NP-MRD: Showing NP-Card for γ-Rubromycin (NP0014025)

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Record Information

Version

1.0

Created at

2021-01-05 23:17:11 UTC

Updated at

2021-07-15 17:16:10 UTC

NP-MRD ID

NP0014025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

γ-Rubromycin

Provided By

NPAtlas

Description

Gamma-Rubromycin, also known as γ-rubromycin, belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. γ-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 gamma-Rubromycin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119523D          

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M  END

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  Mrv1652306242119523D          

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   -6.0331   -0.4402   -1.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0754   -0.9022   -2.9201 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816    0.5146    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2878    1.2211    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2834    2.2870    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2840   -0.0739    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -1.1686    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    2.3270   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.2327    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2725   -2.8267   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027   -2.5034    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -1.2187    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -2.9645   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627   -1.5633   -2.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261   -2.0875   -3.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9036    0.7346    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8764   -0.0312    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2326    1.6361    0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6449    1.4281   -0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1299    0.2738   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  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
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 16  5  1  0  0  0  0
 30 18  1  0  0  0  0
 13  7  1  0  0  0  0
 29 22  1  0  0  0  0
 20  9  1  0  0  0  0
 37 25  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  6 42  1  0  0  0  0
  8 43  1  0  0  0  0
 12 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 24 51  1  0  0  0  0
 28 52  1  0  0  0  0
 35 53  1  0  0  0  0
 35 54  1  0  0  0  0
 35 55  1  0  0  0  0
 36 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2O[C@]3(OC4=C(C([H])=C5C([H])=C(OC(=O)C5=C4O[H])C(=O)OC([H])([H])[H])C([H])([H])C3([H])[H])C([H])([H])C2=C(O[H])C2=C1C(=O)C(OC([H])([H])[H])=C([H])C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H18O12/c1-34-13-7-12(27)16-17(19(13)29)21(31)23-11(18(16)28)8-26(38-23)4-3-9-5-10-6-14(24(32)35-2)36-25(33)15(10)20(30)22(9)37-26/h5-7,28,30-31H,3-4,8H2,1-2H3/t26-/m0/s1

> <INCHI_KEY>
CKLKRRFSZZUFKT-SANMLTNESA-N

> <FORMULA>
C26H18O12

> <MOLECULAR_WEIGHT>
522.418

> <EXACT_MASS>
522.07982602

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
51.517756480467206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-4,9,10'-trihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
4.328296224666666

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.874955223058786

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.586364856894395

> <JCHEM_PKA_STRONGEST_BASIC>
-3.467131632676554

> <JCHEM_POLAR_SURFACE_AREA>
175.11999999999998

> <JCHEM_REFRACTIVITY>
129.64849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-4,9,10'-trihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
   10.0413    1.2434    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6615    0.9692    0.7628 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9598    1.6716   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5453    2.5354   -0.8705 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    1.4599   -0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958    0.5339    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461    0.3529    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7583   -0.5904    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.7674    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7985   -0.0248   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4633    0.9455   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    1.6408   -2.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139    1.1179   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5921    2.0137   -1.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    2.7342   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8711    2.1435   -1.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -0.2334   -0.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597   -1.3575   -0.1204 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7032   -2.4371    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420   -1.7825    1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1685   -1.8554   -1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4874   -1.2581   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6713   -1.1544   -1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551   -1.6511   -2.8498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812   -0.5586   -0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6674   -0.0735    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -0.1754    1.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569    0.2893    2.3231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -0.7884    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -1.0117    0.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703    0.5460    0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8300    1.0050    2.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1234    0.6560    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2427    1.2547    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5502    1.0082    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2031    0.1897   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331   -0.4402   -1.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0754   -0.9022   -2.9201 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816    0.5146    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2878    1.2211    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2834    2.2870    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2840   -0.0739    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -1.1686    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    2.3270   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.2327    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2725   -2.8267   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027   -2.5034    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -1.2187    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -2.9645   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627   -1.5633   -2.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261   -2.0875   -3.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9036    0.7346    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8764   -0.0312    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2326    1.6361    0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6449    1.4281   -0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1299    0.2738   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 18 17  1  6
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 26 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  2  0
 36 37  1  0
 37 38  2  0
 16  5  1  0
 30 18  1  0
 13  7  1  0
 29 22  1  0
 20  9  1  0
 37 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  6 42  1  0
  8 43  1  0
 12 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 24 51  1  0
 28 52  1  0
 35 53  1  0
 35 54  1  0
 35 55  1  0
 36 56  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      10.041   1.243   0.922  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.662   0.969   0.763  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.960   1.672  -0.176  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.545   2.535  -0.871  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.520   1.460  -0.418  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.796   0.534   0.296  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.446   0.353   0.052  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.758  -0.590   0.795  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.434  -0.767   0.554  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.799  -0.025  -0.405  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.463   0.946  -1.183  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.775   1.641  -2.110  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.814   1.118  -0.929  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.592   2.014  -1.595  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.069   2.734  -2.496  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.871   2.143  -1.321  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.438  -0.233  -0.625  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.260  -1.357  -0.120  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.703  -2.437   0.345  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.642  -1.783   1.337  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.169  -1.855  -1.198  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.487  -1.258  -0.810  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.671  -1.154  -1.541  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.755  -1.651  -2.850  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.781  -0.559  -0.982  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.667  -0.074   0.323  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.498  -0.175   1.046  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.357   0.289   2.323  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.369  -0.788   0.460  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.087  -1.012   0.974  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.870   0.546   0.864  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.830   1.005   2.042  0.00  0.00           O+0
HETATM   33  C   UNK     0      -7.123   0.656   0.091  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.243   1.255   0.649  0.00  0.00           O+0
HETATM   35  C   UNK     0      -9.550   1.008   0.215  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.203   0.190  -1.139  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.033  -0.440  -1.732  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.075  -0.902  -2.920  0.00  0.00           O+0
HETATM   39  H   UNK     0      10.682   0.515   0.384  0.00  0.00           H+0
HETATM   40  H   UNK     0      10.288   1.221   2.005  0.00  0.00           H+0
HETATM   41  H   UNK     0      10.283   2.287   0.587  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.284  -0.074   1.071  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.285  -1.169   1.551  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.038   2.327  -2.725  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.102  -3.233   0.817  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.272  -2.827  -0.529  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.303  -2.503   1.841  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.004  -1.219   2.057  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.264  -2.965  -1.071  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.863  -1.563  -2.213  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.926  -2.087  -3.246  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.904   0.735   2.977  0.00  0.00           H+0
HETATM   53  H   UNK     0      -9.876  -0.031   0.290  0.00  0.00           H+0
HETATM   54  H   UNK     0     -10.233   1.636   0.849  0.00  0.00           H+0
HETATM   55  H   UNK     0      -9.645   1.428  -0.810  0.00  0.00           H+0
HETATM   56  H   UNK     0      -8.130   0.274  -1.703  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7   42                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   43                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   44                                                       
CONECT   13   11   14    7                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    5                                                       
CONECT   17   10   18                                                       
CONECT   18   17   19   21   30                                             
CONECT   19   18   20   45   46                                             
CONECT   20   19    9   47   48                                             
CONECT   21   18   22   49   50                                             
CONECT   22   21   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   51                                                       
CONECT   25   23   26   37                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   52                                                       
CONECT   29   27   30   22                                                  
CONECT   30   29   18                                                       
CONECT   31   26   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   53   54   55                                             
CONECT   36   33   37   56                                                  
CONECT   37   36   38   25                                                  
CONECT   38   37                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44   12                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   24                                                            
CONECT   52   28                                                            
CONECT   53   35                                                            
CONECT   54   35                                                            
CONECT   55   35                                                            
CONECT   56   36                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

RDKit          3D

56 61  0  0  0  0  0  0  0  0999 V2000
   10.0413    1.2434    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6615    0.9692    0.7628 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9598    1.6716   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5453    2.5354   -0.8705 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5199    1.4599   -0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7958    0.5339    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461    0.3529    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7583   -0.5904    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.7674    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7985   -0.0248   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4633    0.9455   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    1.6408   -2.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139    1.1179   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5921    2.0137   -1.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    2.7342   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8711    2.1435   -1.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380   -0.2334   -0.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597   -1.3575   -0.1204 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7032   -2.4371    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6420   -1.7825    1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1685   -1.8554   -1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4874   -1.2581   -0.8104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6713   -1.1544   -1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7551   -1.6511   -2.8498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7812   -0.5586   -0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6674   -0.0735    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -0.1754    1.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569    0.2893    2.3231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -0.7884    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -1.0117    0.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8703    0.5460    0.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8300    1.0050    2.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1234    0.6560    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2427    1.2547    0.6493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5502    1.0082    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2031    0.1897   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0331   -0.4402   -1.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0754   -0.9022   -2.9201 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816    0.5146    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2878    1.2211    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2834    2.2870    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2840   -0.0739    1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -1.1686    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385    2.3270   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.2327    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2725   -2.8267   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027   -2.5034    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -1.2187    2.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640   -2.9645   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627   -1.5633   -2.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261   -2.0875   -3.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9036    0.7346    2.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8764   -0.0312    0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2326    1.6361    0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6449    1.4281   -0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1299    0.2738   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 18 17  1  6
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 26 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  2  0
 36 37  1  0
 37 38  2  0
 16  5  1  0
 30 18  1  0
 13  7  1  0
 29 22  1  0
 20  9  1  0
 37 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  6 42  1  0
  8 43  1  0
 12 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 24 51  1  0
 28 52  1  0
 35 53  1  0
 35 54  1  0
 35 55  1  0
 36 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
g-Rubromycin	Generator
Γ-rubromycin	Generator
delta-Rubromycin	MeSH
Methyl (2S)-4,9,10'-trihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylic acid	Generator

Chemical Formula

C₂₆H₁₈O₁₂

Average Mass

522.4180 Da

Monoisotopic Mass

522.07983 Da

IUPAC Name

methyl (2S)-4,9,10'-trihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

Traditional Name

methyl (2S)-4,9,10'-trihydroxy-7-methoxy-5,8,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=CC3=C(O[C@@]4(CC5=C(O)C6=C(C(O)=C5O4)C(=O)C(OC)=CC6=O)CC3)C(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C26H18O12/c1-34-13-7-12(27)16-17(19(13)29)21(31)23-11(18(16)28)8-26(38-23)4-3-9-5-10-6-14(24(32)35-2)36-25(33)15(10)20(30)22(9)37-26/h5-7,28,30-31H,3-4,8H2,1-2H3/t26-/m0/s1

InChI Key

CKLKRRFSZZUFKT-SANMLTNESA-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 pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
Naphthofuran
Naphthoquinone
Isocoumarin
Naphthalene
2-benzopyran
Coumaran
Quinone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Ketal
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Methyl ester
Vinylogous ester
Carboxylic acid ester
Ketone
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Hydrocarbon derivative
Aldehyde
Organic oxygen compound
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	ALOGPS
logP	4.33	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	175.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129.65 m³·mol⁻¹	ChemAxon
Polarizability	51.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020513

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4576520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5464075

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-Rubromycin (NP0014025)

MOL for NP0014025 (γ-Rubromycin)

3D MOL for NP0014025 (γ-Rubromycin)

3D SDF for NP0014025 (γ-Rubromycin)

3D-SDF for NP0014025 (γ-Rubromycin)

PDB for NP0014025 (γ-Rubromycin)

3D PDB for NP0014025 (γ-Rubromycin)

SMILES for NP0014025 (γ-Rubromycin)

INCHI for NP0014025 (γ-Rubromycin)

Structure for NP0014025 (γ-Rubromycin)

3D Structure for NP0014025 (γ-Rubromycin)