NP-MRD: Showing NP-Card for [(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid (NP0295228)

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Record Information

Version

2.0

Created at

2022-09-10 04:07:00 UTC

Updated at

2022-09-10 04:07:00 UTC

NP-MRD ID

NP0295228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

Description

2-[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]Icosa-2,4(13),6(11),14-tetraen-9-yl]acetic acid belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. [(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid is found in Streptomyces thermoviolaceus. Based on a literature review very few articles have been published on 2-[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]Icosa-2,4(13),6(11),14-tetraen-9-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102206072D          

 33 37  0  0  1  0            999 V2000
    5.5693    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2837    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9982   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4272   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5693   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5680   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1465    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2825    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3351    0.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  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  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 25 33  1  6  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    2.2984    3.5243   -0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7189    2.4645    0.6446 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0339    2.1773    0.6138 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597    1.0785   -0.0742 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9500    0.9517    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4570    0.8540    1.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7987    0.9736    2.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8248    0.5993    1.6200 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7756   -0.2112    0.2659 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0980   -0.6015    1.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2968    0.0377    0.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760    1.2657    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4053    1.4695    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581    2.6277    0.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944    0.3510    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8808    0.6305    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    1.9066    0.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7214   -0.4078   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2201   -1.6998   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8755   -1.9750   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028   -3.2684   -0.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0167   -0.9245   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155   -1.1199    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206   -2.2507   -0.1374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572   -2.7305   -0.4651 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2381   -2.6921    0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6760   -1.2976    1.0031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0095   -0.9194    2.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2017   -0.3754   -0.1352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7951    0.8429   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5982   -1.1190   -1.4202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4308   -0.1702   -2.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9724   -2.3118   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7426    3.0733   -1.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228    4.0296   -0.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6170    4.2371    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    2.8167    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2271    1.2153   -1.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3218    0.0325   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4814    1.8054   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4609    0.5026    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0647   -0.9610   -0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990   -0.3247    2.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330    2.2113    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3791   -3.6534   -0.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -3.7388   -0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270   -3.2350    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1481   -3.2504    0.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7574   -1.1791    1.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399   -0.9170    2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7580    0.7296   -0.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6977   -1.3244   -1.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7244   -0.6065   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9999    0.8069   -2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4186    0.0502   -3.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
  4  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 31 33  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 12  2  1  0
 22 15  1  0
 23 11  1  0
 29 18  1  0
 33 25  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  4 38  1  6
  5 39  1  0
  5 40  1  0
  8 41  1  0
  9 42  1  6
 10 43  1  0
 17 44  1  0
 25 46  1  6
 26 47  1  0
 26 48  1  0
 27 49  1  1
 28 50  1  0
 30 51  1  0
 31 52  1  1
 32 53  1  0
 32 54  1  0
 32 55  1  0
 21 45  1  0
M  END


  Mrv1652309102206072D          

 33 37  0  0  1  0            999 V2000
    5.5693    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2837    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2837   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9982   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4272   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7127    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5693   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4259    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1403   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5680   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5680    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1465    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2825    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.6875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3351    0.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  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  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 25 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0295228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](CC(O)=O)[C@@H](O)C2=C1C(=O)C1=C(O)C3=C([C@H]4C[C@@H](O)[C@]3(O)[C@@H](C)O4)C(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-5-11-13(17(26)8(32-5)4-10(24)25)20(29)14-15(18(11)27)21(30)16-12(19(14)28)7-3-9(23)22(16,31)6(2)33-7/h5-9,17,23,26,28,30-31H,3-4H2,1-2H3,(H,24,25)/t5-,6+,7+,8-,9+,17+,22+/m0/s1

> <INCHI_KEY>
WCEOQCLZGCMUEV-MJDCBFFMSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.42913594417943

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

> <JCHEM_LOGP>
-0.20566750000000078

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.082206286828661

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1381898685963576

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4058727899725545

> <JCHEM_POLAR_SURFACE_AREA>
191.04999999999998

> <JCHEM_REFRACTIVITY>
108.65569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.396   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.396   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.730   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.730  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.063  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.397  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.731  -0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.397   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.396  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.396  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.062   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.062   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.729   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.729   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.395   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.061   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.061   3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.728   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.728   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.061  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.061  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.395   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.729  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.729  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.394  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.060  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.060   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.273   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.394   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.394   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.137   1.283   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.625   0.990   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.137   0.257   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   29                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   11   24                                                  
CONECT   24   23                                                            
CONECT   25   19   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   18   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-Pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0,.0,.0,]icosa-2,4(13),6(11),14-tetraen-9-yl]acetate	Generator

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

2-[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

Traditional Name

[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0^{2,15}.0^{4,13}.0^{6,11}]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](CC(O)=O)[C@@H](O)C2=C1C(=O)C1=C(O)C3=C([C@H]4C[C@@H](O)[C@]3(O)[C@@H](C)O4)C(O)=C1C2=O

InChI Identifier

InChI=1S/C22H22O11/c1-5-11-13(17(26)8(32-5)4-10(24)25)20(29)14-15(18(11)27)21(30)16-12(19(14)28)7-3-9(23)22(16,31)6(2)33-7/h5-9,17,23,26,28,30-31H,3-4H2,1-2H3,(H,24,25)/t5-,6+,7+,8-,9+,17+,22+/m0/s1

InChI Key

WCEOQCLZGCMUEV-MJDCBFFMSA-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 thermoviolaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
1,4-anthraquinone
Benzoisochromanequinone
Isochromanequinone
Naphthopyranone
Naphthopyran
Benzopyran
Isochromane
2-benzopyran
Tetralin
Naphthalene
Aryl ketone
Quinone
Pyranone
Pyran
Oxane
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	-0.21	ChemAxon
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.66 m³·mol⁻¹	ChemAxon
Polarizability	44.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

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

136863246

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid (NP0295228)

MOL for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

3D MOL for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

3D SDF for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

3D-SDF for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

PDB for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

3D PDB for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

SMILES for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

INCHI for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

Structure for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)

3D Structure for NP0295228 ([(1s,7s,9s,10s,16r,18r,19r)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.0²,¹⁵.0⁴,¹³.0⁶,¹¹]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid)