NP-MRD: Showing NP-Card for mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside (NP0025718)

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Record Information

Version

1.0

Created at

2021-06-19 17:46:12 UTC

Updated at

2021-06-29 23:50:50 UTC

NP-MRD ID

NP0025718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside

Provided By

JEOL Database JEOL Logo

Description

3-{[(2R,3S,4R,5S,6R)-6-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside is found in Ribes alpinum. It was first documented in 2001 (Gluchoff-Fiasson, K., et al.). Based on a literature review very few articles have been published on 3-{[(2R,3S,4R,5S,6R)-6-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119463D          

 64 67  0  0  0  0            999 V2000
    0.9658    3.2789   -4.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    1.8557   -4.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    1.4404   -3.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3938    1.8265   -2.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372    2.6630   -1.9196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    1.3405   -1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    0.4373   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685   -0.0555   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995    0.2105   -0.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588   -0.1897    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9872    0.0634   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0037   -0.3113    0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2881   -0.0464    0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7150   -0.9318    1.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857   -1.1793    2.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1611   -1.7856    3.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558   -0.8127    1.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6368   -1.5320    2.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357   -0.7044    0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967   -0.9463    0.9365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861   -2.3433    1.0848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0353   -2.9672   -0.1815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496   -2.3860   -0.8950 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2065   -3.1717   -2.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -2.3331   -0.1155 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1876   -1.3791   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754   -1.1401   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -1.7641    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353   -0.0202   -1.3502 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0698    1.1185   -1.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844    1.5632   -0.5358 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905    1.6312   -2.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -1.8478    1.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2893   -2.2010    2.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2302   -3.8593    2.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6613    0.0243   -2.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.5156   -3.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553    0.0771   -5.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0456    3.7631   -4.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    3.5199   -5.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360    3.6738   -4.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868    2.5187   -0.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    1.6671   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2317    0.5501   -1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8895   -0.3671    1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5005   -1.2250    2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -1.8774    3.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8850   -3.3079   -0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2701   -0.4146   -2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9552    0.3519   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0957   -0.7543    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215   -2.0634    1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7578   -1.9895    2.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1179   -3.8418    2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.6800   -3.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    0.5003   -5.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7 38  2  0  0  0  0
 34 35  1  0  0  0  0
 12 14  2  0  0  0  0
 34 26  1  0  0  0  0
 34 36  1  0  0  0  0
 36 22  1  0  0  0  0
  7  6  1  0  0  0  0
 38 39  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  6  2  0  0  0  0
  8  7  1  0  0  0  0
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  6 45  1  0  0  0  0
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 40 64  1  0  0  0  0
 30 56  1  0  0  0  0
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 33 58  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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    0.9171    1.8557   -4.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192119463D          

 64 67  0  0  0  0            999 V2000
    0.9658    3.2789   -4.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    1.8557   -4.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    1.4404   -3.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3938    1.8265   -2.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372    2.6630   -1.9196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    1.3405   -1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    0.4373   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685   -0.0555   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995    0.2105   -0.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588   -0.1897    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5005   -1.2250    2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8850   -3.3079   -0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2701   -0.4146   -2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0  0  0  0
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  8  7  1  0  0  0  0
 12 11  1  0  0  0  0
 18 19  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
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  3  2  1  0  0  0  0
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  2  1  1  0  0  0  0
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 10  9  1  0  0  0  0
 30 31  1  0  0  0  0
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 33 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C(=O)O[C@@]1([H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]([H])(OC2=C(OC3=C([H])C(O[H])=C([H])C(O[H])=C3C2=O)C2=C([H])C(O[H])=C(OC([H])([H])[H])C(O[H])=C2[H])O[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O15/c1-8-21(39-16(32)7-15(30)31)19(34)20(35)25(37-8)40-24-18(33)17-11(27)5-10(26)6-14(17)38-22(24)9-3-12(28)23(36-2)13(29)4-9/h3-6,8,19-21,25-29,34-35H,7H2,1-2H3,(H,30,31)/t8-,19-,20+,21-,25-/m1/s1

> <INCHI_KEY>
ZYSQXSNEDGAKCG-MTBBIAQTSA-N

> <FORMULA>
C25H24O15

> <MOLECULAR_WEIGHT>
564.452

> <EXACT_MASS>
564.111520073

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.40141598191106

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R,3S,4R,5S,6R)-6-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.0777572613333333

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.375448343665798

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6260715934151846

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6916265174757363

> <JCHEM_POLAR_SURFACE_AREA>
238.96999999999997

> <JCHEM_REFRACTIVITY>
129.6906

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R,3S,4R,5S,6R)-6-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    0.9658    3.2789   -4.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2065   -3.1717   -2.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1876   -1.3791   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0698    1.1185   -1.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2893   -2.2010    2.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433   -2.4787    1.9907 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2302   -3.8593    2.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6613    0.0243   -2.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.5156   -3.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7578   -1.9895    2.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1179   -3.8418    2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3602    0.5003   -5.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  8  2  0
  8  9  1  0
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 40 64  1  0
 30 56  1  0
 30 57  1  0
 33 58  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.966   3.279  -4.722  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.917   1.856  -4.606  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.167   1.440  -3.535  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.394   1.827  -2.214  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.437   2.663  -1.920  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.421   1.341  -1.185  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.462   0.437  -1.469  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.369  -0.056  -0.413  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.700   0.211  -0.697  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.659  -0.190   0.195  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.987   0.063  -0.147  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.004  -0.311   0.727  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.288  -0.046   0.355  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.715  -0.932   1.939  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.386  -1.179   2.275  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.161  -1.786   3.482  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.356  -0.813   1.401  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.946  -1.061   1.721  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.637  -1.532   2.812  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.936  -0.704   0.687  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.597  -0.946   0.937  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.286  -2.343   1.085  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.035  -2.967  -0.182  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.050  -2.386  -0.895  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.206  -3.172  -2.196  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.382  -2.333  -0.116  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.188  -1.379  -0.868  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.475  -1.140  -0.529  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.096  -1.764   0.320  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.035  -0.020  -1.350  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.070   1.119  -1.447  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.384   1.563  -0.536  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.990   1.631  -2.690  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.175  -1.848   1.336  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.289  -2.201   2.184  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.943  -2.479   1.991  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.230  -3.859   2.277  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.661   0.024  -2.794  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.842   0.516  -3.804  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.055   0.077  -5.082  0.00  0.00           O+0
HETATM   41  H   UNK     0       0.046   3.763  -4.375  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.089   3.520  -5.782  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.836   3.674  -4.190  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.687   2.519  -0.980  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.256   1.667  -0.161  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.232   0.550  -1.087  0.00  0.00           H+0
HETATM   47  H   UNK     0      -8.890  -0.367   1.049  0.00  0.00           H+0
HETATM   48  H   UNK     0      -7.500  -1.225   2.629  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.189  -1.877   3.606  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.106  -2.910   1.538  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.766  -1.369  -1.183  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.263  -3.178  -2.753  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.457  -4.218  -1.990  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.983  -2.744  -2.837  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.885  -3.308  -0.128  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.270  -0.415  -2.344  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.955   0.352  -0.890  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.213   2.239  -2.684  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.096  -0.754   1.352  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.122  -2.063   1.682  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.758  -1.990   2.954  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.118  -3.842   2.692  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.451  -0.680  -3.046  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.360   0.500  -5.623  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    3    1                                                       
CONECT    3   39    4    2                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   44                                                       
CONECT    6    7    4   45                                                  
CONECT    7   38    6    8                                                  
CONECT    8   20    9    7                                                  
CONECT    9    8   10                                                       
CONECT   10   11   17    9                                                  
CONECT   11   12   10   46                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12   47                                                       
CONECT   14   12   15   48                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   49                                                       
CONECT   17   15   10   18                                                  
CONECT   18   19   17   20                                                  
CONECT   19   18                                                            
CONECT   20    8   21   18                                                  
CONECT   21   20   22                                                       
CONECT   22   36   23   21   50                                             
CONECT   23   22   24                                                       
CONECT   24   23   26   25   51                                             
CONECT   25   24   52   53   54                                             
CONECT   26   34   24   27   55                                             
CONECT   27   28   26                                                       
CONECT   28   27   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28   31   56   57                                             
CONECT   31   30   33   32                                                  
CONECT   32   31                                                            
CONECT   33   31   58                                                       
CONECT   34   35   26   36   59                                             
CONECT   35   34   60                                                       
CONECT   36   34   22   37   61                                             
CONECT   37   36   62                                                       
CONECT   38    7   39   63                                                  
CONECT   39   38    3   40                                                  
CONECT   40   39   64                                                       
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    5                                                            
CONECT   45    6                                                            
CONECT   46   11                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   16                                                            
CONECT   50   22                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   30                                                            
CONECT   57   30                                                            
CONECT   58   33                                                            
CONECT   59   34                                                            
CONECT   60   35                                                            
CONECT   61   36                                                            
CONECT   62   37                                                            
CONECT   63   38                                                            
CONECT   64   40                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  134    0
END

RDKit          3D

64 67  0  0  0  0  0  0  0  0999 V2000
    0.9658    3.2789   -4.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171    1.8557   -4.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1674    1.4404   -3.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3938    1.8265   -2.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372    2.6630   -1.9196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    1.3405   -1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    0.4373   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685   -0.0555   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995    0.2105   -0.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6588   -0.1897    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9872    0.0634   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0037   -0.3113    0.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2881   -0.0464    0.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7150   -0.9318    1.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857   -1.1793    2.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1611   -1.7856    3.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558   -0.8127    1.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9463   -1.0606    1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368   -1.5320    2.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357   -0.7044    0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967   -0.9463    0.9365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861   -2.3433    1.0848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0353   -2.9672   -0.1815 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0496   -2.3860   -0.8950 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2065   -3.1717   -2.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -2.3331   -0.1155 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1876   -1.3791   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754   -1.1401   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -1.7641    0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353   -0.0202   -1.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0698    1.1185   -1.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844    1.5632   -0.5358 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905    1.6312   -2.6900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -1.8478    1.3360 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2893   -2.2010    2.1840 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433   -2.4787    1.9907 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2302   -3.8593    2.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6613    0.0243   -2.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.5156   -3.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553    0.0771   -5.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0456    3.7631   -4.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0894    3.5199   -5.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360    3.6738   -4.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868    2.5187   -0.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    1.6671   -0.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2317    0.5501   -1.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8895   -0.3671    1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5005   -1.2250    2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -1.8774    3.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1063   -2.9101    1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7663   -1.3686   -1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2629   -3.1777   -2.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4566   -4.2184   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -2.7443   -2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850   -3.3079   -0.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2701   -0.4146   -2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9552    0.3519   -0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127    2.2393   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -0.7543    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215   -2.0634    1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7578   -1.9895    2.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1179   -3.8418    2.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4506   -0.6800   -3.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    0.5003   -5.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  8  2  0
  8  9  1  0
  7 38  2  0
 34 35  1  0
 12 14  2  0
 34 26  1  0
 34 36  1  0
 36 22  1  0
  7  6  1  0
 38 39  1  0
 39  3  2  0
  3  4  1  0
  4  6  2  0
  8  7  1  0
 12 11  1  0
 18 19  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 12 13  1  0
 10 11  2  0
  4  5  1  0
 10 17  1  0
 20 21  1  0
 22 23  1  0
  3  2  1  0
 23 24  1  0
  2  1  1  0
 24 26  1  0
 39 40  1  0
 27 28  1  0
 28 30  1  0
 28 29  2  0
 10  9  1  0
 30 31  1  0
 17 18  1  0
 31 33  1  0
 18 20  1  0
 31 32  2  0
 26 27  1  0
 24 25  1  0
 22 21  1  0
 36 37  1  0
 37 62  1  0
 26 55  1  1
 22 50  1  1
 25 52  1  0
 25 53  1  0
 25 54  1  0
 24 51  1  6
 36 61  1  1
 34 59  1  6
 35 60  1  0
 14 48  1  0
 11 46  1  0
 38 63  1  0
  6 45  1  0
 16 49  1  0
 13 47  1  0
  5 44  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
 40 64  1  0
 30 56  1  0
 30 57  1  0
 33 58  1  0
M  END

View in JSmol

Synonyms

Value	Source
3-{[(2R,3S,4R,5S,6R)-6-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₅H₂₄O₁₅

Average Mass

564.4520 Da

Monoisotopic Mass

564.11152 Da

IUPAC Name

3-{[(2R,3S,4R,5S,6R)-6-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[(2R,3S,4R,5S,6R)-6-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C(=O)O[C@@]1([H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]([H])(OC2=C(OC3=C([H])C(O[H])=C([H])C(O[H])=C3C2=O)C2=C([H])C(O[H])=C(OC([H])([H])[H])C(O[H])=C2[H])O[C@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H24O15/c1-8-21(39-16(32)7-15(30)31)19(34)20(35)25(37-8)40-24-18(33)17-11(27)5-10(26)6-14(17)38-22(24)9-3-12(28)23(36-2)13(29)4-9/h3-6,8,19-21,25-29,34-35H,7H2,1-2H3,(H,30,31)/t8-,19-,20+,21-,25-/m1/s1

InChI Key

ZYSQXSNEDGAKCG-MTBBIAQTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ribes alpinum	JEOL database	Gluchoff-Fiasson, K., et al, Chem. Pharm. Bull. 49, 768 (2001)

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Methoxyphenol
Anisole
Resorcinol
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Sugar acid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
1,3-dicarbonyl compound
Dicarboxylic acid or derivatives
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
1,2-diol
Carboxylic acid ester
Secondary alcohol
Oxacycle
Carboxylic acid
Ether
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	2.02	ALOGPS
logP	1.08	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	238.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.69 m³·mol⁻¹	ChemAxon
Polarizability	52.4 Å³	ChemAxon
Number of Rings	4	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8896991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10721653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gluchoff-Fiasson, K., et al. (2001). Gluchoff-Fiasson, K., et al, Chem. Pharm. Bull. 49, 768 (2001). Chem. Pharm. Bull..

Showing NP-Card for mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside (NP0025718)

MOL for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

3D MOL for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

3D SDF for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

3D-SDF for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

PDB for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

3D PDB for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

SMILES for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

INCHI for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

Structure for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)

3D Structure for NP0025718 (mearnsetin 3-O-(4''-O-malonyl)-alpha-L-rhamnopyranoside)