NP-MRD: Showing NP-Card for 8-epi-ophiobolin J (NP0006563)

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Record Information

Version

2.0

Created at

2020-12-09 03:32:39 UTC

Updated at

2021-07-15 16:55:10 UTC

NP-MRD ID

NP0006563

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-epi-ophiobolin J

Provided By

NPAtlas

Description

8-Epi-Ohiobolin J belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position. 8-epi-ophiobolin J is found in Drechslera gigantea. 8-epi-ophiobolin J was first documented in 2006 (PMID: 16962149). Based on a literature review very few articles have been published on 8-epi-Ohiobolin J.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118283D          

 65 68  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118283D          

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   -2.1151    1.6172   -0.1801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4448    0.9734   -0.1952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2557    1.7042    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5188    3.1755    0.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6996    0.9657    1.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2250   -0.4180    1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4843   -1.3830    2.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4586   -0.4451    0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413   -1.5903   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2382   -2.7624    0.7030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1204   -3.3856    1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.8691   -1.2977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0179   -3.2599   -1.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616   -1.4078   -1.1151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4376   -0.1038   -0.4760 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5507   -0.1449    0.8844 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4848   -1.6722    2.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971   -0.4844    3.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0654   -1.9174    3.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2068    1.7507    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2698    1.1033    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6094    0.8333    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2496    1.0553    0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    0.2235   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.4822   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813   -1.7688   -1.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.5964   -2.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526    0.1318   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238   -1.0640   -3.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374    2.1568    0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151    1.7318   -1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751    2.5437   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2431    3.0648   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0045    0.1068   -3.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6571    0.8172   -2.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    1.8346   -3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    2.6925   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117    1.6047    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099    1.0811   -1.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815    3.6209    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6415    3.2708    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898    3.6274   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    1.1963    2.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796   -3.5696   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987   -2.9505    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487   -4.1064    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5577   -1.5344   -2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2220   -3.6449   -0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1510   -2.1760   -0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -1.4749   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -0.2139    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 29  1  1  0  0  0
 29  5  1  0  0  0  0
 28  9  1  0  0  0  0
 28 12  1  0  0  0  0
 21 15  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  6  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
  7 40  1  6  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
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 14 51  1  0  0  0  0
 14 52  1  0  0  0  0
 15 53  1  6  0  0  0
 17 54  1  0  0  0  0
 17 55  1  0  0  0  0
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 23 58  1  0  0  0  0
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 24 60  1  0  0  0  0
 25 61  1  6  0  0  0
 26 62  1  0  0  0  0
 27 63  1  0  0  0  0
 27 64  1  0  0  0  0
 28 65  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0006563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C2\C(=O)C([H])=C(C([H])([H])[H])[C@@]2([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]3(O[C@@]([H])(C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[C@]3([H])C([H])([H])[H])[C@]2([H])C([H])([H])[C@@]\1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-14(2)8-17-10-16(4)25(29-17)7-6-24(5)12-18-15(3)9-21(28)23(18)19(13-26)20(27)11-22(24)25/h8-9,16-18,20,22,26-27H,6-7,10-13H2,1-5H3/b23-19+/t16-,17-,18+,20+,22+,24+,25-/m0/s1

> <INCHI_KEY>
LFYREHKMIHWZQF-VNBBXFQNSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.559

> <EXACT_MASS>
400.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.45386713561865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2S,3S,3'R,5R,7'R,9'R,10'E)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecane]-10',13'-dien-12'-one

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
3.316373189666666

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.21593666354929

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.364898905156569

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7890608129334336

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
116.60009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,3S,3'R,5R,7'R,9'R,10'E)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecane]-10',13'-dien-12'-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    5.6866   -1.1537    3.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0133    2.1755   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2382   -2.7624    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -3.3856    1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1971   -0.4844    3.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2698    1.1033    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6094    0.8333    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057   -1.7110    2.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2496    1.0553    0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    0.2235   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.4822   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813   -1.7688   -1.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.5964   -2.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526    0.1318   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238   -1.0640   -3.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7802   -0.2139    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  9 29  1  1
 29  5  1  0
 28  9  1  0
 28 12  1  0
 21 15  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  6 39  1  0
  7 40  1  6
  8 41  1  0
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 15 53  1  6
 17 54  1  0
 17 55  1  0
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 23 59  1  0
 24 60  1  0
 25 61  1  6
 26 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.687  -1.154   3.102  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.877  -0.365   2.103  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.498   0.890   1.607  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.690  -0.795   1.716  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.922   0.005   0.733  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.278  -0.532  -0.639  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.885  -0.682  -1.275  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.010  -0.206  -2.683  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.052   0.146  -0.378  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.276   1.592  -0.651  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.013   2.176  -1.154  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.071   1.085  -1.111  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.559   0.902  -2.509  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.115   1.617  -0.180  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.445   0.973  -0.195  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.256   1.704   0.814  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.519   3.176   0.703  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.700   0.966   1.769  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.225  -0.418   1.503  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.484  -1.383   2.268  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.459  -0.445   0.288  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.941  -1.590  -0.101  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.238  -2.762   0.703  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.120  -3.386   1.258  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.057  -1.869  -1.298  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.018  -3.260  -1.411  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.662  -1.408  -1.115  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.438  -0.104  -0.476  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.551  -0.145   0.884  0.00  0.00           O+0
HETATM   30  H   UNK     0       6.485  -1.672   2.518  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.197  -0.484   3.814  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.065  -1.917   3.600  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.207   1.751   2.249  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.270   1.103   0.547  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.609   0.833   1.674  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.306  -1.711   2.118  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.250   1.055   0.830  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.853   0.224  -1.175  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.818  -1.482  -0.598  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.681  -1.769  -1.249  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.341   0.596  -2.977  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.053   0.132  -2.950  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.824  -1.064  -3.385  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.637   2.157   0.258  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.115   1.732  -1.394  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.175   2.544  -2.205  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.243   3.065  -0.577  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.004   0.107  -3.027  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.657   0.817  -2.622  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.323   1.835  -3.110  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.260   2.692  -0.427  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.712   1.605   0.854  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.010   1.081  -1.143  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.181   3.621   1.657  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.641   3.271   0.702  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.090   3.627  -0.189  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.307   1.196   2.646  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.380  -3.570  -0.177  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.199  -2.950   1.130  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.449  -4.106   1.826  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.558  -1.534  -2.231  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.222  -3.645  -0.937  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.151  -2.176  -0.456  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.150  -1.475  -2.087  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.780  -0.214   0.599  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   33   34   35                                             
CONECT    4    2    5   36                                                  
CONECT    5    4    6   29   37                                             
CONECT    6    5    7   38   39                                             
CONECT    7    6    8    9   40                                             
CONECT    8    7   41   42   43                                             
CONECT    9    7   10   29   28                                             
CONECT   10    9   11   44   45                                             
CONECT   11   10   12   46   47                                             
CONECT   12   11   13   14   28                                             
CONECT   13   12   48   49   50                                             
CONECT   14   12   15   51   52                                             
CONECT   15   14   16   21   53                                             
CONECT   16   15   17   18                                                  
CONECT   17   16   54   55   56                                             
CONECT   18   16   19   57                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   15                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24   58   59                                             
CONECT   24   23   60                                                       
CONECT   25   22   26   27   61                                             
CONECT   26   25   62                                                       
CONECT   27   25   28   63   64                                             
CONECT   28   27    9   12   65                                             
CONECT   29    9    5                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   11                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   13                                                            
CONECT   51   14                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   17                                                            
CONECT   57   18                                                            
CONECT   58   23                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
CONECT   63   27                                                            
CONECT   64   27                                                            
CONECT   65   28                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
    5.6866   -1.1537    3.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8767   -0.3654    2.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4977    0.8899    1.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -0.7948    1.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    0.0050    0.7332 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2777   -0.5322   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -0.6823   -1.2748 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0098   -0.2064   -2.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521    0.1463   -0.3781 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2756    1.5916   -0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133    2.1755   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714    1.0853   -1.1115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5585    0.9022   -2.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    1.6172   -0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448    0.9734   -0.1952 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.2250   -0.4180    1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6616   -1.4078   -1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4376   -0.1038   -0.4760 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.0654   -1.9174    3.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2068    1.7507    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2698    1.1033    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6094    0.8333    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057   -1.7110    2.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2496    1.0553    0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    0.2235   -1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -1.4822   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813   -1.7688   -1.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3405    0.5964   -2.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526    0.1318   -2.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238   -1.0640   -3.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6374    2.1568    0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151    1.7318   -1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751    2.5437   -2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2431    3.0648   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0045    0.1068   -3.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6571    0.8172   -2.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    1.8346   -3.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    2.6925   -0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117    1.6047    0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099    1.0811   -1.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1815    3.6209    1.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6415    3.2708    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898    3.6274   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3073    1.1963    2.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3796   -3.5696   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987   -2.9505    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4487   -4.1064    1.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5577   -1.5344   -2.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2220   -3.6449   -0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1510   -2.1760   -0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498   -1.4749   -2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -0.2139    0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  9 29  1  1
 29  5  1  0
 28  9  1  0
 28 12  1  0
 21 15  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  6 39  1  0
  7 40  1  6
  8 41  1  0
  8 42  1  0
  8 43  1  0
 10 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  6
 17 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  6
 26 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
8-Epi-ophiobolin J	MeSH
Ophiobolin J	MeSH

Chemical Formula

C₂₅H₃₆O₄

Average Mass

400.5590 Da

Monoisotopic Mass

400.26136 Da

IUPAC Name

(1'R,2S,3S,3'R,5R,7'R,9'R,10'E)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecane]-10',13'-dien-12'-one

Traditional Name

(1'R,2S,3S,3'R,5R,7'R,9'R,10'E)-9'-hydroxy-10'-(hydroxymethyl)-3,3',14'-trimethyl-5-(2-methylprop-1-en-1-yl)spiro[oxolane-2,6'-tricyclo[9.3.0.0^{3,7}]tetradecane]-10',13'-dien-12'-one

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H](O[C@@]11CC[C@]2(C)C[C@@H]3C(C)=CC(=O)\C3=C(CO)\[C@H](O)C[C@@H]12)C=C(C)C

InChI Identifier

InChI=1S/C25H36O4/c1-14(2)8-17-10-16(4)25(29-17)7-6-24(5)12-18-15(3)9-21(28)23(18)19(13-26)20(27)11-22(24)25/h8-9,16-18,20,22,26-27H,6-7,10-13H2,1-5H3/b23-19+/t16-,17-,18+,20+,22+,24+,25-/m0/s1

InChI Key

LFYREHKMIHWZQF-VNBBXFQNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Drechslera gigantea	NPAtlas	16962149

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ophiobolane sesterterpenoids. These are sesterterpnoids with a structure based on the ophiobolane backbone. Ophiobolane is a tricyclic compound consisting of two cyclopentane rings joined by a cyclooctane ring, and carries a methyl group at the 1-, 4-, and 8-position, as well as a 6-methylheptane group at the 12-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Ophiobolane sesterterpenoids

Alternative Parents

Substituents

Ophiobolane sesterterpenoid
Oxolane
Ketone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.89	ALOGPS
logP	3.32	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.6 m³·mol⁻¹	ChemAxon
Polarizability	46.45 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA008478

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101419604

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Evidente A, Andolfi A, Cimmino A, Vurro M, Fracchiolla M, Charudattan R, Motta A: Ophiobolin E and 8-epi-ophiobolin J produced by Drechslera gigantea, a potential mycoherbicide of weedy grasses. Phytochemistry. 2006 Oct;67(20):2281-7. doi: 10.1016/j.phytochem.2006.07.016. Epub 2006 Sep 7. [PubMed:16962149 ]

Showing NP-Card for 8-epi-ophiobolin J (NP0006563)

MOL for NP0006563 (8-epi-ophiobolin J)

3D MOL for NP0006563 (8-epi-ophiobolin J)

3D SDF for NP0006563 (8-epi-ophiobolin J)

3D-SDF for NP0006563 (8-epi-ophiobolin J)

PDB for NP0006563 (8-epi-ophiobolin J)

3D PDB for NP0006563 (8-epi-ophiobolin J)

SMILES for NP0006563 (8-epi-ophiobolin J)

INCHI for NP0006563 (8-epi-ophiobolin J)

Structure for NP0006563 (8-epi-ophiobolin J)

3D Structure for NP0006563 (8-epi-ophiobolin J)