NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate (NP0308283)

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Record Information

Version

2.0

Created at

2022-09-11 01:57:55 UTC

Updated at

2022-09-11 01:57:55 UTC

NP-MRD ID

NP0308283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

Description

2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate is found in Marrubium vulgare. 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521072D          

 37 40  0  0  0  0            999 V2000
   -1.4289   -2.4750    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
   -2.1434   -1.2375    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
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  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
   -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
   -2.8579    0.8250    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
   -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 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
   -0.7145   -0.4125    0.0000 O   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
    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
    1.4289    0.8250    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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  1  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  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
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 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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   -3.1027   -0.5152    1.3006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3022   -0.5428    0.6039 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1181    0.0978   -0.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    0.5605   -1.2560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1075    2.0899   -1.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9307    2.4878   -1.9475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5384    0.0862   -0.8478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4369    1.1323   -1.1760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7202   -0.2291    0.5944 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2721   -1.5296    0.6838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4725   -0.1194    1.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3688    1.0986    2.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.7114    0.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -2.7087    0.8037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -0.6036    0.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4713   -0.5976   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233   -1.0506   -1.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -1.0878   -2.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.5399   -3.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0423   -0.6575   -2.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1254    0.2513   -0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3052    0.7349   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1690    1.1811    1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2334    1.6516    1.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4997    1.6910    1.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5770    2.1636    2.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6812    1.2674    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9382    1.3020   -0.5000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691    0.7968   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9499    0.2364   -0.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8491   -0.1855   -0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6470   -0.1667   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7175   -1.2108    3.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186   -2.4165    3.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014   -2.8973    2.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0740   -2.5852    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4749   -1.6360    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0559    0.2512   -2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0512    2.5320   -0.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9958    2.5285   -1.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    3.1378   -2.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8877   -0.7591   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3784    0.7879   -1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4958    0.4230    1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5802   -0.8849    2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2655    1.4476    2.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3989   -1.3968   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699   -1.8821   -4.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1316   -0.1990   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1594    2.0017    2.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4834    2.1883    1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0175    0.9751   -1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7289    0.4601   -1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6282    0.1925    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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  6  7  1  0
  7  8  1  0
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  2 15  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
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 22 23  1  0
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 26 35  1  0
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 26 27  1  0
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 29 30  2  0
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 30 32  1  0
 32 33  1  0
 32 34  2  0
 13  4  1  0
 37 18  1  0
 34 27  1  0
 36 22  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  6
  4 42  1  6
  6 43  1  6
  7 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  6
 10 48  1  0
 11 49  1  1
 12 50  1  0
 13 51  1  1
 14 52  1  0
 19 53  1  0
 21 54  1  0
 25 55  1  0
 37 61  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
 33 59  1  0
 34 60  1  0
M  END


  Mrv1533004161521072D          

 37 40  0  0  0  0            999 V2000
   -1.4289   -2.4750    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
   -2.1434   -1.2375    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
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  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
   -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
   -2.8579    0.8250    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
   -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 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
   -0.7145   -0.4125    0.0000 O   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
    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
    1.4289    0.8250    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
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    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -3.7125    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
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 25 26  2  0  0  0  0
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 22 28  1  0  0  0  0
 28 29  2  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(OC1OC(CO)C(O)C(O)C1O)C(=O)OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O13/c1-9(34-24-22(32)21(31)20(30)18(8-25)37-24)23(33)35-11-5-14(28)19-15(29)7-16(36-17(19)6-11)10-2-3-12(26)13(27)4-10/h2-7,9,18,20-22,24-28,30-32H,8H2,1H3

> <INCHI_KEY>
UAMQTTPOILAAME-UHFFFAOYSA-N

> <FORMULA>
C24H24O13

> <MOLECULAR_WEIGHT>
520.443

> <EXACT_MASS>
520.121690833

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.56412675903823

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
0.29463065866666693

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.7106328472979

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.909929554737323

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810837081704493

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
122.65569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.335   1.540   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      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    4   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28   18                                                       
CONECT   30   26   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid	Generator

Chemical Formula

C₂₄H₂₄O₁₃

Average Mass

520.4430 Da

Monoisotopic Mass

520.12169 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

Traditional Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate

CAS Registry Number

Not Available

SMILES

CC(OC1OC(CO)C(O)C(O)C1O)C(=O)OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C24H24O13/c1-9(34-24-22(32)21(31)20(30)18(8-25)37-24)23(33)35-11-5-14(28)19-15(29)7-16(36-17(19)6-11)10-2-3-12(26)13(27)4-10/h2-7,9,18,20-22,24-28,30-32H,8H2,1H3

InChI Key

UAMQTTPOILAAME-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
Marrubium vulgare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Fatty acyl
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Carbonyl group
Primary alcohol
Alcohol
Organic oxide
Hydrocarbon derivative
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	1.01	ALOGPS
logP	0.29	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	122.66 m³·mol⁻¹	ChemAxon
Polarizability	50.56 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

74977663

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate (NP0308283)

MOL for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

3D MOL for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

3D SDF for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

3D-SDF for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

PDB for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

3D PDB for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

SMILES for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

INCHI for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

Structure for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)

3D Structure for NP0308283 (2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl 2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoate)