NP-MRD: Showing NP-Card for 5-Hydroxy-7,8-dimethoxyflavone 5-glucoside (NP0052499)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 23:31:16 UTC

Updated at

2022-04-27 23:31:16 UTC

NP-MRD ID

NP0052499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Hydroxy-7,8-dimethoxyflavone 5-glucoside

Description

Andrographidine C 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. Thus, andrographidine C is considered to be a flavonoid. 5-Hydroxy-7,8-dimethoxyflavone 5-glucoside is found in Andrographis paniculata and Andrographis serpyllifolia. 5-Hydroxy-7,8-dimethoxyflavone 5-glucoside was first documented in 2011 (PMID: 21626787). Based on a literature review a small amount of articles have been published on Andrographidine C (PMID: 35147481) (PMID: 33555214) (PMID: 33425994) (PMID: 30754616).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201312D          

 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 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
    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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  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   -2.4750    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
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  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
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  0  0  0
  1 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -0.5812    4.7850    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329    4.0996    0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    2.7040    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3659    1.9078    0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3143    0.4723    0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149   -0.2006    0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5286   -0.8817    0.6737 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1747   -1.2171   -0.5171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4982   -1.4859   -0.4901 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9514   -1.8279   -1.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341   -0.7949   -2.7867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3474   -0.3963    0.1029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3511   -0.8623    0.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4813    0.5533    0.9224 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8517    1.4782    0.1110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366   -0.3226    1.6759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2575   -1.3932    2.1856 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9381   -0.1018    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -1.4698    0.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576   -2.2409    0.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -2.0129    0.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904   -1.1602    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -1.6734   -0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9734   -3.0176   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2918   -3.4672   -0.2532 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3242   -2.5604   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0816   -1.2105   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7832   -0.7848   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237    0.1364    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438    0.7135    0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413    2.0949    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0691    2.8808    0.0796 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487    3.2351   -1.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4103    5.8534    0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0020    4.7516    1.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711    4.3869   -0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3297    2.3617    0.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285   -1.9330    1.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6614   -2.3924    0.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0734   -1.9446   -1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679   -2.7999   -2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8151   -0.8983   -3.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8006    0.1952   -0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4682   -0.3125    1.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1209    1.0979    1.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5064    1.7696   -0.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0287    0.1857    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7294   -1.9268    2.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3785   -3.0876    0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1873   -3.7438   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4647   -4.5278   -0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -2.8761   -0.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8860   -0.4745   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5744    0.2964   -0.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310    3.3284   -1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0957    2.4976   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    4.2142   -1.5408 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 31  3  1  0
 28 23  1  0
 16  7  1  0
 30 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  7 38  1  1
  9 39  1  1
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  6
 13 44  1  0
 14 45  1  1
 15 46  1  0
 16 47  1  1
 17 48  1  0
 21 49  1  0
 33 55  1  0
 33 56  1  0
 33 57  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
M  END


  Mrv1652304282201312D          

 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 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
    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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  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   -2.4750    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
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  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
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  0  0  0
  1 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C2C(=O)C=C(OC2=C1OC)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O10/c1-29-15-9-14(32-23-20(28)19(27)18(26)16(10-24)33-23)17-12(25)8-13(11-6-4-3-5-7-11)31-22(17)21(15)30-2/h3-9,16,18-20,23-24,26-28H,10H2,1-2H3/t16-,18-,19+,20-,23-/m1/s1

> <INCHI_KEY>
WGCQDTNINMCFAY-PUIBNRJISA-N

> <FORMULA>
C23H24O10

> <MOLECULAR_WEIGHT>
460.435

> <EXACT_MASS>
460.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.070429423011554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,8-dimethoxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.08040915233333235

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19189425401811

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199630935323553

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463096186

> <JCHEM_POLAR_SURFACE_AREA>
144.14000000000001

> <JCHEM_REFRACTIVITY>
114.02289999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8-dimethoxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    3   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
CONECT   32    1   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₄O₁₀

Average Mass

460.4350 Da

Monoisotopic Mass

460.13695 Da

IUPAC Name

7,8-dimethoxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

7,8-dimethoxy-2-phenyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C2C(=O)C=C(OC2=C1OC)C1=CC=CC=C1

InChI Identifier

InChI=1S/C23H24O10/c1-29-15-9-14(32-23-20(28)19(27)18(26)16(10-24)33-23)17-12(25)8-13(11-6-4-3-5-7-11)31-22(17)21(15)30-2/h3-9,16,18-20,23-24,26-28H,10H2,1-2H3/t16-,18-,19+,20-,23-/m1/s1

InChI Key

WGCQDTNINMCFAY-PUIBNRJISA-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
Andrographis paniculata	Plant	KNApSAcK
Andrographis serpyllifolia	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-5-o-glycoside
Flavonoid o-glycoside
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
Flavone
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Anisole
Pyranone
Alkyl aryl ether
Pyran
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Vinylogous ester
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Polyol
Acetal
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
Organooxygen compound
Primary 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	0.87	ALOGPS
logP	0.08	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	144.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.02 m³·mol⁻¹	ChemAxon
Polarizability	46.07 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	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

10306100

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tarachand SP, Thirumoorthy G, Lakshmaiah VV, Nagella P: In silico molecular docking study of Andrographis paniculata phytochemicals against TNF-alpha as a potent anti-rheumatoid drug. J Biomol Struct Dyn. 2022 Feb 11:1-11. doi: 10.1080/07391102.2022.2037463. [PubMed:35147481 ]
Singh R, Dhiman M, Saklani A, Immanuel Selvaraj C, Kate AS: Isolation and characterization of a novel flavanone glycoside from an endemic plant Haplanthodes neilgherryensis. J Asian Nat Prod Res. 2022 Jan;24(1):96-101. doi: 10.1080/10286020.2021.1880394. Epub 2021 Feb 8. [PubMed:33555214 ]
Vincent S, Arokiyaraj S, Saravanan M, Dhanraj M: Molecular Docking Studies on the Anti-viral Effects of Compounds From Kabasura Kudineer on SARS-CoV-2 3CL(pro). Front Mol Biosci. 2020 Dec 23;7:613401. doi: 10.3389/fmolb.2020.613401. eCollection 2020. [PubMed:33425994 ]
Sun X, Yan H, Zhang Y, Wang X, Qin D, Yu J: Preparative Separation of Diterpene Lactones and Flavones from Andrographis paniculate Using Off-Line Two-Dimensional High-Speed Counter-Current Chromatography. Molecules. 2019 Feb 11;24(3). pii: molecules24030620. doi: 10.3390/molecules24030620. [PubMed:30754616 ]
Xu C, Wang ZT: [Chemical constituents from roots of Andrographis paniculata]. Yao Xue Xue Bao. 2011 Mar;46(3):317-21. [PubMed:21626787 ]

Showing NP-Card for 5-Hydroxy-7,8-dimethoxyflavone 5-glucoside (NP0052499)

MOL for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

3D MOL for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

3D SDF for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

3D-SDF for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

PDB for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

3D PDB for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

SMILES for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

INCHI for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

Structure for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)

3D Structure for NP0052499 (5-Hydroxy-7,8-dimethoxyflavone 5-glucoside)