NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one (NP0217167)

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Record Information

Version

2.0

Created at

2022-09-05 17:25:38 UTC

Updated at

2022-09-05 17:25:38 UTC

NP-MRD ID

NP0217167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

Description

Quercetin 3-O-alpha-L-rhamnopyranoside 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. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one is found in Embelia schimperi, Euphorbia franchetii, Hypericum aucheri, Maesa lanceolata and Persicaria orientalis. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one was first documented in 2021 (PMID: 34975468). Based on a literature review a small amount of articles have been published on Quercetin 3-O-alpha-L-rhamnopyranoside (PMID: 33572445) (PMID: 33166841).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052219252D          

 32 35  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.1434   -0.4125    0.0000 C   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -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  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
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  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
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  9 10  1  0  0  0  0
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 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.3052   -1.6472    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.9493   -0.6061 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3597   -1.0282   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577    0.0646   -0.3125 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6942   -0.3058    0.7914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -0.7503    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6722    0.0234    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7271    1.4516    0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    2.1155    1.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    3.4766    1.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9011    4.2017    1.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799    5.5534    1.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361    3.5425    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0461    4.2776    0.3617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465    2.2029    0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8431   -0.5396    0.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9713   -1.7914   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2267   -2.3203   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3900   -3.6366   -0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6857   -4.0771   -1.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -4.4648   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315   -4.0023   -0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9907   -4.8578   -0.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953   -2.6669   -0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -2.1036    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -2.7989    0.1558 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2365    1.3459   -0.0216 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8961    1.3290    1.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414    1.4787   -1.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9465    2.7040   -1.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3235    0.3853   -0.7462 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3226    0.3927   -1.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568   -2.1483    0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404   -2.4221    1.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4864   -0.9306    1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1629    1.6201    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7505    6.1316    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8274    3.8672   -0.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6600    1.6855   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597   -1.6316   -0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2720   -4.4381   -0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -5.5175   -1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505   -4.8649   -0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5455    2.2095   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4303    0.8186    1.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.2256   -2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7374    3.2001   -0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107    0.6868    0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108    1.2543   -2.1899 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  2  0
  7 16  1  0
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 17 18  2  0
 18 19  1  0
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 25 26  2  0
  7  8  1  0
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  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  4 27  1  0
 27 28  1  0
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 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  2  1  0
 25  6  1  0
 15  8  1  0
 24 17  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  4 37  1  6
 18 43  1  0
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 21 45  1  0
 23 46  1  0
  9 38  1  0
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 14 41  1  0
 15 42  1  0
 27 47  1  1
 28 48  1  0
 29 49  1  6
 30 50  1  0
 31 51  1  1
 32 52  1  0
M  END


  Mrv1652309052219252D          

 32 35  0  0  1  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    2.1434   -0.4125    0.0000 C   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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -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  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 11 12  1  0  0  0  0
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  8 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0217167

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21+/m1/s1

> <INCHI_KEY>
OXGUCUVFOIWWQJ-AIRRAIBWSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.523441035061275

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one

> <JCHEM_LOGP>
0.9020746706666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.872521648367228

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.372405738137058

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612200408172593

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
107.7318

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
CONECT   16    7   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24    6   26                                                  
CONECT   26   25                                                            
CONECT   27    4   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Quercetin 3-O-a-L-rhamnopyranoside	Generator
Quercetin 3-O-α-L-rhamnopyranoside	Generator

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21+/m1/s1

InChI Key

OXGUCUVFOIWWQJ-AIRRAIBWSA-N

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
Embelia schimperi	LOTUS Database	35616633
Euphorbia franchetii	LOTUS Database	35616633
Hypericum aucheri	LOTUS Database	35616633
Maesa lanceolata	LOTUS Database	35616633
Persicaria orientalis	LOTUS Database	35616633

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
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	0.9	ChemAxon
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.73 m³·mol⁻¹	ChemAxon
Polarizability	42.52 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

C00005440

Chemspider ID

23311302

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

40486293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

De Araujo ERD, Guerra GCB, Andrade AWL, Fernandes JM, Da Silva VC, De Aragao Tavares E, De Araujo AA, de Araujo Junior RF, Zucolotto SM: Gastric Ulcer Healing Property of Bryophyllum pinnatum Leaf Extract in Chronic Model In Vivo and Gastroprotective Activity of Its Major Flavonoid. Front Pharmacol. 2021 Dec 16;12:744192. doi: 10.3389/fphar.2021.744192. eCollection 2021. [PubMed:34975468 ]
de Brito JAG, Pinto LDS, Chaves CF, Ribeiro da Silva AJ, Silva MFDGFD, Cotinguiba F: Chemophenetic Significance of Anomalocalyx uleanus Metabolites are Revealed by Dereplication Using Molecular Networking Tools. Molecules. 2021 Feb 9;26(4):925. doi: 10.3390/molecules26040925. [PubMed:33572445 ]
Morais Fernandes J, Ortiz S, Padilha M Tavares R, Mandova T, Rodrigues D Araujo E, L Andrade AW, Michel S, Grougnet R, Zucolotto SM: Bryophyllum pinnatum markers: CPC isolation, simultaneous quantification by a validated UPLC-DAD method and biological evaluations. J Pharm Biomed Anal. 2021 Jan 30;193:113682. doi: 10.1016/j.jpba.2020.113682. Epub 2020 Oct 12. [PubMed:33166841 ]
LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one (NP0217167)

MOL for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

PDB for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

SMILES for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

INCHI for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

Structure for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0217167 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one)