NP-MRD: Showing NP-Card for methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate (NP0182778)

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Record Information

Version

2.0

Created at

2022-09-03 21:34:13 UTC

Updated at

2022-09-03 21:34:14 UTC

NP-MRD ID

NP0182778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate

Description

(6AR)-1-Methyl-3-(2,6-dideoxy-beta-D-arabino-hexopyranosyloxy)-6,10,11-trioxo-6aalpha,7alpha,10aalpha,12-tetrahydroxy-8-methoxy-6,6a,7,10,10a,11-hexahydro-2-naphthacenecarboxylic acid methyl ester belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4. methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate is found in Streptomyces fradiae. Based on a literature review very few articles have been published on (6aR)-1-Methyl-3-(2,6-dideoxy-beta-D-arabino-hexopyranosyloxy)-6,10,11-trioxo-6aalpha,7alpha,10aalpha,12-tetrahydroxy-8-methoxy-6,6a,7,10,10a,11-hexahydro-2-naphthacenecarboxylic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223342D          

 42 46  0  0  1  0            999 V2000
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
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 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 20 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
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   -2.2976   -0.8044   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440   -0.6501   -0.4625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724    0.4456    0.1099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2052    1.0850   -0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0895    2.1303   -0.2653 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0506    2.5378   -1.1567 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9369    0.3476   -1.0441 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6405    1.0047   -2.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5695    1.3009    2.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7248    2.0976    2.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3213    0.5854    1.3499 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8442    1.0815    2.5518 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6641    1.2475    0.1568 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3057    2.4844   -0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2406    1.5124    0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8325    2.5625    0.9344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4801   -4.0539   -4.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3879   -3.7386   -2.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
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 33 64  1  0
 30 63  1  0
 23 59  1  0
 26 60  1  0
 26 61  1  0
 26 62  1  0
M  END


  Mrv1652309032223342D          

 42 46  0  0  1  0            999 V2000
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 20 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0182778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(O[C@H]2C[C@@H](O)[C@H](O)[C@@H](C)O2)C=C2C=C3C(=O)[C@@]4(O)[C@H](O)C(OC)=CC(=O)[C@@]4(O)C(=O)C3=C(O)C2=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O14/c1-9-18-11(6-14(19(9)26(36)40-4)42-17-7-13(29)21(31)10(2)41-17)5-12-20(22(18)32)25(35)27(37)16(30)8-15(39-3)24(34)28(27,38)23(12)33/h5-6,8,10,13,17,21,24,29,31-32,34,37-38H,7H2,1-4H3/t10-,13-,17+,21-,24-,27-,28-/m1/s1

> <INCHI_KEY>
SYMWSBRGJWUXNP-BJXNODDTSA-N

> <FORMULA>
C28H28O14

> <MOLECULAR_WEIGHT>
588.518

> <EXACT_MASS>
588.147905582

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.027721060340326

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (6aR,7S,10aR)-3-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate

> <JCHEM_LOGP>
0.3914393873333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.83491243666629

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.702298479935213

> <JCHEM_PKA_STRONGEST_BASIC>
-3.252886695346559

> <JCHEM_POLAR_SURFACE_AREA>
226.57999999999996

> <JCHEM_REFRACTIVITY>
140.51399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (6aR,7S,10aR)-3-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7H-tetracene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003   8.470   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
CONECT   17    6   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   41                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18   25                                                  
CONECT   25   24    5   26                                                  
CONECT   26   25                                                            
CONECT   27   21   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   39                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   29   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   20   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(6AR)-1-methyl-3-(2,6-dideoxy-b-D-arabino-hexopyranosyloxy)-6,10,11-trioxo-6aalpha,7a,10aalpha,12-tetrahydroxy-8-methoxy-6,6a,7,10,10a,11-hexahydro-2-naphthacenecarboxylate methyl ester	Generator
(6AR)-1-methyl-3-(2,6-dideoxy-b-D-arabino-hexopyranosyloxy)-6,10,11-trioxo-6aalpha,7a,10aalpha,12-tetrahydroxy-8-methoxy-6,6a,7,10,10a,11-hexahydro-2-naphthacenecarboxylic acid methyl ester	Generator
(6AR)-1-methyl-3-(2,6-dideoxy-beta-D-arabino-hexopyranosyloxy)-6,10,11-trioxo-6aalpha,7alpha,10aalpha,12-tetrahydroxy-8-methoxy-6,6a,7,10,10a,11-hexahydro-2-naphthacenecarboxylate methyl ester	Generator
(6AR)-1-methyl-3-(2,6-dideoxy-β-D-arabino-hexopyranosyloxy)-6,10,11-trioxo-6aalpha,7α,10aalpha,12-tetrahydroxy-8-methoxy-6,6a,7,10,10a,11-hexahydro-2-naphthacenecarboxylate methyl ester	Generator
(6AR)-1-methyl-3-(2,6-dideoxy-β-D-arabino-hexopyranosyloxy)-6,10,11-trioxo-6aalpha,7α,10aalpha,12-tetrahydroxy-8-methoxy-6,6a,7,10,10a,11-hexahydro-2-naphthacenecarboxylic acid methyl ester	Generator

Chemical Formula

C₂₈H₂₈O₁₄

Average Mass

588.5180 Da

Monoisotopic Mass

588.14791 Da

IUPAC Name

methyl (6aR,7S,10aR)-3-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate

Traditional Name

methyl (6aR,7S,10aR)-3-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7H-tetracene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(O[C@H]2C[C@@H](O)[C@H](O)[C@@H](C)O2)C=C2C=C3C(=O)[C@@]4(O)[C@H](O)C(OC)=CC(=O)[C@@]4(O)C(=O)C3=C(O)C2=C1C

InChI Identifier

InChI=1S/C28H28O14/c1-9-18-11(6-14(19(9)26(36)40-4)42-17-7-13(29)21(31)10(2)41-17)5-12-20(22(18)32)25(35)27(37)16(30)8-15(39-3)24(34)28(27,38)23(12)33/h5-6,8,10,13,17,21,24,29,31-32,34,37-38H,7H2,1-4H3/t10-,13-,17+,21-,24-,27-,28-/m1/s1

InChI Key

SYMWSBRGJWUXNP-BJXNODDTSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 fradiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracenequinones. These are polyaromatic hydrocarbon derivatives containing a tetracyclic cycle made up of four linearly fused benzene rings, one of which bears two ketone groups at position 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Tetracenequinone
Anthracene carboxylic acid
Anthracene carboxylic acid or derivatives
9,10-anthraquinone
1,4-anthraquinone
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
Hexose monosaccharide
Glycosyl compound
1-naphthol
O-glycosyl compound
Naphthalene
Tetralin
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Cyclohexenone
Oxane
Monosaccharide
Methyl ester
Tertiary alcohol
Vinylogous acid
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Ketone
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	0.39	ChemAxon
pKa (Strongest Acidic)	7.7	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	226.58 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	140.51 m³·mol⁻¹	ChemAxon
Polarizability	57.03 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100919039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate (NP0182778)

MOL for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

3D MOL for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

3D SDF for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

3D-SDF for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

PDB for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

3D PDB for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

SMILES for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

INCHI for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

Structure for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)

3D Structure for NP0182778 (methyl (6ar,7s,10ar)-3-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-7h-tetracene-2-carboxylate)