NP-MRD: Showing NP-Card for gossypitrin (NP0031683)

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Record Information

Version

2.0

Created at

2021-06-19 22:41:54 UTC

Updated at

2021-06-30 00:00:25 UTC

NP-MRD ID

NP0031683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gossypitrin

Provided By

JEOL Database JEOL Logo

Description

Gossypitrin belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. gossypitrin is found in Abutilon indicum , Restio tetraphyllus, Calorophus lateriflorus, Calorophus minor, Chrysanthemum segetum , Dacrydium spp., Drosera rotundifolia, Equisetum arvense, Equisetum spp., Equisetum telmateia, Hibiscus sabdariffa, Hibiscus spp., Leucanthemopsis flaveola, Millettia zechiana, Papaver nudicaule and Restio complanatus. gossypitrin was first documented in 2002 (PMID: 11933852). Based on a literature review a small amount of articles have been published on Gossypitrin (PMID: 30853999) (PMID: 23831703) (PMID: 16376394) (PMID: 14599345).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100413D          

 54 57  0  0  0  0            999 V2000
    4.3573    1.8715   -0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    1.2316   -0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2364    1.1352   -2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1495    1.7945   -2.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.4306   -2.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083    0.2800   -4.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -0.2269   -4.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5943   -0.3973   -6.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.0622   -6.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566   -0.2296   -8.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0809   -1.8945    3.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
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 15 34  2  0  0  0  0
 25 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 20  1  0  0  0  0
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 12 39  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202100413D          

 54 57  0  0  0  0            999 V2000
    4.3573    1.8715   -0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    1.2316   -0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2364    1.1352   -2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1495    1.7945   -2.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.4306   -2.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083    0.2800   -4.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -0.2269   -4.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5943   -0.3973   -6.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8858   -2.0899    1.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109   -0.1111    2.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    0.5616    1.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    1.2230    2.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7767    2.2287   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3475   -0.7858   -6.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1322    0.0737   -8.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    1.1404   -5.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227    1.0034   -3.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.5334   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958    0.1270    2.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    1.3792    3.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805    1.7070    6.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    0.2828    6.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745    1.3456    5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385   -1.1816    5.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7558   -0.2375    4.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2617   -0.1859    2.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0131   -2.3711    2.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464   -2.5799    3.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -2.2376    0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -0.1056    3.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    1.6527    1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 34  2  0  0  0  0
 25 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 20  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 15 14  1  0  0  0  0
 34  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  2  0  0  0  0
  5 14  1  0  0  0  0
 29 30  1  0  0  0  0
  5  6  1  0  0  0  0
 18 19  1  0  0  0  0
 32 33  1  0  0  0  0
  2  1  2  0  0  0  0
  3  4  1  0  0  0  0
 34 32  1  0  0  0  0
  6  7  2  0  0  0  0
 20 29  1  0  0  0  0
  7  8  1  0  0  0  0
 32 31  2  0  0  0  0
  8  9  2  0  0  0  0
 29 27  1  0  0  0  0
  9 11  1  0  0  0  0
 31 18  1  0  0  0  0
 11 13  2  0  0  0  0
 13  6  1  0  0  0  0
 27 25  1  0  0  0  0
  9 10  1  0  0  0  0
 23 24  1  0  0  0  0
 18 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 15  1  0  0  0  0
 11 12  1  0  0  0  0
 20 19  1  0  0  0  0
 22 23  1  0  0  0  0
 24 46  1  0  0  0  0
  4 35  1  0  0  0  0
 20 42  1  6  0  0  0
 25 47  1  1  0  0  0
 26 48  1  0  0  0  0
 27 49  1  6  0  0  0
 28 50  1  0  0  0  0
 29 51  1  1  0  0  0
 30 52  1  0  0  0  0
 23 44  1  0  0  0  0
 23 45  1  0  0  0  0
 22 43  1  6  0  0  0
 31 53  1  0  0  0  0
 33 54  1  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
 13 40  1  0  0  0  0
 10 38  1  0  0  0  0
 17 41  1  0  0  0  0
 12 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1O[H])C1=C(O[H])C(=O)C2=C(O1)C(O[H])=C(O[C@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])C([H])=C2O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O13/c22-5-11-13(26)16(29)18(31)21(33-11)32-10-4-9(25)12-15(28)17(30)19(34-20(12)14(10)27)6-1-2-7(23)8(24)3-6/h1-4,11,13,16,18,21-27,29-31H,5H2/t11-,13-,16+,18-,21-/m1/s1

> <INCHI_KEY>
ATRBFJXIWFCIMW-ZGNDCXKCSA-N

> <FORMULA>
C21H20O13

> <MOLECULAR_WEIGHT>
480.378

> <EXACT_MASS>
480.090390704

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.26988237598773

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
-0.4153339510000003

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.475061401438754

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.521552997025214

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648395366008158

> <JCHEM_POLAR_SURFACE_AREA>
226.82999999999998

> <JCHEM_REFRACTIVITY>
110.98750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    4.3573    1.8715   -0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    1.2316   -0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2364    1.1352   -2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1495    1.7945   -2.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.4306   -2.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083    0.2800   -4.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -0.2269   -4.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5943   -0.3973   -6.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.0622   -6.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566   -0.2296   -8.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    0.4405   -5.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8555    0.7540   -6.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6363    0.6105   -4.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2601   -0.2133   -1.8186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145   -0.1569   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -0.8329    0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5437   -1.5407   -0.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686   -0.7950    1.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3191   -1.4927    2.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -0.7148    2.7630 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4176   -0.2117    4.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5917    0.5294    4.4832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3459    1.0883    5.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    1.8973    5.8787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309   -0.3706    4.4467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0129    0.3627    4.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9825   -0.9681    3.0479 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0809   -1.8945    3.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7004   -1.6672    2.6025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8858   -2.0899    1.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109   -0.1111    2.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    0.5616    1.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    1.2230    2.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    0.5391    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767    2.2287   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706   -0.4927   -4.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3475   -0.7858   -6.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1322    0.0737   -8.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    1.1404   -5.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227    1.0034   -3.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.5334   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958    0.1270    2.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    1.3792    3.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805    1.7070    6.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    0.2828    6.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745    1.3456    5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385   -1.1816    5.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7558   -0.2375    4.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2617   -0.1859    2.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0131   -2.3711    2.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464   -2.5799    3.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -2.2376    0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -0.1056    3.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    1.6527    1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 34  2  0
 25 22  1  0
 22 21  1  0
 21 20  1  0
 25 26  1  0
 27 28  1  0
 15 14  1  0
 34  2  1  0
  2  3  1  0
  3  5  2  0
  5 14  1  0
 29 30  1  0
  5  6  1  0
 18 19  1  0
 32 33  1  0
  2  1  2  0
  3  4  1  0
 34 32  1  0
  6  7  2  0
 20 29  1  0
  7  8  1  0
 32 31  2  0
  8  9  2  0
 29 27  1  0
  9 11  1  0
 31 18  1  0
 11 13  2  0
 13  6  1  0
 27 25  1  0
  9 10  1  0
 23 24  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 11 12  1  0
 20 19  1  0
 22 23  1  0
 24 46  1  0
  4 35  1  0
 20 42  1  6
 25 47  1  1
 26 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  1
 30 52  1  0
 23 44  1  0
 23 45  1  0
 22 43  1  6
 31 53  1  0
 33 54  1  0
  7 36  1  0
  8 37  1  0
 13 40  1  0
 10 38  1  0
 17 41  1  0
 12 39  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       4.357   1.871  -0.215  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.421   1.232  -0.687  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.236   1.135  -2.153  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.149   1.795  -2.953  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.191   0.431  -2.622  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.908   0.280  -4.063  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.880  -0.227  -4.944  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.594  -0.397  -6.301  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.336  -0.062  -6.774  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.057  -0.230  -8.100  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.363   0.441  -5.916  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.856   0.754  -6.453  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.636   0.611  -4.562  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.260  -0.213  -1.819  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.415  -0.157  -0.456  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.477  -0.833   0.326  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.544  -1.541  -0.254  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.569  -0.795   1.718  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.319  -1.493   2.489  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.498  -0.715   2.763  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.418  -0.212   4.101  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.592   0.529   4.483  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.346   1.088   5.888  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.167   1.897   5.879  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.831  -0.371   4.447  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.013   0.363   4.770  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.982  -0.968   3.048  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.081  -1.895   3.051  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.700  -1.667   2.603  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.886  -2.090   1.240  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.611  -0.111   2.340  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.548   0.562   1.560  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.543   1.223   2.226  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.450   0.539   0.163  0.00  0.00           C+0
HETATM   35  H   UNK     0       4.777   2.229  -2.337  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.871  -0.493  -4.581  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.348  -0.786  -6.980  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.132   0.074  -8.198  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.411   1.140  -5.755  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.123   1.003  -3.893  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.388  -1.533  -1.219  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.596   0.127   2.061  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.701   1.379   3.796  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.180   1.707   6.230  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.181   0.283   6.612  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.475   1.346   5.467  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.739  -1.182   5.180  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.756  -0.238   4.553  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.262  -0.186   2.330  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.013  -2.371   2.198  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.546  -2.580   3.191  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.988  -2.238   0.869  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.695  -0.106   3.424  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.136   1.653   1.571  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   34    3    1                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3   35                                                       
CONECT    5    3   14    6                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7    9   37                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   38                                                       
CONECT   11    9   13   12                                                  
CONECT   12   11   39                                                       
CONECT   13   11    6   40                                                  
CONECT   14   15    5                                                       
CONECT   15   34   14   16                                                  
CONECT   16   18   17   15                                                  
CONECT   17   16   41                                                       
CONECT   18   19   31   16                                                  
CONECT   19   18   20                                                       
CONECT   20   21   29   19   42                                             
CONECT   21   22   20                                                       
CONECT   22   25   21   23   43                                             
CONECT   23   24   22   44   45                                             
CONECT   24   23   46                                                       
CONECT   25   22   26   27   47                                             
CONECT   26   25   48                                                       
CONECT   27   28   29   25   49                                             
CONECT   28   27   50                                                       
CONECT   29   30   20   27   51                                             
CONECT   30   29   52                                                       
CONECT   31   32   18   53                                                  
CONECT   32   33   34   31                                                  
CONECT   33   32   54                                                       
CONECT   34   15    2   32                                                  
CONECT   35    4                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38   10                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   17                                                            
CONECT   42   20                                                            
CONECT   43   22                                                            
CONECT   44   23                                                            
CONECT   45   23                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
CONECT   54   33                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
    4.3573    1.8715   -0.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4211    1.2316   -0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2364    1.1352   -2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1495    1.7945   -2.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912    0.4306   -2.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083    0.2800   -4.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799   -0.2269   -4.9442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5943   -0.3973   -6.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.0622   -6.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566   -0.2296   -8.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627    0.4405   -5.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8555    0.7540   -6.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6363    0.6105   -4.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2601   -0.2133   -1.8186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145   -0.1569   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -0.8329    0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5437   -1.5407   -0.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5686   -0.7950    1.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3191   -1.4927    2.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -0.7148    2.7630 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4176   -0.2117    4.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5917    0.5294    4.4832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3459    1.0883    5.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    1.8973    5.8787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8309   -0.3706    4.4467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0129    0.3627    4.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9825   -0.9681    3.0479 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0809   -1.8945    3.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7004   -1.6672    2.6025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8858   -2.0899    1.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109   -0.1111    2.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    0.5616    1.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    1.2230    2.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497    0.5391    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767    2.2287   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8706   -0.4927   -4.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3475   -0.7858   -6.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1322    0.0737   -8.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    1.1404   -5.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227    1.0034   -3.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.5334   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958    0.1270    2.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7009    1.3792    3.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1805    1.7070    6.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    0.2828    6.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745    1.3456    5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385   -1.1816    5.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7558   -0.2375    4.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2617   -0.1859    2.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0131   -2.3711    2.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464   -2.5799    3.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -2.2376    0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -0.1056    3.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    1.6527    1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 34  2  0
 25 22  1  0
 22 21  1  0
 21 20  1  0
 25 26  1  0
 27 28  1  0
 15 14  1  0
 34  2  1  0
  2  3  1  0
  3  5  2  0
  5 14  1  0
 29 30  1  0
  5  6  1  0
 18 19  1  0
 32 33  1  0
  2  1  2  0
  3  4  1  0
 34 32  1  0
  6  7  2  0
 20 29  1  0
  7  8  1  0
 32 31  2  0
  8  9  2  0
 29 27  1  0
  9 11  1  0
 31 18  1  0
 11 13  2  0
 13  6  1  0
 27 25  1  0
  9 10  1  0
 23 24  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 11 12  1  0
 20 19  1  0
 22 23  1  0
 24 46  1  0
  4 35  1  0
 20 42  1  6
 25 47  1  1
 26 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  1
 30 52  1  0
 23 44  1  0
 23 45  1  0
 22 43  1  6
 31 53  1  0
 33 54  1  0
  7 36  1  0
  8 37  1  0
 13 40  1  0
 10 38  1  0
 17 41  1  0
 12 39  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₁₃

Average Mass

480.3780 Da

Monoisotopic Mass

480.09039 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1O[H])C1=C(O[H])C(=O)C2=C(O1)C(O[H])=C(O[C@]1([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])C([H])=C2O[H]

InChI Identifier

InChI=1S/C21H20O13/c22-5-11-13(26)16(29)18(31)21(33-11)32-10-4-9(25)12-15(28)17(30)19(34-20(12)14(10)27)6-1-2-7(23)8(24)3-6/h1-4,11,13,16,18,21-27,29-31H,5H2/t11-,13-,16+,18-,21-/m1/s1

InChI Key

ATRBFJXIWFCIMW-ZGNDCXKCSA-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
Abutilon indicum	Plant	KNApSAcK
Baloskion tetraphyllum	Plant	KNApSAcK
Calorophus lateriflorus	Plant	KNApSAcK
Calorophus minor	Plant	KNApSAcK
Chrysanthemum segetum	Plant	KNApSAcK
Dacrydium spp.	Plant	KNApSAcK
Drosera rotundifolia	LOTUS Database	35616633
Equisetum arvense	LOTUS Database	35616633
Equisetum spp.	Plant	KNApSAcK
Equisetum telmateia	LOTUS Database	35616633
Hibiscus sabdariffa	LOTUS Database	35616633
Hibiscus spp.	Plant	KNApSAcK
Leucanthemopsis flaveola	Plant	KNApSAcK
Millettia zechiana	Plant	KNApSAcK
Papaver nudicaule	JEOL database	Schliemann, W., et al, Phytochemistry 67, 191 (2006)
Restio complanatus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3-hydroxyflavone
Hydroxyflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
8-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
Benzopyran
1-benzopyran
Catechol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Acetal
Polyol
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
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	0.43	ALOGPS
logP	-0.42	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.52	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	226.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.99 m³·mol⁻¹	ChemAxon
Polarizability	45.27 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10306183

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6452123

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ay E, Hunyadi A, Mezei M, Minarovits J, Hohmann J: Flavonol 7-O-Glucoside Herbacitrin Inhibits HIV-1 Replication through Simultaneous Integrase and Reverse Transcriptase Inhibition. Evid Based Complement Alternat Med. 2019 Feb 3;2019:1064793. doi: 10.1155/2019/1064793. eCollection 2019. [PubMed:30853999 ]
Braunberger C, Zehl M, Conrad J, Fischer S, Adhami HR, Beifuss U, Krenn L: LC-NMR, NMR, and LC-MS identification and LC-DAD quantification of flavonoids and ellagic acid derivatives in Drosera peltata. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Aug 1;932:111-6. doi: 10.1016/j.jchromb.2013.06.015. Epub 2013 Jun 17. [PubMed:23831703 ]
Schliemann W, Schneider B, Wray V, Schmidt J, Nimtz M, Porzel A, Bohm H: Flavonols and an indole alkaloid skeleton bearing identical acylated glycosidic groups from yellow petals of Papaver nudicaule. Phytochemistry. 2006 Jan;67(2):191-201. doi: 10.1016/j.phytochem.2005.11.002. Epub 2005 Dec 22. [PubMed:16376394 ]
Perez-Trueba G, Ramos-Guanche C, Martinez-Sanchez B, Marquez-Hernandez I, Giuliani A, Martinez-Sanchez G: Protective effect of gossypitrin on carbon tetrachloride-induced in vivo hepatotoxicity. Redox Rep. 2003;8(4):215-21. doi: 10.1179/135100003225002718. [PubMed:14599345 ]
Kolodziej H, Pertz HH, Humke A: Main constituents of a commercial Drosera fluid extract and their antagonist activity at muscarinic M3 receptors in guinea-pig ileum. Pharmazie. 2002 Mar;57(3):201-3. [PubMed:11933852 ]
Schliemann, W., et al. (2006). Schliemann, W., et al, Phytochemistry 67, 191 (2006) . Phytochem..

Showing NP-Card for gossypitrin (NP0031683)

MOL for NP0031683 (gossypitrin)

3D MOL for NP0031683 (gossypitrin)

3D SDF for NP0031683 (gossypitrin)

3D-SDF for NP0031683 (gossypitrin)

PDB for NP0031683 (gossypitrin)

3D PDB for NP0031683 (gossypitrin)

SMILES for NP0031683 (gossypitrin)

INCHI for NP0031683 (gossypitrin)

Structure for NP0031683 (gossypitrin)

3D Structure for NP0031683 (gossypitrin)