NP-MRD: Showing NP-Card for Drophiobolin B (NP0044596)

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Record Information

Version

2.0

Created at

2022-02-24 21:08:16 UTC

Updated at

2026-02-14 20:01:43 UTC

NP-MRD ID

NP0044596

Natural Product DOI

https://doi.org/10.57994/6913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Drophiobolin B

Description

Drophiobiolin b 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. Thus, drophiobiolin b is considered to be an isoprenoid. Drophiobolin B was first documented in 2020 (PMID: 33074690). Based on a literature review very few articles have been published on Drophiobiolin b.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302242222082D          

 31 34  0  0  1  0            999 V2000
    4.6265    2.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519    1.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1498    0.3066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3556    0.5297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398   -0.3418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0989   -1.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927   -0.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9242    0.0219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9556    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985   -0.2627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9233   -1.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085    0.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7494    1.0712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0341    1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5058    2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6929    2.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905    3.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953   -1.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    0.0703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8915    0.4742    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0743    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650    1.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8627    0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233   -0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633   -1.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9187    1.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5843    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1804    2.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014    2.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  6 19  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  2  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
    4.8454    1.7882    0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4506    1.5529    1.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0572    2.4166    2.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    0.5872    1.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896   -0.2602    0.7362 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0069   -1.7185    1.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841   -2.2200    0.4890 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0298   -3.2550   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0902   -1.0431   -0.1438 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4340   -0.8219   -1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6483    0.4817   -1.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121    0.0016   -1.2680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3885   -0.6069   -2.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980    1.1710   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814    0.9914   -0.7739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6342    2.2986   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3840    3.3997   -1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4787    2.4002    0.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4946    1.1776    1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2405    1.0509    2.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391    0.2972    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3741   -0.8906    0.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032   -1.2127    2.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0168   -1.4691    3.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -1.9841    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9862   -3.0913    0.9270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1682   -2.1648   -0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3889   -0.8955   -0.1286 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6616    0.0358    0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4700    0.9701   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799    2.7438   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.8889   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8916    3.4779    2.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5838    2.2958    3.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1592    2.2911    2.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    0.4180    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992   -0.1152   -0.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791   -2.2141    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0517   -1.8178    2.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -2.6457    1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630   -2.7554   -1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368   -3.4552   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5190   -4.1425   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887   -1.6284   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811   -0.6341   -1.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5813    0.7345   -2.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910    1.2475   -1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451    0.2603   -3.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2667   -1.2151   -2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -1.1534   -3.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2181    1.4186    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358    2.0520   -1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619    0.4269   -1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3392    3.8669   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9174    2.9802   -2.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    4.1402   -1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889    3.2829    0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6727   -0.5321    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5090   -2.2716    2.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730   -1.9294    3.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345   -2.9988    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3795   -2.5922   -1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6358   -0.4119    0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 12  1  0
 12 13  1  6
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9 29  1  1
 29  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  9 28  1  0
 28 27  1  0
 27 25  1  0
 25 26  2  0
 25 22  1  0
 22 23  1  0
 23 24  1  0
 22 21  2  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 21 15  1  0
 16 15  1  0
 28 12  1  0
  7  9  1  0
 15 53  1  6
 14 51  1  0
 14 52  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 11 46  1  0
 11 47  1  0
 10 44  1  0
 10 45  1  0
  5 37  1  6
  6 38  1  0
  6 39  1  0
  7 40  1  1
  8 41  1  0
  8 42  1  0
  8 43  1  0
  4 36  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
 28 63  1  1
 27 61  1  0
 27 62  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 18 57  1  0
 17 54  1  0
 17 55  1  0
 17 56  1  0
M  END


  Mrv1652302242222082D          

 31 34  0  0  1  0            999 V2000
    4.6265    2.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4035    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0519    1.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1498    0.3066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3556    0.5297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398   -0.3418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0989   -1.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8927   -0.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9242    0.0219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9556    0.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985   -0.2627    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9233   -1.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085    0.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7494    1.0712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0341    1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5058    2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6929    2.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7905    3.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953   -1.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8206   -0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722    0.0703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8915    0.4742    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0743    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650    1.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8627    0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4233   -0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633   -1.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9187    1.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5843    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1804    2.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014    2.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  6 19  1  1  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  2  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]3(C)CC[C@@]4(O[C@H](C[C@@H]4C)C=C(C)C)[C@]3([H])CC(=O)\C(CO)=C1\C(=O)C=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O4/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/h8-9,16-18,22,26H,6-7,10-13H2,1-5H3/b23-19+/t16-,17-,18+,22+,24+,25-/m0/s1

> <INCHI_KEY>
VSGIUTNUGKJBMM-QUMYQEGPSA-N

> <FORMULA>
C25H34O4

> <MOLECULAR_WEIGHT>
398.543

> <EXACT_MASS>
398.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.82282608845021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2S,3S,3'R,5R,7'R)-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'-diene-9',12'-dione

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.879900895333333

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.687723354207712

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.735161624332342

> <JCHEM_PKA_STRONGEST_BASIC>
-2.836487435939265

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
115.77779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,3S,3'R,5R,7'R)-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'-diene-9',12'-dione

> <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  O   UNK     0       8.636   4.536   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.220   3.054   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.430   2.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.613   0.572   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       8.130   0.989   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       8.661  -0.638   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.518  -1.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.000  -1.498   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.058   0.041   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.117   1.580   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.504  -0.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.924  -1.972   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.456   0.720   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.599   2.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.130   3.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.144   4.628   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.627   4.365   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.676   6.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.018  -2.037   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.132  -0.821   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.921   0.131   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       7.264   0.885   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       5.739   1.660   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.228   1.959   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.477   0.615   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.524  -0.515   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.225  -2.026   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.582   3.357   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.691   2.871   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.937   4.214   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.723   5.538   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    9                                             
CONECT    5    4                                                            
CONECT    6    4    7   19   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10   11                                             
CONECT   10    9   14                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    6                                                            
CONECT   20    6   21                                                       
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   24                                                            
CONECT   29   23    2   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₄

Average Mass

398.5430 Da

Monoisotopic Mass

398.24571 Da

IUPAC Name

(1'R,2S,3S,3'R,5R,7'R)-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'-diene-9',12'-dione

Traditional Name

(1'R,2S,3S,3'R,5R,7'R)-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'-diene-9',12'-dione

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3(C)CC[C@@]4(O[C@H](C[C@@H]4C)C=C(C)C)[C@]3([H])CC(=O)\C(CO)=C1\C(=O)C=C2C

InChI Identifier

InChI=1S/C25H34O4/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/h8-9,16-18,22,26H,6-7,10-13H2,1-5H3/b23-19+/t16-,17-,18+,22+,24+,25-/m0/s1

InChI Key

VSGIUTNUGKJBMM-QUMYQEGPSA-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, 400.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Drechslera gigantea		Not Available
Drechslera gigantea	Linington's dataset npmrd_submissions_20220207	33074690

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
Tetrahydrofuran
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	3.1	ALOGPS
logP	3.88	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.74	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.78 m³·mol⁻¹	ChemAxon
Polarizability	45.82 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

113385751

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

Zatout R, Masi M, Sangermano F, Vurro M, Zonno MC, Santoro E, Calabro V, Superchi S, Evidente A: Drophiobiolins A and B, Bioactive Ophiobolan Sestertepenoids Produced by Dreschslera gigantea. J Nat Prod. 2020 Nov 25;83(11):3387-3396. doi: 10.1021/acs.jnatprod.0c00836. Epub 2020 Oct 19. [PubMed:33074690 ]
DOI: 10.1021/acs.jnatprod.0c00836
PMID: 33074690

Showing NP-Card for Drophiobolin B (NP0044596)

MOL for NP0044596 (Drophiobolin B)

3D MOL for NP0044596 (Drophiobolin B)

3D SDF for NP0044596 (Drophiobolin B)

3D-SDF for NP0044596 (Drophiobolin B)

PDB for NP0044596 (Drophiobolin B)

3D PDB for NP0044596 (Drophiobolin B)

SMILES for NP0044596 (Drophiobolin B)

INCHI for NP0044596 (Drophiobolin B)

Structure for NP0044596 (Drophiobolin B)

3D Structure for NP0044596 (Drophiobolin B)