NP-MRD: Showing NP-Card for (8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one (NP0250059)

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Record Information

Version

2.0

Created at

2022-09-07 12:47:33 UTC

Updated at

2022-09-07 12:47:33 UTC

NP-MRD ID

NP0250059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one

Description

(8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one is found in Boswellia ovalifoliolata.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120273D          

 44 46  0  0  0  0            999 V2000
    0.8669    4.9876   -1.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    3.8568   -1.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783    2.6217   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    2.3826   -1.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471    1.0710   -1.9791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067   -0.0212   -1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1881    0.2180   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606    1.5240   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    1.7494   -0.6110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954    0.8848    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -0.0151    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415   -1.0629    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -1.1945    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -0.2074    2.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    0.8381    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -2.4447    3.0380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6352   -3.6202    2.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6593   -4.7428    3.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -3.2817    2.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -3.1884    2.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -3.1620    0.5964 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4928   -2.3477    0.3882 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9589   -2.3871   -1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -1.3901   -1.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    4.9871   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    5.8838   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533    5.0415   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807    3.1938   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.9137   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -0.6219   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.0525   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -1.8057    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.2834    3.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3719    1.5649    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -2.2474    4.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120   -2.7218    3.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381   -3.9255    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -4.5541    3.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -4.1807    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.6912    0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3423   -1.3214    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011   -2.7558    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -3.3504   -1.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -1.5851   -2.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  5  4  1  0  0  0  0
  9 10  1  0  0  0  0
  4  3  2  0  0  0  0
 10 11  2  0  0  0  0
  6 24  1  0  0  0  0
 11 12  1  0  0  0  0
  8  7  2  0  0  0  0
 12 13  2  0  0  0  0
 24 23  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
 23 22  1  0  0  0  0
 13 16  1  0  0  0  0
  7  6  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 22 21  1  0  0  0  0
 19 20  2  0  0  0  0
  3  8  1  0  0  0  0
 17 18  1  0  0  0  0
 21 19  1  0  0  0  0
  3  2  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  1  0  0  0  0
  4 28  1  0  0  0  0
  7 30  1  0  0  0  0
  5 29  1  0  0  0  0
 24 44  1  0  0  0  0
 23 43  1  0  0  0  0
 22 41  1  0  0  0  0
 22 42  1  0  0  0  0
 21 39  1  0  0  0  0
 21 40  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 14 33  1  0  0  0  0
 15 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  6  0  0  0
 18 38  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
M  END

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    0.8669    4.9876   -1.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    3.8568   -1.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783    2.6217   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    2.3826   -1.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471    1.0710   -1.9791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067   -0.0212   -1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1881    0.2180   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606    1.5240   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    1.7494   -0.6110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954    0.8848    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -0.0151    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415   -1.0629    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -1.1945    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -0.2074    2.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    0.8381    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -2.4447    3.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -3.6202    2.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6593   -4.7428    3.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -3.2817    2.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -3.1884    2.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -3.1620    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4928   -2.3477    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9589   -2.3871   -1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -1.3901   -1.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    4.9871   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    5.8838   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533    5.0415   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807    3.1938   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.9137   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -0.6219   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.0525   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -1.8057    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.2834    3.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3719    1.5649    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -2.2474    4.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120   -2.7218    3.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381   -3.9255    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -4.5541    3.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -4.1807    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.6912    0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3423   -1.3214    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011   -2.7558    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -3.3504   -1.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -1.5851   -2.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  5  4  1  0
  9 10  1  0
  4  3  2  0
 10 11  2  0
  6 24  1  0
 11 12  1  0
  8  7  2  0
 12 13  2  0
 24 23  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 23 22  1  0
 13 16  1  0
  7  6  1  0
 16 17  1  0
 17 19  1  0
 22 21  1  0
 19 20  2  0
  3  8  1  0
 17 18  1  0
 21 19  1  0
  3  2  1  0
  6  5  2  0
  2  1  1  0
  4 28  1  0
  7 30  1  0
  5 29  1  0
 24 44  1  0
 23 43  1  0
 22 41  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652306192120273D          

 44 46  0  0  0  0            999 V2000
    0.8669    4.9876   -1.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    3.8568   -1.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783    2.6217   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    2.3826   -1.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471    1.0710   -1.9791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067   -0.0212   -1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1881    0.2180   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606    1.5240   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    1.7494   -0.6110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954    0.8848    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -0.0151    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415   -1.0629    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -1.1945    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -0.2074    2.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    0.8381    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -2.4447    3.0380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6352   -3.6202    2.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6593   -4.7428    3.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -3.2817    2.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -3.1884    2.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -3.1620    0.5964 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4928   -2.3477    0.3882 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9589   -2.3871   -1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -1.3901   -1.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    4.9871   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    5.8838   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533    5.0415   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807    3.1938   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.9137   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -0.6219   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.0525   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -1.8057    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.2834    3.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3719    1.5649    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -2.2474    4.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120   -2.7218    3.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381   -3.9255    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -4.5541    3.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -4.1807    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.6912    0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3423   -1.3214    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011   -2.7558    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -3.3504   -1.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -1.5851   -2.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  5  4  1  0  0  0  0
  9 10  1  0  0  0  0
  4  3  2  0  0  0  0
 10 11  2  0  0  0  0
  6 24  1  0  0  0  0
 11 12  1  0  0  0  0
  8  7  2  0  0  0  0
 12 13  2  0  0  0  0
 24 23  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
 23 22  1  0  0  0  0
 13 16  1  0  0  0  0
  7  6  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 22 21  1  0  0  0  0
 19 20  2  0  0  0  0
  3  8  1  0  0  0  0
 17 18  1  0  0  0  0
 21 19  1  0  0  0  0
  3  2  1  0  0  0  0
  6  5  2  0  0  0  0
  2  1  1  0  0  0  0
  4 28  1  0  0  0  0
  7 30  1  0  0  0  0
  5 29  1  0  0  0  0
 24 44  1  0  0  0  0
 23 43  1  0  0  0  0
 22 41  1  0  0  0  0
 22 42  1  0  0  0  0
 21 39  1  0  0  0  0
 21 40  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 14 33  1  0  0  0  0
 15 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  6  0  0  0
 18 38  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
M  END
> <DATABASE_ID>
NP0250059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=O)C([H])([H])C([H])([H])\C([H])=C([H])/C2=C([H])C([H])=C(OC([H])([H])[H])C(OC3=C([H])C([H])=C(C([H])=C3[H])C1([H])[H])=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-23-19-11-8-14-4-2-3-5-17(21)18(22)12-15-6-9-16(10-7-15)24-20(19)13-14/h2,4,6-11,13,18,22H,3,5,12H2,1H3/b4-2-/t18-/m0/s1

> <INCHI_KEY>
BLQMQLZCNMRVFZ-VEXQSBSHSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.376

> <EXACT_MASS>
324.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
34.60806148595521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8Z,13S)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.7723166316666665

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.777487643622784

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.326848054302065

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5306338822625554

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
93.2974

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8Z,13S)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    0.8669    4.9876   -1.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    3.8568   -1.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783    2.6217   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    2.3826   -1.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471    1.0710   -1.9791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067   -0.0212   -1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1881    0.2180   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606    1.5240   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    1.7494   -0.6110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954    0.8848    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -0.0151    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415   -1.0629    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -1.1945    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -0.2074    2.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    0.8381    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -2.4447    3.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -3.6202    2.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6593   -4.7428    3.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -3.2817    2.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -3.1884    2.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -3.1620    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4928   -2.3477    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9589   -2.3871   -1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -1.3901   -1.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    4.9871   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    5.8838   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533    5.0415   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807    3.1938   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.9137   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -0.6219   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.0525   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -1.8057    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.2834    3.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3719    1.5649    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -2.2474    4.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120   -2.7218    3.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381   -3.9255    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -4.5541    3.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -4.1807    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.6912    0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3423   -1.3214    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011   -2.7558    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -3.3504   -1.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -1.5851   -2.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  5  4  1  0
  9 10  1  0
  4  3  2  0
 10 11  2  0
  6 24  1  0
 11 12  1  0
  8  7  2  0
 12 13  2  0
 24 23  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 23 22  1  0
 13 16  1  0
  7  6  1  0
 16 17  1  0
 17 19  1  0
 22 21  1  0
 19 20  2  0
  3  8  1  0
 17 18  1  0
 21 19  1  0
  3  2  1  0
  6  5  2  0
  2  1  1  0
  4 28  1  0
  7 30  1  0
  5 29  1  0
 24 44  1  0
 23 43  1  0
 22 41  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.867   4.988  -1.345  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.045   3.857  -1.093  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.578   2.622  -1.346  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.885   2.383  -1.787  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.347   1.071  -1.979  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.507  -0.021  -1.754  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.188   0.218  -1.374  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.261   1.524  -1.116  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.536   1.749  -0.611  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.895   0.885   0.403  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.934  -0.015   0.170  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.142  -1.063   1.066  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.322  -1.194   2.198  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.367  -0.207   2.480  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.158   0.838   1.587  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.368  -2.445   3.038  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.635  -3.620   2.374  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.659  -4.743   3.259  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.170  -3.282   2.063  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.653  -3.188   2.978  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.216  -3.162   0.596  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.493  -2.348   0.388  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.959  -2.387  -1.048  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.993  -1.390  -1.950  0.00  0.00           C+0
HETATM   25  H   UNK     0       1.748   4.987  -0.695  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.283   5.884  -1.113  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.153   5.042  -2.401  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.581   3.194  -1.974  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.376   0.914  -2.297  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.488  -0.622  -1.247  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.519   0.053  -0.743  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.906  -1.806   0.847  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.732  -0.283   3.361  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.372   1.565   1.773  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.941  -2.247   4.031  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.412  -2.722   3.232  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.138  -3.926   1.450  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.998  -4.554   3.955  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.335  -4.181   0.209  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.611  -2.691   0.054  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.342  -1.321   0.740  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.301  -2.756   1.008  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.360  -3.350  -1.364  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.418  -1.585  -2.934  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    4    8    2                                                  
CONECT    4    5    3   28                                                  
CONECT    5    4    6   29                                                  
CONECT    6   24    7    5                                                  
CONECT    7    8    6   30                                                  
CONECT    8    9    7    3                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   31                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   10   34                                                  
CONECT   16   13   17   35   36                                             
CONECT   17   16   19   18   37                                             
CONECT   18   17   38                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   22   19   39   40                                             
CONECT   22   23   21   41   42                                             
CONECT   23   24   22   43                                                  
CONECT   24    6   23   44                                                  
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   21                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   24                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

RDKit          3D

44 46  0  0  0  0  0  0  0  0999 V2000
    0.8669    4.9876   -1.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    3.8568   -1.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783    2.6217   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    2.3826   -1.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471    1.0710   -1.9791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067   -0.0212   -1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1881    0.2180   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606    1.5240   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5360    1.7494   -0.6110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8954    0.8848    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336   -0.0151    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415   -1.0629    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -1.1945    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -0.2074    2.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580    0.8381    1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3677   -2.4447    3.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352   -3.6202    2.3739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6593   -4.7428    3.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697   -3.2817    2.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -3.1884    2.9785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -3.1620    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4928   -2.3477    0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9589   -2.3871   -1.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9930   -1.3901   -1.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    4.9871   -0.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2834    5.8838   -1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533    5.0415   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807    3.1938   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.9137   -2.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876   -0.6219   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    0.0525   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -1.8057    0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -0.2834    3.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3719    1.5649    1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413   -2.2474    4.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4120   -2.7218    3.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381   -3.9255    1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9979   -4.5541    3.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345   -4.1807    0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -2.6912    0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3423   -1.3214    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3011   -2.7558    1.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -3.3504   -1.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -1.5851   -2.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  5  4  1  0
  9 10  1  0
  4  3  2  0
 10 11  2  0
  6 24  1  0
 11 12  1  0
  8  7  2  0
 12 13  2  0
 24 23  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 23 22  1  0
 13 16  1  0
  7  6  1  0
 16 17  1  0
 17 19  1  0
 22 21  1  0
 19 20  2  0
  3  8  1  0
 17 18  1  0
 21 19  1  0
  3  2  1  0
  6  5  2  0
  2  1  1  0
  4 28  1  0
  7 30  1  0
  5 29  1  0
 24 44  1  0
 23 43  1  0
 22 41  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₄

Average Mass

324.3760 Da

Monoisotopic Mass

324.13616 Da

IUPAC Name

(8Z,13S)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one

Traditional Name

(8Z,13S)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(=O)C([H])([H])C([H])([H])\C([H])=C([H])/C2=C([H])C([H])=C(OC([H])([H])[H])C(OC3=C([H])C([H])=C(C([H])=C3[H])C1([H])[H])=C2[H]

InChI Identifier

InChI=1S/C20H20O4/c1-23-19-11-8-14-4-2-3-5-17(21)18(22)12-15-6-9-16(10-7-15)24-20(19)13-14/h2,4,6-11,13,18,22H,3,5,12H2,1H3/b4-2-/t18-/m0/s1

InChI Key

BLQMQLZCNMRVFZ-VEXQSBSHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Boswellia ovalifoliolata	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	3.36	ALOGPS
logP	3.77	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.3 m³·mol⁻¹	ChemAxon
Polarizability	34.61 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one (NP0250059)

MOL for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

3D MOL for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

3D SDF for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

3D-SDF for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

PDB for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

3D PDB for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

SMILES for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

INCHI for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

Structure for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)

3D Structure for NP0250059 ((8e,13s)-13-hydroxy-4-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,8,15,18-heptaen-12-one)