NP-MRD: Showing NP-Card for 17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione (NP0233211)

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Record Information

Version

2.0

Created at

2022-09-06 14:43:53 UTC

Updated at

2022-09-06 14:43:54 UTC

NP-MRD ID

NP0233211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione

Description

17-[(3,4,5-Trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]Henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. 17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione is found in Gnidia glauca. 17-[(3,4,5-Trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]Henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251509242D          

 34 39  0  0  0  0            999 V2000
    8.5803    3.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8040    2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6578    2.0624    0.0000 O   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
    6.7353    0.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9590    0.6918    0.0000 C   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
    5.0365   -0.3994    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
    4.5527    0.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    1.4777    0.0000 O   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
    3.0001    0.3865    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
    3.3183   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955   -0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -1.4203    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
    0.9111   -0.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1189   -0.1584    0.0000 C   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  0  0  0  0  0  0  0  0  0  0
    0.3212    2.0149    0.0000 O   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
    1.5067    0.1822    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
    5.3289    1.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2515    2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4752    2.0364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3977    3.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677    3.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1740    3.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3202    4.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

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   -5.8092   -0.1851    1.4131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4722   -0.1005    1.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1311    0.4786    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1218    0.7883    1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.8063    1.5580 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306    0.5493    1.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221    0.8895    1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -0.1016   -0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5188   -0.4663   -0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507   -1.0592   -1.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2726   -1.1118   -1.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1901   -1.6318   -2.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5381   -1.5537   -2.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978   -0.9511   -1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3423   -0.8589   -1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7511   -0.2582    0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8098    0.2473    0.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1427    0.8137    2.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5581    0.1327    0.6546 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1060   -0.4312   -0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7554   -0.5156   -0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5228    1.9307    0.5297 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.6914   -2.1773    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2961   -1.7309    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3991    0.3973    2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7459    0.0957   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -0.4470   -1.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2427   -1.0084   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1802    1.3067    2.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8721   -2.1124   -3.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2618   -1.9533   -3.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0823   -1.2559   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8105   -0.1879    0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167    2.7040    0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6597    3.1002    2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2717    1.4158   -1.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3096    3.2278   -1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0542   -0.5720   -0.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9391    1.1176   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
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  5  6  1  0
  6  7  2  0
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 11 42  1  0
 29 47  1  6
 30 48  1  0
 31 49  1  6
 32 50  1  0
 33 51  1  6
 34 52  1  0
M  END


  Mrv1533004251509242D          

 34 39  0  0  0  0            999 V2000
    8.5803    3.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8040    2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6578    2.0624    0.0000 O   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
    6.7353    0.9711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9590    0.6918    0.0000 C   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
    5.0365   -0.3994    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
    4.5527    0.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9226    1.4777    0.0000 O   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
    3.0001    0.3865    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
    3.3183   -0.9099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4955   -0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -1.4203    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
    0.9111   -0.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2515    2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3977    3.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677    3.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1740    3.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3202    4.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0  0  0  0
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  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0233211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2=CC=C3C4=C(C5=C6OC(=O)C=CC6=CC=C5O4)C(=O)OC3=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H18O10/c1-9-18(26)19(27)20(28)24(30-9)31-11-4-5-12-14(8-11)33-23(29)17-16-13(32-22(12)17)6-2-10-3-7-15(25)34-21(10)16/h2-9,18-20,24,26-28H,1H3

> <INCHI_KEY>
CGPMFXUKNVLABW-UHFFFAOYSA-N

> <FORMULA>
C24H18O10

> <MOLECULAR_WEIGHT>
466.398

> <EXACT_MASS>
466.08999678

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
45.970945407003796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2,6,8,10,14,16,18-octaene-5,21-dione

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.2898423166666668

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.268672541952725

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.21362119982513

> <JCHEM_PKA_STRONGEST_BASIC>
-3.062919966300136

> <JCHEM_POLAR_SURFACE_AREA>
144.89000000000001

> <JCHEM_REFRACTIVITY>
113.7299

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2,6,8,10,14,16,18-octaene-5,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      16.017   5.887   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.568   5.365   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.295   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.845   3.328   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.572   1.813   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.123   1.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.850  -0.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.401  -0.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.225   0.249   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.498   1.764   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.322   2.758   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.873   2.237   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.697   3.231   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.600   0.721   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.776  -0.273   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.194  -1.699   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.658  -1.585   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.547  -2.651   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.068  -2.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.701  -0.726   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.222  -0.296   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.145   1.200   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.967   2.266   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.600   3.761   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.445   1.836   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.812   0.340   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.291  -0.090   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.947   2.286   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.669   4.323   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.220   3.801   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.942   5.838   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.766   6.832   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.391   6.360   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.664   7.875   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26   14   17                                                  
CONECT   28   10    6                                                       
CONECT   29    4   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₁₈O₁₀

Average Mass

466.3980 Da

Monoisotopic Mass

466.09000 Da

IUPAC Name

17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2,6,8,10,14,16,18-octaene-5,21-dione

Traditional Name

17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2,6,8,10,14,16,18-octaene-5,21-dione

CAS Registry Number

Not Available

SMILES

CC1OC(OC2=CC=C3C4=C(C5=C6OC(=O)C=CC6=CC=C5O4)C(=O)OC3=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C24H18O10/c1-9-18(26)19(27)20(28)24(30-9)31-11-4-5-12-14(8-11)33-23(29)17-16-13(32-22(12)17)6-2-10-3-7-15(25)34-21(10)16/h2-9,18-20,24,26-28H,1H3

InChI Key

CGPMFXUKNVLABW-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
Lasiosiphon glaucus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Phenolic glycoside
Angular furanocoumarin
Furanocoumarin
Hexose monosaccharide
Coumarin
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Benzofuran
Furopyran
Pyranone
Pyran
Benzenoid
Monosaccharide
Oxane
Heteroaromatic compound
Furan
Lactone
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.95	ALOGPS
logP	1.29	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	144.89 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	113.73 m³·mol⁻¹	ChemAxon
Polarizability	45.97 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

12897366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione (NP0233211)

MOL for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

3D MOL for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

3D SDF for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

3D-SDF for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

PDB for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

3D PDB for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

SMILES for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

INCHI for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

Structure for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)

3D Structure for NP0233211 (17-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0³,⁸.0¹⁴,¹⁹]henicosa-1(13),2(11),3(8),6,9,14(19),15,17-octaene-5,21-dione)