NP-MRD: Showing NP-Card for myrciacitrin i (NP0150829)

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Record Information

Version

2.0

Created at

2022-09-02 07:02:57 UTC

Updated at

2022-09-02 07:02:57 UTC

NP-MRD ID

NP0150829

Secondary Accession Numbers

None

Natural Product Identification

Common Name

myrciacitrin i

Description

Myrciacitrin I belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Myrciacitrin I is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. myrciacitrin i is found in Myrcia multiflora. myrciacitrin i was first documented in 1998 (PMID: 9468642). Based on a literature review very few articles have been published on myrciacitrin I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022209022D          

 34 37  0  0  1  0            999 V2000
   -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
    0.0000   -2.4750    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
    0.0000    0.8250    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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  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
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  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
   -3.5724   -0.4125    0.0000 C   0  0  2  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
   -2.8579    0.0000    0.0000 C   0  0  1  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
    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
    2.8579   -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
    3.5724    2.0625    0.0000 O   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
    3.5724   -1.2375    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -2.2698   -2.0809    1.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -1.6202    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1823   -1.7533    1.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186   -2.2363    3.1232 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4028   -1.3973    1.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206   -0.9173   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3864   -0.7860   -0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5376   -0.2927   -2.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -1.1360   -0.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410   -0.9934   -0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934    0.3005   -0.8414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2881    0.4063    0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    1.1599    0.4125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9001    1.3545    1.8633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0370    2.1674    1.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4889    0.2482   -0.2753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7723    0.8055   -0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0560    0.0507   -1.6970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2187   -1.2514   -2.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331    0.5399   -1.9402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6347    1.8840   -2.3013 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8228   -0.6214   -0.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6907   -0.0146    0.5075 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0313    0.3063   -0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7986    1.3154    0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9766    1.7065   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7823    2.7020    0.4096 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3390    1.0840   -1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5626    0.0595   -1.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4200   -0.3090   -1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5800   -1.3186   -1.7018 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845   -0.2800    1.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6339   -1.4486    2.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -2.4152    2.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725   -1.4624    2.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -3.1386    1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0063   -2.2144    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8767   -2.3441    3.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5563   -0.5508   -2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5144    0.8360   -2.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2421   -0.5940   -2.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    1.0407   -0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4258    2.0987   -0.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1778    0.3783    2.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942    1.8570    2.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8002    3.0959    1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4529   -0.7454    0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1734    0.4432    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902    0.7201   -2.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0825   -1.3165   -2.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    0.0012   -2.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8134    2.3477   -2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2437    1.1222    0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241    1.8344    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5246    2.3727    1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2360    1.3806   -1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8326   -0.4522   -2.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -1.7577   -2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5382   -0.7166    2.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785    0.5453    2.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6 22  1  0
 22 23  1  0
 23 32  1  0
 32 33  1  0
 33 34  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9  2  1  0
 20 11  1  0
 33  5  1  0
 30 24  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
 23 53  1  1
 32 59  1  0
 32 60  1  0
 25 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
 11 42  1  1
 13 43  1  6
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  1
 17 48  1  0
 18 49  1  6
 19 50  1  0
 20 51  1  6
 21 52  1  0
M  END


  Mrv1652309022209022D          

 34 37  0  0  1  0            999 V2000
   -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
    0.0000   -2.4750    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
    0.0000    0.8250    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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  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
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  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
   -3.5724   -0.4125    0.0000 C   0  0  2  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
   -2.8579    0.0000    0.0000 C   0  0  1  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
    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
    2.8579   -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
    3.5724    2.0625    0.0000 O   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
    3.5724   -1.2375    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0150829

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C2=C(O[C@@H](CC2=O)C2=CC(O)=CC=C2O)C(C)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O11/c1-8-17(28)16-13(27)6-14(11-5-10(25)3-4-12(11)26)32-22(16)9(2)21(8)34-23-20(31)19(30)18(29)15(7-24)33-23/h3-5,14-15,18-20,23-26,28-31H,6-7H2,1-2H3/t14-,15+,18+,19-,20+,23-/m0/s1

> <INCHI_KEY>
XIMHLIFRXMEWEW-HMFSKKNISA-N

> <FORMULA>
C23H26O11

> <MOLECULAR_WEIGHT>
478.45

> <EXACT_MASS>
478.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.67116418067684

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
1.290317414

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.732025640559412

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.121044348989129

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923461062435

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
115.4975

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   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       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   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  O   UNK     0      -2.667   0.000   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  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+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      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   33                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    6   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   24   31                                                  
CONECT   31   30                                                            
CONECT   32   23   33                                                       
CONECT   33   32    5   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2S)-6,8-Dimethyl-5,7,2',5'-tetrahydroxyflavanone-7-O-beta-D-glucopyranoside	ChEBI
(2S)-6,8-Dimethyl-5,7,2',5'-tetrahydroxyflavanone-7-O-b-D-glucopyranoside	Generator
(2S)-6,8-Dimethyl-5,7,2',5'-tetrahydroxyflavanone-7-O-β-D-glucopyranoside	Generator

Chemical Formula

C₂₃H₂₆O₁₁

Average Mass

478.4500 Da

Monoisotopic Mass

478.14751 Da

IUPAC Name

(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-2-(2,5-dihydroxyphenyl)-5-hydroxy-6,8-dimethyl-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

CC1=C(O)C2=C(O[C@@H](CC2=O)C2=CC(O)=CC=C2O)C(C)=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H26O11/c1-8-17(28)16-13(27)6-14(11-5-10(25)3-4-12(11)26)32-22(16)9(2)21(8)34-23-20(31)19(30)18(29)15(7-24)33-23/h3-5,14-15,18-20,23-26,28-31H,6-7H2,1-2H3/t14-,15+,18+,19-,20+,23-/m0/s1

InChI Key

XIMHLIFRXMEWEW-HMFSKKNISA-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
Myrcia multiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Chromane
Benzopyran
Aryl alkyl ketone
Aryl ketone
Hydroquinone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Ether
Polyol
Acetal
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:66417 )
monosaccharide derivative (CHEBI:66417 )
trihydroxyflavanone (CHEBI:66417 )
flavanone glycoside (CHEBI:66417 )

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	0.21	ALOGPS
logP	1.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-3	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	115.5 m³·mol⁻¹	ChemAxon
Polarizability	46.67 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

C00051681

Chemspider ID

159249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

183137

PDB ID

Not Available

ChEBI ID

66417

Good Scents ID

Not Available

References

General References

Yoshikawa M, Shimada H, Nishida N, Li Y, Toguchida I, Yamahara J, Matsuda H: Antidiabetic principles of natural medicines. II. Aldose reductase and alpha-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): structures of myrciacitrins I and II and myrciaphenones A and B. Chem Pharm Bull (Tokyo). 1998 Jan;46(1):113-9. doi: 10.1248/cpb.46.113. [PubMed:9468642 ]
LOTUS database [Link]

Showing NP-Card for myrciacitrin i (NP0150829)

MOL for NP0150829 (myrciacitrin i)

3D MOL for NP0150829 (myrciacitrin i)

3D SDF for NP0150829 (myrciacitrin i)

3D-SDF for NP0150829 (myrciacitrin i)

PDB for NP0150829 (myrciacitrin i)

3D PDB for NP0150829 (myrciacitrin i)

SMILES for NP0150829 (myrciacitrin i)

INCHI for NP0150829 (myrciacitrin i)

Structure for NP0150829 (myrciacitrin i)

3D Structure for NP0150829 (myrciacitrin i)