NP-MRD: Showing NP-Card for 13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol (NP0158077)

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Record Information

Version

2.0

Created at

2022-09-02 15:36:26 UTC

Updated at

2022-09-02 15:36:26 UTC

NP-MRD ID

NP0158077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol

Description

13-[5,6-Dihydroxy-2-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol is found in Lespedeza cyrtobotrya. 13-[5,6-Dihydroxy-2-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520212D          

 60 67  0  0  0  0            999 V2000
   -4.2215   14.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6084   13.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799   12.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1668   12.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3384   11.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7253   11.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968   10.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2837    9.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    9.7716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1277    9.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431    8.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    9.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547    9.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678    9.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524    9.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962   10.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1715    7.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131    7.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    7.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5692    7.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    8.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4552    8.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2399    8.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8530    9.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814    9.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2945   10.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1230   11.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7361   11.8935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131    6.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715    6.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262    6.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1400    5.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936    4.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    5.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2707    5.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6832    4.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    4.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9207    4.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7457    4.0731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    3.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6832    6.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082    6.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2707    6.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6832    7.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    6.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0332    6.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4255    4.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2890    5.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0035    4.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179    5.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324    4.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324    3.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449    4.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7146    3.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179    3.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0035    3.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2890    3.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4255    3.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1400    3.5745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238   14.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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  1  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  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
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  2  0  0  0  0
 31 46  1  0  0  0  0
 34 46  1  0  0  0  0
 32 47  1  0  0  0  0
 47 48  2  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 52 55  1  0  0  0  0
 55 56  1  0  0  0  0
 49 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 47 58  1  0  0  0  0
 58 59  1  0  0  0  0
  2 60  1  0  0  0  0
M  END

     RDKit          3D

110117  0  0  0  0  0  0  0  0999 V2000
    9.4956    2.4334    1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7087    1.4293    2.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0571    1.9306    3.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6013    0.1258    2.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2601   -0.4533    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0425   -1.2990    0.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8457   -0.7975    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6864   -1.5398    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7421   -2.8256    1.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9213   -3.3812    1.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0520   -2.5793    1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2352   -3.1495    1.9259 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5659   -3.5389    1.0205 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2645   -2.9678    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2482   -1.4842    0.9078 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1366   -1.0092    0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.6054    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939   -0.1578   -0.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    0.5657   -0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    1.8400   -0.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -0.0579   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7000    0.4598   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1472    1.8229    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0776    2.0699    1.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6042    3.2949    1.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2072    4.3866    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3168    4.1829   -0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9325    2.8307   -1.6902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7550    5.5914    0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9125    6.5130    1.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1715    6.8963    2.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1103    4.7028    2.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5923    3.5185    2.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5766   -0.5505   -0.0560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9979   -1.6953   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5009   -2.9797   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349   -3.3003   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5098   -3.3331    1.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1354   -4.4283    1.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7077   -4.4492    2.9706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2621   -5.6285    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -4.0486   -0.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1908   -5.3218   -0.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983   -3.8317   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4116   -4.8337   -1.0529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8126   -2.5159   -0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6365   -1.4547   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5782    0.1840   -6.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6121   -0.9408   -1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -1.4114   -1.2187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406   -0.9658    0.0665 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8268    3.4431    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0652    2.1706    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3947    2.5083    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1723    1.9953    3.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6964    2.9901    3.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6279    1.3040    4.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8239    0.2148    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004231520212D          

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M  END
> <DATABASE_ID>
NP0158077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC2=C(OCC3C2OC2=C(CC=C(C)C)C(O)=C(C=C32)C(=O)C2=C(OC3=C(CC=C(C)C)C(O)=C(O)C=C23)C2=CC3=C(OC(C)(C)C=C3)C=C2O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C50H50O10/c1-24(2)9-12-27-17-33-41(21-37(27)51)57-23-36-31-19-35(43(54)29(13-10-25(3)4)46(31)58-48(33)36)45(56)42-34-20-39(53)44(55)30(14-11-26(5)6)47(34)59-49(42)32-18-28-15-16-50(7,8)60-40(28)22-38(32)52/h9-11,15-22,36,48,51-55H,12-14,23H2,1-8H3

> <INCHI_KEY>
IYUZDUFYWMTORD-UHFFFAOYSA-N

> <FORMULA>
C50H50O10

> <MOLECULAR_WEIGHT>
810.94

> <EXACT_MASS>
810.34039781

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
88.21267744970767

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol

> <ALOGPS_LOGP>
7.31

> <JCHEM_LOGP>
11.374660699000003

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.7065878697279055

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.842006505703814

> <JCHEM_PKA_STRONGEST_BASIC>
-2.978982894670775

> <JCHEM_POLAR_SURFACE_AREA>
159.04999999999998

> <JCHEM_REFRACTIVITY>
236.07360000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -7.880  26.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.736  25.690   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.056  24.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.911  23.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.232  21.647   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.087  20.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.407  19.110   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.263  18.079   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.731  18.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.105  16.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.640  16.358   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.504  17.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.969  16.912   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.113  17.943   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.578  17.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.793  19.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.320  14.851   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.144  14.375   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.465  13.821   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.929  14.297   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.249  15.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.583  16.573   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.048  16.097   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -7.192  17.128   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.872  18.634   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.016  19.664   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.696  21.171   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.841  22.201   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.144  12.315   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.320  11.839   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.289  11.284   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.128   9.752   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.535   9.126   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.565  10.271   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.105  10.271   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.875   8.937   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.415   8.937   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.185   7.603   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -10.725   7.603   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.415   6.270   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.875  11.604   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.415  11.604   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -6.105  12.938   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.875  14.272   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -4.565  12.938   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.795  11.604   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -0.794   8.982   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.539   9.752   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.873   8.982   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.207   9.752   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.540   8.982   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.540   7.442   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       6.057   7.710   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.067   5.995   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       3.207   6.672   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       1.873   7.442   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.539   6.672   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -0.794   7.442   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -2.128   6.672   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -5.271  26.166   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   60                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   10   22                                                  
CONECT   22   21    8   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26    5   28                                                  
CONECT   28   27                                                            
CONECT   29   19   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   46                                                  
CONECT   32   31   33   47                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   46                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   35   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   31   34                                                  
CONECT   47   32   48   58                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   56                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52   56                                                       
CONECT   56   55   49   57                                                  
CONECT   57   56   58                                                       
CONECT   58   57   47   59                                                  
CONECT   59   58                                                            
CONECT   60    2                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  134    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₀H₅₀O₁₀

Average Mass

810.9400 Da

Monoisotopic Mass

810.34040 Da

IUPAC Name

13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC2=C(OCC3C2OC2=C(CC=C(C)C)C(O)=C(C=C32)C(=O)C2=C(OC3=C(CC=C(C)C)C(O)=C(O)C=C23)C2=CC3=C(OC(C)(C)C=C3)C=C2O)C=C1O

InChI Identifier

InChI=1S/C50H50O10/c1-24(2)9-12-27-17-33-41(21-37(27)51)57-23-36-31-19-35(43(54)29(13-10-25(3)4)46(31)58-48(33)36)45(56)42-34-20-39(53)44(55)30(14-11-26(5)6)47(34)59-49(42)32-18-28-15-16-50(7,8)60-40(28)22-38(32)52/h9-11,15-22,36,48,51-55H,12-14,23H2,1-8H3

InChI Key

IYUZDUFYWMTORD-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
Lespedeza cyrtobotrya	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
7-prenylated 2-arybenzofuran
Pterocarpan
Furanoisoflavonoid skeleton
Isoflavanol
Isoflavonoid
Isoflavan
2,2-dimethyl-1-benzopyran
1-benzopyran
Chromane
Benzopyran
Coumaran
Benzofuran
Aryl ketone
3-aroylfuran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Furan
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	7.31	ALOGPS
logP	11.37	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	6.84	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	159.05 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	236.07 m³·mol⁻¹	ChemAxon
Polarizability	88.21 Å³	ChemAxon
Number of Rings	8	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

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

74429595

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol (NP0158077)

MOL for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D MOL for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D SDF for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D-SDF for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

PDB for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D PDB for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

SMILES for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

INCHI for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

Structure for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D Structure for NP0158077 (13-[5,6-dihydroxy-2-(7-hydroxy-2,2-dimethylchromen-6-yl)-7-(3-methylbut-2-en-1-yl)-1-benzofuran-3-carbonyl]-4,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)