NP-MRD: Showing NP-Card for 4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid (NP0324326)

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Record Information

Version

2.0

Created at

2022-09-12 04:20:28 UTC

Updated at

2022-09-12 04:20:29 UTC

NP-MRD ID

NP0324326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid

Description

4-Hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid belongs to the class of organic compounds known as dibenzo-p-dioxins. Dibenzo-p-dioxins are compounds containing a dibenzo-p-dioxin moiety, which consists of two benzene connected by a para-dioxin ring. 4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid is found in Siphoneugena densiflora. Based on a literature review very few articles have been published on 4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206202D          

 35 38  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  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
    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   -1.6500    0.0000 C   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 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
    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
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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 O   0  0  0  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
    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 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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 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
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  2  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
  5 35  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -0.3583    3.5037   -1.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961    2.3822   -0.9910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548    1.5723   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7701    1.8035   -0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8143    1.0045   -0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -0.0829    0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2408   -0.3249    0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852   -1.4109    1.4874 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -2.6639    0.9225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928    0.4838    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1239    0.2556    0.5917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0348   -0.5207   -0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796   -0.5306    0.5703 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8406    0.7574    0.6475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0608    0.9362    1.2183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6263    2.2554    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7291    2.1394   -0.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0389   -0.1539    1.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4974   -0.5634    2.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6465   -1.3719    0.3815 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4985   -2.4773    1.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3457   -1.2626   -0.3706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8689   -2.4934   -0.7513 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981   -0.9053    0.7716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9171   -0.6574    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741   -1.4460    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764   -2.5448    1.6526 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2757   -1.1857    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5647   -0.0897   -0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9352    0.1984   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1485    1.1916   -1.4743 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9656   -0.6090   -0.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4951    0.6818   -0.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1903    0.4311   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1345    1.2480   -0.8308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884    4.3087   -1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393    3.8153   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2625    3.2008   -2.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    2.6487   -1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -2.6020   -0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -3.1475    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6644   -3.2723    0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544   -0.0676   -1.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905   -1.5476   -0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3428   -1.0079    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8844    1.1595    2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6376    2.4364    1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9098    3.0693    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2757    1.3587   -0.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9732    0.2497    0.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8815    0.2329    2.8367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4138   -1.7073   -0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3591   -2.1018    2.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4921   -0.5843   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4237   -2.4028   -1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7367   -2.7618    1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0510   -1.8464    0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8695   -0.5203   -0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6717    1.5390   -1.3837 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
  4  5  1  0
  5  6  2  0
  6 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 33  1  0
 33 34  2  0
 34 35  1  0
 29 30  1  0
 30 32  1  0
 30 31  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 10  3  1  0
 22 13  1  0
 35  5  1  0
 34 25  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
 27 56  1  0
 28 57  1  0
 33 59  1  0
 32 58  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  1
 15 46  1  1
 16 47  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  6
 19 51  1  0
 20 52  1  6
 21 53  1  0
 22 54  1  6
 23 55  1  0
M  END


  Mrv1652309122206202D          

 35 38  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  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
    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   -1.6500    0.0000 C   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 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
    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
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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 O   0  0  0  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
    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 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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
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 29 30  1  0  0  0  0
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 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  2  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
  5 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(OC3=C(O)C=C(C=C3O2)C(O)=O)C(OC)=C1OCC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O13/c1-30-10-5-12-20(35-18-9(24)3-8(22(28)29)4-11(18)33-12)21(31-2)19(10)32-7-14-16(26)17(27)15(25)13(6-23)34-14/h3-5,13-17,23-27H,6-7H2,1-2H3,(H,28,29)

> <INCHI_KEY>
QSKHZQUOPBBPSH-UHFFFAOYSA-N

> <FORMULA>
C22H24O13

> <MOLECULAR_WEIGHT>
496.421

> <EXACT_MASS>
496.121690833

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
48.36672321746514

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid

> <JCHEM_LOGP>
-0.7984949943333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.049728416130062

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.833504704419449

> <JCHEM_PKA_STRONGEST_BASIC>
-2.978895842224465

> <JCHEM_POLAR_SURFACE_AREA>
193.82999999999998

> <JCHEM_REFRACTIVITY>
113.70299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001  -0.770   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  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24    6   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29   34                                                       
CONECT   34   33   25   35                                                  
CONECT   35   34    5                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylate	Generator

Chemical Formula

C₂₂H₂₄O₁₃

Average Mass

496.4210 Da

Monoisotopic Mass

496.12169 Da

IUPAC Name

4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid

Traditional Name

4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(OC3=C(O)C=C(C=C3O2)C(O)=O)C(OC)=C1OCC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H24O13/c1-30-10-5-12-20(35-18-9(24)3-8(22(28)29)4-11(18)33-12)21(31-2)19(10)32-7-14-16(26)17(27)15(25)13(6-23)34-14/h3-5,13-17,23-27H,6-7H2,1-2H3,(H,28,29)

InChI Key

QSKHZQUOPBBPSH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, 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
Siphoneugena densiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzo-p-dioxins. Dibenzo-p-dioxins are compounds containing a dibenzo-p-dioxin moiety, which consists of two benzene connected by a para-dioxin ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxins

Sub Class

Benzo-p-dioxins

Direct Parent

Dibenzo-p-dioxins

Alternative Parents

Substituents

Dibenzo-p-dioxin
Gallic acid or derivatives
Glycosyl compound
Diaryl ether
C-glycosyl compound
Hydroxybenzoic acid
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	-0.8	ChemAxon
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	193.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	113.7 m³·mol⁻¹	ChemAxon
Polarizability	48.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162820318

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid (NP0324326)

MOL for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

3D MOL for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

3D SDF for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

3D-SDF for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

PDB for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

3D PDB for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

SMILES for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

INCHI for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

Structure for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)

3D Structure for NP0324326 (4-hydroxy-6,8-dimethoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methoxy}oxanthrene-2-carboxylic acid)