NP-MRD: Showing NP-Card for 5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one (NP0303781)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-10 18:25:23 UTC

Updated at

2022-09-10 18:25:23 UTC

NP-MRD ID

NP0303781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

5-Hydroxy-2-(3-hydroxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxy-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one is found in Sium suave. It was first documented in 2022 (PMID: 36116068). Based on a literature review a significant number of articles have been published on 5-hydroxy-2-(3-hydroxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxy-4H-chromen-4-one (PMID: 36116067) (PMID: 36116066) (PMID: 36116065) (PMID: 36116064) (PMID: 36116063) (PMID: 36116062).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220252D          

 35 38  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
    0.0000    0.0000    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
    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 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
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    0.0000   -2.4750    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  8 26  1  0  0  0  0
  7 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  3 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    5.4941   -1.6656   -5.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3619   -0.8167   -4.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8444   -0.1633   -3.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360   -0.3603   -2.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0058    0.2595   -1.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607    0.0582   -1.3478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1714    0.6191   -0.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    0.2919   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596    0.8152    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.4993    1.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9596   -0.3665    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2804   -0.7429    0.5195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1936   -0.3554    1.4816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2789    0.3518    0.9590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0136    0.8020    2.0594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8395    2.0187    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7400    1.7324    0.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8250   -0.3567    2.5343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6768   -0.0014    3.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9230   -1.4620    2.9609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6152   -2.6779    2.7476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6235   -1.5680    2.2555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6273   -1.7950    3.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252   -0.8957   -0.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9063   -1.7799   -1.5329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -0.5800   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9189    1.4571    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2523    1.7035    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8916    2.4838    0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8315    1.1111   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1454    1.3136   -1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9691    2.1346   -0.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6741    0.6686   -2.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0037    0.8710   -2.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0525    0.0539   -2.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0319   -1.9143   -5.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2831   -2.6054   -4.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5580   -1.1596   -5.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8728   -1.0199   -3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422    1.4978    1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176    0.9325    2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7151    0.3339    2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3032    1.0880    2.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1375    2.8241    1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4020    2.3074    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5694    1.3858    1.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4592   -0.6926    1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1398    0.5160    4.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003   -1.4179    4.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2348   -3.3681    3.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5574   -2.4540    1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6664   -0.9814    3.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3866   -2.1705   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6472   -0.9996   -1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    1.9423    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9216    2.6934    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1456   -0.8468   -2.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0096    0.6239   -2.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8756   -0.1727   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 33  2  0
 33 34  1  0
 34 35  1  0
 33 31  1  0
 31 32  1  0
 31 30  2  0
 30 28  1  0
 28 29  2  0
 28 27  1  0
 27  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24 25  1  0
 24 26  2  0
  4  3  1  0
 26  8  1  0
  5 30  1  0
 22 13  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 35 57  1  0
 35 58  1  0
 35 59  1  0
 32 56  1  0
 27 55  1  0
  4 39  1  0
  9 40  1  0
 10 41  1  0
 13 42  1  1
 15 43  1  1
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  6
 19 48  1  0
 20 49  1  1
 21 50  1  0
 22 51  1  6
 23 52  1  0
 25 53  1  0
 26 54  1  0
M  END


  Mrv1652309102220252D          

 35 38  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
    0.0000    0.0000    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
    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 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
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    0.0000   -2.4750    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  8 26  1  0  0  0  0
  7 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  3 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O12/c1-31-15-7-14-17(19(28)22(15)32-2)11(26)6-13(33-14)9-3-4-12(10(25)5-9)34-23-21(30)20(29)18(27)16(8-24)35-23/h3-7,16,18,20-21,23-25,27-30H,8H2,1-2H3/t16-,18-,20+,21-,23-/m0/s1

> <INCHI_KEY>
GLTCTFBPNQJRQT-UTMPCQRGSA-N

> <FORMULA>
C23H24O12

> <MOLECULAR_WEIGHT>
492.433

> <EXACT_MASS>
492.126776213

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
48.41425461670321

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.1232785089999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.409620082522073

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.92206471918321

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549038426

> <JCHEM_POLAR_SURFACE_AREA>
184.6

> <JCHEM_REFRACTIVITY>
117.98469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.338   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24   11   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    8                                                       
CONECT   27    7   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    5   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₄O₁₂

Average Mass

492.4330 Da

Monoisotopic Mass

492.12678 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)C(O)=C1

InChI Identifier

InChI=1S/C23H24O12/c1-31-15-7-14-17(19(28)22(15)32-2)11(26)6-13(33-14)9-3-4-12(10(25)5-9)34-23-21(30)20(29)18(27)16(8-24)35-23/h3-7,16,18,20-21,23-25,27-30H,8H2,1-2H3/t16-,18-,20+,21-,23-/m0/s1

InChI Key

GLTCTFBPNQJRQT-UTMPCQRGSA-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
Sium suave	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-4p-o-glycoside
Flavonoid o-glycoside
6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Phenol ether
Anisole
Phenoxy compound
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Oxane
Pyran
Monosaccharide
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
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	0.12	ChemAxon
pKa (Strongest Acidic)	7.92	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.98 m³·mol⁻¹	ChemAxon
Polarizability	48.41 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	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

11972311

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Anraku T: Anoxia/reoxygenation enhances spontaneous contractile activity via TRPA1 channel and COX2 activation in isolated rat whole bladder. Neurourol Urodyn. 2022 Sep 18. doi: 10.1002/nau.25045. [PubMed:36116068 ]
DeLong JP, Cressler CE: Stochasticity directs adaptive evolution toward nonequilibrium evolutionary attractors. Ecology. 2022 Sep 18:e3873. doi: 10.1002/ecy.3873. [PubMed:36116067 ]
Liu H, Shu F, Xu H, Ji C, Wang Y, Lou X, Luo P, Xiao S, Xia Z, Lv K: Ablative fractional carbon dioxide laser improves quality of life in patients with extensive burn scars: A nested case-control study. Lasers Surg Med. 2022 Sep 18. doi: 10.1002/lsm.23603. [PubMed:36116066 ]
Forcillo J, Robert-Halabi M, Soulez G, Potvin J: Transcatheter occlusion of a left ventricular outflow tract pseudoaneurysm using a "plug and coil" strategy. J Card Surg. 2022 Sep 18. doi: 10.1111/jocs.16963. [PubMed:36116065 ]
Onur R, Bayrak O, Coskun B, Tahra A, Ocakoglu G, Buyuran G, Mega E, Gungor Ugurlucan F, Ozturk GB: Clinical preferences and treatment attitudes among urologists, gynecologists, and geriatricians: An independent online questionnaire survey for comparison of treatment choices in the management of overactive bladder. Neurourol Urodyn. 2022 Sep 18. doi: 10.1002/nau.25050. [PubMed:36116064 ]
Enemchukwu E, Cameron A: Management of complex OAB patients: A call to action. Neurourol Urodyn. 2022 Nov;41(8):1938-1939. doi: 10.1002/nau.25048. Epub 2022 Sep 18. [PubMed:36116063 ]
Binder MS, Wu Y, Baker JW, Rowe JF, Wyatt DA, Choate C, Poelzing S, Joseph M: A retrospective comparison of albumin versus mannitol priming fluid with relation to postoperative atrial fibrillation. J Card Surg. 2022 Nov;37(11):3485-3491. doi: 10.1111/jocs.16960. Epub 2022 Sep 18. [PubMed:36116062 ]
Hirani R, Ohira S, Spielvogel D, De La Pena C, Kai M: Insertion of durable left ventricular assist device with repair of ischemic ventricular septal rupture. J Card Surg. 2022 Nov;37(11):3896-3898. doi: 10.1111/jocs.16952. Epub 2022 Sep 18. [PubMed:36116061 ]
Perrig PL, Lambertucci SA, Donadio E, Smith JA, Middleton AD, Pauli JN: Risk effects cascade up to an obligate scavenger. Ecology. 2022 Sep 18:e3871. doi: 10.1002/ecy.3871. [PubMed:36116060 ]
Llerena-Velastegui J, Vaca-Perez P, Vasavada A: Surgical treatment of primary cardiac tumors in the contemporary era: A single-center analysis. J Card Surg. 2022 Nov;37(11):4003. doi: 10.1111/jocs.16961. Epub 2022 Sep 18. [PubMed:36116059 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one (NP0303781)

MOL for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

3D MOL for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

3D SDF for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

3D-SDF for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

PDB for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

3D PDB for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

SMILES for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

INCHI for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

Structure for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)

3D Structure for NP0303781 (5-hydroxy-2-(3-hydroxy-4-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-6,7-dimethoxychromen-4-one)