NP-MRD: Showing NP-Card for cytisoside (NP0303023)

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Record Information

Version

2.0

Created at

2022-09-10 17:00:05 UTC

Updated at

2022-09-10 17:00:05 UTC

NP-MRD ID

NP0303023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cytisoside

Description

Cytisoside 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. cytisoside is found in Peganum harmala. cytisoside was first documented in 2008 (PMID: 18409044). Based on a literature review a small amount of articles have been published on Cytisoside (PMID: 30475503) (PMID: 23006992).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102219002D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    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
   -1.4289   -2.4750    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
   -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  0  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  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
    2.1434   -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  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 29  2  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    6.7450    1.4501   -3.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4010    1.7735   -3.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5768    1.1717   -2.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092    0.1900   -1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -0.4030   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8301   -0.0324   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413   -0.6219    0.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4619   -1.4895    1.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7021   -2.0745    2.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2121   -2.8657    3.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536   -1.8027    2.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4329   -2.3874    3.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870   -3.2400    4.6638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513   -2.0928    3.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2782   -1.2430    2.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -0.9741    2.8959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907   -0.6269    1.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743    0.2300    0.8530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2620   -0.4687    0.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    0.2768   -0.5099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4436   -0.5285   -1.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4014   -0.9821   -2.4856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6126    1.6527   -0.8257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0569    2.5931    0.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1543    1.8155   -1.0457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8160    1.6176   -2.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3381    0.8283   -0.1913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8206   -0.1485   -1.0415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1522   -0.9301    1.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541   -0.4085    0.9288 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058    0.9557   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630    1.5481   -1.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2580    2.3513   -3.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2298    1.2290   -2.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8403    0.5860   -3.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.1408   -1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5416   -1.1727    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -1.7129    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3498   -3.6947    5.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800   -2.5463    4.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1171   -0.3636    2.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492    1.0611    1.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0254    0.4020    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1172    0.0891   -2.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0606   -1.4225   -1.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820   -1.9526   -2.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1146    1.9368   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198    2.7454   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856    2.8697   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416    1.6228   -2.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5241    1.4103    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569    0.2812   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    1.3115   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793    2.3272   -2.6242 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  2  0
  6 31  1  0
 31 32  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 17 29  2  0
 29 30  1  0
 32  3  1  0
 30  7  1  0
 29 11  1  0
 27 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
 31 53  1  0
 32 54  1  0
  8 38  1  0
 13 39  1  0
 14 40  1  0
 16 41  1  0
 18 42  1  1
 20 43  1  1
 21 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  6
 24 48  1  0
 25 49  1  1
 26 50  1  0
 27 51  1  1
 28 52  1  0
M  END


  Mrv1652309102219002D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    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
   -1.4289   -2.4750    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
   -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  0  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  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
    2.1434   -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  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 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
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 29  2  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
  7 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C([C@@H]3OC(CO)[C@@H](O)[C@H](O)C3O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-30-10-4-2-9(3-5-10)14-7-13(26)16-11(24)6-12(25)17(21(16)31-14)22-20(29)19(28)18(27)15(8-23)32-22/h2-7,15,18-20,22-25,27-29H,8H2,1H3/t15?,18-,19+,20?,22+/m1/s1

> <INCHI_KEY>
ADCCDGCXRFALSQ-OEMYLOCWSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.46635215511388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.09526228466666686

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.090714640858776

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.173980455892479

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791926292654134

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
110.51450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
cytisoside

> <JCHEM_VEBER_RULE>
0

$$$$

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

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

Traditional Name

cytisoside

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C([C@@H]3OC(CO)[C@@H](O)[C@H](O)C3O)=C2O1

InChI Identifier

InChI=1S/C22H22O10/c1-30-10-4-2-9(3-5-10)14-7-13(26)16-11(24)6-12(25)17(21(16)31-14)22-20(29)19(28)18(27)15(8-23)32-22/h2-7,15,18-20,22-25,27-29H,8H2,1H3/t15?,18-,19+,20?,22+/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110433 )

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	0.095	ChemAxon
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	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	43.47 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

C00006127

Chemspider ID

24843472

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257872

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Seo CS, Shin HK: Simultaneous Determination of the Five Marker Compounds in Melandriumfirmum using High-Performance Liquid Chromatography with Photodiode-Array Detection. Nat Prod Commun. 2016 Nov;11(11):1667-1669. [PubMed:30475503 ]
Diab Y, Atalla K, Elbanna K: Antimicrobial screening of some Egyptian plants and active flavones from Lagerstroemia indica leaves. Drug Discov Ther. 2012 Aug;6(4):212-7. [PubMed:23006992 ]
Zheng MS, Hwang NK, Kim DH, Moon TC, Son JK, Chang HW: Chemical constituents of Melandrium firmum Rohrbach and their anti-inflammatory activity. Arch Pharm Res. 2008 Mar;31(3):318-22. doi: 10.1007/s12272-001-1158-9. Epub 2008 Apr 13. [PubMed:18409044 ]
LOTUS database [Link]

Showing NP-Card for cytisoside (NP0303023)

MOL for NP0303023 (cytisoside)

3D MOL for NP0303023 (cytisoside)

3D SDF for NP0303023 (cytisoside)

3D-SDF for NP0303023 (cytisoside)

PDB for NP0303023 (cytisoside)

3D PDB for NP0303023 (cytisoside)

SMILES for NP0303023 (cytisoside)

INCHI for NP0303023 (cytisoside)

Structure for NP0303023 (cytisoside)

3D Structure for NP0303023 (cytisoside)