NP-MRD: Showing NP-Card for methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate (NP0239316)

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Record Information

Version

1.0

Created at

2022-09-06 22:53:20 UTC

Updated at

2022-09-06 22:53:20 UTC

NP-MRD ID

NP0239316

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate

Description

Methyl (2S,3S,4R,5R,6S)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate is found in Helicteres isora. Based on a literature review very few articles have been published on methyl (2S,3S,4R,5R,6S)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072200532D          

 35 38  0  0  1  0            999 V2000
   -0.7145   -5.3625    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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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  1  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
    1.4289   -2.4750    0.0000 C   0  0  1  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
    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   -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
    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
    7.1447   -2.4750    0.0000 C   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
    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
    2.1434   -2.8875    0.0000 C   0  0  2  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   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 19 27  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  2  0  0  0  0
 14 29  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.1578    0.2047   -2.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0799   -0.1415   -1.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9017   -1.4567   -0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343   -2.2956   -1.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -1.8671    0.0663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0387   -0.8061    0.3980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673   -0.0662    1.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4472    1.3375    1.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5069    2.1458    1.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5950    1.6479    2.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634    3.4645    0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856    4.0204    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5484    5.3131   -0.1459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3998    3.2244   -0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6978    3.6775   -0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702    4.8507   -1.1343 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7350    2.7674   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7118    1.4702   -0.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8099    0.5232   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396    0.8866   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685   -0.0479   -1.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8650   -1.3363   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8831   -2.2799   -1.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0599   -1.9676   -2.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7232   -1.7012   -0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6482   -3.0098    0.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7249   -0.7836   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281    1.0906    0.1561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3740    1.8950    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838   -0.5991    2.3177 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4561   -0.0648    3.6150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -2.0934    2.5406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0692   -2.6392    3.4275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072   -2.7191    1.1769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7196   -3.9829    1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0201   -0.4386   -1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8761    0.0217   -3.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4323    1.2578   -2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1507   -2.5517   -0.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4507   -0.1716    2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4119    2.1939    2.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    4.1011    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147    5.9542   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    3.1558   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715    1.8728   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8485    0.2478   -2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5188   -2.9069   -2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8138   -1.5021   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -1.3223   -2.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8022   -3.2674    0.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8296   -1.0468    0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.6224    1.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7808   -0.5493    4.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -2.2214    2.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7029   -3.4847    3.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -2.8850    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1410   -4.4967    0.4688 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 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  7  8  1  0
  8 29  2  0
 29 28  1  0
 28 18  1  0
 18 17  2  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  2  0
 34  5  1  0
  9  8  1  0
 27 19  1  0
 14 29  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  6
  7 40  1  1
 30 52  1  6
 31 53  1  0
 32 54  1  1
 33 55  1  0
 34 56  1  6
 35 57  1  0
 17 44  1  0
 13 43  1  0
 11 42  1  0
 10 41  1  0
 20 45  1  0
 21 46  1  0
 24 47  1  0
 24 48  1  0
 24 49  1  0
 26 50  1  0
 27 51  1  0
M  END


  Mrv1652309072200532D          

 35 38  0  0  1  0            999 V2000
   -0.7145   -5.3625    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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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  1  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
    1.4289   -2.4750    0.0000 C   0  0  1  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
    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   -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
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    3.5724   -1.2375    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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    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
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    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
    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
    2.1434   -2.8875    0.0000 C   0  0  2  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   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  2  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
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 21 22  2  0  0  0  0
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  8 29  2  0  0  0  0
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  7 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0239316

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(OC)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O12/c1-32-13-4-3-8(5-9(13)24)14-7-12(27)15-10(25)6-11(26)16(20(15)34-14)21-18(29)17(28)19(30)22(35-21)23(31)33-2/h3-7,17-19,21-22,24-26,28-30H,1-2H3/t17-,18-,19+,21+,22+/m1/s1

> <INCHI_KEY>
WHWSCJLBWILGIF-DGYCAGFBSA-N

> <FORMULA>
C23H22O12

> <MOLECULAR_WEIGHT>
490.417

> <EXACT_MASS>
490.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.745238628685

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3S,4R,5R,6S)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate

> <JCHEM_LOGP>
0.25786555700000025

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.07593882769363

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1735915387463525

> <JCHEM_PKA_STRONGEST_BASIC>
-3.657012179512093

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
117.13190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3S,4R,5R,6S)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -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   29                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   29                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   19                                                       
CONECT   28   18   29                                                       
CONECT   29   28    8   14                                                  
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 (2S,3S,4R,5R,6S)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₂O₁₂

Average Mass

490.4170 Da

Monoisotopic Mass

490.11113 Da

IUPAC Name

methyl (2S,3S,4R,5R,6S)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate

Traditional Name

methyl (2S,3S,4R,5R,6S)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(OC)C(O)=C1

InChI Identifier

InChI=1S/C23H22O12/c1-32-13-4-3-8(5-9(13)24)14-7-12(27)15-10(25)6-11(26)16(20(15)34-14)21-18(29)17(28)19(30)22(35-21)23(31)33-2/h3-7,17-19,21-22,24-26,28-30H,1-2H3/t17-,18-,19+,21+,22+/m1/s1

InChI Key

WHWSCJLBWILGIF-DGYCAGFBSA-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
Helicteres isora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
3'-hydroxyflavonoid
Phenolic glycoside
C-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Methoxyphenol
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Hydroxy acid
Heteroaromatic compound
Vinylogous acid
Methyl ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Polyol
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	0.26	ChemAxon
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.13 m³·mol⁻¹	ChemAxon
Polarizability	46.75 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

162933403

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate (NP0239316)

MOL for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

3D MOL for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

3D SDF for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

3D-SDF for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

PDB for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

3D PDB for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

SMILES for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

INCHI for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

Structure for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)

3D Structure for NP0239316 (methyl (2s,3s,4r,5r,6s)-6-[5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-8-yl]-3,4,5-trihydroxyoxane-2-carboxylate)