NP-MRD: Showing NP-Card for Pelargonidin 3-(6''-acetylglucoside) (NP0054514)

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Record Information

Version

2.0

Created at

2022-04-28 00:50:41 UTC

Updated at

2022-04-28 00:50:41 UTC

NP-MRD ID

NP0054514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pelargonidin 3-(6''-acetylglucoside)

Description

2-(4-Hydroxyphenyl)-3-(6-O-acetyl-beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Thus, 2-(4-hydroxyphenyl)-3-(6-O-acetyl-beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium is considered to be a flavonoid. Pelargonidin 3-(6''-acetylglucoside) is found in Verbena x hybrida. Based on a literature review very few articles have been published on 2-(4-Hydroxyphenyl)-3-(6-O-acetyl-beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282202502D          

 34 37  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  3  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  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
    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
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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    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
   -1.4289    0.0000    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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  6  0  0  0
 14 24  1  1  0  0  0
 13 25  1  6  0  0  0
  8 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 29 32  1  0  0  0  0
  3 33  1  0  0  0  0
  1 34  1  0  0  0  0
M  CHG  1   7   1
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    6.9903   -2.3911    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4927   -2.4235    0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9143   -3.4274    0.6711 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7473   -1.3902   -0.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3317   -1.4074   -0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9005   -0.0892   -1.0462 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5648    0.0319   -1.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8752    0.8277   -0.2772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3157    0.2210    0.0310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    0.5294   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732    1.7136   -0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2969    1.9956   -0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6819    3.1523   -1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583    4.0398   -2.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0498    3.3783   -1.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0110    2.5152   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3763    2.7486   -1.4678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614    1.3686   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2317    1.0994   -0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8541    0.0145    0.0773 O   0  0  0  0  0  3  0  0  0  0  0  0
   -2.5847   -0.3364    0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -1.5941    0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1249   -2.1154    1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108   -3.3516    1.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1504   -4.0414    2.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0082   -5.2514    2.9590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4048   -3.5410    2.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4802   -2.3375    1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862    1.1984    0.9483 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9201    2.1410    1.6739 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9062    1.9233    0.4689 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6911    2.4309    1.4952 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6615    1.0403   -0.4503 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2606    1.8547   -1.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3993   -3.4014    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3710   -1.8957   -0.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3582   -1.7719    1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9577   -2.2736   -0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633   -1.5112    0.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3036   -0.2025   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015    1.7843   -0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1670    2.3310   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781    3.9335   -2.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3604    4.2829   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9374    3.2390   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3501    0.6871   -0.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374   -1.5894    1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0047   -3.6884    2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8062   -5.7943    3.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3163   -4.0788    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4839   -1.9443    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8698    0.3722    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.9133    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    2.8071   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1707    3.2556    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5390    0.6248    0.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    1.3937   -2.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
  8 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  6  1  0
 21 10  1  0
 28 22  1  0
 19 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  6
  8 41  1  6
 11 42  1  0
 14 43  1  0
 15 44  1  0
 17 45  1  0
 18 46  1  0
 23 47  1  0
 24 48  1  0
 26 49  1  0
 27 50  1  0
 28 51  1  0
 29 52  1  1
 30 53  1  0
 31 54  1  6
 32 55  1  0
 33 56  1  1
 34 57  1  0
M  CHG  1  20   1
M  END

  Mrv1652304282202502D          

 34 37  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  3  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  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
    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
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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    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
   -1.4289    0.0000    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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  6  0  0  0
 14 24  1  1  0  0  0
 13 25  1  6  0  0  0
  8 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
 29 32  1  0  0  0  0
  3 33  1  0  0  0  0
  1 34  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0054514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O11/c1-10(24)31-9-18-19(28)20(29)21(30)23(34-18)33-17-8-14-15(27)6-13(26)7-16(14)32-22(17)11-2-4-12(25)5-3-11/h2-8,18-21,23,28-30H,9H2,1H3,(H2-,25,26,27)/p+1/t18-,19-,20+,21-,23-/m1/s1

> <INCHI_KEY>
SYFJGOZRUVEOJC-ZFVIQDPVSA-O

> <FORMULA>
C23H23O11

> <MOLECULAR_WEIGHT>
475.425

> <EXACT_MASS>
475.123487981

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.08891571403615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.1004999999999994

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.535853469013329

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.396818380179358

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649102880226849

> <JCHEM_POLAR_SURFACE_AREA>
179.27999999999997

> <JCHEM_REFRACTIVITY>
123.4281

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

> <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  -0.770   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  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15                                                            
CONECT   24   14                                                            
CONECT   25   13                                                            
CONECT   26    8   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29                                                            
CONECT   33    3                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-(4-Hydroxyphenyl)-3-(6-O-acetyl-b-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium	Generator
2-(4-Hydroxyphenyl)-3-(6-O-acetyl-β-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium	Generator

Chemical Formula

C₂₃H₂₃O₁₁

Average Mass

475.4250 Da

Monoisotopic Mass

475.12349 Da

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H22O11/c1-10(24)31-9-18-19(28)20(29)21(30)23(34-18)33-17-8-14-15(27)6-13(26)7-16(14)32-22(17)11-2-4-12(25)5-3-11/h2-8,18-21,23,28-30H,9H2,1H3,(H2-,25,26,27)/p+1/t18-,19-,20+,21-,23-/m1/s1

InChI Key

SYFJGOZRUVEOJC-ZFVIQDPVSA-O

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
Verbena hybrida	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organic cation
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	1.83	ALOGPS
logP	1.1	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.43 m³·mol⁻¹	ChemAxon
Polarizability	46.09 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	Yes	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

28284424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23584711

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pelargonidin 3-(6''-acetylglucoside) (NP0054514)

MOL for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

3D MOL for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

3D SDF for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

3D-SDF for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

PDB for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

3D PDB for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

SMILES for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

INCHI for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

Structure for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))

3D Structure for NP0054514 (Pelargonidin 3-(6''-acetylglucoside))