NP-MRD: Showing NP-Card for scoparin (NP0175730)

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Record Information

Version

2.0

Created at

2022-09-03 13:16:13 UTC

Updated at

2022-09-03 13:16:13 UTC

NP-MRD ID

NP0175730

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scoparin

Description

Scoparin belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Thus, scoparin is considered to be a flavonoid. scoparin is found in Passiflora coactilis and Setaria italica. scoparin was first documented in 2006 (PMID: 17061839). Based on a literature review a small amount of articles have been published on Scoparin (PMID: 26593535) (PMID: 24295703) (PMID: 30634246) (PMID: 17923995).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032215162D          

 33 36  0  0  1  0            999 V2000
   -2.8579   -1.6500    0.0000 C   0  0  0  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
   -1.4289   -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
    0.0000   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   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
    3.5724   -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
    4.2868   -1.6500    0.0000 O   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 C   0  0  2  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
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  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
    2.1434   -1.2375    0.0000 C   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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  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
 14 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 16 28  2  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
  6 29  1  0  0  0  0
  5 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    4.7534    2.4273    2.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5655    1.6565    1.9470 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3743    0.8906    0.9288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    0.3486    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006   -0.4553   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -1.0716   -1.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9805   -2.1206   -2.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769   -2.7996   -2.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1818   -3.7385   -3.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267   -2.4474   -2.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3540   -3.1069   -2.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765   -4.1143   -3.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216   -2.7415   -2.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8268   -1.7442   -1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1406   -1.3633   -1.3096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416   -1.0228   -0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1906   -0.0218   -0.0686 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3737    1.2616   -0.4851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861    1.9027    0.3522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3282    3.4142    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919    3.8273   -1.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064    1.6806    1.8232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4216    1.6995    2.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4445    0.4132    2.2406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0762    0.3373    3.5178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3244    0.1029    1.1879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7740   -1.1385    1.5565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4837   -1.4186   -1.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455   -0.7782   -0.7999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2011   -0.7266   -1.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471   -0.2362   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5444    0.5773    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7493    1.1228    0.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2161    1.8542    3.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9315    3.0456    3.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5697    3.2021    2.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540    0.5960    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9703   -2.4517   -2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -4.6352   -4.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4199   -3.2865   -3.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679   -1.8838   -1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380   -0.2934    0.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2858    1.5057    0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4278    3.9200    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1488    3.7569    0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010    3.0905   -1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6327    2.5710    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7197    0.7764    2.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1657   -0.4690    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5800   -0.4590    3.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104    0.8904    1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -1.3654    2.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904   -1.3625   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3482   -0.4746   -1.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5958    0.8554    0.0523 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 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 16 28  2  0
 28 29  1  0
 32  3  1  0
 29  6  1  0
 28 10  1  0
 26 17  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
 30 53  1  0
 31 54  1  0
 33 55  1  0
  7 38  1  0
 12 39  1  0
 13 40  1  0
 15 41  1  0
 17 42  1  1
 19 43  1  6
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  1
 23 48  1  0
 24 49  1  1
 25 50  1  0
 26 51  1  6
 27 52  1  0
M  END


  Mrv1652309032215162D          

 33 36  0  0  1  0            999 V2000
   -2.8579   -1.6500    0.0000 C   0  0  0  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
   -1.4289   -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
    0.0000   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   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
    3.5724   -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
    4.2868   -1.6500    0.0000 O   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 C   0  0  2  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
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  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
    2.1434   -1.2375    0.0000 C   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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  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
 14 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 16 28  2  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
  6 29  1  0  0  0  0
  5 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175730

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=CC(=O)C2=C(O)C=C(O)C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2O1

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

> <INCHI_KEY>
YXHFXGHAELQJGK-PGPONNFDSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.44994009458543

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

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
-0.20830303699999952

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.05854019901611

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.173534371630948

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791926292654134

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
112.49540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -0.770   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   28                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   28                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   17   27                                                  
CONECT   27   26                                                            
CONECT   28   16   10   29                                                  
CONECT   29   28    6                                                       
CONECT   30    5   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    3   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

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=CC(=O)C2=C(O)C=C(O)C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2O1

InChI Identifier

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

InChI Key

YXHFXGHAELQJGK-PGPONNFDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, 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
Passiflora coactilis	LOTUS Database	35616633
Setaria italica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Methoxyphenol
Benzopyran
Methoxybenzene
Phenoxy compound
Phenol ether
Anisole
Alkyl aryl ether
Pyranone
1-hydroxy-2-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

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	0.48	ALOGPS
logP	-0.21	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.5 m³·mol⁻¹	ChemAxon
Polarizability	44.45 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

C00001058

Chemspider ID

16736463

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20055255

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Barreca D, Gattuso G, Lagana G, Leuzzi U, Bellocco E: C- and O-glycosyl flavonoids in Sanguinello and Tarocco blood orange (Citrus sinensis (L.) Osbeck) juice: Identification and influence on antioxidant properties and acetylcholinesterase activity. Food Chem. 2016 Apr 1;196:619-27. doi: 10.1016/j.foodchem.2015.09.098. Epub 2015 Sep 30. [PubMed:26593535 ]
Barreca D, Bellocco E, Leuzzi U, Gattuso G: First evidence of C- and O-glycosyl flavone in blood orange (Citrus sinensis (L.) Osbeck) juice and their influence on antioxidant properties. Food Chem. 2014 Apr 15;149:244-52. doi: 10.1016/j.foodchem.2013.10.096. Epub 2013 Oct 30. [PubMed:24295703 ]
Barreca D, Bellocco E, Caristi C, Leuzzi U, Gattuso G: Flavonoid profile and radical-scavenging activity of Mediterranean sweet lemon (Citrus limetta Risso) juice. Food Chem. 2011 Nov 15;129(2):417-422. doi: 10.1016/j.foodchem.2011.04.093. Epub 2011 May 4. [PubMed:30634246 ]
Johann S, Oliveira VL, Pizzolatti MG, Schripsema J, Braz-Filho R, Branco A, Smania A Jr: Antimicrobial activity of wax and hexane extracts from Citrus spp. peels. Mem Inst Oswaldo Cruz. 2007 Sep;102(6):681-5. doi: 10.1590/s0074-02762007005000087. [PubMed:17923995 ]
Schauss AG, Wu X, Prior RL, Ou B, Patel D, Huang D, Kababick JP: Phytochemical and nutrient composition of the freeze-dried amazonian palm berry, Euterpe oleraceae mart. (acai). J Agric Food Chem. 2006 Nov 1;54(22):8598-603. doi: 10.1021/jf060976g. [PubMed:17061839 ]
LOTUS database [Link]

Showing NP-Card for scoparin (NP0175730)

MOL for NP0175730 (scoparin)

3D MOL for NP0175730 (scoparin)

3D SDF for NP0175730 (scoparin)

3D-SDF for NP0175730 (scoparin)

PDB for NP0175730 (scoparin)

3D PDB for NP0175730 (scoparin)

SMILES for NP0175730 (scoparin)

INCHI for NP0175730 (scoparin)

Structure for NP0175730 (scoparin)

3D Structure for NP0175730 (scoparin)