NP-MRD: Showing NP-Card for (2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside (NP0060559)

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Record Information

Version

2.0

Created at

2022-04-28 05:35:00 UTC

Updated at

2022-04-28 05:35:01 UTC

NP-MRD ID

NP0060559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside

Description

(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. (2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside is found in Aspalathus linearis . Based on a literature review very few articles have been published on (2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207352D          

 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 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 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  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    2.0625    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
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   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
    0.0000    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  2  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
    2.8579   -1.6500    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
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
   -1.4289   -1.6500    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
  7  6  1  1  0  0  0
  7  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
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 22 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 27 30  1  0  0  0  0
 26 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    1.1478   -2.3451   -1.8525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -1.3095   -1.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271   -0.7562   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483   -0.6689    0.0857 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7878   -0.6738    0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4313   -1.9300    0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7764   -2.0313    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5298   -0.8653    0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9310   -1.0109    0.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9460    0.3713    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6689    1.5423    0.6373 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5516    0.4539    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    0.3490    0.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201    0.3563    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3725    1.1811    1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093    1.1649    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607    2.0373    1.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.3238   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042    0.2363   -0.2350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5931   -0.9443   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9508   -0.8156    0.2764 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0965   -0.7945    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4220    0.2533    2.4115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6284    0.3916   -0.2493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9731    1.3238    0.7318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9953    1.0717   -1.4123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5141    0.5796   -2.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4901    1.0224   -1.4417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9577    2.2678   -1.5540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -0.5205   -0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015   -1.3375   -1.6564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6224   -0.4869   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -1.3649   -2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437    0.3108   -1.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -1.6875    0.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8202   -2.8410    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3240   -2.9907    0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5321   -0.2141    0.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1976    2.4274    0.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579    1.4246    0.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130    1.8486    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501    2.6657    2.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4326    0.9300    0.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -1.7623   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1903   -0.7201    2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7083   -1.7487    2.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6479   -0.0823    2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6373    0.0251   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8219    2.2330    0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2944    2.1424   -1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0969   -0.2783   -2.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517    0.3849   -2.3859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151    2.8717   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9719   -2.0103   -2.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 19 18  1  0
 18 30  2  0
 30 31  1  0
 30 32  1  0
 32 14  2  0
 14 13  1  0
 13  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 24 21  1  0
 16 18  1  0
  2 32  1  0
  6  5  1  0
 23 47  1  0
 22 45  1  0
 22 46  1  0
 21 44  1  6
 19 43  1  1
 28 52  1  6
 29 53  1  0
 26 50  1  1
 27 51  1  0
 24 48  1  6
 25 49  1  0
 31 54  1  0
  4 35  1  1
  3 33  1  0
  3 34  1  0
 12 40  1  0
 11 39  1  0
  9 38  1  0
  7 37  1  0
  6 36  1  0
 15 41  1  0
 17 42  1  0
M  END


  Mrv1652304282207352D          

 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 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 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  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    2.0625    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
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   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
    0.0000    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  2  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
    2.8579   -1.6500    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
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
   -1.4289   -1.6500    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
  7  6  1  1  0  0  0
  7  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
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 22 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 27 30  1  0  0  0  0
 26 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(O[C@@H](CC2=O)C2=CC(O)=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-3,5,12,14,17,19-24,26-30H,4,6H2/t12-,14-,17+,19-,20+,21-/m0/s1

> <INCHI_KEY>
FNJRUYGFVNGXTL-QQWMYQIUSA-N

> <FORMULA>
C21H22O11

> <MOLECULAR_WEIGHT>
450.396

> <EXACT_MASS>
450.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.054486770582045

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-0.22577817633333408

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.849608352464454

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.421984499163939

> <JCHEM_PKA_STRONGEST_BASIC>
-3.644730891778007

> <JCHEM_POLAR_SURFACE_AREA>
197.36999999999998

> <JCHEM_REFRACTIVITY>
106.389

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-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  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -3.080   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  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    8                                                            
CONECT   18    5                                                            
CONECT   19    4   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22    3                                                       
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   27                                                            
CONECT   31   26                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₁₁

Average Mass

450.3960 Da

Monoisotopic Mass

450.11621 Da

IUPAC Name

(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C(O)C2=C(O[C@@H](CC2=O)C2=CC(O)=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C21H22O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-3,5,12,14,17,19-24,26-30H,4,6H2/t12-,14-,17+,19-,20+,21-/m0/s1

InChI Key

FNJRUYGFVNGXTL-QQWMYQIUSA-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
Aspalathus linearis	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
Hydroxyflavonoid
Flavanone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
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	-0.1	ALOGPS
logP	-0.23	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.42	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.39 m³·mol⁻¹	ChemAxon
Polarizability	44.05 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

162904320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside (NP0060559)

MOL for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

3D MOL for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

3D SDF for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

3D-SDF for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

PDB for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

3D PDB for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

SMILES for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

INCHI for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

Structure for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)

3D Structure for NP0060559 ((2S)-5,7,3',4'-Tetrahydroxyflavanone 6-C-glucoside)