NP-MRD: Showing NP-Card for Cyathusal B (NP0007076)

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Record Information

Version

2.0

Created at

2020-12-09 03:57:58 UTC

Updated at

2021-07-15 16:56:35 UTC

NP-MRD ID

NP0007076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyathusal B

Provided By

NPAtlas

Description

Cyathusal B belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. Cyathusal B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Cyathusal B is found in Cyathus stercoreus. Based on a literature review very few articles have been published on cyathusal B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242118373D          

 39 41  0  0  0  0            999 V2000
    6.9853    1.2889   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870    1.2715   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041    0.1457    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    0.1226    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846   -1.0829    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.0652    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    0.1650    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560    1.3175   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    2.4352   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6940    1.2407   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.1843    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347    1.3404   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    2.5684   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    1.2991   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7253    2.4124   -0.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5645    0.0629    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9329    0.0051    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7559   -0.1426   -1.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -1.0839    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410   -2.3743    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258   -2.7958    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -1.0523    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7644   -2.3541    0.3447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1284   -2.8576    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -2.2298    0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989    1.3975   -1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4097    0.4106    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    2.1750    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158    2.1801   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -0.7860    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -2.0292    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723    3.4399   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810    3.3346   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7986    0.1906   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552   -1.2011   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    0.4665   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077   -2.9508   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -3.0873   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.3619    2.3182 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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 10  4  1  0  0  0  0
 22 11  1  0  0  0  0
 25  6  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  0  0  0  0
  5 31  1  0  0  0  0
 13 32  1  0  0  0  0
 15 33  1  0  0  0  0
 18 34  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
 23 38  1  6  0  0  0
 24 39  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    6.9853    1.2889   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870    1.2715   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041    0.1457    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    0.1226    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846   -1.0829    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.0652    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    0.1650    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560    1.3175   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    2.4352   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6940    1.2407   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.1843    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347    1.3404   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    2.5684   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    1.2991   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7253    2.4124   -0.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5645    0.0629    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9329    0.0051    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7559   -0.1426   -1.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -1.0839    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410   -2.3743    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258   -2.7958    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -1.0523    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7644   -2.3541    0.3447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1284   -2.8576    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -2.2298    0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989    1.3975   -1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4097    0.4106    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    2.1750    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158    2.1801   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -0.7860    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -2.0292    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723    3.4399   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810    3.3346   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7986    0.1906   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552   -1.2011   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    0.4665   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077   -2.9508   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -3.0873   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.3619    2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 10  4  1  0
 22 11  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  5 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 23 38  1  6
 24 39  1  0
M  END

  Mrv1652306242118373D          

 39 41  0  0  0  0            999 V2000
    6.9853    1.2889   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870    1.2715   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041    0.1457    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    0.1226    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846   -1.0829    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.0652    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    0.1650    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560    1.3175   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    2.4352   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6940    1.2407   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.1843    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347    1.3404   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    2.5684   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    1.2991   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7253    2.4124   -0.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5645    0.0629    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9329    0.0051    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7559   -0.1426   -1.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -1.0839    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410   -2.3743    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258   -2.7958    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -1.0523    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7644   -2.3541    0.3447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1284   -2.8576    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -2.2298    0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989    1.3975   -1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4097    0.4106    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    2.1750    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158    2.1801   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -0.7860    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -2.0292    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723    3.4399   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810    3.3346   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7986    0.1906   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552   -1.2011   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    0.4665   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077   -2.9508   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -3.0873   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.3619    2.3182 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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 10  4  1  0  0  0  0
 22 11  1  0  0  0  0
 25  6  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  0  0  0  0
  5 31  1  0  0  0  0
 13 32  1  0  0  0  0
 15 33  1  0  0  0  0
 18 34  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
 20 37  1  0  0  0  0
 23 38  1  6  0  0  0
 24 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C(C([H])=O)=C2C(=C1O[H])C1=C(O[C@@]2([H])O[H])C([H])=C(OC1=O)C(\[H])=C(/[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O8/c1-3-4-7-5-9-11(17(22)24-7)12-10(16(21)25-9)8(6-18)15(23-2)14(20)13(12)19/h3-6,16,19-21H,1-2H3/b4-3+/t16-/m1/s1

> <INCHI_KEY>
YLBKRHCXWXNKBF-ONEGZZNKSA-N

> <FORMULA>
C17H14O8

> <MOLECULAR_WEIGHT>
346.291

> <EXACT_MASS>
346.068867411

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.89418160039493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R)-6,9,10-trihydroxy-8-methoxy-1-oxo-3-[(1E)-prop-1-en-1-yl]-1H,6H-pyrano[4,3-c]isochromene-7-carbaldehyde

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.425777493

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.222564656450572

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.417028396729458

> <JCHEM_PKA_STRONGEST_BASIC>
-4.484088221623542

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
89.6913

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6,9,10-trihydroxy-8-methoxy-1-oxo-3-[(1E)-prop-1-en-1-yl]-6H-pyrano[4,3-c]isochromene-7-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    6.9853    1.2889   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870    1.2715   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041    0.1457    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    0.1226    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846   -1.0829    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.0652    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    0.1650    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560    1.3175   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    2.4352   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6940    1.2407   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.1843    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347    1.3404   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    2.5684   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    1.2991   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7253    2.4124   -0.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5645    0.0629    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9329    0.0051    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7559   -0.1426   -1.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -1.0839    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410   -2.3743    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258   -2.7958    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -1.0523    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7644   -2.3541    0.3447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1284   -2.8576    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -2.2298    0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989    1.3975   -1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4097    0.4106    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    2.1750    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158    2.1801   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -0.7860    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -2.0292    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723    3.4399   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810    3.3346   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7986    0.1906   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552   -1.2011   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    0.4665   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077   -2.9508   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -3.0873   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.3619    2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 10  4  1  0
 22 11  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  5 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 23 38  1  6
 24 39  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       6.985   1.289  -0.043  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.487   1.272  -0.037  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.804   0.146   0.078  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.325   0.123   0.084  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.685  -1.083   0.207  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.316  -1.065   0.209  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.648   0.165   0.088  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.356   1.317  -0.029  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.872   2.435  -0.140  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.694   1.241  -0.026  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.823   0.184   0.091  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.535   1.340  -0.023  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.976   2.568  -0.148  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.917   1.299  -0.015  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.725   2.412  -0.124  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.564   0.063   0.111  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.933   0.005   0.121  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.756  -0.143  -1.002  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.839  -1.084   0.224  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.541  -2.374   0.355  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.826  -2.796   1.488  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.465  -1.052   0.216  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.764  -2.354   0.345  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.128  -2.858   1.616  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.607  -2.230   0.328  0.00  0.00           O+0
HETATM   26  H   UNK     0       7.399   1.397  -1.054  0.00  0.00           H+0
HETATM   27  H   UNK     0       7.410   0.411   0.445  0.00  0.00           H+0
HETATM   28  H   UNK     0       7.309   2.175   0.575  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.916   2.180  -0.126  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.333  -0.786   0.169  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.202  -2.029   0.300  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.472   3.440  -0.233  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.381   3.335  -0.217  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.799   0.191  -0.729  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.855  -1.201  -1.299  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.463   0.467  -1.868  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.808  -2.951  -0.505  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.171  -3.087  -0.387  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.607  -2.362   2.318  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3   29                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6   31                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4                                                       
CONECT   11    7   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   32                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14   33                                                       
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   34   35   36                                             
CONECT   19   16   20   22                                                  
CONECT   20   19   21   37                                                  
CONECT   21   20                                                            
CONECT   22   19   23   11                                                  
CONECT   23   22   24   25   38                                             
CONECT   24   23   39                                                       
CONECT   25   23    6                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    3                                                            
CONECT   31    5                                                            
CONECT   32   13                                                            
CONECT   33   15                                                            
CONECT   34   18                                                            
CONECT   35   18                                                            
CONECT   36   18                                                            
CONECT   37   20                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
    6.9853    1.2889   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4870    1.2715   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041    0.1457    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    0.1226    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846   -1.0829    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.0652    0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    0.1650    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560    1.3175   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8715    2.4352   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6940    1.2407   -0.0256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    0.1843    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5347    1.3404   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9756    2.5684   -0.1476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9169    1.2991   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7253    2.4124   -0.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5645    0.0629    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9329    0.0051    0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7559   -0.1426   -1.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -1.0839    0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410   -2.3743    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258   -2.7958    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -1.0523    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7644   -2.3541    0.3447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1284   -2.8576    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -2.2298    0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989    1.3975   -1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4097    0.4106    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094    2.1750    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158    2.1801   -0.1263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -0.7860    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -2.0292    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4723    3.4399   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3810    3.3346   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7986    0.1906   -0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8552   -1.2011   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4635    0.4665   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8077   -2.9508   -0.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -3.0873   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6066   -2.3619    2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 19 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 10  4  1  0
 22 11  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  5 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 23 38  1  6
 24 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₈

Average Mass

346.2910 Da

Monoisotopic Mass

346.06887 Da

IUPAC Name

(6R)-6,9,10-trihydroxy-8-methoxy-1-oxo-3-[(1E)-prop-1-en-1-yl]-1H,6H-pyrano[4,3-c]isochromene-7-carbaldehyde

Traditional Name

(6R)-6,9,10-trihydroxy-8-methoxy-1-oxo-3-[(1E)-prop-1-en-1-yl]-6H-pyrano[4,3-c]isochromene-7-carbaldehyde

CAS Registry Number

Not Available

SMILES

COC1=C(C=O)C2=C(C(O)=C1O)C1=C(OC2O)C=C(OC1=O)\C=C\C

InChI Identifier

InChI=1S/C17H14O8/c1-3-4-7-5-9-11(17(22)24-7)12-10(16(21)25-9)8(6-18)15(23-2)14(20)13(12)19/h3-6,16,19-21H,1-2H3/b4-3+

InChI Key

YLBKRHCXWXNKBF-ONEGZZNKSA-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
Cyathus stercoreus	NPAtlas	17511503

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Aryl-aldehyde
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Hemiacetal
Lactone
Polyol
Ether
Oxacycle
Organooxygen compound
Organic oxygen compound
Aldehyde
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:65703 )
organic heterotricyclic compound (CHEBI:65703 )
polyphenol (CHEBI:65703 )
polyketide (CHEBI:65703 )
delta-lactone (CHEBI:65703 )
cyclic ether (CHEBI:65703 )
arenecarbaldehyde (CHEBI:65703 )

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	2.06	ALOGPS
logP	1.43	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.42	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.69 m³·mol⁻¹	ChemAxon
Polarizability	33.89 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA002429

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038885

Chemspider ID

20568538

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16737097

PDB ID

Not Available

ChEBI ID

65703

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cyathusal B (NP0007076)

MOL for NP0007076 (Cyathusal B)

3D MOL for NP0007076 (Cyathusal B)

3D SDF for NP0007076 (Cyathusal B)

3D-SDF for NP0007076 (Cyathusal B)

PDB for NP0007076 (Cyathusal B)

3D PDB for NP0007076 (Cyathusal B)

SMILES for NP0007076 (Cyathusal B)

INCHI for NP0007076 (Cyathusal B)

Structure for NP0007076 (Cyathusal B)

3D Structure for NP0007076 (Cyathusal B)