NP-MRD: Showing NP-Card for Boletopsin C (NP0009116)

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Record Information

Version

2.0

Created at

2020-12-09 06:33:52 UTC

Updated at

2021-07-15 17:02:21 UTC

NP-MRD ID

NP0009116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Boletopsin C

Provided By

NPAtlas

Description

Boletopsin C belongs to the class of organic compounds known as phenylbenzofurans. These are organic aromatic compounds that contain a phenyl group attached to a benzofuran moiety. Benzofuran is a bicyclic compound containing a benzene fused to a furan. Boletopsin C is found in Boletopsis and Boletopsis leucomelas. Boletopsin C was first documented in 2010 (PMID: 20380423). Based on a literature review very few articles have been published on Boletopsin C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106323D          

 43 46  0  0  0  0            999 V2000
   -1.6941    3.8804   -0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553    2.6488   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    2.5789    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    1.4831   -1.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2657    0.3812   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.6899   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -0.8063   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -1.6827   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8405   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936   -1.0902   -0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5381   -1.2720   -0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255   -0.2130    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204    0.5289    1.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -0.0793    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.7355    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -2.8234    1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723   -1.7120    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -2.7116    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -0.5961    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.4563   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059    1.3429   -0.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    0.9875   -0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.6118   -0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053    0.9854   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637    1.6077   -0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4846   -0.2457    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361   -0.8759    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -0.8606    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -0.2641    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    4.1289   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960    3.7655   -0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2104   -2.2592   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6027    0.4536    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    0.6253    1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390   -3.6234    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541   -3.5297    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380    2.5705   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7031    1.1439    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5802   -1.7933    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1750   -1.8445    1.1559 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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  8 33  1  0  0  0  0
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 27 42  1  0  0  0  0
 28 43  1  0  0  0  0
M  END

     RDKit          3D

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   -1.0553    2.6488   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    2.5789    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    1.4831   -1.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2657    0.3812   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.6899   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -0.8063   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -1.6827   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8405   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936   -1.0902   -0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5381   -1.2720   -0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255   -0.2130    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204    0.5289    1.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -0.0793    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.7355    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -2.8234    1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723   -1.7120    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -2.7116    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -0.5961    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.4563   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059    1.3429   -0.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    0.9875   -0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.6118   -0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053    0.9854   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637    1.6077   -0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4846   -0.2457    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361   -0.8759    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -0.8606    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -0.2641    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7960    3.7655   -0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2104   -2.2592   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172   -2.5251   -2.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2859   -0.7981   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6027    0.4536    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    0.6253    1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390   -3.6234    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5802   -1.7933    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1750   -1.8445    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
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 14  7  1  0
 29 19  1  0
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 28 43  1  0
M  END


  Mrv1652306242106323D          

 43 46  0  0  0  0            999 V2000
   -1.6941    3.8804   -0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553    2.6488   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    2.5789    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    1.4831   -1.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2657    0.3812   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.6899   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -0.8063   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -1.6827   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8405   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936   -1.0902   -0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5381   -1.2720   -0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6204    0.5289    1.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2942   -1.7355    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8202   -2.7116    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -0.5961    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.4563   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059    1.3429   -0.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    0.9875   -0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6390   -3.6234    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541   -3.5297    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5802   -1.7933    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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  2  0  0  0  0
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 10 12  1  0  0  0  0
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 28 29  2  0  0  0  0
 20  5  1  0  0  0  0
 29 22  1  0  0  0  0
 14  7  1  0  0  0  0
 29 19  1  0  0  0  0
  1 30  1  0  0  0  0
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  1 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  0  0  0  0
 11 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  0  0  0  0
 16 38  1  0  0  0  0
 18 39  1  0  0  0  0
 23 40  1  0  0  0  0
 25 41  1  0  0  0  0
 27 42  1  0  0  0  0
 28 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1O[H])C1=C(OC(=O)C([H])([H])[H])C2=C(C3=C([H])C(O[H])=C(O[H])C([H])=C3O2)C(O[H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O9/c1-7(21)28-19-15(8-2-3-10(22)11(23)4-8)17(26)18(27)16-9-5-12(24)13(25)6-14(9)29-20(16)19/h2-6,22-27H,1H3

> <INCHI_KEY>
ITQQDEWZQMZXBV-UHFFFAOYSA-N

> <FORMULA>
C20H14O9

> <MOLECULAR_WEIGHT>
398.323

> <EXACT_MASS>
398.063782031

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
39.22941506585252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(3,4-dihydroxyphenyl)-3,4,11,12-tetrahydroxy-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2(7),3,5,9,11-hexaen-6-yl acetate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.5843415033333335

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.762795283655207

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.908875379192749

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9360083428077255

> <JCHEM_POLAR_SURFACE_AREA>
160.82

> <JCHEM_REFRACTIVITY>
99.38080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3,4-dihydroxyphenyl)-3,4,11,12-tetrahydroxy-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2(7),3,5,9,11-hexaen-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -1.6941    3.8804   -0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553    2.6488   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    2.5789    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    1.4831   -1.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2657    0.3812   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.6899   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -0.8063   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -1.6827   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8405   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936   -1.0902   -0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5381   -1.2720   -0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255   -0.2130    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204    0.5289    1.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -0.0793    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.7355    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -2.8234    1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723   -1.7120    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -2.7116    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -0.5961    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.4563   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059    1.3429   -0.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    0.9875   -0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.6118   -0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053    0.9854   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637    1.6077   -0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4846   -0.2457    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361   -0.8759    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -0.8606    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -0.2641    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    4.1289   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960    3.7655   -0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758    4.6912   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2104   -2.2592   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172   -2.5251   -2.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2859   -0.7981   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6027    0.4536    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    0.6253    1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390   -3.6234    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541   -3.5297    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380    2.5705   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7031    1.1439    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5802   -1.7933    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1750   -1.8445    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  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  1  0
 12 14  2  0
  6 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 20  5  1  0
 29 22  1  0
 14  7  1  0
 29 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 23 40  1  0
 25 41  1  0
 27 42  1  0
 28 43  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.694   3.880  -0.799  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.055   2.649  -0.303  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.599   2.579   0.895  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.893   1.483  -1.064  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.266   0.381  -0.453  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.990  -0.690  -0.007  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.441  -0.806  -0.174  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.959  -1.683  -1.138  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.277  -1.841  -1.389  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.194  -1.090  -0.648  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.538  -1.272  -0.928  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.726  -0.213   0.314  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.620   0.529   1.043  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.344  -0.079   0.543  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.294  -1.736   0.595  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.008  -2.823   1.052  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.072  -1.712   0.743  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.820  -2.712   1.331  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.777  -0.596   0.270  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.125   0.456  -0.330  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.006   1.343  -0.673  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.224   0.988  -0.358  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.459   1.612  -0.535  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.605   0.985  -0.095  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.864   1.608  -0.268  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.485  -0.246   0.506  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.636  -0.876   0.948  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.264  -0.861   0.678  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.117  -0.264   0.255  0.00  0.00           C+0
HETATM   30  H   UNK     0      -1.245   4.129  -1.780  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.796   3.765  -0.840  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.476   4.691  -0.067  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.210  -2.259  -1.694  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.617  -2.525  -2.140  0.00  0.00           H+0
HETATM   35  H   UNK     0      -7.286  -0.798  -0.472  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.603   0.454   0.905  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.035   0.625   1.306  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.639  -3.623   1.488  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.354  -3.530   1.687  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.538   2.571  -1.010  0.00  0.00           H+0
HETATM   41  H   UNK     0       7.703   1.144   0.056  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.580  -1.793   1.395  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.175  -1.845   1.156  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   33                                                  
CONECT    9    8   10   34                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   35                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12   36                                                       
CONECT   14   12    7   37                                                  
CONECT   15    6   16   17                                                  
CONECT   16   15   38                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17   39                                                       
CONECT   19   17   20   29                                                  
CONECT   20   19   21    5                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24   40                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   41                                                       
CONECT   26   24   27   28                                                  
CONECT   27   26   42                                                       
CONECT   28   26   29   43                                                  
CONECT   29   28   22   19                                                  
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   11                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   23                                                            
CONECT   41   25                                                            
CONECT   42   27                                                            
CONECT   43   28                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

RDKit          3D

43 46  0  0  0  0  0  0  0  0999 V2000
   -1.6941    3.8804   -0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553    2.6488   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5994    2.5789    0.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    1.4831   -1.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2657    0.3812   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -0.6899   -0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -0.8063   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -1.6827   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767   -1.8405   -1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1936   -1.0902   -0.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5381   -1.2720   -0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255   -0.2130    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204    0.5289    1.0426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -0.0793    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.7355    0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -2.8234    1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723   -1.7120    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202   -2.7116    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774   -0.5961    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.4563   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0059    1.3429   -0.6726 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    0.9875   -0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    1.6118   -0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053    0.9854   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8637    1.6077   -0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4846   -0.2457    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361   -0.8759    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -0.8606    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1168   -0.2641    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2446    4.1289   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960    3.7655   -0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758    4.6912   -0.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2104   -2.2592   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172   -2.5251   -2.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2859   -0.7981   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6027    0.4536    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0352    0.6253    1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6390   -3.6234    1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541   -3.5297    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380    2.5705   -1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7031    1.1439    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5802   -1.7933    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1750   -1.8445    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  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  1  0
 12 14  2  0
  6 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 20  5  1  0
 29 22  1  0
 14  7  1  0
 29 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 23 40  1  0
 25 41  1  0
 27 42  1  0
 28 43  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-(3,4-Dihydroxyphenyl)-3,4,11,12-tetrahydroxy-8-oxatricyclo[7.4.0.0,]trideca-1(9),2,4,6,10,12-hexaen-6-yl acetic acid	Generator

Chemical Formula

C₂₀H₁₄O₉

Average Mass

398.3230 Da

Monoisotopic Mass

398.06378 Da

IUPAC Name

5-(3,4-dihydroxyphenyl)-3,4,11,12-tetrahydroxy-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2(7),3,5,9,11-hexaen-6-yl acetate

Traditional Name

5-(3,4-dihydroxyphenyl)-3,4,11,12-tetrahydroxy-8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2(7),3,5,9,11-hexaen-6-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=C(C(O)=C(O)C2=C1OC1=CC(O)=C(O)C=C21)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C20H14O9/c1-7(21)28-19-15(8-2-3-10(22)11(23)4-8)17(26)18(27)16-9-5-12(24)13(25)6-14(9)29-20(16)19/h2-6,22-27H,1H3

InChI Key

ITQQDEWZQMZXBV-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Boletopsis	NPAtlas	20380423
Boletopsis leucomelas	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzofurans. These are organic aromatic compounds that contain a phenyl group attached to a benzofuran moiety. Benzofuran is a bicyclic compound containing a benzene fused to a furan.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Phenylbenzofurans

Direct Parent

Phenylbenzofurans

Alternative Parents

Substituents

Phenylbenzofuran
Biphenol
Dibenzofuran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Polyol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
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	2.78	ALOGPS
logP	2.58	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	160.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.38 m³·mol⁻¹	ChemAxon
Polarizability	39.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005148

HMDB ID

HMDB0178603

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054657

Chemspider ID

24671195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46831715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kaneko A, Tsukada M, Fukai M, Suzuki T, Nishio K, Miki K, Kinoshita K, Takahashi K, Koyama K: KDR Kinase Inhibitor Isolated from the Mushroom Boletopsis leucomelas. J Nat Prod. 2010 May 28;73(5):1002-4. doi: 10.1021/np100113e. [PubMed:20380423 ]

Showing NP-Card for Boletopsin C (NP0009116)

MOL for NP0009116 (Boletopsin C)

3D MOL for NP0009116 (Boletopsin C)

3D SDF for NP0009116 (Boletopsin C)

3D-SDF for NP0009116 (Boletopsin C)

PDB for NP0009116 (Boletopsin C)

3D PDB for NP0009116 (Boletopsin C)

SMILES for NP0009116 (Boletopsin C)

INCHI for NP0009116 (Boletopsin C)

Structure for NP0009116 (Boletopsin C)

3D Structure for NP0009116 (Boletopsin C)