NP-MRD: Showing NP-Card for Isoscoparin (NP0138629)

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Record Information

Version

2.0

Created at

2022-06-29 17:38:21 UTC

Updated at

2022-06-29 17:38:21 UTC

NP-MRD ID

NP0138629

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoscoparin

Description

Isoscoparin belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, isoscoparin is considered to be a flavonoid. Isoscoparin 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. Isoscoparin is found in Arrhenatherum elatius, Eremogone kansuensis, Barbarea vulgaris, Centaurea montana, Cerastium arvense, Citrullus colocynthis, Cyclanthera pedata, Cymbopogon citratus, Gentiana depressa, Gentiana sino-ornata, Gentianopsis lanceolata, Isatis tinctoria, Passiflora palmeri, Silene latifolia and Trichophorum cespitosum. Isoscoparin was first documented in 2013 (PMID: 23265286). Based on a literature review a significant number of articles have been published on isoscoparin (PMID: 28958514) (PMID: 30363098) (PMID: 27685157) (PMID: 23849114) (PMID: 27373652) (PMID: 35638105).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652306292219382D          

 33 36  0  0  1  0            999 V2000
   -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 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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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
   -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
    0.0000   -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
    0.7145   -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
    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
    2.1434   -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   -1.6500    0.0000 C   0  0  1  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
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 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
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 18  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
 17 32  1  0  0  0  0
  4 33  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -7.3162    1.0984   -2.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6742    0.2677   -1.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7609   -0.2723   -0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3850   -0.0744   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4614   -0.5982    0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0297   -0.3874    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341    0.1558   -0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553    0.3321   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    0.8205   -2.1995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2735   -0.0238   -0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100    0.1048   -0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6388    0.6056   -1.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9126   -0.2803    0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -0.0501    0.7583 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4782    1.2316    0.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6370    1.7024   -0.2511 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6621    2.3677   -1.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971    1.5618   -2.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    0.7348   -0.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3180    0.6770    1.0325 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3969   -0.6389   -0.6959 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4996   -0.8744   -2.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923   -0.9788   -0.1292 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4129   -2.0491    0.8431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2993   -0.7659    1.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0787   -1.1432    3.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0614   -0.9161    2.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -0.5430    1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1485   -0.6954    1.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9250   -1.3695    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2799   -1.5928    1.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1919   -1.0574    0.8177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5861   -1.2863    0.9706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1829    1.6502   -2.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8764    0.4858   -3.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5301    1.8549   -1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0880    0.5658   -1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993    0.4550   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523    0.9171   -2.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882   -0.0003    1.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9904    2.5193    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7651    2.5923   -1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1671    3.3840   -1.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2855    2.0747   -3.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6098    1.1548   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1104    1.2941    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1947   -1.3158   -0.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2842   -1.8207   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687   -1.5830   -0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -1.6053    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179   -1.5112    3.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -1.3242    2.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2106   -1.7945    2.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5993   -2.1957    2.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8741   -1.8607    1.7507 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 30  2  0
 30  5  1  0
  5  4  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 28  2  0
 28 29  1  0
 28 27  1  0
 27 25  2  0
 25 26  1  0
 25 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 13 11  2  0
 11 12  1  0
  4  3  1  0
 29  6  1  0
 23 14  1  0
 11 10  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 33 55  1  0
 31 54  1  0
 30 53  1  0
  4 37  1  0
  7 38  1  0
 27 52  1  0
 26 51  1  0
 14 40  1  1
 16 41  1  1
 17 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  6
 20 46  1  0
 21 47  1  1
 22 48  1  0
 23 49  1  6
 24 50  1  0
 12 39  1  0
M  END

  Mrv1652306292219382D          

 33 36  0  0  1  0            999 V2000
   -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 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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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
   -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
    0.0000   -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
    0.7145   -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
    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
    2.1434   -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   -1.6500    0.0000 C   0  0  1  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
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 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
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 18  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
 17 32  1  0  0  0  0
  4 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138629

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O1)C=C(O)C([C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C2O

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

> <INCHI_KEY>
KOMUHHCFAXYRPO-DGHBBABESA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.842904593131166

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-[(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>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.740645013217149

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.138409688641091

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979192626943843

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
112.49539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoscoparin

> <JCHEM_VEBER_RULE>
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HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   13   20                                                  
CONECT   20   19                                                            
CONECT   21   18   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   17                                                            
CONECT   33    4                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
C-Glucosyl-6 chrysoeriol	ChEBI
Chrysoeriol 6-C-glucoside	ChEBI

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

20013-23-4

SMILES

COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O1)C=C(O)C([C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C2O

InChI Identifier

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

InChI Key

KOMUHHCFAXYRPO-DGHBBABESA-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
A. elatiusa, A. lilacinum	LOTUS Database	35616633
Arenaria kansuensis	LOTUS Database	35616633
Barbarea vulgaris	LOTUS Database	35616633
Centaurea montana	LOTUS Database	35616633
Cerastium arvense	LOTUS Database	35616633
Citrullus colocynthis	LOTUS Database	35616633
Cyclanthera pedata	LOTUS Database	35616633
Cymbopogon citratus	LOTUS Database	35616633
Gentiana depressa	LOTUS Database	35616633
Gentiana sino-ornata	LOTUS Database	35616633
Gentianopsis lanceolata	LOTUS Database	35616633
Isatis tinctoria	LOTUS Database	35616633
Passiflora palmeri	LOTUS Database	35616633
Silene latifolia	LOTUS Database	35616633
Trichophorum cespitosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-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 C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenol ether
Phenoxy compound
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:18200 )
C-glycosyl compound (CHEBI:18200 )
monomethoxyflavone (CHEBI:18200 )
trihydroxyflavone (CHEBI:18200 )
flavones (C05990 )
Flavones and Flavonols (C05990 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442611

PDB ID

Not Available

ChEBI ID

18200

Good Scents ID

Not Available

References

General References

Kim B, Woo S, Kim MJ, Kwon SW, Lee J, Sung SH, Koh HJ: Identification and quantification of flavonoids in yellow grain mutant of rice (Oryza sativa L.). Food Chem. 2018 Feb 15;241:154-162. doi: 10.1016/j.foodchem.2017.08.089. Epub 2017 Aug 30. [PubMed:28958514 ]
Zhan ZH, Matsuo A, Kim CS: Studies on probing stimulants for the green rice leafhopper, Nephotettix nigropictus (Stal) (Hemiptera: Cicadellidae), in the rice plant (Oryza sativa L.). J Pestic Sci. 2016 Nov 20;41(4):163-166. doi: 10.1584/jpestics.D16-052. [PubMed:30363098 ]
Zhan ZH, Matsuo A, Oku Y, Tebayashi SI, Kim CS: Studies on the probing stimulants for the white-backed planthopper, Sogatella furcifera (Homoptera: Delphacidae) in rice plant (Oryza sativa L.). Biosci Biotechnol Biochem. 2016 Dec;80(12):2285-2290. doi: 10.1080/09168451.2016.1220820. Epub 2016 Aug 12. [PubMed:27685157 ]
Zhou M, Geng HC, Zhang HB, Dong K, Wang WG, Du X, Li XN, He F, Qin HB, Li Y, Pu JX, Sun HD: Scopariusins, a new class of ent-halimane diterpenoids isolated from Isodon scoparius, and biomimetic synthesis of scopariusin A and isoscoparin N. Org Lett. 2013 Jan 18;15(2):314-7. doi: 10.1021/ol303226c. Epub 2012 Dec 24. [PubMed:23265286 ]
Jung ES, Lee S, Lim SH, Ha SH, Liu KH, Lee CH: Metabolite profiling of the short-term responses of rice leaves (Oryza sativa cv. Ilmi) cultivated under different LED lights and its correlations with antioxidant activities. Plant Sci. 2013 Sep;210:61-9. doi: 10.1016/j.plantsci.2013.05.004. Epub 2013 May 14. [PubMed:23849114 ]
Yang Z, Nakabayashi R, Mori T, Takamatsu S, Kitanaka S, Saito K: Metabolome Analysis of Oryza sativa (Rice) Using Liquid Chromatography-Mass Spectrometry for Characterizing Organ Specificity of Flavonoids with Anti-inflammatory and Anti-oxidant Activity. Chem Pharm Bull (Tokyo). 2016;64(7):952-6. doi: 10.1248/cpb.c16-00180. [PubMed:27373652 ]
Huang X, Jiang H, Liang Q, Ma Y, Wang X: Determination of isoscoparin in mouse blood using UPLC-MS/MS and its pharmacokinetics. Biomed Chromatogr. 2022 Sep;36(9):e5419. doi: 10.1002/bmc.5419. Epub 2022 Jun 6. [PubMed:35638105 ]
Pasdaran A, Butovska D, Kerr P, Naychov Z, Aneva I, Kozuharova E: Gentians, natural remedies for future of visceral pain control; an ethnopharmacological review with an in silico approach. Biol Futur. 2022 Jun;73(2):219-227. doi: 10.1007/s42977-022-00114-7. Epub 2022 Mar 23. [PubMed:35318616 ]
Garibay-Hernandez A, Kessler N, Jozefowicz AM, Turksoy GM, Lohwasser U, Mock HP: Untargeted metabotyping to study phenylpropanoid diversity in crop plants. Physiol Plant. 2021 Nov;173(3):680-697. doi: 10.1111/ppl.13458. Epub 2021 May 27. [PubMed:33963574 ]
Cuo N, Rui GU, Lin FU, Ke-Ru W, Rong D, Cai-Hong Z: [Determination of content of iridoids and flavonoids in Tibetan medicine "Lanhua Longdan" by quantitative analysis of multi-components by single marker (QAMS)]. Zhongguo Zhong Yao Za Zhi. 2020 Sep;45(18):4423-4428. doi: 10.19540/j.cnki.cjcmm.20200603.202. [PubMed:33164372 ]
Luyen BT, Tai BH, Thao NP, Cha JY, Lee YM, Kim YH: A new phenolic component from Triticum aestivum sprouts and its effects on LPS-stimulated production of nitric oxide and TNF-alpha in RAW 264.7 cells. Phytother Res. 2014 Jul;28(7):1064-70. doi: 10.1002/ptr.5097. [PubMed:25165783 ]
Poudel B, Nepali S, Xin M, Ki HH, Kim YH, Kim DK, Lee YM: Flavonoids from Triticum aestivum inhibit adipogenesis in 3T3-L1 cells by upregulating the insig pathway. Mol Med Rep. 2015 Aug;12(2):3139-45. doi: 10.3892/mmr.2015.3700. Epub 2015 Apr 29. [PubMed:25936595 ]
Park MJ, Ra JE, Seo KH, Jang KC, Han SI, Lee JH, Kang YH, Nam MH, Seo WD: Identification and evaluation of flavone-glucosides isolated from barley sprouts and their inhibitory activity against bacterial neuraminidase. Nat Prod Commun. 2014 Oct;9(10):1469-72. [PubMed:25522538 ]

Showing NP-Card for Isoscoparin (NP0138629)

MOL for NP0138629 (Isoscoparin)

3D MOL for NP0138629 (Isoscoparin)

3D SDF for NP0138629 (Isoscoparin)

3D-SDF for NP0138629 (Isoscoparin)

PDB for NP0138629 (Isoscoparin)

3D PDB for NP0138629 (Isoscoparin)

SMILES for NP0138629 (Isoscoparin)

INCHI for NP0138629 (Isoscoparin)

Structure for NP0138629 (Isoscoparin)

3D Structure for NP0138629 (Isoscoparin)