NP-MRD: Showing NP-Card for (1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione (NP0298280)

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Record Information

Version

2.0

Created at

2022-09-10 09:24:27 UTC

Updated at

2022-09-10 09:24:28 UTC

NP-MRD ID

NP0298280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione

Description

Kobophenol B belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione is found in Carex pendula and Carex pumila. Based on a literature review very few articles have been published on Kobophenol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211242D          

 68 80  0  0  1  0            999 V2000
    1.2271   -3.0943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2610   -2.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804   -1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286   -0.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0234   -0.1053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0735    0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6702    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790    2.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293    2.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210    3.3276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519    2.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149    1.0023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4730    0.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8554    1.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7030    2.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    1.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1215    1.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7391    0.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    0.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110   -0.4925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7815   -1.3406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5712   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461   -0.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1507   -2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8508   -2.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5774    0.2447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.3404   -0.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846   -0.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976    0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8453    0.1463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    0.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394    0.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3162   -0.2571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1784   -1.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8139   -1.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -2.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2072   -3.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027   -2.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2672   -2.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5633   -2.7154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050   -1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0552    0.1095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7862   -0.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4829    0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2139   -0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2483   -1.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0484   -1.3568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8206   -1.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7789   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619   -2.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9862   -2.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940   -3.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275   -1.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0445   -0.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  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
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
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 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
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 14 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
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 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 22 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 33 31  1  6  0  0  0
  4 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
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 35 41  1  0  0  0  0
 19 42  1  0  0  0  0
 42 43  1  6  0  0  0
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 44 45  1  0  0  0  0
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 47 48  1  0  0  0  0
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 48 50  2  0  0  0  0
 43 50  1  0  0  0  0
 42 51  1  0  0  0  0
 51 52  1  1  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 57 58  2  0  0  0  0
 52 58  1  0  0  0  0
 51 59  1  0  0  0  0
 18 59  1  0  0  0  0
  7 60  1  0  0  0  0
 60 61  1  0  0  0  0
  5 61  1  0  0  0  0
 61 62  1  6  0  0  0
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 65 66  1  0  0  0  0
 65 67  1  0  0  0  0
 67 68  2  0  0  0  0
 62 68  1  0  0  0  0
M  END

     RDKit          3D

108120  0  0  0  0  0  0  0  0999 V2000
    1.7875    0.7793    3.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6117    0.7795    2.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -0.3452    1.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -0.1668   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1912   -0.9974   -0.6251 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8807   -1.5230   -2.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399   -2.4754   -2.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125   -2.9749   -3.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0450   -2.5085   -4.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585   -3.0373   -5.8167 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0931   -1.5614   -4.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9828   -1.0340   -2.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683   -0.1321   -2.7862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4187   -0.6389   -2.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359   -1.4317   -3.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9600   -1.5033   -1.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2555   -0.7164   -0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -0.2539   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5132    1.4257    0.9504 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0392    1.1353    2.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975   -0.0239    2.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0032    0.8380    4.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070    0.7351    6.1867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620    2.0360    4.2493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    2.1703    2.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102211242D          

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M  END
> <DATABASE_ID>
NP0298280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1OC2=CC(O)=C3[C@H]4[C@H](C5=CC=C(O)C=C5)[C@]56[C@@H]([C@H]([C@H](C5=O)C(=O)C=C6[C@H]5[C@@H](OC6=C5C4=CC(O)=C6)C4=CC=C(O)C=C4)C4=CC=C(O)C=C4)C3=C2[C@H]1C1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C56H40O12/c57-29-9-1-24(2-10-29)42-48-38(64)22-37-46-44-36(20-35(63)21-40(44)67-54(46)27-7-15-32(60)16-8-27)45-47-39(65)23-41-49(50(47)52(42)56(37,55(48)66)51(45)25-3-11-30(58)12-4-25)43(28-17-33(61)19-34(62)18-28)53(68-41)26-5-13-31(59)14-6-26/h1-23,42-43,45-46,48,51-54,57-63,65H/t42-,43+,45-,46+,48+,51-,52-,53-,54-,56+/m0/s1

> <INCHI_KEY>
QENCSSQOFHZZCZ-PSGPQVICSA-N

> <FORMULA>
C56H40O12

> <MOLECULAR_WEIGHT>
904.924

> <EXACT_MASS>
904.251976728

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
92.07996647303072

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,7R,8R,15S,21R,22R,25S,26R,27R)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1^{3,25}.1^{7,10}.0^{1,6}.0^{16,24}.0^{19,23}.0^{14,28}]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione

> <JCHEM_LOGP>
9.388623058666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
13

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.96603302290265

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.591986233126603

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4923943309274845

> <JCHEM_POLAR_SURFACE_AREA>
214.43999999999997

> <JCHEM_REFRACTIVITY>
249.96949999999987

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,7R,8R,15S,21R,22R,25S,26R,27R)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1^{3,25}.1^{7,10}.0^{1,6}.0^{16,24}.0^{19,23}.0^{14,28}]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       2.291  -5.776   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.354  -4.064   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.083  -3.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.360  -1.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.044  -0.197   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.137   1.421   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.251   2.174   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.267   3.781   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.055   4.604   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.039   6.211   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.404   3.855   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.455   2.287   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.014   1.871   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.616   1.857   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.330   3.222   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.046   4.800   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.869   3.286   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.694   1.985   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.980   0.621   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.441   0.557   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.687  -0.919   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.192  -2.502   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.666  -2.948   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.553  -1.528   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.263  -2.339   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.615  -3.838   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.921  -4.840   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.309  -5.011   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.018  -4.447   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.907  -3.532   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.378  -2.340   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.148  -3.159   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.017  -0.963   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.944   0.457   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.404   0.456   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.635  -0.878   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.905  -0.879   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.676   0.454   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.445   0.273   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.906   1.788   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.634   1.789   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.057  -0.480   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.800  -1.998   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.986  -2.980   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.729  -4.499   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       9.720  -5.902   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       7.285  -5.035   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.099  -4.053   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.785  -5.069   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       6.356  -2.535   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       9.436   0.204   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.801  -0.509   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      12.101   0.315   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      13.466  -0.399   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      13.530  -1.937   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      15.024  -2.533   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      12.230  -2.762   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.865  -2.048   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       9.212   1.728   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -2.323   1.012   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -1.563  -0.353   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -2.278  -1.717   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -1.454  -3.018   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -2.169  -4.382   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -3.708  -4.445   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -4.469  -5.846   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      -4.531  -3.144   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      -3.816  -1.780   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6   61                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8   60                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14   34                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   59                                                  
CONECT   19   18   20   42                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20   22   33                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   22    2   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    4   21   34                                             
CONECT   34   33   13   35                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35                                                       
CONECT   42   19   43   51                                                  
CONECT   43   42   44   50                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   43                                                       
CONECT   51   42   52   59                                                  
CONECT   52   51   53   58                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57   52                                                       
CONECT   59   51   18                                                       
CONECT   60    7   61                                                       
CONECT   61   60    5   62                                                  
CONECT   62   61   63   68                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65   68                                                       
CONECT   68   67   62                                                       
MASTER        0    0    0    0    0    0    0    0   68    0  160    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₆H₄₀O₁₂

Average Mass

904.9240 Da

Monoisotopic Mass

904.25198 Da

IUPAC Name

(1R,3S,7R,8R,15S,21R,22R,25S,26R,27R)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1^{3,25}.1^{7,10}.0^{1,6}.0^{16,24}.0^{19,23}.0^{14,28}]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1OC2=CC(O)=C3[C@H]4[C@H](C5=CC=C(O)C=C5)[C@]56[C@@H]([C@H]([C@H](C5=O)C(=O)C=C6[C@H]5[C@@H](OC6=C5C4=CC(O)=C6)C4=CC=C(O)C=C4)C4=CC=C(O)C=C4)C3=C2[C@H]1C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C56H40O12/c57-29-9-1-24(2-10-29)42-48-38(64)22-37-46-44-36(20-35(63)21-40(44)67-54(46)27-7-15-32(60)16-8-27)45-47-39(65)23-41-49(50(47)52(42)56(37,55(48)66)51(45)25-3-11-30(58)12-4-25)43(28-17-33(61)19-34(62)18-28)53(68-41)26-5-13-31(59)14-6-26/h1-23,42-43,45-46,48,51-54,57-63,65H/t42-,43+,45-,46+,48+,51-,52-,53-,54-,56+/m0/s1

InChI Key

QENCSSQOFHZZCZ-PSGPQVICSA-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
Carex pendula	LOTUS Database	35616633
Carex pumila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
4-prenylated 2-arybenzofuran
Linear 1,7-diphenylheptane skeleton
1-aryltetralin lignan
Neolignan skeleton
Phenylnaphthalene
1-phenylcoumaran
Stilbene
Naphthofuran
Tetralin
Benzofuran
Coumaran
Resorcinol
1,3-diketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexenone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
1,3-dicarbonyl compound
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	9.39	ChemAxon
pKa (Strongest Acidic)	8.59	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	214.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	249.97 m³·mol⁻¹	ChemAxon
Polarizability	92.08 Å³	ChemAxon
Number of Rings	13	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

C00015803

Chemspider ID

24534557

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636952

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione (NP0298280)

MOL for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

3D MOL for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

3D SDF for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

3D-SDF for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

PDB for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

3D PDB for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

SMILES for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

INCHI for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

Structure for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)

3D Structure for NP0298280 ((1r,3s,7r,8r,15s,21r,22r,25s,26r,27r)-22-(3,5-dihydroxyphenyl)-12,17-dihydroxy-8,21,26,27-tetrakis(4-hydroxyphenyl)-9,20-dioxaoctacyclo[13.10.1.1³,²⁵.1⁷,¹⁰.0¹,⁶.0¹⁶,²⁴.0¹⁹,²³.0¹⁴,²⁸]octacosa-5,10(28),11,13,16,18,23-heptaene-2,4-dione)