NP-MRD: Showing NP-Card for thrigonosomone A (NP0038130)

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Record Information

Version

2.0

Created at

2021-06-20 20:54:10 UTC

Updated at

2021-06-30 00:10:45 UTC

NP-MRD ID

NP0038130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

thrigonosomone A

Provided By

JEOL Database JEOL Logo

Description

Thrigonosomone A belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom). thrigonosomone A is found in Trigonostemon lii Y.T. Chang. thrigonosomone A was first documented in 2009 (Hu, X.-J., et al.). Based on a literature review very few articles have been published on Thrigonosomone A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122543D          

 42 44  0  0  0  0            999 V2000
    1.0086    3.3809   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.9768   -1.2987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.6244   -0.6141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6606    1.7658   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6428    2.2889   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432    1.2539   -2.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965    0.7911   -3.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    1.3859   -4.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1831   -0.6081   -2.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2461   -0.8813   -3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667   -1.5574   -3.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -0.8585   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.1896   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -2.4983    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -3.8157    1.0419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -1.4998    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -1.8393    3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079   -0.8762    4.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.3071    5.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    0.4558    3.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.4896    4.5387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    0.8141    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -0.1420    1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.1743   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1716    3.7753   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.8941   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    3.5634   -2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    2.3045    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -0.1908   -2.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -0.7584   -4.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801   -1.9005   -2.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -2.6019   -3.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -1.5106   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.2850   -4.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -3.0046   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618   -4.3804    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.8926    3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -2.3979    5.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678   -0.9465    6.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.9161    5.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.1350    5.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.8810    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
 24  3  1  0  0  0  0
 16 23  1  0  0  0  0
  3  4  1  0  0  0  0
 16 17  1  0  0  0  0
  4  6  1  0  0  0  0
 23 24  2  0  0  0  0
  9  7  1  0  0  0  0
  7  6  1  0  0  0  0
 20 22  2  0  0  0  0
  7  8  2  0  0  0  0
 24 12  1  0  0  0  0
  4  5  2  0  0  0  0
 17 18  2  0  0  0  0
  3  2  1  0  0  0  0
 12 13  2  0  0  0  0
  9 10  1  6  0  0  0
 18 20  1  0  0  0  0
  9 11  1  0  0  0  0
 13 14  1  0  0  0  0
  2  1  1  0  0  0  0
 14 16  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 14 15  1  0  0  0  0
 12  9  1  0  0  0  0
 18 19  1  0  0  0  0
 22 42  1  0  0  0  0
 17 37  1  0  0  0  0
 13 35  1  0  0  0  0
  3 28  1  1  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 21 41  1  0  0  0  0
 15 36  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.0086    3.3809   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.9768   -1.2987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.6244   -0.6141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6606    1.7658   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6428    2.2889   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432    1.2539   -2.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965    0.7911   -3.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    1.3859   -4.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1831   -0.6081   -2.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2461   -0.8813   -3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667   -1.5574   -3.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -0.8585   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.1896   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -2.4983    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -3.8157    1.0419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -1.4998    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -1.8393    3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079   -0.8762    4.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.3071    5.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    0.4558    3.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.4896    4.5387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    0.8141    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -0.1420    1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.1743   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1716    3.7753   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.8941   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    3.5634   -2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    2.3045    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -0.1908   -2.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -0.7584   -4.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801   -1.9005   -2.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -2.6019   -3.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -1.5106   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.2850   -4.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -3.0046   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618   -4.3804    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.8926    3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -2.3979    5.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678   -0.9465    6.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.9161    5.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.1350    5.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.8810    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
 24  3  1  0
 16 23  1  0
  3  4  1  0
 16 17  1  0
  4  6  1  0
 23 24  2  0
  9  7  1  0
  7  6  1  0
 20 22  2  0
  7  8  2  0
 24 12  1  0
  4  5  2  0
 17 18  2  0
  3  2  1  0
 12 13  2  0
  9 10  1  6
 18 20  1  0
  9 11  1  0
 13 14  1  0
  2  1  1  0
 14 16  2  0
 20 21  1  0
 22 23  1  0
 14 15  1  0
 12  9  1  0
 18 19  1  0
 22 42  1  0
 17 37  1  0
 13 35  1  0
  3 28  1  1
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 41  1  0
 15 36  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv1652306202122543D          

 42 44  0  0  0  0            999 V2000
    1.0086    3.3809   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.9768   -1.2987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.6244   -0.6141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6606    1.7658   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6428    2.2889   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432    1.2539   -2.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965    0.7911   -3.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    1.3859   -4.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1831   -0.6081   -2.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2461   -0.8813   -3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667   -1.5574   -3.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -0.8585   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.1896   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -2.4983    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -3.8157    1.0419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -1.4998    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -1.8393    3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079   -0.8762    4.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.3071    5.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    0.4558    3.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.4896    4.5387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    0.8141    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -0.1420    1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.1743   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1716    3.7753   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.8941   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    3.5634   -2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    2.3045    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -0.1908   -2.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -0.7584   -4.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801   -1.9005   -2.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -2.6019   -3.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -1.5106   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.2850   -4.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -3.0046   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618   -4.3804    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.8926    3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -2.3979    5.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678   -0.9465    6.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.9161    5.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.1350    5.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.8810    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
 24  3  1  0  0  0  0
 16 23  1  0  0  0  0
  3  4  1  0  0  0  0
 16 17  1  0  0  0  0
  4  6  1  0  0  0  0
 23 24  2  0  0  0  0
  9  7  1  0  0  0  0
  7  6  1  0  0  0  0
 20 22  2  0  0  0  0
  7  8  2  0  0  0  0
 24 12  1  0  0  0  0
  4  5  2  0  0  0  0
 17 18  2  0  0  0  0
  3  2  1  0  0  0  0
 12 13  2  0  0  0  0
  9 10  1  6  0  0  0
 18 20  1  0  0  0  0
  9 11  1  0  0  0  0
 13 14  1  0  0  0  0
  2  1  1  0  0  0  0
 14 16  2  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 14 15  1  0  0  0  0
 12  9  1  0  0  0  0
 18 19  1  0  0  0  0
 22 42  1  0  0  0  0
 17 37  1  0  0  0  0
 13 35  1  0  0  0  0
  3 28  1  1  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 21 41  1  0  0  0  0
 15 36  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C3C(=C([H])C(O[H])=C2C([H])=C1C([H])([H])[H])C(C(=O)OC(=O)[C@]3([H])OC([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-8-5-9-10(6-12(8)19)14-11(7-13(9)20)18(2,3)17(22)24-16(21)15(14)23-4/h5-7,15,19-20H,1-4H3/t15-/m1/s1

> <INCHI_KEY>
RUWQKGHNIXMWSA-OAHLLOKOSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.624137731675674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-7,10-dihydroxy-1-methoxy-5,5,9-trimethyl-1H,2H,4H,5H-naphtho[1,2-d]oxepine-2,4-dione

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.305650531

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.154151498192142

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.028181598058945

> <JCHEM_PKA_STRONGEST_BASIC>
-4.225160293738772

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
86.0859

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-7,10-dihydroxy-1-methoxy-5,5,9-trimethyl-1H-naphtho[1,2-d]oxepine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.0086    3.3809   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.9768   -1.2987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.6244   -0.6141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6606    1.7658   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6428    2.2889   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432    1.2539   -2.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965    0.7911   -3.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    1.3859   -4.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1831   -0.6081   -2.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2461   -0.8813   -3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667   -1.5574   -3.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -0.8585   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.1896   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -2.4983    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -3.8157    1.0419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -1.4998    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -1.8393    3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079   -0.8762    4.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.3071    5.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    0.4558    3.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.4896    4.5387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    0.8141    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -0.1420    1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.1743   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1716    3.7753   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.8941   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    3.5634   -2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    2.3045    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -0.1908   -2.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -0.7584   -4.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801   -1.9005   -2.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -2.6019   -3.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -1.5106   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.2850   -4.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -3.0046   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618   -4.3804    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.8926    3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -2.3979    5.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678   -0.9465    6.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.9161    5.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.1350    5.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.8810    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
 24  3  1  0
 16 23  1  0
  3  4  1  0
 16 17  1  0
  4  6  1  0
 23 24  2  0
  9  7  1  0
  7  6  1  0
 20 22  2  0
  7  8  2  0
 24 12  1  0
  4  5  2  0
 17 18  2  0
  3  2  1  0
 12 13  2  0
  9 10  1  6
 18 20  1  0
  9 11  1  0
 13 14  1  0
  2  1  1  0
 14 16  2  0
 20 21  1  0
 22 23  1  0
 14 15  1  0
 12  9  1  0
 18 19  1  0
 22 42  1  0
 17 37  1  0
 13 35  1  0
  3 28  1  1
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 41  1  0
 15 36  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.009   3.381  -1.490  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.875   1.977  -1.299  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.320   1.624  -0.614  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.661   1.766  -1.359  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.643   2.289  -0.834  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.743   1.254  -2.607  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.597   0.791  -3.149  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.065   1.386  -4.082  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.183  -0.608  -2.671  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.246  -0.881  -3.195  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.167  -1.557  -3.399  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.174  -0.859  -1.141  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.082  -2.190  -0.692  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.011  -2.498   0.663  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.069  -3.816   1.042  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.003  -1.500   1.645  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.082  -1.839   3.016  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.108  -0.876   4.031  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.200  -1.307   5.463  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.053   0.456   3.646  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.081   1.490   4.539  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.034   0.814   2.297  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.074  -0.142   1.248  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.176   0.174  -0.158  0.00  0.00           C+0
HETATM   25  H   UNK     0       0.172   3.775  -2.074  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.072   3.894  -0.526  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.934   3.563  -2.043  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.413   2.305   0.234  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.971  -0.191  -2.748  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.307  -0.758  -4.283  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.580  -1.901  -2.970  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.839  -2.602  -3.378  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.166  -1.511  -2.950  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.273  -1.285  -4.457  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.044  -3.005  -1.409  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.062  -4.380   0.253  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.132  -2.893   3.293  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.224  -2.398   5.558  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.668  -0.947   6.025  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.116  -0.916   5.918  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.134   1.135   5.440  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.059   1.881   2.101  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3   24    4    2   28                                             
CONECT    4    3    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    9    6    8                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9   29   30   31                                             
CONECT   11    9   32   33   34                                             
CONECT   12   24   13    9                                                  
CONECT   13   12   14   35                                                  
CONECT   14   13   16   15                                                  
CONECT   15   14   36                                                       
CONECT   16   23   17   14                                                  
CONECT   17   16   18   37                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   38   39   40                                             
CONECT   20   22   18   21                                                  
CONECT   21   20   41                                                       
CONECT   22   20   23   42                                                  
CONECT   23   16   24   22                                                  
CONECT   24    3   23   12                                                  
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29   10                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   13                                                            
CONECT   36   15                                                            
CONECT   37   17                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   19                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

RDKit          3D

42 44  0  0  0  0  0  0  0  0999 V2000
    1.0086    3.3809   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    1.9768   -1.2987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197    1.6244   -0.6141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6606    1.7658   -1.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6428    2.2889   -0.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7432    1.2539   -2.6070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965    0.7911   -3.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    1.3859   -4.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1831   -0.6081   -2.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2461   -0.8813   -3.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667   -1.5574   -3.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -0.8585   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0819   -2.1896   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -2.4983    0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -3.8157    1.0419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028   -1.4998    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -1.8393    3.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079   -0.8762    4.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003   -1.3071    5.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0527    0.4558    3.6457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    1.4896    4.5387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0341    0.8141    2.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0742   -0.1420    1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1762    0.1743   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1716    3.7753   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722    3.8941   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343    3.5634   -2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    2.3045    0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -0.1908   -2.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068   -0.7584   -4.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801   -1.9005   -2.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -2.6019   -3.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663   -1.5106   -2.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.2850   -4.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -3.0046   -1.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618   -4.3804    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.8926    3.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -2.3979    5.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678   -0.9465    6.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161   -0.9161    5.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1337    1.1350    5.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.8810    2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
 24  3  1  0
 16 23  1  0
  3  4  1  0
 16 17  1  0
  4  6  1  0
 23 24  2  0
  9  7  1  0
  7  6  1  0
 20 22  2  0
  7  8  2  0
 24 12  1  0
  4  5  2  0
 17 18  2  0
  3  2  1  0
 12 13  2  0
  9 10  1  6
 18 20  1  0
  9 11  1  0
 13 14  1  0
  2  1  1  0
 14 16  2  0
 20 21  1  0
 22 23  1  0
 14 15  1  0
 12  9  1  0
 18 19  1  0
 22 42  1  0
 17 37  1  0
 13 35  1  0
  3 28  1  1
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 21 41  1  0
 15 36  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3360 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

(1R)-7,10-dihydroxy-1-methoxy-5,5,9-trimethyl-1H,2H,4H,5H-naphtho[1,2-d]oxepine-2,4-dione

Traditional Name

(1R)-7,10-dihydroxy-1-methoxy-5,5,9-trimethyl-1H-naphtho[1,2-d]oxepine-2,4-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C3C(=C([H])C(O[H])=C2C([H])=C1C([H])([H])[H])C(C(=O)OC(=O)[C@]3([H])OC([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C18H18O6/c1-8-5-9-10(6-12(8)19)14-11(7-13(9)20)18(2,3)17(22)24-16(21)15(14)23-4/h5-7,15,19-20H,1-4H3/t15-/m1/s1

InChI Key

RUWQKGHNIXMWSA-OAHLLOKOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃/CD₃OD (1:2), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃/CD₃OD (1:2), 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
Trigonostemon lii	JEOL database	Hu, X.-J., et al, Tetrahedron Lett. 50, 2917 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Not Available

Direct Parent

Benzoxepines

Alternative Parents

Substituents

Benzoxepine
2-naphthol
1-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Benzenoid
Carboxylic acid anhydride
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.69	ALOGPS
logP	3.31	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.09 m³·mol⁻¹	ChemAxon
Polarizability	33.62 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101462743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu, X.-J., et al. (2009). Hu, X.-J., et al, Tetrahedron Lett. 50, 2917 (2009). Tetrahedron Lett.

Showing NP-Card for thrigonosomone A (NP0038130)

MOL for NP0038130 (thrigonosomone A)

3D MOL for NP0038130 (thrigonosomone A)

3D SDF for NP0038130 (thrigonosomone A)

3D-SDF for NP0038130 (thrigonosomone A)

PDB for NP0038130 (thrigonosomone A)

3D PDB for NP0038130 (thrigonosomone A)

SMILES for NP0038130 (thrigonosomone A)

INCHI for NP0038130 (thrigonosomone A)

Structure for NP0038130 (thrigonosomone A)

3D Structure for NP0038130 (thrigonosomone A)