NP-MRD: Showing NP-Card for (5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one (NP0166412)

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Record Information

Version

2.0

Created at

2022-09-03 01:47:28 UTC

Updated at

2022-09-03 01:47:28 UTC

NP-MRD ID

NP0166412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one

Description

Calyflorenone C belongs to the class of organic compounds known as 6-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 6-position. (5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one was first documented in 2004 (PMID: 15003423). Based on a literature review very few articles have been published on Calyflorenone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032203472D          

 46 52  0  0  1  0            999 V2000
    4.8452    2.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0689    2.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5527    0.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4064    0.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6301   -0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    0.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464    1.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5163    1.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    2.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989   -0.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871    0.7693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1613    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    0.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111   -0.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1078   -1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5122   -1.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -1.4203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0966   -2.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5010   -2.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955   -0.8493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7748   -1.6256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -1.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3183   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1189   -0.1584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4766   -0.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777    0.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5178    1.2137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3212    2.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710    2.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677    3.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721    3.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    3.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    2.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3100    0.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0365   -0.3994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8902   -1.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8127   -0.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9590    0.6918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7353    0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8815    1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6578    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2878    1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1416    0.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3653    0.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289    1.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
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 16 18  1  0  0  0  0
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 19 20  1  0  0  0  0
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  6 24  1  0  0  0  0
 15 25  1  0  0  0  0
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 29 30  2  0  0  0  0
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 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 28 35  1  0  0  0  0
 14 35  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
 39 46  1  0  0  0  0
  4 46  1  0  0  0  0
M  END

     RDKit          3D

 82 88  0  0  0  0  0  0  0  0999 V2000
    2.5183    3.5155    1.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328    2.9455    0.3302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6512    1.5864    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    0.7160   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554   -0.6128   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9987   -1.0463    0.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0765   -0.1781    0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    1.1778    0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938    2.1073    1.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674    2.4584    2.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -0.9415    0.9587 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.2452   -4.7886    1.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2402   -4.1395    2.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702   -2.2937    0.1007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5337   -0.6693   -2.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.3554    0.8088   -2.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4400    1.4491   -0.6616 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7027    2.1384   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8619    3.5084   -0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0424    4.1696   -0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1338    3.4866    0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9889    2.1331    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8001    1.4672    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2022   -1.6163   -0.8860 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7066   -2.3090    0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4018   -0.9702   -1.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6188    1.9364   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8416    2.4774   -1.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6176    1.8189   -1.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3079   -2.2782    3.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1924    3.4208   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5891    2.1986   -2.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7064   -0.8486   -2.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
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 45 82  1  0
M  END


  Mrv1652309032203472D          

 46 52  0  0  1  0            999 V2000
    4.8452    2.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0689    2.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5527    0.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4064    0.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6301   -0.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0001    0.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464    1.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5163    1.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    2.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989   -0.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1871    0.7693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1613    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    0.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111   -0.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1078   -1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5122   -1.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -1.4203    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0966   -2.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5010   -2.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955   -0.8493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7748   -1.6256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5868   -1.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3183   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1189   -0.1584    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4766   -0.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777    0.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5178    1.2137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3212    2.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710    2.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677    3.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721    3.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7201    3.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167    2.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3100    0.9834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0365   -0.3994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8902   -1.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8127   -0.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9590    0.6918    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7353    0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8815    1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6578    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2878    1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1416    0.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3653    0.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289    1.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
  6 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 28 35  1  0  0  0  0
 14 35  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
 39 46  1  0  0  0  0
  4 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0166412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C(=O)C2=C(O[C@@H](C[C@H]2O)C2=CC=CC=C2)C2(OC)C3=C(OC)C(OC)=C4O[C@@H](C[C@@H](O)C4=C3O[C@]12OC)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H36O11/c1-39-30-26-28(25-21(37)17-22(18-12-8-6-9-13-18)44-29(25)31(30)40-2)46-35(43-5)33(41-3)27(38)24-20(36)16-23(19-14-10-7-11-15-19)45-32(24)34(26,35)42-4/h6-15,20-23,33,36-37H,16-17H2,1-5H3/t20-,21-,22+,23+,33+,34?,35-/m1/s1

> <INCHI_KEY>
YBOJMAVDKNXHBU-YIBOUZAVSA-N

> <FORMULA>
C35H36O11

> <MOLECULAR_WEIGHT>
632.662

> <EXACT_MASS>
632.225761979

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
65.86695486642154

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,7R,10S,11R,15R,17S)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{14,19}]henicosa-1(21),3(8),13,19-tetraen-9-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.151175547666666

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.047469171514535

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.508355697293187

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1526038616946463

> <JCHEM_POLAR_SURFACE_AREA>
131.37000000000003

> <JCHEM_REFRACTIVITY>
164.50649999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,7R,10S,11R,15R,17S)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{14,19}]henicosa-1(21),3(8),13,19-tetraen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       9.044   4.795   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.595   4.274   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.322   2.758   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.498   1.764   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.225   0.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.776  -0.273   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.600   0.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.873   2.237   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.697   3.231   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.970   4.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.291  -0.090   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.083   1.436   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.034   2.975   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.812   0.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.701  -0.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.068  -2.221   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.956  -3.287   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.547  -2.651   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.914  -4.147   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.802  -5.212   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.658  -1.585   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.180  -3.035   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.695  -3.307   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.194  -1.699   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.222  -0.296   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.890  -1.361   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.145   1.200   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.967   2.266   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.600   3.761   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.879   4.191   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.246   5.687   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.135   6.752   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.344   6.323   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.711   4.827   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.445   1.836   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.401  -0.746   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.128  -2.261   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.850  -0.224   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.123   1.291   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.572   1.813   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.845   3.328   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.295   3.850   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.471   2.856   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      15.198   1.340   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.749   0.819   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       9.947   2.286   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   46                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   14   21                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   35                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   11   22   24                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21    6                                                       
CONECT   25   15   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   28   14                                                       
CONECT   36    5   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   46                                                  
CONECT   40   39   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   40                                                       
CONECT   46   39    4                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₆O₁₁

Average Mass

632.6620 Da

Monoisotopic Mass

632.22576 Da

IUPAC Name

(5S,7R,10S,11R,15R,17S)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{14,19}]henicosa-1(21),3(8),13,19-tetraen-9-one

Traditional Name

(5S,7R,10S,11R,15R,17S)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0^{2,11}.0^{3,8}.0^{14,19}]henicosa-1(21),3(8),13,19-tetraen-9-one

CAS Registry Number

Not Available

SMILES

CO[C@H]1C(=O)C2=C(O[C@@H](C[C@H]2O)C2=CC=CC=C2)C2(OC)C3=C(OC)C(OC)=C4O[C@@H](C[C@@H](O)C4=C3O[C@]12OC)C1=CC=CC=C1

InChI Identifier

InChI=1S/C35H36O11/c1-39-30-26-28(25-21(37)17-22(18-12-8-6-9-13-18)44-29(25)31(30)40-2)46-35(43-5)33(41-3)27(38)24-20(36)16-23(19-14-10-7-11-15-19)45-32(24)34(26,35)42-4/h6-15,20-23,33,36-37H,16-17H2,1-5H3/t20-,21-,22+,23+,33+,34?,35-/m1/s1

InChI Key

YBOJMAVDKNXHBU-YIBOUZAVSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

6-prenylated flavans

Alternative Parents

Substituents

6-prenylated flavan
Furanoflavonoid or dihydroflavonoid
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
4-hydroxyflavonoid
Hydroxyflavonoid
Flavan-4-ol
Benzopyran
Chromane
1-benzopyran
Coumaran
Anisole
Alkyl aryl ether
Ketal
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Vinylogous ester
Secondary alcohol
Ketone
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Acetal
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.72	ALOGPS
logP	3.15	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.51	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	164.51 m³·mol⁻¹	ChemAxon
Polarizability	65.87 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00014749

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101727394

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mayer R: Five biflavonoids from Calycopteris floribunda (Combretaceae). Phytochemistry. 2004 Mar;65(5):593-601. doi: 10.1016/j.phytochem.2004.01.001. [PubMed:15003423 ]
LOTUS database [Link]

Showing NP-Card for (5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one (NP0166412)

MOL for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

3D MOL for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

3D SDF for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

3D-SDF for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

PDB for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

3D PDB for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

SMILES for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

INCHI for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

Structure for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)

3D Structure for NP0166412 ((5s,7r,10s,11r,15r,17s)-7,15-dihydroxy-2,10,11,20,21-pentamethoxy-5,17-diphenyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(21),3(8),13,19-tetraen-9-one)