NP-MRD: Showing NP-Card for Scutellarein 7-glucoside (NP0052563)

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Record Information

Version

2.0

Created at

2022-04-27 23:33:44 UTC

Updated at

2022-04-27 23:33:44 UTC

NP-MRD ID

NP0052563

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Scutellarein 7-glucoside

Description

Plantaginin 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, plantaginin is considered to be a flavonoid. Plantaginin 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. Scutellarein 7-glucoside is found in Anaphalis sinica, Betonica officinalis , Buddleja madagascariensis, Crocus chrysanthus, Crocus sativus , Halophila johnsonii, Helichrysum arenarium, Juniperus spp., Lantana trifolia, Origanum majorana, Persicaria hydropiper, Plantago asiatica, Plantago major and Scutellaria indica. Scutellarein 7-glucoside was first documented in 1989 (PMID: 2488968). Based on a literature review a small amount of articles have been published on plantaginin (PMID: 10048707) (PMID: 18958424).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201332D          

 32 35  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
    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
    0.0000   -2.4750    0.0000 O   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
   -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  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    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
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  3 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  6  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
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 25 30  1  1  0  0  0
 24 31  1  6  0  0  0
 23 32  1  1  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -3.0001   -3.9361   -0.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9935   -2.6959   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2195   -2.0074   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1961   -0.6433   -0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4432    0.1386   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3795    1.5279   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5028    2.3172   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7542    1.7445   -0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8955    2.5465   -0.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8255    0.3763   -0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6900   -0.4164   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0374   -0.0363   -0.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8714   -0.6463   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    0.0659   -0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696   -0.5329   -0.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6275    0.2927   -0.1239 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9937    0.1529   -0.1129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4284    0.5292    1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8165    0.3530    1.1579 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3693    0.1435    2.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7435   -0.0193    2.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3641    1.6101    0.5158 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7369    1.7088    0.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9005    1.6323   -0.8990 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8582    2.9932   -1.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6299    0.9626   -1.2050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8205    0.0806   -2.2950 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6152   -1.8888   -0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119   -2.5482   -0.3662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5718   -2.6504   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428   -3.9911   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -2.0154   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1359   -2.5749   -0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3809    1.9565   -0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4063    3.3905   -0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3128    2.7546    0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7824   -0.0882   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7836   -1.5004   -0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7669    1.1334   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2835   -0.9075   -0.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0604   -0.5053    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9619   -0.7919    2.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366    1.0080    3.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0769   -0.4894    3.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8703    2.4665    1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1137    2.2103   -0.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455    1.2089   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246    2.9745   -2.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8863    1.7121   -1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393   -0.8079   -1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9259   -3.5324   -0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0137   -4.7653   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 17 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 19  1  0
 14 15  1  0
 11  5  1  0
 13 32  1  0
 21 44  1  0
 20 42  1  0
 20 43  1  0
 19 41  1  6
 17 40  1  6
 29 51  1  0
 31 52  1  0
  3 33  1  0
 14 39  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 26 49  1  6
 27 50  1  0
 24 47  1  6
 25 48  1  0
 22 45  1  1
 23 46  1  0
M  END


  Mrv1652304282201332D          

 32 35  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
    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
    0.0000   -2.4750    0.0000 O   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
   -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  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    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
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
  3 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
 22 21  1  6  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
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 25 30  1  1  0  0  0
 24 31  1  6  0  0  0
 23 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0052563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-14-17(26)19(28)20(29)21(32-14)31-13-6-12-15(18(27)16(13)25)10(24)5-11(30-12)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21-/m1/s1

> <INCHI_KEY>
VUGRLRAUZWGZJP-IAAKTDFRSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.1601088239107

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
0.1350557186666665

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.752512152218651

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.51628615385011

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549784256

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
107.03919999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-2-(4-hydroxyphenyl)-7-{[(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       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668  -0.770   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      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    3                                                            
CONECT   20    2                                                            
CONECT   21    1   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31   24                                                            
CONECT   32   23                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Scutellarein 7beta-D-glucopyranoside	ChEBI
Scutellarein 7b-D-glucopyranoside	Generator
Scutellarein 7β-D-glucopyranoside	Generator

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-14-17(26)19(28)20(29)21(32-14)31-13-6-12-15(18(27)16(13)25)10(24)5-11(30-12)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21-/m1/s1

InChI Key

VUGRLRAUZWGZJP-IAAKTDFRSA-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
Anaphalis sinica	LOTUS Database	35616633
Betonica officinalis	Plant	KNApSAcK
Buddleja madagascariensis	LOTUS Database	35616633
Crocus chrysanthus	Plant	KNApSAcK
Crocus sativus	Plant	KNApSAcK
Halophila johnsonii	Plant	KNApSAcK
Helichrysum arenarium	LOTUS Database	35616633
Juniperus spp.	Plant	KNApSAcK
Lantana trifolia	LOTUS Database	35616633
Origanum majorana	LOTUS Database	35616633
Persicaria hydropiper	LOTUS Database	35616633
Plantago asiatica	LOTUS Database	35616633
Plantago major	LOTUS Database	35616633
Scutellaria indica	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
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monosaccharide
Oxane
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:80895 )
glycosyloxyflavone (CHEBI:80895 )
trihydroxyflavone (CHEBI:80895 )

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	0.62	ALOGPS
logP	0.14	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.04 m³·mol⁻¹	ChemAxon
Polarizability	43.16 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

C00004231

Chemspider ID

10188631

KEGG Compound ID

C17056

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320623

PDB ID

Not Available

ChEBI ID

80895

Good Scents ID

Not Available

References

General References

Yokozawa T, Dong E, Kawai Y, Gemba M, Shimizu M: Protective effects of some flavonoids on the renal cellular membrane. Exp Toxicol Pathol. 1999 Jan;51(1):9-14. doi: 10.1016/S0940-2993(99)80050-5. [PubMed:10048707 ]
Dai LM, Zhao CC, Jin HZ, Tang J, Shen YH, Li HL, Peng CY, Zhang WD: A new ferulic acid ester and other constituents from Dracocephalum peregrinum. Arch Pharm Res. 2008 Oct;31(10):1325-9. doi: 10.1007/s12272-001-2113-2. Epub 2008 Oct 29. [PubMed:18958424 ]
Komoda Y, Chujo H, Ishihara S, Uchida M: HPLC quantitative analysis of plantaginin in Shazenso (Plantago asiatica L.) extracts and isolation of plantamajoside. Tokyo Ika Shika Daigaku Iyo Kizai Kenkyusho Hokoku. 1989;23:81-5. [PubMed:2488968 ]

Showing NP-Card for Scutellarein 7-glucoside (NP0052563)

MOL for NP0052563 (Scutellarein 7-glucoside)

3D MOL for NP0052563 (Scutellarein 7-glucoside)

3D SDF for NP0052563 (Scutellarein 7-glucoside)

3D-SDF for NP0052563 (Scutellarein 7-glucoside)

PDB for NP0052563 (Scutellarein 7-glucoside)

3D PDB for NP0052563 (Scutellarein 7-glucoside)

SMILES for NP0052563 (Scutellarein 7-glucoside)

INCHI for NP0052563 (Scutellarein 7-glucoside)

Structure for NP0052563 (Scutellarein 7-glucoside)

3D Structure for NP0052563 (Scutellarein 7-glucoside)