NP-MRD: Showing NP-Card for cyanidin 3-o-β-d-galactoside (NP0269548)

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Record Information

Version

2.0

Created at

2022-09-08 15:04:57 UTC

Updated at

2022-09-08 15:04:57 UTC

NP-MRD ID

NP0269548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyanidin 3-o-β-d-galactoside

Description

Cyanidin 3-galactoside, also known as idaein, 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. Cyanidin 3-galactoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-galactoside is found, on average, in the highest concentration in a few different foods, such as black chokeberries, lingonberries, and bilberries and in a lower concentration in american cranberries, highbush blueberries, and gooseberries. Cyanidin 3-galactoside has also been detected, but not quantified in, several different foods, such as sweet cherries, sparkleberries, summer grapes, nuts, and red raspberries. This could make cyanidin 3-galactoside a potential biomarker for the consumption of these foods. cyanidin 3-o-β-d-galactoside is found in Acalypha hispida, Camellia sinensis, Cornus suecica, Fagopyrum megacarpum, Malus pumila, Ribes rubrum, Rubus idaeus, Vaccinium angustifolium, Vaccinium arboreum, Vaccinium corymbosum, Vaccinium macrocarpon, Vaccinium myrtillus, Vaccinium padifolium and Visnea mocanera. cyanidin 3-o-β-d-galactoside was first documented in 2009 (PMID: 19351112). An anthocyanin cation that is cyanidin(1+) carrying a single beta-D-galactosyl substituent at position 3.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241221522D          

 32 35  0  0  0  0            999 V2000
   -5.5693    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693   -1.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8548   -1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8548   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1403    0.2225    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -4.1403   -1.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969    1.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114    1.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825    1.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693   -2.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5680    1.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9981    0.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969    2.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -2.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -3.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7114   -3.9025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9970   -3.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9970   -2.6650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7114   -2.2525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7114   -1.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825   -2.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825   -3.9025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114   -4.7275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -3.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -4.7275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
  9 27  1  0  0  0  0
 12 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 24 29  1  1  0  0  0
 23 30  1  1  0  0  0
 22 31  1  1  0  0  0
 31 32  1  0  0  0  0
M  CHG  1   7   1
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    2.4866    2.6240    2.1015 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3506    1.9436    1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    0.4960    1.6268 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0463    0.0136    1.5363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6191   -0.5238    0.3500 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3571   -0.0082    0.0687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460   -0.6196    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770   -1.9764    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2138   -2.5847    0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3812   -3.9320    0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2554   -4.6665    0.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6298   -4.5177    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7279   -3.7483    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9837   -4.3467   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5553   -2.4118   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3058   -1.8068   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -0.5427   -0.3326 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.9753    0.1033   -0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233    1.5269   -0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    2.1192   -0.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490    3.4535   -1.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447    4.2496   -1.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424    5.6169   -1.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    3.6976   -0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1109    4.4840   -0.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9341    2.3383   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5259   -0.3787   -0.8237 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3446   -1.4867   -1.6884 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -0.2365   -0.5714 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5045    0.9776   -1.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441   -0.3931    0.8858 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5759   -0.1938    1.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    3.5732    1.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862    2.0786    0.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3313    2.4029    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6104    0.4720    2.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5166   -1.6096    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -2.6070    0.5000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569   -5.6623    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793   -5.5716    0.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5241   -4.3768    0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3961   -1.7870   -0.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259    1.4985   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3392    3.8588   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    6.1906   -1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880    4.0712   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0538    1.9800   -0.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866    0.4943   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503   -2.2827   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5831   -1.0280   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883    0.8907   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -1.4465    1.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1787   -0.4098    0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 16  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 26  2  0
 26 24  1  0
 24 25  1  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 20  2  0
  5 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  3  1  0
 18  7  1  0
 20 19  1  0
 10  9  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  5 37  1  1
  8 38  1  0
 15 42  1  0
 14 41  1  0
 12 40  1  0
 11 39  1  0
 26 47  1  0
 25 46  1  0
 23 45  1  0
 21 44  1  0
 20 43  1  0
 27 48  1  6
 28 49  1  0
 29 50  1  6
 30 51  1  0
 31 52  1  1
 32 53  1  0
M  CHG  1  17   1
M  END


  Mrv0541 02241221522D          

 32 35  0  0  0  0            999 V2000
   -5.5693    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2837   -1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693   -1.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8548   -1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8548   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1403    0.2225    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -4.1403   -1.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969    1.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114    1.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969   -0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825    0.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825    1.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5693   -2.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5680    1.4600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9981    0.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969    2.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -2.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4259   -3.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7114   -3.9025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9970   -3.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9970   -2.6650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7114   -2.2525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7114   -1.4275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825   -2.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825   -3.9025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114   -4.7275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -3.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -4.7275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
  9 27  1  0  0  0  0
 12 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 24 29  1  1  0  0  0
 23 30  1  1  0  0  0
 22 31  1  1  0  0  0
 31 32  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0269548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17+,18+,19-,21-/m1/s1

> <INCHI_KEY>
RKWHWFONKJEUEF-WVXKDWSHSA-O

> <FORMULA>
C21H21O11

> <MOLECULAR_WEIGHT>
449.3848

> <EXACT_MASS>
449.108386514

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
43.04246655712965

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
0.38699999999999934

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.457961070975373

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.388329617449456

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923799280262

> <JCHEM_POLAR_SURFACE_AREA>
193.44

> <JCHEM_REFRACTIVITY>
116.25749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyanidin 3-O-β-D-galactoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -10.396   0.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.730  -0.355   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.730  -1.895   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.396  -2.665   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.062  -1.895   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.062  -0.355   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.729   0.415   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0      -7.729  -2.665   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.395  -1.895   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.395  -0.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.061   0.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.728   2.725   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.061   1.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.728  -0.355   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.394   0.415   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.394   1.955   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.396  -4.205   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.060   2.725   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0     -13.063   0.415   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.728   4.265   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.395  -4.975   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.395  -6.515   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.061  -7.285   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.728  -6.515   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.728  -4.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.061  -4.205   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.061  -2.665   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.394  -4.205   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.394  -7.285   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.061  -8.825   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -7.729  -7.285   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.729  -8.825   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   20                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   18                                                  
CONECT   17    4                                                            
CONECT   18   16                                                            
CONECT   19    2                                                            
CONECT   20   12                                                            
CONECT   21   22   26                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   21   25   27                                                  
CONECT   27    9   26                                                       
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   22   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Cyanidin 3-O-galactoside	ChEBI
Cyanidin 3-O-beta-D-galactoside	Kegg
Cyanidin 3-O-b-D-galactoside	Generator
Cyanidin 3-O-β-D-galactoside	Generator
Cyanidin 3-O-beta-D-galactopyranoside	HMDB
Idaein	HMDB
Idein	HMDB
Cy3-gal	MeSH
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-chromeniumyl beta-D-galactopyranoside chloride	MeSH
Cyanidin 3-galactoside	MeSH

Chemical Formula

C₂₁H₂₁O₁₁

Average Mass

449.3848 Da

Monoisotopic Mass

449.10839 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

Traditional Name

cyanidin 3-O-β-D-galactoside

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17+,18+,19-,21-/m1/s1

InChI Key

RKWHWFONKJEUEF-WVXKDWSHSA-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, 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
Acalypha hispida	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Cornus suecica	LOTUS Database	35616633
Fagopyrum megacarpum	LOTUS Database	35616633
Malus pumila	LOTUS Database	35616633
Ribes rubrum	LOTUS Database	35616633
Rubus idaeus	LOTUS Database	35616633
Vaccinium angustifolium	LOTUS Database	35616633
Vaccinium arboreum	LOTUS Database	35616633
Vaccinium corymbosum	LOTUS Database	35616633
Vaccinium macrocarpon	LOTUS Database	35616633
Vaccinium myrtillus	LOTUS Database	35616633
Vaccinium padifolium	LOTUS Database	35616633
Visnea mocanera	LOTUS Database	35616633

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
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:27475 )
anthocyanin cation (CHEBI:27475 )
beta-D-galactoside (CHEBI:27475 )
Anthocyanidins (C08647 )
Anthocyanidins and anthocyanins (C08647 )

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	0.98	ALOGPS
logP	0.39	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	193.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.26 m³·mol⁻¹	ChemAxon
Polarizability	43.04 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

HMDB0037977

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441699

PDB ID

Not Available

ChEBI ID

27475

Good Scents ID

Not Available

References

General References

Lehtonen HM, Rantala M, Suomela JP, Viitanen M, Kallio H: Urinary excretion of the main anthocyanin in lingonberry (Vaccinium vitis-idaea), cyanidin 3-O-galactoside, and its metabolites. J Agric Food Chem. 2009 May 27;57(10):4447-51. doi: 10.1021/jf900894k. Epub 2009 Apr 7. [PubMed:19351112 ]
LOTUS database [Link]

Showing NP-Card for cyanidin 3-o-β-d-galactoside (NP0269548)

MOL for NP0269548 (cyanidin 3-o-β-d-galactoside)

3D MOL for NP0269548 (cyanidin 3-o-β-d-galactoside)

3D SDF for NP0269548 (cyanidin 3-o-β-d-galactoside)

3D-SDF for NP0269548 (cyanidin 3-o-β-d-galactoside)

PDB for NP0269548 (cyanidin 3-o-β-d-galactoside)

3D PDB for NP0269548 (cyanidin 3-o-β-d-galactoside)

SMILES for NP0269548 (cyanidin 3-o-β-d-galactoside)

INCHI for NP0269548 (cyanidin 3-o-β-d-galactoside)

Structure for NP0269548 (cyanidin 3-o-β-d-galactoside)

3D Structure for NP0269548 (cyanidin 3-o-β-d-galactoside)