NP-MRD: Showing NP-Card for Taxifolin 3-apioside (NP0055972)

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Record Information

Version

2.0

Created at

2022-04-28 01:52:47 UTC

Updated at

2022-04-28 01:52:47 UTC

NP-MRD ID

NP0055972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taxifolin 3-apioside

Description

(2S,3R)-3-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. Taxifolin 3-apioside is found in Rosa davurica . Based on a literature review very few articles have been published on (2S,3R)-3-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203522D          

 31 34  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 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
    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 O   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  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5253   -2.9599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -3.7445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4454   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -2.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205   -4.0880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3652   -4.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -4.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  1  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  1  0  0  0
 16 20  1  6  0  0  0
 20 21  1  0  0  0  0
 15 22  1  6  0  0  0
  9 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -0.3118    1.3050   -2.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426    1.3706   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742    2.2760   -0.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    3.3082   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    3.5338   -2.6071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    4.1472   -0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5403    3.9620    0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5204    4.7682    1.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0218    2.9372    1.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    2.0822    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5093    1.0641    1.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944    0.0049    0.9881 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6471   -1.0280    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5709   -1.6323   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958   -2.6104   -1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5161   -2.9989   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4403   -3.9692   -0.6108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6040   -2.3879    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6372   -2.7893    1.8533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6929   -1.4455    1.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    0.5187   -0.0684 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0364   -0.3778   -0.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672   -0.1012   -0.4901 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0544    0.1532   -1.6769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3965    0.0382   -1.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3823   -1.3006   -0.5632 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4544   -2.3035   -1.5307 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4896   -1.4167    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3617   -2.6580    1.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -1.2805    0.1508 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2651   -1.0441    1.5017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308    3.1467   -3.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853    4.9398   -1.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2839    5.6192    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3474    2.7513    2.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.4028    1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8195   -1.4031   -1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -3.0754   -2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1643   -4.2125    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6917   -2.3412    2.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7516   -0.9670    2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895    1.2833    0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5056    0.8170    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0964    0.0787   -2.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5985    0.8121   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2379   -2.0885   -2.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4916   -1.3233    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824   -0.6425    1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9456   -2.6057    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869   -2.2219    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -0.2898    1.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 26  1  0
 26 27  1  6
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 12  1  0
 12 11  1  0
 11 10  1  0
 10  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  3  2  1  0
  2  1  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 23 30  1  0
 30 31  1  0
 30 26  1  0
  2 21  1  0
 20 13  1  0
  9 10  1  0
 29 49  1  0
 28 47  1  0
 28 48  1  0
 27 46  1  0
 25 44  1  0
 25 45  1  0
 23 43  1  1
 21 42  1  1
 12 36  1  1
  5 32  1  0
  6 33  1  0
  8 34  1  0
  9 35  1  0
 14 37  1  0
 15 38  1  0
 17 39  1  0
 19 40  1  0
 20 41  1  0
 30 50  1  1
 31 51  1  0
M  END


  Mrv1652304282203522D          

 31 34  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 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
    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 O   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  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5253   -2.9599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -3.7445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4454   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -2.9599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205   -4.0880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3652   -4.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224   -4.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  1  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  1  0  0  0
 16 20  1  6  0  0  0
 20 21  1  0  0  0  0
 15 22  1  6  0  0  0
  9 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@]1(O)CO[C@@H](O[C@@H]2[C@@H](OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O11/c21-6-20(28)7-29-19(18(20)27)31-17-15(26)14-12(25)4-9(22)5-13(14)30-16(17)8-1-2-10(23)11(24)3-8/h1-5,16-19,21-25,27-28H,6-7H2/t16-,17-,18-,19-,20-/m0/s1

> <INCHI_KEY>
HNNSDCGSWVUYQI-HVTWWXFQSA-N

> <FORMULA>
C20H20O11

> <MOLECULAR_WEIGHT>
436.369

> <EXACT_MASS>
436.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.09831862091747

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-3-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.14

> <JCHEM_LOGP>
0.5398852079999998

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.000362865530894

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.741320266387223

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423792503642884

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
101.2791

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+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       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.581  -5.525   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.105  -6.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.565  -6.990   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.089  -5.525   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.505  -7.631   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.282  -8.520   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.695  -9.131   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.045  -5.049   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   19   20                                             
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   16                                                            
CONECT   20   16   21                                                       
CONECT   21   20                                                            
CONECT   22   15                                                            
CONECT   23    9   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27                                                            
CONECT   30   26                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₁₁

Average Mass

436.3690 Da

Monoisotopic Mass

436.10056 Da

IUPAC Name

(2S,3R)-3-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S,3R)-3-{[(2S,3R,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC[C@]1(O)CO[C@@H](O[C@@H]2[C@@H](OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C(O)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C20H20O11/c21-6-20(28)7-29-19(18(20)27)31-17-15(26)14-12(25)4-9(22)5-13(14)30-16(17)8-1-2-10(23)11(24)3-8/h1-5,16-19,21-25,27-28H,6-7H2/t16-,17-,18-,19-,20-/m0/s1

InChI Key

HNNSDCGSWVUYQI-HVTWWXFQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Rosa davurica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanonols

Alternative Parents

Substituents

Hydroxyflavonoid
Flavanonol
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Pentose monosaccharide
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	0.14	ALOGPS
logP	0.54	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.28 m³·mol⁻¹	ChemAxon
Polarizability	41.1 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162981127

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Taxifolin 3-apioside (NP0055972)

MOL for NP0055972 (Taxifolin 3-apioside)

3D MOL for NP0055972 (Taxifolin 3-apioside)

3D SDF for NP0055972 (Taxifolin 3-apioside)

3D-SDF for NP0055972 (Taxifolin 3-apioside)

PDB for NP0055972 (Taxifolin 3-apioside)

3D PDB for NP0055972 (Taxifolin 3-apioside)

SMILES for NP0055972 (Taxifolin 3-apioside)

INCHI for NP0055972 (Taxifolin 3-apioside)

Structure for NP0055972 (Taxifolin 3-apioside)

3D Structure for NP0055972 (Taxifolin 3-apioside)