NP-MRD: Showing NP-Card for 5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione (NP0244488)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 05:18:00 UTC

Updated at

2022-09-07 05:18:00 UTC

NP-MRD ID

NP0244488

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione

Description

5,13,16,18-Tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]Henicosa-2(7),9,15,17,19-pentaene-8,14-dione belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. 5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione is found in Daphne feddei and Daphne genkwa. 5,13,16,18-Tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]Henicosa-2(7),9,15,17,19-pentaene-8,14-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171504592D          

 41 47  0  0  0  0            999 V2000
    3.3674    3.2947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902    2.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6447    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332    1.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    1.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    1.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5440    1.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287    1.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5002    0.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2848    0.6544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8871    0.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2064    0.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7204    1.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -1.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2679   -1.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -0.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706    3.2723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139   -2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6689   -3.3934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -1.2111    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
M  END

     RDKit          3D

 63 69  0  0  0  0  0  0  0  0999 V2000
   -1.2358   -3.9564    2.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6784   -2.9001    1.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -2.6686    2.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2753   -1.5435    1.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5715   -0.9865    1.7148 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8092   -0.4275    0.4037 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6794   -1.3983   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6593   -2.1068    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132   -3.0030   -0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4461   -3.2607   -1.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3189   -4.1757   -2.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992   -2.5870   -2.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6287   -1.6678   -1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -0.3249   -0.1923 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0667   -1.3647   -1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2668    1.0223   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414    1.2326   -1.9710 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4053    2.1505    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8308    3.3919   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1554    3.6405   -1.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538    4.4639    0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    4.2265    1.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7305    5.2514    2.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    2.9838    2.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0861    1.9254    1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613    0.6906    1.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -0.4588    1.0448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8794   -0.7473    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -1.8754    1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094   -2.0125    0.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1606   -1.7311   -0.4756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5123   -2.7415   -1.1899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6433   -0.3642   -0.8646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8061    0.5424   -1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070    0.8706   -2.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3825    1.7098   -2.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0109    2.2636   -1.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1113    3.1222   -1.5245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5319    1.9527   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493    1.1076    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067    0.1200    0.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3553   -3.4291    2.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879    0.5778    0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7338   -1.9232    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2619   -3.5356    0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2178   -3.8679   -2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4451   -2.7900   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235   -1.1697   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528   -1.0416   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489    3.0259   -2.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2918    5.4337    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    5.8156    3.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486    2.7702    3.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324   -1.3692    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2057   -3.0873    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2549   -1.8173   -0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624   -2.7156   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1147   -0.4571   -1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8136    0.4351   -3.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7865    1.9758   -3.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5449    3.5076   -0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0485    2.4058    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048    0.8899    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 31 30  1  0
 30 29  1  0
 29 28  2  0
 28 41  1  0
 41 33  1  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  2  0
 28 27  1  0
 27 26  1  1
 26 25  1  0
 25 24  2  0
 24 22  1  0
 22 23  1  0
 22 21  2  0
 21 19  1  0
 19 20  1  0
 19 18  2  0
 18 16  1  0
 16 17  2  0
 16 14  1  0
 14 15  1  6
 14  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 33 31  1  0
 40 34  1  0
 14 27  1  0
 13  7  1  0
  2 29  1  0
  4 27  1  0
 18 25  1  0
 32 57  1  0
 31 56  1  1
 30 54  1  0
 30 55  1  0
 33 58  1  6
 35 59  1  0
 36 60  1  0
 38 61  1  0
 39 62  1  0
 40 63  1  0
 24 53  1  0
 23 52  1  0
 21 51  1  0
 20 50  1  0
 15 49  1  0
  6 43  1  1
  3 42  1  0
  8 44  1  0
  9 45  1  0
 11 46  1  0
 12 47  1  0
 13 48  1  0
M  END


  Mrv1533004171504592D          

 41 47  0  0  0  0            999 V2000
    3.3674    3.2947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902    2.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6447    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332    1.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    1.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    1.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5440    1.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3287    1.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5002    0.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2848    0.6544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8871    0.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2064    0.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7204    1.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -1.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2679   -1.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -0.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706    3.2723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6480   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930   -2.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139   -2.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6689   -3.3934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -1.2111    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244488

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(OC1C1=CC=C(O)C=C1)C13OC4=CC(O)=CC(O)=C4C(=O)C1(O)C(OC3=CC2=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O11/c31-15-5-1-13(2-6-15)25-21(36)11-18-19(34)12-23-30(28(18)40-25)29(38,27(39-23)14-3-7-16(32)8-4-14)26(37)24-20(35)9-17(33)10-22(24)41-30/h1-10,12,21,25,27,31-33,35-36,38H,11H2

> <INCHI_KEY>
JTLAASAWWOBQSW-UHFFFAOYSA-N

> <FORMULA>
C30H22O11

> <MOLECULAR_WEIGHT>
558.495

> <EXACT_MASS>
558.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
53.31678998939488

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.5319845076666665

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.95004374025292

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.700445920778875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2364219820572133

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
142.18619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       6.286   6.150   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.553   4.631   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.088   5.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.070   2.669   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.729   2.095   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.873   3.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.338   2.649   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.482   3.680   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.947   3.204   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.267   1.697   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.732   1.221   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.123   0.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.852   1.044   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.453   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.811   2.636   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.318  -2.401   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.233  -2.231   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.989  -1.719   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.250   0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.065   6.108   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.179  -1.941   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.210  -3.085   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.734  -4.550   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.773  -4.870   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.249  -6.334   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.803  -3.725   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.327  -2.261   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    5   16   27   31                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   15   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   15   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32    4   34                                                  
CONECT   34   33                                                            
CONECT   35   29   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                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₁

Average Mass

558.4950 Da

Monoisotopic Mass

558.11621 Da

IUPAC Name

5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione

Traditional Name

5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione

CAS Registry Number

Not Available

SMILES

OC1CC2=C(OC1C1=CC=C(O)C=C1)C13OC4=CC(O)=CC(O)=C4C(=O)C1(O)C(OC3=CC2=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H22O11/c31-15-5-1-13(2-6-15)25-21(36)11-18-19(34)12-23-30(28(18)40-25)29(38,27(39-23)14-3-7-16(32)8-4-14)26(37)24-20(35)9-17(33)10-22(24)41-30/h1-10,12,21,25,27,31-33,35-36,38H,11H2

InChI Key

JTLAASAWWOBQSW-UHFFFAOYSA-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
Daphne feddei	LOTUS Database	35616633
Daphne genkwa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Benzofuran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxolane
Vinylogous ester
Tertiary alcohol
Vinylogous acid
Ketone
Secondary alcohol
Ether
Oxacycle
Polyol
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
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	2.94	ALOGPS
logP	2.53	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.7	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	142.19 m³·mol⁻¹	ChemAxon
Polarizability	53.32 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	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

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

75144957

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione (NP0244488)

MOL for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

3D MOL for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

3D SDF for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

3D-SDF for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

PDB for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

3D PDB for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

SMILES for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

INCHI for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

Structure for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)

3D Structure for NP0244488 (5,13,16,18-tetrahydroxy-4,12-bis(4-hydroxyphenyl)-3,11,21-trioxapentacyclo[11.8.0.0¹,¹⁰.0²,⁷.0¹⁵,²⁰]henicosa-2(7),9,15,17,19-pentaene-8,14-dione)