NP-MRD: Showing NP-Card for methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate (NP0203148)

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Record Information

Version

2.0

Created at

2022-09-04 22:32:13 UTC

Updated at

2022-09-04 22:32:13 UTC

NP-MRD ID

NP0203148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

Description

Methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate is found in Periploca sepium, Pimenta dioica, Potentilla anserina, Tamarix nilotica and Theobroma grandiflorum. Methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241507022D          

 35 38  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    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 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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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 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
    0.0000    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
   -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 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
   -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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    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
  3  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 22 29  1  0  0  0  0
  7 30  1  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  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    3.6326    1.0613   -3.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428    0.2442   -2.6106 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7411   -0.5438   -3.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672   -0.5654   -4.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7398   -1.3750   -2.5486 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6742   -0.9527   -1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -1.7128   -0.4538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3377   -0.9142   -0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    0.4168    0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    0.8665    1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    0.0221    2.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117    0.6435    3.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3973   -0.0467    5.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7174   -1.3845    5.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -2.0398    6.3664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1558   -2.0289    3.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -3.3555    4.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656   -1.3008    2.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9504    2.2009    1.7038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281    3.0668    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    4.4308    1.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9932    5.3624    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8810    6.7116    0.3721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1819    4.9314   -1.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    3.6043   -1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    3.1241   -2.8652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2095    2.6754   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    1.3291   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4748    0.9376   -1.9839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5533   -3.0128   -1.0869 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2786   -3.8784   -0.2747 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -3.6664   -1.5308 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6478   -3.5312   -0.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988   -2.7984   -2.6337 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7162   -2.7989   -2.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899    1.6615   -4.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1930    1.6548   -2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945    0.3997   -3.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.3297   -3.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762   -1.8551    0.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608    1.6660    3.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440    0.4994    5.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376   -1.5086    7.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994   -3.9365    3.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.8229    1.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746    4.7048    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    7.1811    0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2417    5.6928   -2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5758    3.7437   -3.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010   -2.8236   -2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -4.3965   -0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520   -4.7058   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756   -4.4069    0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0175   -3.2035   -3.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974   -2.9372   -1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  7 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34  5  1  0
 28  9  1  0
 18 11  1  0
 27 20  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  6
  7 40  1  1
 21 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 30 50  1  6
 31 51  1  0
 32 52  1  6
 33 53  1  0
 34 54  1  6
 35 55  1  0
M  END


  Mrv1533004241507022D          

 35 38  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    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 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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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 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
    0.0000    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
   -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 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
   -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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    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
  3  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 22 29  1  0  0  0  0
  7 30  1  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  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O13/c1-32-21(31)20-16(29)15(28)17(30)22(35-20)34-19-14(27)13-11(26)5-8(23)6-12(13)33-18(19)7-2-3-9(24)10(25)4-7/h2-6,15-17,20,22-26,28-30H,1H3

> <INCHI_KEY>
DAKHAONGVOPWRO-UHFFFAOYSA-N

> <FORMULA>
C22H20O13

> <MOLECULAR_WEIGHT>
492.389

> <EXACT_MASS>
492.090390704

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.47435714310927

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
0.32133329800000027

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.872517957421475

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372404057017655

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868341799172812

> <JCHEM_POLAR_SURFACE_AREA>
212.66999999999996

> <JCHEM_REFRACTIVITY>
113.91199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+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  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19    9   21                                                  
CONECT   21   20                                                            
CONECT   22   10   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22                                                       
CONECT   30    7   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    5   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₀O₁₃

Average Mass

492.3890 Da

Monoisotopic Mass

492.09039 Da

IUPAC Name

methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

Traditional Name

methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H20O13/c1-32-21(31)20-16(29)15(28)17(30)22(35-20)34-19-14(27)13-11(26)5-8(23)6-12(13)33-18(19)7-2-3-9(24)10(25)4-7/h2-6,15-17,20,22-26,28-30H,1H3

InChI Key

DAKHAONGVOPWRO-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
Periploca sepium	LOTUS Database	35616633
Pimenta dioica	LOTUS Database	35616633
Potentilla anserina	LOTUS Database	35616633
Tamarix nilotica	LOTUS Database	35616633
Theobroma grandiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Carboxylic acid ester
Ketimine
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Imine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
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	1.48	ALOGPS
logP	0.32	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.7	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	5	ChemAxon
Refractivity	113.91 m³·mol⁻¹	ChemAxon
Polarizability	45.47 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	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

73829983

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate (NP0203148)

MOL for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D MOL for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D SDF for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D-SDF for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

PDB for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D PDB for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

SMILES for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

INCHI for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

Structure for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)

3D Structure for NP0203148 (methyl 6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate)