NP-MRD: Showing NP-Card for 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0187675)

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Record Information

Version

2.0

Created at

2022-09-04 03:53:33 UTC

Updated at

2022-09-04 03:53:33 UTC

NP-MRD ID

NP0187675

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

Acacetin-7-O-beta-D-galactopyranoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Thus, acacetin-7-O-beta-D-galactopyranoside is considered to be a flavonoid. Acacetin-7-O-beta-D-galactopyranoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Chrysanthemum indicum and Chrysanthemum morifolium. 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one was first documented in 1994 (PMID: 8158164). Based on a literature review a small amount of articles have been published on acacetin-7-O-beta-D-galactopyranoside (PMID: 22226544) (PMID: 9781305).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205532D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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  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
   -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 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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  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
    3.5724   -2.8875    0.0000 C   0  0  1  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   -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
    1.4289   -1.6500    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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    8.5495    3.2865    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5561    1.8665    0.0551 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3428    1.1574    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3121   -0.2144    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0919   -0.9123    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001   -0.2476    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113   -0.9551    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817   -2.3212    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -2.9767    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334   -4.2047    0.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1269   -2.1994    0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298   -2.7584    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2370   -4.1341    0.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2288   -1.9196    0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1472   -0.5481    0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086    0.3271    0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -0.0372    0.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1961    0.3594   -0.9931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184   -0.0633   -0.8711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1421   -0.2599   -2.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0990    0.9683   -2.9163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2506    0.9895   -0.0750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4137    2.0972   -0.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3969    1.4126    1.0725 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9203    2.7281    0.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    0.4897    1.4057 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6984   -0.5254    2.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582   -0.0408    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2899   -0.8295    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911   -0.2731    0.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9458    1.1375    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1394    1.8272    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1814    3.7381    0.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8840    3.5916   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5396    3.7010   -0.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2392   -0.7707    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1170   -1.9942    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3854   -2.9227    0.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -4.6291    0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2106   -2.3986    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6710   -1.1309    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864   -1.0357   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1764   -0.6218   -2.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864   -1.0415   -2.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9310    1.0013   -3.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2414    0.5936    0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5047    2.4567   -1.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0689    1.4610    1.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152    2.7832    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5210    1.0842    1.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0348   -1.2432    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697    1.0318    0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9963    1.6744    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1656    2.9127    0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 31  1  0
 31 32  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 28  1  0
 28 29  2  0
 29 30  1  0
 32  3  1  0
 30  7  1  0
 29 11  1  0
 26 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
 31 53  1  0
 32 54  1  0
  8 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  1
 19 42  1  1
 20 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 24 48  1  1
 25 49  1  0
 26 50  1  1
 27 51  1  0
 28 52  1  0
M  END


  Mrv1652309042205532D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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  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
   -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 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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  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
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.8579   -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
    1.4289   -1.6500    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   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 15 28  1  0  0  0  0
 28 29  2  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187675

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)15-8-14(25)18-13(24)6-12(7-16(18)31-15)30-22-21(28)20(27)19(26)17(9-23)32-22/h2-8,17,19-24,26-28H,9H2,1H3/t17-,19+,20+,21-,22-/m1/s1

> <INCHI_KEY>
NLZCOTZRUWYPTP-WHCFWRGISA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.077851687254935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.5845150963333339

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200113032927037

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3142197967002165

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758667

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
109.54060000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-(4-methoxyphenyl)-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   29                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   15   29                                                       
CONECT   29   28   11   30                                                  
CONECT   30   29    7                                                       
CONECT   31    6   32                                                       
CONECT   32   31    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-4'-methoxyflavone-7-O-beta-D-galactopyranoside	ChEBI
7-(beta-D-Galactopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
5,7-Dihydroxy-4'-methoxyflavone-7-O-b-D-galactopyranoside	Generator
5,7-Dihydroxy-4'-methoxyflavone-7-O-β-D-galactopyranoside	Generator
7-(b-D-Galactopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	Generator
7-(Β-D-galactopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	Generator
Acacetin-7-O-b-D-galactopyranoside	Generator
Acacetin-7-O-β-D-galactopyranoside	Generator

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

5-hydroxy-2-(4-methoxyphenyl)-7-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)15-8-14(25)18-13(24)6-12(7-16(18)31-15)30-22-21(28)20(27)19(26)17(9-23)32-22/h2-8,17,19-24,26-28H,9H2,1H3/t17-,19+,20+,21-,22-/m1/s1

InChI Key

NLZCOTZRUWYPTP-WHCFWRGISA-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
Chrysanthemum indicum	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Monosaccharide
Oxane
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Organic oxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-galactoside (CHEBI:65361 )
monomethoxyflavone (CHEBI:65361 )
glycosyloxyflavone (CHEBI:65361 )
monohydroxyflavone (CHEBI:65361 )

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	0.58	ChemAxon
pKa (Strongest Acidic)	7.31	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.54 m³·mol⁻¹	ChemAxon
Polarizability	44.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

4586973

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5480899

PDB ID

Not Available

ChEBI ID

65361

Good Scents ID

Not Available

References

General References

Zacharia JT, Hayashi M: Facile synthesis of acacetin-7-O-beta-D-galactopyranoside. Carbohydr Res. 2012 Feb 1;348:91-4. doi: 10.1016/j.carres.2011.11.015. Epub 2011 Dec 8. [PubMed:22226544 ]
Hu CQ, Chen K, Shi Q, Kilkuskie RE, Cheng YC, Lee KH: Anti-AIDS agents, 10. Acacetin-7-O-beta-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids. J Nat Prod. 1994 Jan;57(1):42-51. doi: 10.1021/np50103a006. [PubMed:8158164 ]
Wang HK, Xia Y, Yang ZY, Natschke SL, Lee KH: Recent advances in the discovery and development of flavonoids and their analogues as antitumor and anti-HIV agents. Adv Exp Med Biol. 1998;439:191-225. doi: 10.1007/978-1-4615-5335-9_15. [PubMed:9781305 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0187675)

MOL for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0187675 (5-hydroxy-2-(4-methoxyphenyl)-7-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)