NP-MRD: Showing NP-Card for (6R)-16,17-Dihydroophiobolin H (NP0044638)

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Record Information

Version

2.0

Created at

2022-02-24 21:10:10 UTC

Updated at

2026-02-14 16:01:44 UTC

NP-MRD ID

NP0044638

Natural Product DOI

https://doi.org/10.57994/6893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6R)-16,17-Dihydroophiobolin H

Description

(1S,3R,6R,7S,13R,15R,16R)-3,15-dimethyl-6-[(2S)-6-methylhept-5-en-2-yl]-12-oxatetracyclo[8.5.1.0³,⁷.0¹³,¹⁶]Hexadec-9-ene-13,15-diol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (6R)-16,17-Dihydroophiobolin H was first documented in 2020 (PMID: 33322904). Based on a literature review very few articles have been published on (1S,3R,6R,7S,13R,15R,16R)-3,15-dimethyl-6-[(2S)-6-methylhept-5-en-2-yl]-12-oxatetracyclo[8.5.1.0³,⁷.0¹³,¹⁶]Hexadec-9-ene-13,15-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302242222102D          

 32 35  0  0  1  0            999 V2000
    3.3285   -0.8383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3968    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3198    1.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.4084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0817    2.1493    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8977    0.5093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    2.1599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9626    2.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7317    2.7301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3650    0.3157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668   -1.0396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6148   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9738   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2287   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0357   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0976   -3.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7386   -3.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 12 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
  2 25  1  6  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    5.2590    0.8732    1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8995    0.2746    0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3229   -0.2354    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4278    0.1209   -0.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1671    0.4270   -1.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9127    0.5495   -0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891   -0.7433   -0.0304 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6218   -1.9036   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2494   -0.7473    0.7445 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2702    0.4432    1.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    1.4797    1.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6717    0.6971    0.3383 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9572    1.4458   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057    0.7159    1.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870    0.5713    0.4792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4527   -0.9150    0.3249 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9508   -1.3950   -0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7624   -1.5103   -1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3087   -1.2588   -1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867   -0.6864    0.1463 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1302   -1.8152   -1.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2253   -1.1635   -1.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9571   -1.0293    0.1514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4583   -2.1340    0.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    0.2533    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3928    1.0660    1.2154 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6171    2.5441    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2459    0.7186    2.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8172    1.8809    1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383    0.2445    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0579    1.0881    2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9690    0.5664    0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4967   -0.4654    1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4593   -1.1414    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1817   -0.3771   -1.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616   -0.2821   -2.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778    1.4090   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0039    1.3273    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472    0.9449   -1.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058   -0.9877    0.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283   -2.1050   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217   -1.6853   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2965   -2.8333   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280   -1.6498    1.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    0.1288    2.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2683    0.8479    1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690    2.2523    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0664    2.0480    1.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091    1.9730   -1.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3784    0.9046   -1.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    2.2977   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -0.0968    1.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334    1.6909    1.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989    0.9922   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193   -1.4814    1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8274   -1.9228   -2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979   -2.3008   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -0.6926   -2.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597   -1.3396    0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2696   -2.9030   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -1.4866   -2.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3947   -2.9085    0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0728    0.8395   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2866    0.0177    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6767    2.8139    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0014    3.0868    1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216    2.8478    0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5936   -0.1865    2.6778 H   0  0  0  0  0  0  0  0  0  0  0  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
 17 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  1
 17 18  2  0
 18 19  1  0
 19 20  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
 20  9  1  0
 20 12  1  0
 26 15  1  0
 23 16  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  6
 16 55  1  1
 21 60  1  0
 21 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  1
  7 40  1  1
  8 41  1  0
  8 42  1  0
  8 43  1  0
  6 38  1  0
  6 39  1  0
  5 36  1  0
  5 37  1  0
  4 35  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
M  END


  Mrv1652302242222102D          

 32 35  0  0  1  0            999 V2000
    3.3285   -0.8383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3968    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3198    1.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.4084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0817    2.1493    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8977    0.5093    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    2.1599    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9626    2.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7317    2.7301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3650    0.3157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668   -1.0396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6148   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9738   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2287   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0357   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2906   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0976   -3.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7386   -3.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 12 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
  2 25  1  6  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@]2(C)C[C@@]3([H])[C@]4([H])\C(CO[C@]4(O)C[C@@]3(C)O)=C/C[C@@]12[H])[C@@H](C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O3/c1-16(2)7-6-8-17(3)19-11-12-23(4)13-21-22-18(9-10-20(19)23)14-28-25(22,27)15-24(21,5)26/h7,9,17,19-22,26-27H,6,8,10-15H2,1-5H3/b18-9-/t17-,19+,20-,21-,22-,23+,24+,25+/m0/s1

> <INCHI_KEY>
AJADRAOGQKSOHA-IISQMHTBSA-N

> <FORMULA>
C25H40O3

> <MOLECULAR_WEIGHT>
388.592

> <EXACT_MASS>
388.297745148

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.52953653160537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,6R,7S,13R,15R,16R)-3,15-dimethyl-6-[(2S)-6-methylhept-5-en-2-yl]-12-oxatetracyclo[8.5.1.0^{3,7}.0^{13,16}]hexadec-9-ene-13,15-diol

> <ALOGPS_LOGP>
4.89

> <JCHEM_LOGP>
4.903613188999999

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.700482495644401

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.664882373275992

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9802545716903586

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
115.12759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6R,7S,13R,15R,16R)-3,15-dimethyl-6-[(2S)-6-methylhept-5-en-2-yl]-12-oxatetracyclo[8.5.1.0^{3,7}.0^{13,16}]hexadec-9-ene-13,15-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-22         0                                  
HETATM    1  H   UNK     0       6.213  -1.565   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       7.302  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.207   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.302   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.838   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.197   3.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.749   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.209   2.629   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       3.886   4.012   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       3.542   0.951   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.250   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.810   2.492   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.655   3.556   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.120   4.032   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.797   5.538   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.233   5.096   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.209  -1.089   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.749  -1.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.838   0.000   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.415   0.589   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       7.778  -1.941   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.748  -3.085   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.284  -2.261   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.760  -3.725   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.267  -4.046   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.742  -5.510   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.249  -5.830   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.712  -6.655   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23   25                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   23                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   18                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   15                                             
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    8   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2    5   24                                             
CONECT   24   23                                                            
CONECT   25    2   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀O₃

Average Mass

388.5920 Da

Monoisotopic Mass

388.29775 Da

IUPAC Name

(1S,3R,6R,7S,13R,15R,16R)-3,15-dimethyl-6-[(2S)-6-methylhept-5-en-2-yl]-12-oxatetracyclo[8.5.1.0^{3,7}.0^{13,16}]hexadec-9-ene-13,15-diol

Traditional Name

(1S,3R,6R,7S,13R,15R,16R)-3,15-dimethyl-6-[(2S)-6-methylhept-5-en-2-yl]-12-oxatetracyclo[8.5.1.0^{3,7}.0^{13,16}]hexadec-9-ene-13,15-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@]2(C)C[C@@]3([H])[C@]4([H])\C(CO[C@]4(O)C[C@@]3(C)O)=C/C[C@@]12[H])[C@@H](C)CCC=C(C)C

InChI Identifier

InChI=1S/C25H40O3/c1-16(2)7-6-8-17(3)19-11-12-23(4)13-21-22-18(9-10-20(19)23)14-28-25(22,27)15-24(21,5)26/h7,9,17,19-22,26-27H,6,8,10-15H2,1-5H3/b18-9-/t17-,19+,20-,21-,22-,23+,24+,25+/m0/s1

InChI Key

AJADRAOGQKSOHA-IISQMHTBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aspergillus	Linington's dataset npmrd_submissions_20220207	33322904
Aspergillus insuetus SD-512		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	4.89	ALOGPS
logP	4.9	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.13 m³·mol⁻¹	ChemAxon
Polarizability	46.53 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

99740766

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chi LP, Li XM, Wan YP, Li X, Wang BG: Ophiobolin Sesterterpenoids and Farnesylated Phthalide Derivatives from the Deep Sea Cold-Seep-Derived Fungus Aspergillus insuetus SD-512. J Nat Prod. 2020 Dec 24;83(12):3652-3660. doi: 10.1021/acs.jnatprod.0c00860. Epub 2020 Dec 15. [PubMed:33322904 ]
DOI: 10.1021/acs.jnatprod.0c00860
PMID: 33322904

Showing NP-Card for (6R)-16,17-Dihydroophiobolin H (NP0044638)

MOL for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

3D MOL for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

3D SDF for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

3D-SDF for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

PDB for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

3D PDB for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

SMILES for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

INCHI for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

Structure for NP0044638 ((6R)-16,17-Dihydroophiobolin H)

3D Structure for NP0044638 ((6R)-16,17-Dihydroophiobolin H)