NP-MRD: Showing NP-Card for 3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one (NP0283180)

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Record Information

Version

2.0

Created at

2022-09-09 10:19:55 UTC

Updated at

2022-09-09 10:19:56 UTC

NP-MRD ID

NP0283180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one

Description

3-{[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. 3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one is found in Ageratina calophylla. 3-{[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231519262D          

 34 37  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    1.4289    0.0000    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
    2.8579    0.0000    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -2.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -4.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5063   -3.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -4.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9543   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7389   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.0000   -1.6500    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
    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
    5.7158   -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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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
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 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  5 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
  3 24  1  0  0  0  0
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 25 26  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    6.7160    0.8870   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1094   -0.3599   -0.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307   -0.5711   -0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282    0.4510   -0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542    0.2516   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    1.2411   -0.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940    1.0850   -0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5346    2.2668    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8805    2.3500   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6131    3.4890    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9587    4.6263    0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7372    5.7514    0.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    4.6069    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720    5.7362    1.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852    3.4367    0.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565   -0.1450   -0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5888   -0.4894   -0.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -0.9101    1.0714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3068   -2.3376    0.9673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2282   -2.3773   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2427   -1.2775    0.1690 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4112   -0.4284   -0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5261   -1.9215    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3723   -2.7718    1.6804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574   -0.5259    1.2907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9257   -1.0416    2.5414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6179   -1.2255   -0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1747   -2.3981   -0.5494 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706   -1.0392   -0.4734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8510   -2.0983   -0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278   -3.3714   -0.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007   -1.8359   -0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0673   -2.9106   -0.8896 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4391   -3.2943   -2.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995    1.6423   -1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8514    1.1851    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7356    0.8062   -0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104    1.4575   -0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351    1.5070   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028    3.5075    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3421    6.5911    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    6.5902    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1601    3.4524    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4273   -0.7190    1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7147   -3.3817   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -2.1762   -1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1046   -0.7646   -1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2251   -1.0960    0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0396   -2.4297   -0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2297   -3.2427    1.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6734    0.5616    1.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4394   -1.8954    2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8749   -4.1964   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7624   -2.4081   -2.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724   -3.8920   -2.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3513   -3.9476   -2.0662 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 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  1  0
 29 27  1  0
 27 28  2  0
 27 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
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 21 22  1  6
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 23 24  1  0
 21 25  1  0
 25 26  1  0
 16  7  2  0
  7  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 32  3  1  0
 25 18  1  0
 15  8  1  0
  6  5  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
 31 53  1  0
 34 54  1  0
 34 55  1  0
 34 56  1  0
 18 44  1  1
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 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  1
 26 52  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
M  END


  Mrv1533004231519262D          

 34 37  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    1.4289    0.0000    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
    2.8579    0.0000    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -2.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -4.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5063   -3.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -4.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9543   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7389   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.0000   -1.6500    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
    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
    5.7158   -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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 10 17  1  0  0  0  0
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  5 21  2  0  0  0  0
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 22 24  2  0  0  0  0
  3 24  1  0  0  0  0
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 25 26  1  0  0  0  0
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 27 28  2  0  0  0  0
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 29 30  2  0  0  0  0
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 27 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1OC)C(=O)C(OC1OCC(O)(CO)C1O)=C(O2)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O12/c1-30-13-6-12-14(15(26)18(13)31-2)16(27)19(34-21-20(28)22(29,7-23)8-32-21)17(33-12)9-3-4-10(24)11(25)5-9/h3-6,20-21,23-26,28-29H,7-8H2,1-2H3

> <INCHI_KEY>
OEAMGGHFQBSAKZ-UHFFFAOYSA-N

> <FORMULA>
C22H22O12

> <MOLECULAR_WEIGHT>
478.406

> <EXACT_MASS>
478.111126148

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.926044349131374

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.33772407999999976

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.615769530591509

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.668734191623877

> <JCHEM_PKA_STRONGEST_BASIC>
-3.142388183026722

> <JCHEM_POLAR_SURFACE_AREA>
184.59999999999997

> <JCHEM_REFRACTIVITY>
114.47789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.756  -5.525   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.232  -6.990   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.772  -6.990   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.611  -8.521   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.278  -7.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.754  -8.775   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.248  -5.525   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.713  -5.049   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13   10   18                                                  
CONECT   18   17                                                            
CONECT   19    8   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    5   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27    7   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₂

Average Mass

478.4060 Da

Monoisotopic Mass

478.11113 Da

IUPAC Name

3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one

Traditional Name

3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1OC)C(=O)C(OC1OCC(O)(CO)C1O)=C(O2)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C22H22O12/c1-30-13-6-12-14(15(26)18(13)31-2)16(27)19(34-21-20(28)22(29,7-23)8-32-21)17(33-12)9-3-4-10(24)11(25)5-9/h3-6,20-21,23-26,28-29H,7-8H2,1-2H3

InChI Key

OEAMGGHFQBSAKZ-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
Ageratina calophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
O-glycosyl compound
Glycosyl compound
Chromone
Pentose monosaccharide
Benzopyran
1-benzopyran
Anisole
Catechol
Pyranone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Tertiary alcohol
Vinylogous acid
Oxolane
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
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	1.17	ALOGPS
logP	0.34	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.48 m³·mol⁻¹	ChemAxon
Polarizability	45.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

74978475

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one (NP0283180)

MOL for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

3D MOL for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

3D SDF for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

3D-SDF for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

PDB for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

3D PDB for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

SMILES for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

INCHI for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

Structure for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)

3D Structure for NP0283180 (3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one)