NP-MRD: Showing NP-Card for Delphinidin 3-(6''-malonylglucoside) 5-glucoside (NP0049529)

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Record Information

Version

2.0

Created at

2022-03-17 21:13:58 UTC

Updated at

2022-03-17 21:13:58 UTC

NP-MRD ID

NP0049529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Delphinidin 3-(6''-malonylglucoside) 5-glucoside

Description

Delphinidin 3-(6''-malonylglucoside) 5-glucoside belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Delphinidin 3-(6''-malonylglucoside) 5-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, delphinidin 3-(6''-malonylglucoside) 5-glucoside has been detected, but not quantified in, several different foods, such as chicories, coffee and coffee products, green vegetables, and herbs and spices. Delphinidin 3-(6''-malonylglucoside) 5-glucoside is found in Dianthus caryophyllus . This could make delphinidin 3-(6''-malonylglucoside) 5-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04261302192D          

 50 54  0  0  0  0            999 V2000
   -5.9518   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6663   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6663   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2373   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2373   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229   -1.1196    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -4.5229   -2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3807   -1.1196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -3.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794    0.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505    0.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505   -1.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3807   -3.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0952   -4.0072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0952   -4.8322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3807   -5.2447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6663   -4.8322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6663   -4.0072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9518   -5.2447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8097   -3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8097   -5.2447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3807   -6.0697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5241   -4.0072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -4.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -4.8321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0939   -5.2446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3794   -4.8322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3794   -4.0072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0939   -3.5946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0939   -2.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -3.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229   -5.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939   -6.0696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -5.2447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -8.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9353   -8.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -7.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9353   -6.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -6.0696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7603   -8.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7603   -6.7841    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
  5  6  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
  2 17  1  0  0  0  0
  4 18  1  0  0  0  0
  9 39  1  0  0  0  0
 12 19  1  0  0  0  0
 16 20  1  0  0  0  0
 15 21  1  0  0  0  0
 27 18  1  1  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 29  1  1  0  0  0
 25 24  1  0  0  0  0
 24 30  1  6  0  0  0
 25 26  1  0  0  0  0
 25 31  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  1  6  0  0  0
 29 32  1  0  0  0  0
 33 34  1  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 34 41  1  1  0  0  0
 36 35  1  0  0  0  0
 35 42  1  6  0  0  0
 36 37  1  0  0  0  0
 36 43  1  1  0  0  0
 37 38  1  0  0  0  0
 37 40  1  6  0  0  0
 38 39  1  1  0  0  0
 41 48  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 45 49  1  0  0  0  0
 47 50  2  0  0  0  0
M  CHG  1   7   1
M  END


  Mrv0541 04261302192D          

 50 54  0  0  0  0            999 V2000
   -5.9518   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6663   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6663   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2373   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2373   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229   -1.1196    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -4.5229   -2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3807   -1.1196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9518   -3.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794    0.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505    0.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505   -1.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3807   -3.5946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0952   -4.0072    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0952   -4.8322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3807   -5.2447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6663   -4.8322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6663   -4.0072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9518   -5.2447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8097   -3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8097   -5.2447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3807   -6.0697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5241   -4.0072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -4.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -4.8321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0939   -5.2446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3794   -4.8322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3794   -4.0072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0939   -3.5946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0939   -2.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -3.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5229   -5.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0939   -6.0696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6650   -5.2447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -8.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9353   -8.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -7.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9353   -6.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228   -6.0696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7603   -8.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7603   -6.7841    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
  5  6  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
  2 17  1  0  0  0  0
  4 18  1  0  0  0  0
  9 39  1  0  0  0  0
 12 19  1  0  0  0  0
 16 20  1  0  0  0  0
 15 21  1  0  0  0  0
 27 18  1  1  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 29  1  1  0  0  0
 25 24  1  0  0  0  0
 24 30  1  6  0  0  0
 25 26  1  0  0  0  0
 25 31  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  1  6  0  0  0
 29 32  1  0  0  0  0
 33 34  1  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 34 41  1  1  0  0  0
 36 35  1  0  0  0  0
 35 42  1  6  0  0  0
 36 37  1  0  0  0  0
 36 43  1  1  0  0  0
 37 38  1  0  0  0  0
 37 40  1  6  0  0  0
 38 39  1  1  0  0  0
 41 48  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 45 49  1  0  0  0  0
 47 50  2  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
NP0049529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=CC3=C2C=C(O[C@@H]2O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(=[O+]3)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O20/c31-7-17-22(39)24(41)26(43)29(49-17)47-15-4-10(32)3-14-11(15)5-16(28(46-14)9-1-12(33)21(38)13(34)2-9)48-30-27(44)25(42)23(40)18(50-30)8-45-20(37)6-19(35)36/h1-5,17-18,22-27,29-31,39-44H,6-8H2,(H4-,32,33,34,35,36,38)/p+1/t17-,18-,22-,23-,24+,25+,26-,27-,29-,30-/m1/s1

> <INCHI_KEY>
KKMPMQKPBOCHRG-YEQKKNNOSA-O

> <FORMULA>
C30H33O20

> <MOLECULAR_WEIGHT>
713.571

> <EXACT_MASS>
713.156518496

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
66.2958478476717

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
-2.2722

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.612828382447817

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.291680664959328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6789695878870257

> <JCHEM_POLAR_SURFACE_AREA>
336.19

> <JCHEM_REFRACTIVITY>
165.87840000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-13         0                                  
HETATM    1  C   UNK     0     -11.110  -2.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.444  -2.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.444  -4.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.110  -5.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.776  -4.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.776  -2.860   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.443  -2.090   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0      -8.443  -5.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.109  -4.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.109  -2.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.775  -2.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.442   0.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.775  -0.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.442  -2.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.108  -2.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.108  -0.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.777  -2.090   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -11.110  -6.710   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.442   1.760   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.774   0.220   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.774  -2.860   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -13.777  -6.710   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -15.111  -7.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.111  -9.020   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.777  -9.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.444  -9.020   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -12.444  -7.480   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -11.110  -9.790   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -16.445  -6.710   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -16.445  -9.790   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -13.777 -11.330   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -17.778  -7.480   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -7.109  -7.480   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.109  -9.020   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.775  -9.790   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.442  -9.020   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.442  -7.480   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.775  -6.710   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.775  -5.170   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.108  -6.710   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -8.443  -9.790   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.775 -11.330   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -3.108  -9.790   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -8.443 -16.665   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -9.213 -15.331   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.443 -13.997   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.213 -12.664   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -8.443 -11.330   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -10.753 -15.331   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -10.753 -12.664   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   19                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   12   15   20                                                  
CONECT   17    2                                                            
CONECT   18    4   27                                                       
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21   15                                                            
CONECT   22   23   27                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   18   22   26                                                  
CONECT   28   26                                                            
CONECT   29   23   32                                                       
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32   29                                                            
CONECT   33   34   38                                                       
CONECT   34   33   35   41                                                  
CONECT   35   34   36   42                                                  
CONECT   36   35   37   43                                                  
CONECT   37   36   38   40                                                  
CONECT   38   33   37   39                                                  
CONECT   39    9   38                                                       
CONECT   40   37                                                            
CONECT   41   34   48                                                       
CONECT   42   35                                                            
CONECT   43   36                                                            
CONECT   44   45                                                            
CONECT   45   44   46   49                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   50                                                  
CONECT   48   41   47                                                       
CONECT   49   45                                                            
CONECT   50   47                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  108    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₃O₂₀

Average Mass

713.5710 Da

Monoisotopic Mass

713.15652 Da

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

CAS Registry Number

104078-08-2

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=CC3=C2C=C(O[C@@H]2O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(=[O+]3)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C30H32O20/c31-7-17-22(39)24(41)26(43)29(49-17)47-15-4-10(32)3-14-11(15)5-16(28(46-14)9-1-12(33)21(38)13(34)2-9)48-30-27(44)25(42)23(40)18(50-30)8-45-20(37)6-19(35)36/h1-5,17-18,22-27,29-31,39-44H,6-8H2,(H4-,32,33,34,35,36,38)/p+1/t17-,18-,22-,23-,24+,25+,26-,27-,29-,30-/m1/s1

InChI Key

KKMPMQKPBOCHRG-YEQKKNNOSA-O

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cichorium intybus	FooDB	KNAPSACK
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Dianthus caryophyllus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-5-O-glycosides

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.51	ALOGPS
logP	-2.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	336.19 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	165.88 m³·mol⁻¹	ChemAxon
Polarizability	66.3 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0039938

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019600

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

11972332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Delphinidin 3-(6''-malonylglucoside) 5-glucoside (NP0049529)

MOL for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

3D MOL for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

3D SDF for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

3D-SDF for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

PDB for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

3D PDB for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

SMILES for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

INCHI for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

Structure for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)

3D Structure for NP0049529 (Delphinidin 3-(6''-malonylglucoside) 5-glucoside)