NP-MRD: Showing NP-Card for xanthouroleuconaphin (NP0042181)

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Record Information

Version

2.0

Created at

2021-06-20 23:54:31 UTC

Updated at

2021-06-30 00:17:07 UTC

NP-MRD ID

NP0042181

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xanthouroleuconaphin

Provided By

JEOL Database JEOL Logo

Description

Xanthouroleuconaphin belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities. xanthouroleuconaphin is found in Uroleucon nigrotuberculatum. xanthouroleuconaphin was first documented in 2013 (Nishimura, T., et al.). Based on a literature review very few articles have been published on Xanthouroleuconaphin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101543D          

 56 59  0  0  0  0            999 V2000
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    2.4760    3.4094    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3382    2.4817    2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212101543D          

 56 59  0  0  0  0            999 V2000
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    3.2159    4.5177    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    3.0073    0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    2.9761   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075   -0.5615    1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188    0.9626    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.5697    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732   -1.6820    4.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838   -2.5514    4.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2322   -0.8569    3.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612   -5.5835    4.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307   -3.8473    3.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489   -4.4684    4.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047   -5.5892    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -4.8547   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -2.2190   -3.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283    0.0224   -4.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.6915   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -0.8085    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2046    0.5287    3.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303    2.5290    3.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    4.5075    3.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1521    4.6018    3.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 17  2  0  0  0  0
  7  5  1  0  0  0  0
 17 18  1  0  0  0  0
 32 30  1  0  0  0  0
 18 20  2  0  0  0  0
  5  4  2  0  0  0  0
 20 21  1  0  0  0  0
 30 29  2  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
  4 33  1  0  0  0  0
 27 28  1  0  0  0  0
 33 32  2  0  0  0  0
 30 31  1  0  0  0  0
 33 34  1  0  0  0  0
 27 26  2  0  0  0  0
  4  2  1  0  0  0  0
  8  9  2  0  0  0  0
  2  1  1  0  0  0  0
 32 25  1  0  0  0  0
  2  3  2  0  0  0  0
  9 11  1  0  0  0  0
  5  6  1  0  0  0  0
 26 25  1  0  0  0  0
 21 22  1  0  0  0  0
 11 15  2  0  0  0  0
 18 19  1  0  0  0  0
 15 17  1  0  0  0  0
 15 16  1  0  0  0  0
 24  8  1  0  0  0  0
 11 12  1  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 25  7  2  0  0  0  0
 12 14  2  0  0  0  0
 29 27  1  0  0  0  0
  9 10  1  0  0  0  0
 29 54  1  0  0  0  0
 26 52  1  0  0  0  0
 20 49  1  0  0  0  0
 23 51  1  0  0  0  0
 28 53  1  0  0  0  0
 31 55  1  0  0  0  0
 34 56  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
 22 50  1  0  0  0  0
 19 48  1  0  0  0  0
 16 47  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 13 46  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042181

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C3=C(C(C(=O)C([H])([H])[H])=C(O[H])C4=C3C([H])=C(O[H])C([H])=C4O[H])C([H])([H])[H])C(=C(C(=O)C([H])([H])[H])C(O[H])=C2C(O[H])=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O8/c1-9-19(11(3)27)25(33)23-15(5-13(29)7-17(23)31)21(9)22-10(2)20(12(4)28)26(34)24-16(22)6-14(30)8-18(24)32/h5-8,29-34H,1-4H3

> <INCHI_KEY>
NVPMMQYSHXYHEF-UHFFFAOYSA-N

> <FORMULA>
C26H22O8

> <MOLECULAR_WEIGHT>
462.454

> <EXACT_MASS>
462.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
47.36375929949944

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{3'-acetyl-4,4',5,5',7,7'-hexahydroxy-2,2'-dimethyl-[1,1'-binaphthalene]-3-yl}ethan-1-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
5.220170577333333

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.304634010311531

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.78082263868659

> <JCHEM_PKA_STRONGEST_BASIC>
-5.3725536657314

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
126.86799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{3'-acetyl-4,4',5,5',7,7'-hexahydroxy-2,2'-dimethyl-[1,1'-binaphthalene]-3-yl}ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    3.1178    3.4686    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760    3.4094    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    4.1741    2.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382    2.4817    2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    1.1288    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276    0.4928    1.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698    0.3602    1.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559   -1.0649    1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -2.1101    2.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -1.7818    3.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -3.4425    1.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3278   -4.6035    2.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -4.6150    4.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0241   -5.5693    2.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445   -3.7294    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889   -5.0390    0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7146   -0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -2.9728   -1.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356   -4.2459   -2.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -1.9619   -2.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.6552   -2.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6760    0.3837   -3.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930   -0.3584   -1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650   -1.3664   -0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    0.9401    2.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325    0.2168    2.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3702    0.7741    3.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4856   -0.0047    3.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3568    2.0722    3.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1854    2.8110    3.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2579    4.0980    3.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    2.2814    2.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1969    3.0216    2.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2103    4.3198    3.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    4.5177    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    3.0073    0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    2.9761   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075   -0.5615    1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188    0.9626    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.5697    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732   -1.6820    4.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838   -2.5514    4.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2322   -0.8569    3.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612   -5.5835    4.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307   -3.8473    3.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489   -4.4684    4.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047   -5.5892    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -4.8547   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -2.2190   -3.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283    0.0224   -4.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.6915   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -0.8085    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2046    0.5287    3.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303    2.5290    3.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    4.5075    3.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1521    4.6018    3.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 17  2  0
  7  5  1  0
 17 18  1  0
 32 30  1  0
 18 20  2  0
  5  4  2  0
 20 21  1  0
 30 29  2  0
 21 23  2  0
 23 24  1  0
  4 33  1  0
 27 28  1  0
 33 32  2  0
 30 31  1  0
 33 34  1  0
 27 26  2  0
  4  2  1  0
  8  9  2  0
  2  1  1  0
 32 25  1  0
  2  3  2  0
  9 11  1  0
  5  6  1  0
 26 25  1  0
 21 22  1  0
 11 15  2  0
 18 19  1  0
 15 17  1  0
 15 16  1  0
 24  8  1  0
 11 12  1  0
  7  8  1  0
 12 13  1  0
 25  7  2  0
 12 14  2  0
 29 27  1  0
  9 10  1  0
 29 54  1  0
 26 52  1  0
 20 49  1  0
 23 51  1  0
 28 53  1  0
 31 55  1  0
 34 56  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  6 38  1  0
  6 39  1  0
  6 40  1  0
 22 50  1  0
 19 48  1  0
 16 47  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.118   3.469   0.455  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.476   3.409   1.815  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.797   4.174   2.725  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.338   2.482   2.051  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.364   1.129   1.673  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.628   0.493   1.140  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.170   0.360   1.801  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.156  -1.065   1.344  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.362  -2.110   2.292  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.657  -1.782   3.737  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.284  -3.442   1.853  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.328  -4.604   2.781  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.555  -4.615   4.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.024  -5.569   2.467  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.145  -3.729   0.483  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.189  -5.039   0.034  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.049  -2.715  -0.484  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.238  -2.973  -1.871  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.236  -4.246  -2.387  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.444  -1.962  -2.803  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.474  -0.655  -2.362  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.676   0.384  -3.221  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.293  -0.358  -1.016  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.065  -1.366  -0.044  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.019   0.940   2.363  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.232   0.217   2.490  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.370   0.774   3.065  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.486  -0.005   3.152  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.357   2.072   3.531  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.185   2.811   3.406  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.258   4.098   3.880  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.000   2.281   2.824  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.197   3.022   2.670  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.210   4.320   3.154  0.00  0.00           O+0
HETATM   35  H   UNK     0       3.216   4.518   0.160  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.107   3.007   0.490  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.501   2.976  -0.301  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.708  -0.562   1.421  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.519   0.963   1.568  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.663   0.570   0.050  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.273  -1.682   4.304  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.284  -2.551   4.199  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.232  -0.857   3.840  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.061  -5.583   4.056  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.331  -3.847   3.940  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.049  -4.468   4.898  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.605  -5.589   0.740  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.102  -4.855  -1.630  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.582  -2.219  -3.847  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.828   0.022  -4.111  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.337   0.692  -0.734  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.313  -0.809   2.135  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.205   0.529   3.532  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.230   2.529   3.983  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.383   4.508   3.714  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.152   4.602   3.243  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5   33    2                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5   38   39   40                                             
CONECT    7    5    8   25                                                  
CONECT    8    9   24    7                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9   41   42   43                                             
CONECT   11    9   15   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   44   45   46                                             
CONECT   14   12                                                            
CONECT   15   11   17   16                                                  
CONECT   16   15   47                                                       
CONECT   17   24   18   15                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   48                                                       
CONECT   20   18   21   49                                                  
CONECT   21   20   23   22                                                  
CONECT   22   21   50                                                       
CONECT   23   21   24   51                                                  
CONECT   24   17   23    8                                                  
CONECT   25   32   26    7                                                  
CONECT   26   27   25   52                                                  
CONECT   27   28   26   29                                                  
CONECT   28   27   53                                                       
CONECT   29   30   27   54                                                  
CONECT   30   32   29   31                                                  
CONECT   31   30   55                                                       
CONECT   32   30   33   25                                                  
CONECT   33    4   32   34                                                  
CONECT   34   33   56                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   16                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   26                                                            
CONECT   53   28                                                            
CONECT   54   29                                                            
CONECT   55   31                                                            
CONECT   56   34                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  118    0
END

RDKit          3D

56 59  0  0  0  0  0  0  0  0999 V2000
    3.1178    3.4686    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760    3.4094    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    4.1741    2.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382    2.4817    2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    1.1288    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276    0.4928    1.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698    0.3602    1.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1559   -1.0649    1.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -2.1101    2.2916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -1.7818    3.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -3.4425    1.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3278   -4.6035    2.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -4.6150    4.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0241   -5.5693    2.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445   -3.7294    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889   -5.0390    0.0341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7146   -0.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -2.9728   -1.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2356   -4.2459   -2.3866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -1.9619   -2.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4738   -0.6552   -2.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6760    0.3837   -3.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930   -0.3584   -1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650   -1.3664   -0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    0.9401    2.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325    0.2168    2.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3702    0.7741    3.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4856   -0.0047    3.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3568    2.0722    3.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1854    2.8110    3.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2579    4.0980    3.8801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996    2.2814    2.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1969    3.0216    2.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2103    4.3198    3.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159    4.5177    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    3.0073    0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    2.9761   -0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075   -0.5615    1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188    0.9626    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.5697    0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732   -1.6820    4.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838   -2.5514    4.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2322   -0.8569    3.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612   -5.5835    4.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307   -3.8473    3.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489   -4.4684    4.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047   -5.5892    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -4.8547   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -2.2190   -3.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283    0.0224   -4.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.6915   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -0.8085    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2046    0.5287    3.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303    2.5290    3.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    4.5075    3.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1521    4.6018    3.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 17  2  0
  7  5  1  0
 17 18  1  0
 32 30  1  0
 18 20  2  0
  5  4  2  0
 20 21  1  0
 30 29  2  0
 21 23  2  0
 23 24  1  0
  4 33  1  0
 27 28  1  0
 33 32  2  0
 30 31  1  0
 33 34  1  0
 27 26  2  0
  4  2  1  0
  8  9  2  0
  2  1  1  0
 32 25  1  0
  2  3  2  0
  9 11  1  0
  5  6  1  0
 26 25  1  0
 21 22  1  0
 11 15  2  0
 18 19  1  0
 15 17  1  0
 15 16  1  0
 24  8  1  0
 11 12  1  0
  7  8  1  0
 12 13  1  0
 25  7  2  0
 12 14  2  0
 29 27  1  0
  9 10  1  0
 29 54  1  0
 26 52  1  0
 20 49  1  0
 23 51  1  0
 28 53  1  0
 31 55  1  0
 34 56  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  6 38  1  0
  6 39  1  0
  6 40  1  0
 22 50  1  0
 19 48  1  0
 16 47  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₂O₈

Average Mass

462.4540 Da

Monoisotopic Mass

462.13147 Da

IUPAC Name

1-{3'-acetyl-4,4',5,5',7,7'-hexahydroxy-2,2'-dimethyl-[1,1'-binaphthalene]-3-yl}ethan-1-one

Traditional Name

1-{3'-acetyl-4,4',5,5',7,7'-hexahydroxy-2,2'-dimethyl-[1,1'-binaphthalene]-3-yl}ethanone

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C3=C(C(C(=O)C([H])([H])[H])=C(O[H])C4=C3C([H])=C(O[H])C([H])=C4O[H])C([H])([H])[H])C(=C(C(=O)C([H])([H])[H])C(O[H])=C2C(O[H])=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H22O8/c1-9-19(11(3)27)25(33)23-15(5-13(29)7-17(23)31)21(9)22-10(2)20(12(4)28)26(34)24-16(22)6-14(30)8-18(24)32/h5-8,29-34H,1-4H3

InChI Key

NVPMMQYSHXYHEF-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Uroleucon nigrotuberculatum	JEOL database	Nishimura, T., et al, Tetrahedron 69, 1808 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylnaphthalene lignans. These are lignans containing the arylnaphthalene skeleton, especially 9-(2H-1,3-benzodioxol-5-yl)-1H,3H-naphtho[2,3-c]furan-1-one or a derivative thereof. Arylnaphthalene lignans occur in nature and exhibit diverse biological activities.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Arylnaphthalene lignans

Sub Class

Not Available

Direct Parent

Arylnaphthalene lignans

Alternative Parents

Substituents

Arylnaphthalene lignan skeleton
Biphenol
1-naphthol
2-naphthol
Naphthalene
Acetophenone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Ketone
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.55	ALOGPS
logP	5.22	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.87 m³·mol⁻¹	ChemAxon
Polarizability	47.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28945560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71567818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nishimura, T., et al. (2013). Nishimura, T., et al, Tetrahedron 69, 1808 (2013). Tetrahedron.

Showing NP-Card for xanthouroleuconaphin (NP0042181)

MOL for NP0042181 (xanthouroleuconaphin)

3D MOL for NP0042181 (xanthouroleuconaphin)

3D SDF for NP0042181 (xanthouroleuconaphin)

3D-SDF for NP0042181 (xanthouroleuconaphin)

PDB for NP0042181 (xanthouroleuconaphin)

3D PDB for NP0042181 (xanthouroleuconaphin)

SMILES for NP0042181 (xanthouroleuconaphin)

INCHI for NP0042181 (xanthouroleuconaphin)

Structure for NP0042181 (xanthouroleuconaphin)

3D Structure for NP0042181 (xanthouroleuconaphin)