NP-MRD: Showing NP-Card for 8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one (NP0054063)

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Record Information

Version

2.0

Created at

2022-04-28 00:32:15 UTC

Updated at

2022-04-28 00:32:15 UTC

NP-MRD ID

NP0054063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one

Description

8-C-beta-d-glucopyranosyldiosmetin 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. Thus, 8-c-beta-D-glucopyranosyldiosmetin is considered to be a flavonoid. 8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one is found in Citrus spp., Lupinus spp. and Passiflora coactilis. Based on a literature review very few articles have been published on 8-c-beta-d-glucopyranosyldiosmetin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202322D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    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 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
    0.0000    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
   -1.4289    0.8250    0.0000 O   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
    2.1434   -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
    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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  7  6  1  1  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  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
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 31  1  0  0  0  0
  3 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    7.0310   -2.9975    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6781   -3.1279    0.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8580   -2.0121    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2501   -0.7335    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3318    0.3118    0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068    0.1147    0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293    1.2279    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    2.5005    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5822    3.5520    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    4.7363    0.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2661    3.2736   -0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160    4.3190   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3473    5.6392    0.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348    3.9962   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    2.7225   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273    2.3925   -0.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    1.6082   -0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9633    0.2796   -0.8395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3467    0.3214   -0.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315   -0.8968   -0.9696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4206   -0.7133   -0.9855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9747   -0.3097    0.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5793   -1.9635    0.0457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5824   -3.1851   -0.6105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2352   -1.6981    0.6615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3186   -1.0464    1.8692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026   -0.8979   -0.2720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8824   -1.8237   -1.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    1.9414   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776    0.9849   -0.2000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.1673   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -2.2156   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0126   -3.4831   -0.3502 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5956   -3.8496    0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4619   -2.0892    0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1759   -2.9781    1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.5384    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    1.2988    0.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4906    2.7558    0.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4212    6.1634    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956    4.7737   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876    3.1461   -0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8429    0.1601   -1.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5884   -1.1346   -1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9414   -1.6304   -1.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7233    0.0711   -1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5847    0.4679    0.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3226   -2.0250    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268   -3.6773   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408   -2.6711    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -0.8510    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4453   -0.6670    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0625   -2.7383   -0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874   -1.3612   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6293   -4.2756   -0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 32  2  0
 32 33  1  0
 32 31  1  0
 31  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
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  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
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 17 18  1  0
 18 19  1  0
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 21 22  1  0
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 23 25  1  0
 25 26  1  0
 25 27  1  0
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 17 29  2  0
 29 30  1  0
  4  3  1  0
 30  7  1  0
 29 11  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 33 55  1  0
 31 54  1  0
  5 38  1  0
  4 37  1  0
  8 39  1  0
 13 40  1  0
 14 41  1  0
 16 42  1  0
 18 43  1  6
 20 44  1  6
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  1
 24 49  1  0
 25 50  1  1
 26 51  1  0
 27 52  1  1
 28 53  1  0
M  END


  Mrv1652304282202322D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    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 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
    0.0000    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
   -1.4289    0.8250    0.0000 O   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
    2.1434   -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
    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 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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  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
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 31  1  0  0  0  0
  3 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054063

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-31-13-3-2-8(4-9(13)24)14-6-12(27)16-10(25)5-11(26)17(21(16)32-14)22-20(30)19(29)18(28)15(7-23)33-22/h2-6,15,18-20,22-26,28-30H,7H2,1H3/t15-,18-,19+,20-,22+/m1/s1

> <INCHI_KEY>
NSUGQZFWSLTJRI-PGPONNFDSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.643998258991715

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-0.20830303699999952

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.0759639032211

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.17376023418302

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791926292654134

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
112.49539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

> <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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   33                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    8                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26   30                                                       
CONECT   30   29                                                            
CONECT   31   25                                                            
CONECT   32    3                                                            
CONECT   33    1                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
8-c-b-D-Glucopyranosyldiosmetin	Generator
8-c-Β-D-glucopyranosyldiosmetin	Generator

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H22O11/c1-31-13-3-2-8(4-9(13)24)14-6-12(27)16-10(25)5-11(26)17(21(16)32-14)22-20(30)19(29)18(28)15(7-23)33-22/h2-6,15,18-20,22-26,28-30H,7H2,1H3/t15-,18-,19+,20-,22+/m1/s1

InChI Key

NSUGQZFWSLTJRI-PGPONNFDSA-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
Citrus spp.	Plant	KNApSAcK
Lupinus spp.	Plant	KNApSAcK
Passiflora coactilis	Plant	KNApSAcK

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
3'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Pyranone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Polyol
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
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	0.5	ALOGPS
logP	-0.21	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.5 m³·mol⁻¹	ChemAxon
Polarizability	44.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

C00006121

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

101387091

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one (NP0054063)

MOL for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D MOL for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D SDF for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D-SDF for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

PDB for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D PDB for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

SMILES for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

INCHI for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

Structure for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D Structure for NP0054063 (8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one)