NP-MRD: Showing NP-Card for dehydroaustinol (NP0233508)

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Record Information

Version

2.0

Created at

2022-09-06 15:08:14 UTC

Updated at

2022-09-06 15:08:14 UTC

NP-MRD ID

NP0233508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dehydroaustinol

Description

Dehydroaustinol, also known as austinol, belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. dehydroaustinol is found in Penicillium simplicissimum. dehydroaustinol was first documented in 2017 (PMID: 28674377). Based on a literature review a small amount of articles have been published on dehydroaustinol (PMID: 34343886) (PMID: 33563821) (PMID: 30044771) (PMID: 28467349).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217082D          

 33 38  0  0  1  0            999 V2000
    1.4599   -1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -1.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802   -0.1167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2412   -0.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4258   -1.4954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -0.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5399    0.4110    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0147    1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.4266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2648    0.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395   -0.1893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6314   -0.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8272   -1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2276    0.1498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8238    0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6158    0.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6035   -0.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153   -0.8829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4234   -0.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -1.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6293   -0.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319    0.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    0.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0738    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7244   -1.1703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3524   -1.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706   -1.4412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7669   -2.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038   -1.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    0.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  1  0  0  0
 11 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 61 66  0  0  0  0  0  0  0  0999 V2000
   -3.6519   -1.3048    1.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7907   -0.9625    0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    0.3854    0.4290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8763    1.4837    1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    1.5846    2.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9779    2.5125    0.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    1.9821   -1.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1026    2.9303   -2.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2329    0.6415   -1.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9267    0.5279   -1.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -0.4156   -0.5746 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1486   -0.3929   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750   -1.3228   -1.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0387    0.5740   -0.0694 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3591    1.6358   -1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068    1.7719   -1.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5808    0.8379   -1.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7148    0.9445   -1.9940 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3388   -0.1690   -0.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3341   -0.0035    0.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616   -1.3098    1.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376    0.9520    1.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4074    1.2836    1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0358    1.5580    0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    0.2359    0.7334 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4537   -0.6302    1.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -1.7788   -0.7672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0887   -2.7116   -0.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2952   -1.9941   -0.3237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5917   -3.3808    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -1.7071   -1.4844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0715   -0.3330   -1.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7773    0.0819   -2.7587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9995   -2.3274    1.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0636   -0.6207    2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956    1.9308   -1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    2.3794   -2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6231    3.6936   -1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7312    3.4688   -2.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1232   -2.0898   -2.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7438   -1.3534   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614    2.3668   -1.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6320    2.5858   -2.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -1.9823    0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1651   -1.8155    1.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276   -1.1270    2.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367    0.6983    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5367    0.7412    2.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013    1.9905    1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5610    0.7237    2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917    2.3022    1.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4585    2.2280    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555    2.0199   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3297   -1.2168    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.0470    2.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390   -1.3833    1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8398   -2.0104   -1.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0904   -3.5896   -0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -4.0869   -0.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903   -3.5512    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -3.5288    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  3  4  1  1
  3  2  1  0
  2  1  2  3
  2 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  2  0
 32  9  1  0
  9 10  1  6
 11 10  1  6
 11 27  1  0
 27 28  1  0
 11 12  1  0
 12 13  2  3
 14 12  1  6
 14 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  9  7  1  0
 25 11  1  0
  9  3  1  0
 20 14  1  0
 25  3  1  0
 27 29  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  7 36  1  6
  1 34  1  0
  1 35  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 27 57  1  6
 28 58  1  0
 13 40  1  0
 13 41  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 15 42  1  0
 16 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
M  END


  Mrv1652309062217082D          

 33 38  0  0  1  0            999 V2000
    1.4599   -1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -1.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802   -0.1167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2412   -0.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4258   -1.4954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -0.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5399    0.4110    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0147    1.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    0.4266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2648    0.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395   -0.1893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6314   -0.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8272   -1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2276    0.1498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8238    0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6158    0.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8115   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6035   -0.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2153   -0.8829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4234   -0.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -1.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6293   -0.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319    0.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    1.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    0.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0738    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7244   -1.1703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3524   -1.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706   -1.4412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7669   -2.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038   -1.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    0.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  1  0  0  0
 11 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0233508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC(=O)[C@@]23C(=C)[C@@]4(C)OC(=O)[C@@]12O[C@@]1([C@H]4O)C(=C)[C@]2(CC[C@@]31C)C=CC(=O)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O8/c1-12-21(7)16(27)24-13(2)22(9-8-15(26)31-19(22,4)5)11-10-20(24,6)23(12)17(28)30-14(3)25(23,33-24)18(29)32-21/h8-9,14,16,27H,1-2,10-11H2,3-7H3/t14-,16-,20-,21+,22+,23+,24+,25-/m0/s1

> <INCHI_KEY>
IQBUQLYYAHHCGX-LRSNFHFMSA-N

> <FORMULA>
C25H28O8

> <MOLECULAR_WEIGHT>
456.491

> <EXACT_MASS>
456.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.06114933208504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5S,7S,8S,9R,12S,13S)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

> <JCHEM_LOGP>
2.0779141956666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.740392045754692

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7871525191868978

> <JCHEM_POLAR_SURFACE_AREA>
108.36

> <JCHEM_REFRACTIVITY>
112.66229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7S,8S,9R,12S,13S)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.725  -1.884   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.938  -1.875   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.510  -0.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.317  -1.290   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.661  -2.791   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.673  -0.815   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.008   0.767   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.028   1.955   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.668   0.796   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.228   1.415   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.300  -0.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.779  -0.785   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.144  -2.281   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.892   0.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.004   1.344   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.483   0.912   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.848  -0.584   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.326  -1.015   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.735  -1.648   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.257  -1.216   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.774  -2.679   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.775  -1.634   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.526   1.776   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.048   2.207   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.935   1.143   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.871   2.256   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.085  -2.185   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.258  -3.183   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.305  -2.690   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.298  -4.230   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.687  -2.215   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.589  -0.417   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.135   0.091   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4    9   25                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10   32                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   25   27                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20   23                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    3   11   26                                             
CONECT   26   25                                                            
CONECT   27   11   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    2   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    9   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
Austinol	MeSH

Chemical Formula

C₂₅H₂₈O₈

Average Mass

456.4910 Da

Monoisotopic Mass

456.17842 Da

IUPAC Name

(1R,2S,5S,7S,8S,9R,12S,13S)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-2',6'-dihydro-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

Traditional Name

(1R,2S,5S,7S,8S,9R,12S,13S)-8-hydroxy-2,2',2',9,13-pentamethyl-6,16-dimethylidene-10,14,17-trioxaspiro[pentacyclo[7.6.1.1^{7,12}.0^{1,12}.0^{2,7}]heptadecane-5,3'-pyran]-6',11,15-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC(=O)[C@@]23C(=C)[C@@]4(C)OC(=O)[C@@]12O[C@@]1([C@H]4O)C(=C)[C@]2(CC[C@@]31C)C=CC(=O)OC2(C)C

InChI Identifier

InChI=1S/C25H28O8/c1-12-21(7)16(27)24-13(2)22(9-8-15(26)31-19(22,4)5)11-10-20(24,6)23(12)17(28)30-14(3)25(23,33-24)18(29)32-21/h8-9,14,16,27H,1-2,10-11H2,3-7H3/t14-,16-,20-,21+,22+,23+,24+,25-/m0/s1

InChI Key

IQBUQLYYAHHCGX-LRSNFHFMSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Penicillium simplicissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Tricarboxylic acid or derivatives
Furofuran
1,4-dioxepane
Delta valerolactone
Dihydropyranone
Dioxepane
Delta_valerolactone
Oxepane
Gamma butyrolactone
Oxane
Pyran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Ether
Dialkyl ether
Oxacycle
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

meroterpenoid (CHEBI:64421 )

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	2.08	ChemAxon
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	112.66 m³·mol⁻¹	ChemAxon
Polarizability	45.06 Å³	ChemAxon
Number of Rings	6	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

28184634

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56955928

PDB ID

Not Available

ChEBI ID

64421

Good Scents ID

Not Available

References

General References

Mo S, Yin J, Ye Z, Li F, Lin S, Zhang S, Yang B, Yao J, Wang J, Hu Z, Zhang Y: Asperanstinoids A-E: Undescribed 3,5-dimethylorsellinic acid-based meroterpenoids from Aspergillus calidoustus. Phytochemistry. 2021 Jul 31;190:112892. doi: 10.1016/j.phytochem.2021.112892. [PubMed:34343886 ]
Wu MY, Mead ME, Lee MK, Neuhaus GF, Adpressa DA, Martien JI, Son YE, Moon H, Amador-Noguez D, Han KH, Rokas A, Loesgen S, Yu JH, Park HS: Transcriptomic, Protein-DNA Interaction, and Metabolomic Studies of VosA, VelB, and WetA in Aspergillus nidulans Asexual Spores. mBio. 2021 Feb 9;12(1). pii: mBio.03128-20. doi: 10.1128/mBio.03128-20. [PubMed:33563821 ]
Thieme KG, Gerke J, Sasse C, Valerius O, Thieme S, Karimi R, Heinrich AK, Finkernagel F, Smith K, Bode HB, Freitag M, Ram AFJ, Braus GH: Velvet domain protein VosA represses the zinc cluster transcription factor SclB regulatory network for Aspergillus nidulans asexual development, oxidative stress response and secondary metabolism. PLoS Genet. 2018 Jul 25;14(7):e1007511. doi: 10.1371/journal.pgen.1007511. eCollection 2018 Jul. [PubMed:30044771 ]
Itoh E, Shigemoto R, Oinuma KI, Shimizu M, Masuo S, Takaya N: Sirtuin A regulates secondary metabolite production by Aspergillus nidulans. J Gen Appl Microbiol. 2017 Sep 5;63(4):228-235. doi: 10.2323/jgam.2016.11.002. Epub 2017 Jul 1. [PubMed:28674377 ]
Long Y, Cui H, Liu X, Xiao Z, Wen S, She Z, Huang X: Acetylcholinesterase Inhibitory Meroterpenoid from a Mangrove Endophytic Fungus Aspergillus sp. 16-5c. Molecules. 2017 May 3;22(5). pii: molecules22050727. doi: 10.3390/molecules22050727. [PubMed:28467349 ]
LOTUS database [Link]

Showing NP-Card for dehydroaustinol (NP0233508)

MOL for NP0233508 (dehydroaustinol)

3D MOL for NP0233508 (dehydroaustinol)

3D SDF for NP0233508 (dehydroaustinol)

3D-SDF for NP0233508 (dehydroaustinol)

PDB for NP0233508 (dehydroaustinol)

3D PDB for NP0233508 (dehydroaustinol)

SMILES for NP0233508 (dehydroaustinol)

INCHI for NP0233508 (dehydroaustinol)

Structure for NP0233508 (dehydroaustinol)

3D Structure for NP0233508 (dehydroaustinol)