ-iso-Rubromycin (NP0014024)

MOL for NP0014024 (γ-iso-Rubromycin)

3D MOL for NP0014024 (γ-iso-Rubromycin)

3D SDF for NP0014024 (γ-iso-Rubromycin)

3D-SDF for NP0014024 (γ-iso-Rubromycin)

PDB for NP0014024 (γ-iso-Rubromycin)

3D PDB for NP0014024 (γ-iso-Rubromycin)

SMILES for NP0014024 (γ-iso-Rubromycin)

INCHI for NP0014024 (γ-iso-Rubromycin)

Structure for NP0014024 (γ-iso-Rubromycin)

3D Structure for NP0014024 (γ-iso-Rubromycin)