NP-MRD: Showing NP-Card for 5-Methylcyanidin 3-glucoside (NP0054478)

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Record Information

Version

2.0

Created at

2022-04-28 00:49:15 UTC

Updated at

2022-04-28 00:49:15 UTC

NP-MRD ID

NP0054478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Methylcyanidin 3-glucoside

Description

7-Hydroxy-5-methoxy-2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-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. 5-Methylcyanidin 3-glucoside is found in Egeria densa. Based on a literature review very few articles have been published on 7-Hydroxy-5-methoxy-2-(3,4-dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-1-benzopyrylium.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202492D          

 33 36  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
    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   -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
    0.7145   -2.8875    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  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
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 13 22  1  6  0  0  0
  8 23  1  0  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
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  CHG  1   7   1
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -1.8061   -5.0082   -1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5161   -3.6924   -1.1220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5619   -2.8151   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -3.2171   -1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8705   -2.3171   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1814   -2.7426   -1.1273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5890   -1.0493   -0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2605   -0.6519   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9798    0.5528    0.0981 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.7401    1.0119    0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768    2.3934    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5041    3.0317    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4734    4.3782    1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    5.0813    1.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690    6.4221    2.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8305    4.4619    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    5.1315    1.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8280    3.1493    0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6631    0.1802    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991    0.5915    0.3396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -0.0256    0.2268 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5544   -0.0840    1.4090 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343   -1.0474    1.2314 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2423   -1.4055    2.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8797   -0.3441    3.0997 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5507   -0.6613    0.1904 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4095   -1.7528    0.0248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7967   -0.4182   -1.1238 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6628    0.0077   -2.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    0.6205   -0.8021 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0402    1.0127   -1.9373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424   -1.1213   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2363   -1.5414   -0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3510   -5.5095   -0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8498   -5.5353   -1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -5.0135   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1178   -4.2217   -1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7401   -3.1588   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906   -0.3486   -0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    2.5678    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718    4.8622    1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    7.0054    2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    6.0758    1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767    2.6454    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6992   -1.0746   -0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0232   -1.9622    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5420   -1.9250    3.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0290   -2.1543    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5122    0.0578    2.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1467    0.2102    0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247   -1.4800   -0.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2875   -1.3616   -1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787    0.6656   -2.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581    1.4622   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365    1.8721   -2.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376   -1.8107   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 33  2  0
 33 32  1  0
 32 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 19 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
  4  3  1  0
 18 11  1  0
  8 33  1  0
 30 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 32 56  1  0
 21 45  1  6
 23 46  1  6
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  1
 27 51  1  0
 28 52  1  6
 29 53  1  0
 30 54  1  1
 31 55  1  0
  7 39  1  0
  6 38  1  0
  4 37  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
M  CHG  1   9   1
M  END


  Mrv1652304282202492D          

 33 36  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
    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   -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
    0.7145   -2.8875    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  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
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 13 22  1  6  0  0  0
  8 23  1  0  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
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0054478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=[O+]C2=CC(O)=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-30-14-5-10(24)6-15-11(14)7-16(21(31-15)9-2-3-12(25)13(26)4-9)32-22-20(29)19(28)18(27)17(8-23)33-22/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26)/p+1/t17-,18-,19+,20-,22-/m1/s1

> <INCHI_KEY>
ZEPNHKUGGSKVDG-OUUKCGNVSA-O

> <FORMULA>
C22H23O11

> <MOLECULAR_WEIGHT>
463.414

> <EXACT_MASS>
463.123487981

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.834838346639835

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
0.41869999999999963

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.994947189384648

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.6812622205965555

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923799280262

> <JCHEM_POLAR_SURFACE_AREA>
182.43999999999997

> <JCHEM_REFRACTIVITY>
120.73979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -4.620   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
HETATM   32  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   33                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22   13                                                            
CONECT   23    8   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    3   32                                                       
CONECT   32   31                                                            
CONECT   33    1                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-5-methoxy-2-(3,4-dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-1-benzopyrylium	Generator
7-Hydroxy-5-methoxy-2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-1-benzopyrylium	Generator

Chemical Formula

C₂₂H₂₃O₁₁

Average Mass

463.4140 Da

Monoisotopic Mass

463.12349 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

Traditional Name

2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

COC1=C2C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=[O+]C2=CC(O)=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C22H22O11/c1-30-14-5-10(24)6-15-11(14)7-16(21(31-15)9-2-3-12(25)13(26)4-9)32-22-20(29)19(28)18(27)17(8-23)33-22/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26)/p+1/t17-,18-,19+,20-,22-/m1/s1

InChI Key

ZEPNHKUGGSKVDG-OUUKCGNVSA-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
Egeria densa	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
5-methoxyflavonoid-skeleton
Hydroxyflavonoid
7-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Catechol
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	1.18	ALOGPS
logP	0.42	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.68	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	182.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.74 m³·mol⁻¹	ChemAxon
Polarizability	44.83 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

102357775

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-Methylcyanidin 3-glucoside (NP0054478)

MOL for NP0054478 (5-Methylcyanidin 3-glucoside)

3D MOL for NP0054478 (5-Methylcyanidin 3-glucoside)

3D SDF for NP0054478 (5-Methylcyanidin 3-glucoside)

3D-SDF for NP0054478 (5-Methylcyanidin 3-glucoside)

PDB for NP0054478 (5-Methylcyanidin 3-glucoside)

3D PDB for NP0054478 (5-Methylcyanidin 3-glucoside)

SMILES for NP0054478 (5-Methylcyanidin 3-glucoside)

INCHI for NP0054478 (5-Methylcyanidin 3-glucoside)

Structure for NP0054478 (5-Methylcyanidin 3-glucoside)

3D Structure for NP0054478 (5-Methylcyanidin 3-glucoside)