NP-MRD: Showing NP-Card for methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate (NP0269433)

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Record Information

Version

2.0

Created at

2022-09-08 14:54:53 UTC

Updated at

2022-09-08 14:54:54 UTC

NP-MRD ID

NP0269433

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate

Description

11-Hydroxysulfurmycinone 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 (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate was first documented in 2004 (PMID: 15497950). Based on a literature review very few articles have been published on 11-hydroxysulfurmycinone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082216542D          

 33 36  0  0  1  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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  2  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
    3.5724    2.0625    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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  1  0  0  0  0  0  0  0  0  0
    6.5403    0.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9774    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3648    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4146    2.1955    0.0000 O   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  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 C   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
    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  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
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  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
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -2.5725    3.7082   -0.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    2.3760   -0.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0689    1.8485    0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    2.6876    1.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.4620    0.9825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4314    0.1194    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7031    0.7463    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5594    1.6279    1.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    0.4459    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -0.4510   -0.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9240   -1.0622   -1.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888   -1.9580   -2.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2994   -0.7630   -0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942   -1.4492   -1.2459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5510   -2.7266   -0.6951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7590   -0.6476   -0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8235   -0.5156    0.5732 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4257   -1.7472    1.1502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1170   -0.0738    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2891   -0.8962    0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2660   -2.2187    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3825   -0.4679    1.2251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671   -0.7955   -1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3869   -1.6184   -2.2471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6006   -0.2015   -0.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8271   -0.5353   -1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9930   -1.4154   -2.4080 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9498    0.0994   -0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8603    0.9909    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6356    1.2965    0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4979    0.6944    0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829    1.0393    0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598    1.8662    1.7586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358    3.7929   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7014    4.3048    0.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073    4.1984   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698    0.3537    2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    2.1530    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3424   -2.4560   -2.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272   -1.5745   -2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661   -3.0529   -0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5813   -1.2057   -1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6083    0.3240   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -1.9064    2.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2728    0.9977    0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9868   -0.0309    2.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3131   -2.7455    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0039   -2.9211    0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7012   -2.0968   -0.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -1.9298   -2.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8978   -0.1538   -1.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7268    1.4851    0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5113    1.9985    1.5590 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  1  0
  6  7  2  0
  7  8  1  0
  7  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  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 10 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 17  5  1  0
 31 25  1  0
 13  6  1  0
 32  9  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
  8 38  1  0
 12 39  1  0
 14 40  1  6
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 27 50  1  0
 28 51  1  0
 29 52  1  0
 30 53  1  0
M  END


  Mrv1652309082216542D          

 33 36  0  0  1  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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  2  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
    3.5724    2.0625    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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  1  0  0  0  0  0  0  0  0  0
    6.5403    0.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9774    1.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3648    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4146    2.1955    0.0000 O   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  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 C   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
    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  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
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  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
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0269433

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C2=C(O)C3=C(C(O)=C2[C@@H](O)C[C@]1(O)CC(C)=O)C(=O)C1=C(O)C=CC=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O10/c1-8(24)6-23(32)7-11(26)13-14(17(23)22(31)33-2)21(30)15-16(20(13)29)19(28)12-9(18(15)27)4-3-5-10(12)25/h3-5,11,17,25-26,29-30,32H,6-7H2,1-2H3/t11-,17-,23+/m0/s1

> <INCHI_KEY>
SSGMOZLPXXJLNJ-RLAVILMUSA-N

> <FORMULA>
C23H20O10

> <MOLECULAR_WEIGHT>
456.403

> <EXACT_MASS>
456.105646844

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.046375154541984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,4S)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

> <JCHEM_LOGP>
2.212877026

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.520640396208952

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.899857536358922

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3067422339442665

> <JCHEM_POLAR_SURFACE_AREA>
178.66

> <JCHEM_REFRACTIVITY>
112.79699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,4S)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1H-tetracene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.208   1.594   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.486   2.846   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.025   2.792   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.748   1.433   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.841   4.098   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   33  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   17                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    5   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   10   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31    9   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
11-Hydroxysulphurmycinone	Generator

Chemical Formula

C₂₃H₂₀O₁₀

Average Mass

456.4030 Da

Monoisotopic Mass

456.10565 Da

IUPAC Name

methyl (1R,2S,4S)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

Traditional Name

methyl (1R,2S,4S)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1H-tetracene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C2=C(O)C3=C(C(O)=C2[C@@H](O)C[C@]1(O)CC(C)=O)C(=O)C1=C(O)C=CC=C1C3=O

InChI Identifier

InChI=1S/C23H20O10/c1-8(24)6-23(32)7-11(26)13-14(17(23)22(31)33-2)21(30)15-16(20(13)29)19(28)12-9(18(15)27)4-3-5-10(12)25/h3-5,11,17,25-26,29-30,32H,6-7H2,1-2H3/t11-,17-,23+/m0/s1

InChI Key

SSGMOZLPXXJLNJ-RLAVILMUSA-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

Not Available

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
Anthracene
1-naphthalenecarboxylic acid or derivatives
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Beta-hydroxy ketone
Vinylogous acid
Methyl ester
Tertiary alcohol
Ketone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.21	ChemAxon
pKa (Strongest Acidic)	7.9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	178.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.8 m³·mol⁻¹	ChemAxon
Polarizability	44.05 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10364832

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23251486

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Clark B, Capon RJ, Stewart M, Lacey E, Tennant S, Gill JH: Blanchaquinone: a new anthraquinone from an Australian Streptomyces sp. J Nat Prod. 2004 Oct;67(10):1729-31. doi: 10.1021/np049826v. [PubMed:15497950 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate (NP0269433)

MOL for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D MOL for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D SDF for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D-SDF for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

PDB for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D PDB for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

SMILES for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

INCHI for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

Structure for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)

3D Structure for NP0269433 (methyl (1r,2s,4s)-2,4,5,7,12-pentahydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1h-tetracene-1-carboxylate)