NP-MRD: Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one (NP0176654)

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Record Information

Version

2.0

Created at

2022-09-03 14:21:12 UTC

Updated at

2022-09-03 14:21:12 UTC

NP-MRD ID

NP0176654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

Description

Afzelin, also known as deacyl-SL0101, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, afzelin is considered to be a flavonoid. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one is found in Acer truncatum, Achillea biebersteinii, Artemisia vulgaris, Betula pubescens, Brickellia diffusa, Carduus pycnocephalus, Cassinia laevis, Clibadium surinamense, Cornus controversa, Cryptomeria japonica, Flemingia stricta, Ginkgo biloba, Licania pyrifolia, Ochradenus baccatus, Phoebe formosana, Rodgersia sambucifolia, Sedum sediforme, Tripterospermum chinense, Vancouveria hexandra, Vicia cracca and Zingiber ottensii. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one was first documented in 2021 (PMID: 34681197). Based on a literature review a significant number of articles have been published on Afzelin (PMID: 35889247) (PMID: 35891565) (PMID: 35889506) (PMID: 35733130) (PMID: 35668920) (PMID: 35593082).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032216212D          

 31 34  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   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
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  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
    0.0000    0.0000    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 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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    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 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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  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
   -0.7145   -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
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  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
  9 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
  8 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  2  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -3.0229    1.7097   -1.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1101    1.5375    0.1360 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9013    1.2002    0.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -0.0489    0.4929 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5524   -0.1114   -0.6116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377   -0.6027   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756    0.2435   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7393    1.6887   -0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8626    2.3571    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    3.7248    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    4.5067   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    5.9142    0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7633    3.8822   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317    2.5052   -0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9595   -0.3812   -0.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1072   -1.6721   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3729   -2.2033   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914   -3.5718   -0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887   -4.0770    0.0252 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5439   -4.4250   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2409   -3.9376   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -4.8273   -0.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0668   -2.5599   -0.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -1.9887   -0.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711   -2.7082   -0.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5153   -1.1103    0.4325 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9805   -1.4042   -0.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6901   -0.5659    1.2587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6247   -1.5496    1.5013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2340    0.6100    0.5183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1919    1.2454    1.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1901    1.0935   -1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0057    2.7542   -1.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9570    1.2628   -1.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    2.5436    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8378   -0.3480    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035    1.7864    0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7824    4.2585    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102    6.3194    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0861    4.4823   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1390    2.0796   -1.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -1.5883    0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1513   -4.2988    0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072   -5.5122   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2830   -4.8139   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2249   -2.0560    0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3905   -1.2888   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2212   -0.1892    2.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9460   -1.4179    2.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7819    0.2375   -0.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0732    1.3151    0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  4 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30  2  1  0
 24  6  1  0
 14  8  1  0
 23 16  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  1
  4 36  1  1
 17 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 26 46  1  1
 27 47  1  0
 28 48  1  1
 29 49  1  0
 30 50  1  6
 31 51  1  0
M  END

  Mrv1652309032216212D          

 31 34  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   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
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  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
    0.0000    0.0000    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 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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    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 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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  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
   -0.7145   -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
    0.0000   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  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
  9 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
  8 14  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  2  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0176654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21+/m0/s1

> <INCHI_KEY>
SOSLMHZOJATCCP-MKMJNHTISA-N

> <FORMULA>
C21H20O10

> <MOLECULAR_WEIGHT>
432.381

> <EXACT_MASS>
432.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.622665332074895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.2056399923333339

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.869705133213711

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372348629689458

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612200408172593

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
105.75089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}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       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+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       0.000   0.000   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      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001   2.310   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -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      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    7   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23    6   25                                                  
CONECT   25   24                                                            
CONECT   26    4   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    2   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Deacyl-SL0101	MeSH
Kaempferol-3-rhamnoside	MeSH

Chemical Formula

C₂₁H₂₀O₁₀

Average Mass

432.3810 Da

Monoisotopic Mass

432.10565 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21+/m0/s1

InChI Key

SOSLMHZOJATCCP-MKMJNHTISA-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
Acer truncatum	LOTUS Database	35616633
Achillea biebersteinii	LOTUS Database	35616633
Artemisia vulgaris	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Brickellia diffusa	LOTUS Database	35616633
Carduus pycnocephalus	LOTUS Database	35616633
Cassinia laevis	LOTUS Database	35616633
Clibadium surinamense	LOTUS Database	35616633
Cornus controversa	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Flemingia stricta	LOTUS Database	35616633
Ginkgo biloba	LOTUS Database	35616633
Licania pyrifolia	LOTUS Database	35616633
Ochradenus baccatus	LOTUS Database	35616633
Phoebe formosana	LOTUS Database	35616633
Rodgersia sambucifolia	LOTUS Database	35616633
Sedum sediforme	LOTUS Database	35616633
Tripterospermum chinense	LOTUS Database	35616633
Vancouveria hexandra	LOTUS Database	35616633
Vicia cracca	LOTUS Database	35616633
Zingiber ottensii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Polyol
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
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	1.21	ChemAxon
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	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	3	ChemAxon
Refractivity	105.75 m³·mol⁻¹	ChemAxon
Polarizability	41.62 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

C00005140

Chemspider ID

67490786

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Afzelin

METLIN ID

Not Available

PubChem Compound

15558501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sultana A, Hossain MJ, Kuddus MR, Rashid MA, Zahan MS, Mitra S, Roy A, Alam S, Sarker MMR, Naina Mohamed I: Ethnobotanical Uses, Phytochemistry, Toxicology, and Pharmacological Properties of Euphorbia neriifolia Linn. against Infectious Diseases: A Comprehensive Review. Molecules. 2022 Jul 8;27(14):4374. doi: 10.3390/molecules27144374. [PubMed:35889247 ]
Liu J, Yuan S, Yao Y, Wang J, Scalabrino G, Jiang S, Sheridan H: Network Pharmacology and Molecular Docking Elucidate the Underlying Pharmacological Mechanisms of the Herb Houttuynia cordata in Treating Pneumonia Caused by SARS-CoV-2. Viruses. 2022 Jul 21;14(7):1588. doi: 10.3390/v14071588. [PubMed:35891565 ]
Jung J, Kim H, Lee S, Hong M, Hwang D: Antioxidant and Anti-Inflammatory Activity of Filipendula glaberrima Nakai Ethanolic Extract and Its Chemical Composition. Molecules. 2022 Jul 20;27(14):4628. doi: 10.3390/molecules27144628. [PubMed:35889506 ]
Akter M, Parvin MS, Hasan MM, Rahman MAA, Islam ME: Anti-tumor and antioxidant activity of kaempferol-3-O-alpha-L-rhamnoside (Afzelin) isolated from Pithecellobium dulce leaves. BMC Complement Med Ther. 2022 Jun 22;22(1):169. doi: 10.1186/s12906-022-03633-x. [PubMed:35733130 ]
Makati AC, Ananda AN, Putri JA, Amellia SF, Setiawan B: Molecular docking of ethanol extracts of katuk leaf (Sauropus androgynus) on functional proteins of severe acute respiratory syndrome coronavirus 2. S Afr J Bot. 2022 Sep;149:1-5. doi: 10.1016/j.sajb.2022.04.044. Epub 2022 Jun 1. [PubMed:35668920 ]
Duan PB, Xiao PT, Yang X, Hao JH, Li K, Liu EH: Screening of hypoglycemic components in Platycladi Cacumen by phytochemical investigation, spectrum-effect relationship, and chemometric methods. J Sep Sci. 2022 Jul;45(14):2591-2602. doi: 10.1002/jssc.202200221. Epub 2022 May 31. [PubMed:35593082 ]
Elsayed HE, Ebrahim HY, Mady MS, Khattab MA, El-Sayed EK, Moharram FA: Ethnopharmacological impact of Melaleuca rugulosa (Link) Craven leaves extract on liver inflammation. J Ethnopharmacol. 2022 Jun 28;292:115215. doi: 10.1016/j.jep.2022.115215. Epub 2022 Mar 23. [PubMed:35337921 ]
Lee Y, Park YJ, Lee B, Park E, Kim H, Choi CW, Kim MS: Ribes fasciculatum Ameliorates High-Fat-Diet-Induced Obesity by Elevating Peripheral Thermogenic Signaling. Molecules. 2022 Mar 2;27(5):1649. doi: 10.3390/molecules27051649. [PubMed:35268752 ]
Raj V, Lee JH, Shim JJ, Lee J: Antiviral activities of 4H-chromen-4-one scaffold-containing flavonoids against SARS-CoV-2 using computational and in vitro approaches. J Mol Liq. 2022 May 1;353:118775. doi: 10.1016/j.molliq.2022.118775. Epub 2022 Feb 17. [PubMed:35194277 ]
Lyko L, Olech M, Nowak R: LC-ESI-MS/MS Characterization of Concentrated Polyphenolic Fractions from Rhododendron luteum and Their Anti-Inflammatory and Antioxidant Activities. Molecules. 2022 Jan 26;27(3):827. doi: 10.3390/molecules27030827. [PubMed:35164090 ]
Pushkala VP, Sulekha SMP, Mathukumar S, Ragavi B, Sowmiya U: Molecular Docking Analysis of Siddha Formulation Parangipattai Chooranam Against Vaginal Candidiasis. Appl Biochem Biotechnol. 2022 Mar;194(3):1039-1050. doi: 10.1007/s12010-022-03813-y. Epub 2022 Jan 8. [PubMed:34997904 ]
Darwish RS, Hammoda HM, Ghareeb DA, Abdelhamid ASA, Harraz FM, Shawky E: Chemical profiling and identification of anti-inflammatory biomarkers of oriental Thuja (Platycladus orientalis) using UPLC/MS/MS and network pharmacology-based analyses. Nat Prod Res. 2022 Sep;36(18):4782-4786. doi: 10.1080/14786419.2021.2010198. Epub 2021 Dec 5. [PubMed:34866494 ]
Radziejewska I, Supruniuk K, Czarnomysy R, Buzun K, Bielawska A: Anti-Cancer Potential of Afzelin towards AGS Gastric Cancer Cells. Pharmaceuticals (Basel). 2021 Sep 25;14(10):973. doi: 10.3390/ph14100973. [PubMed:34681197 ]
Mady MS, Elsayed HE, El-Sayed EK, Hussein AA, Ebrahim HY, Moharram FA: Polyphenolic profile and ethno pharmacological activities of Callistemonsubulatus (Cheel) Craven leaves cultivated in Egypt. J Ethnopharmacol. 2022 Feb 10;284:114698. doi: 10.1016/j.jep.2021.114698. Epub 2021 Sep 29. [PubMed:34600075 ]
Kim M, Shin S, Ryu D, Cho E, Yoo J, Park D, Jung E: Evaluating the Sun Protection Factor of Cosmetic Formulations Containing Afzelin. Chem Pharm Bull (Tokyo). 2021 Nov 1;69(11):1039-1044. doi: 10.1248/cpb.c21-00398. Epub 2021 Aug 28. [PubMed:34456215 ]
LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one (NP0176654)

MOL for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

PDB for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

SMILES for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

INCHI for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

Structure for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0176654 (5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)