NP-MRD: Showing NP-Card for 3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one (NP0060233)

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Record Information

Version

2.0

Created at

2022-04-28 05:19:28 UTC

Updated at

2022-04-28 05:19:29 UTC

NP-MRD ID

NP0060233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one

Description

(2S,3R,4R,5S,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one is found in Ammi majus . Based on a literature review very few articles have been published on (2S,3R,4R,5S,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207192D          

 58 63  0  0  1  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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  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
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    3.3000    0.0000 O   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
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    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
   -7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   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
    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
    2.1434   -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
    2.8579   -1.6500    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 29 34  1  6  0  0  0
 28 35  1  1  0  0  0
 27 36  1  6  0  0  0
 21 37  1  6  0  0  0
 20 38  1  1  0  0  0
 19 39  1  6  0  0  0
 40 39  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 40 45  1  0  0  0  0
 44 46  1  6  0  0  0
 43 47  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 42 51  1  1  0  0  0
 41 52  1  1  0  0  0
 13 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 12 56  2  0  0  0  0
 55 57  1  0  0  0  0
 53 58  1  0  0  0  0
M  END

     RDKit          3D

102107  0  0  0  0  0  0  0  0999 V2000
   -1.8489    6.8296    3.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0943    5.6850    4.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8768    4.2800    2.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8878    3.0313    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6364    2.9425    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    4.0933   -0.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562    4.2142   -1.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4978    5.4474   -2.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2866    5.6182   -3.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414    6.9005   -4.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0194    4.5105   -4.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9663    3.2293   -3.9396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6969    2.1858   -4.7627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874    3.1068   -2.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1498    1.9018   -1.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    0.8621   -2.5755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3784    1.8150   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072    0.5514    0.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1398   -0.0584    0.4838 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.1342   -0.7642   -0.8982 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7584   -1.9637   -1.8809 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0209   -1.8010   -2.4885 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6409   -3.1141   -2.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4527   -2.2502    1.6521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5065   -1.3499    1.3378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6202   -1.9613    0.8450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5237   -1.9090   -0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7332   -3.4155    1.2485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1102   -3.7343    1.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.1655   -4.8815    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3804    2.1396    3.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5975    3.5361    5.7541 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4876    7.6922    4.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0342    6.6681    2.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817    5.1297    1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7135    6.3136   -1.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1826    7.0264   -5.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8499    4.6206   -5.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4906    0.6923    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582    0.2591    0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6935    0.2942   -1.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001   -1.5318   -1.9590 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5705   -2.9430   -3.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3500   -2.8514    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5613   -1.4411    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5256   -1.9191   -1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8850   -1.0824   -1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282207192D          

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 55 57  1  0  0  0  0
 53 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@H](O)[C@@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C36H44O22/c1-11-30(53-12(2)38)27(47)29(49)35(52-11)58-33-26(46)23(43)20(10-51-34-28(48)25(45)22(42)19(9-37)55-34)56-36(33)57-32-24(44)21-16(41)7-14(39)8-18(21)54-31(32)13-4-5-15(40)17(6-13)50-3/h4-8,11,19-20,22-23,25-30,33-37,39-43,45-49H,9-10H2,1-3H3/t11-,19+,20+,22+,23+,25-,26-,27+,28+,29-,30-,33+,34+,35-,36-/m0/s1

> <INCHI_KEY>
VJEVXTUVNQQJJL-BMBQPZFGSA-N

> <FORMULA>
C36H44O22

> <MOLECULAR_WEIGHT>
828.726

> <EXACT_MASS>
828.232423057

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
79.26976859748603

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-2.0525771543333327

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.9340657594914665

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.374287436273095

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678613072130494

> <JCHEM_POLAR_SURFACE_AREA>
339.74

> <JCHEM_REFRACTIVITY>
186.1922

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         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  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0     -12.003   2.310   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9                                                       
CONECT    9    8                                                            
CONECT   10    2   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   56                                                  
CONECT   13   12   14   53                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   39                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22   37                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29                                                            
CONECT   35   28                                                            
CONECT   36   27                                                            
CONECT   37   21                                                            
CONECT   38   20                                                            
CONECT   39   19   40                                                       
CONECT   40   39   41   45                                                  
CONECT   41   40   42   52                                                  
CONECT   42   41   43   51                                                  
CONECT   43   42   44   47                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44   40                                                       
CONECT   46   44                                                            
CONECT   47   43   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   42                                                            
CONECT   52   41                                                            
CONECT   53   13   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55   12                                                       
CONECT   57   55                                                            
CONECT   58   53                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R,5S,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetic acid	Generator

Chemical Formula

C₃₆H₄₄O₂₂

Average Mass

828.7260 Da

Monoisotopic Mass

828.23242 Da

IUPAC Name

Traditional Name

(2S,3R,4R,5S,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@H](O)[C@@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C36H44O22/c1-11-30(53-12(2)38)27(47)29(49)35(52-11)58-33-26(46)23(43)20(10-51-34-28(48)25(45)22(42)19(9-37)55-34)56-36(33)57-32-24(44)21-16(41)7-14(39)8-18(21)54-31(32)13-4-5-15(40)17(6-13)50-3/h4-8,11,19-20,22-23,25-30,33-37,39-43,45-49H,9-10H2,1-3H3/t11-,19+,20+,22+,23+,25-,26-,27+,28+,29-,30-,33+,34+,35-,36-/m0/s1

InChI Key

VJEVXTUVNQQJJL-BMBQPZFGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ammi majus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Oligosaccharide
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Methoxyphenol
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.11	ALOGPS
logP	-2.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	339.74 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	186.19 m³·mol⁻¹	ChemAxon
Polarizability	79.27 Å³	ChemAxon
Number of Rings	6	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

162891880

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one (NP0060233)

MOL for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D MOL for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D SDF for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D-SDF for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

PDB for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D PDB for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

SMILES for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

INCHI for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

Structure for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)

3D Structure for NP0060233 (3-[(O-4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-[beta-D-glucopyranosyl-(1->6)]-beta-D-glucopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one)