NP-MRD: Showing NP-Card for isoswertisin (NP0157876)

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Record Information

Version

2.0

Created at

2022-09-02 15:21:55 UTC

Updated at

2022-09-02 15:21:55 UTC

NP-MRD ID

NP0157876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isoswertisin

Description

Isoswertisin 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. isoswertisin is found in Andrographis paniculata, Deschampsia antarctica, Galipea trifoliata, Gnetum buchholzianum, Gnetum gnemon, Passiflora sexflora, Trollius chinensis, Wilbrandia ebracteata and Zantedeschia aethiopica. isoswertisin was first documented in 2015 (PMID: 26281588). Based on a literature review a small amount of articles have been published on Isoswertisin (PMID: 32214429) (PMID: 26956555) (PMID: 26262599) (PMID: 25789809).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217212D          

 32 35  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  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
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  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
    0.7145   -2.8875    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
  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
  5  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
 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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 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
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -3.2842   -4.1144   -1.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206   -3.0327   -1.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063   -3.0060   -0.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6599   -4.1519   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5964   -4.1276    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2011   -5.2850    0.7566 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1535   -2.8943    0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -2.7774    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0489   -3.7987    1.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9114   -1.5060    1.5651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -0.3646    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294    0.9413    1.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374    2.0418    0.7811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390    3.3315    0.9557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832    3.5399    1.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3924    4.8431    2.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3787    2.4669    2.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8684    1.1652    2.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427   -0.5440    0.6810 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810   -1.6981    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441   -1.7487   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410   -0.5918   -0.5387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9062    0.1723   -1.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7028    1.1991   -1.9542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9541    2.5273   -2.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1399    2.4647   -2.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    1.3536   -1.2341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4477    2.6713   -1.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9501    1.1728    0.2624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9639    2.3530    0.9577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    0.3652    0.6130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6595    1.1974    0.9114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8086   -3.8551   -2.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324   -5.0551   -1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1176   -4.2519   -0.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1145   -5.1189   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -5.5873    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8704   -1.4328    2.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5517    1.9649    0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4216    4.1803    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    5.2203    1.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1936    2.6058    3.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2775    0.3386    2.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193   -0.8841   -0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9907    0.9567   -3.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6313    2.9142   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573    3.3047   -2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8848    3.0479   -2.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    0.6914   -1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3534    2.7218   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7771    0.5131    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    2.4878    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9270   -0.2469    1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526    1.3193    1.9061 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 21  3  1  0
 31 22  1  0
 18 12  1  0
 20  7  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 10 38  1  0
 22 44  1  6
 24 45  1  6
 25 46  1  0
 25 47  1  0
 26 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  1
 30 52  1  0
 31 53  1  1
 32 54  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
M  END


  Mrv1652309022217212D          

 32 35  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  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
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  2  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
    0.7145   -2.8875    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
  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
  5  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
 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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 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
 24 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1[C@@H]1OC(CO)[C@H](O)[C@H](O)C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-30-14-7-12(26)16-11(25)6-13(9-2-4-10(24)5-3-9)31-21(16)17(14)22-20(29)19(28)18(27)15(8-23)32-22/h2-7,15,18-20,22-24,26-29H,8H2,1H3/t15?,18-,19-,20?,22-/m0/s1

> <INCHI_KEY>
HHPLIFSIFJSIBY-UHJXJGFFSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.170915771761486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-[(2S,4R,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.09526228466666686

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.740576506864675

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2903101015406095

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979192630016531

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
110.51450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoswertisin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -5.390   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  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19   11   20                                                       
CONECT   20   19    7   21                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

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

Traditional Name

isoswertisin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1[C@@H]1OC(CO)[C@H](O)[C@H](O)C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C22H22O10/c1-30-14-7-12(26)16-11(25)6-13(9-2-4-10(24)5-3-9)31-21(16)17(14)22-20(29)19(28)18(27)15(8-23)32-22/h2-7,15,18-20,22-24,26-29H,8H2,1H3/t15?,18-,19-,20?,22-/m0/s1

InChI Key

HHPLIFSIFJSIBY-UHJXJGFFSA-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
Andrographis paniculata	LOTUS Database	35616633
Deschampsia antarctica	LOTUS Database	35616633
Galipea trifoliata	LOTUS Database	35616633
Gnetum buchholzianum	LOTUS Database	35616633
Gnetum gnemon	LOTUS Database	35616633
Passiflora sexflora	LOTUS Database	35616633
Trollius chinensis	LOTUS Database	35616633
Wilbrandia ebracteata	LOTUS Database	35616633
Zantedeschia aethiopica	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
7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Phenol ether
Anisole
Pyranone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
1,2-diol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110973 )

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	0.61	ALOGPS
logP	0.095	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.51 m³·mol⁻¹	ChemAxon
Polarizability	43.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

C00006129

Chemspider ID

24843935

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44258317

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fang M, Liu S, Wang Q, Gu X, Ding P, Wang W, Ding Y, Liu J, Wang R: Qualitative and Quantitative Analysis of 24 Components in Jinlianhua Decoction by UPLC-MS/MS. Chromatographia. 2019;82(12):1801-1825. doi: 10.1007/s10337-019-03806-w. Epub 2019 Sep 28. [PubMed:32214429 ]
Chiluka R, Gamble AB, Lucas NT, Hawkins BC, Bhumkar A, Achanta PS, Bobbala RK: Flavone C-glycosides from Trichuriella monsoniae (L.f.) Bennet. Nat Prod Res. 2016 Oct;30(19):2235-7. doi: 10.1080/14786419.2016.1149707. Epub 2016 Mar 8. [PubMed:26956555 ]
Chen KX, Zhao LM, Ji CJ, Tan NH: [Flavone C-glycosides from seeds of Ziziphus jujuba var. spinosa]. Zhongguo Zhong Yao Za Zhi. 2015 Apr;40(8):1503-7. [PubMed:26281588 ]
Qin Y, Liang Y, Ren D, Qiu X, Li X: Separation of phenolic acids and flavonoids from Trollius chinensis Bunge by high speed counter-current chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Sep 15;1001:82-9. doi: 10.1016/j.jchromb.2015.07.051. Epub 2015 Aug 1. [PubMed:26262599 ]
Liu L, Guo L, Zhao C, Wu X, Wang R, Liu C: Characterization of the intestinal absorption of seven flavonoids from the flowers of Trollius chinensis using the Caco-2 cell monolayer model. PLoS One. 2015 Mar 19;10(3):e0119263. doi: 10.1371/journal.pone.0119263. eCollection 2015. [PubMed:25789809 ]
LOTUS database [Link]

Showing NP-Card for isoswertisin (NP0157876)

MOL for NP0157876 (isoswertisin)

3D MOL for NP0157876 (isoswertisin)

3D SDF for NP0157876 (isoswertisin)

3D-SDF for NP0157876 (isoswertisin)

PDB for NP0157876 (isoswertisin)

3D PDB for NP0157876 (isoswertisin)

SMILES for NP0157876 (isoswertisin)

INCHI for NP0157876 (isoswertisin)

Structure for NP0157876 (isoswertisin)

3D Structure for NP0157876 (isoswertisin)