NP-MRD: Showing NP-Card for Alternapyrone (NP0006147)

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Record Information

Version

2.0

Created at

2020-12-09 03:12:06 UTC

Updated at

2021-07-15 16:53:58 UTC

NP-MRD ID

NP0006147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alternapyrone

Provided By

NPAtlas

Description

Alternapyrone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Alternapyrone is found in Alternaria solani. Alternapyrone was first documented in 2005 (PMID: 16356847). Based on a literature review a small amount of articles have been published on alternapyrone (PMID: 19100326) (PMID: 27388157).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242118253D          

 75 75  0  0  0  0            999 V2000
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   -8.9348   -0.7317    1.3760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8101   -0.4148    2.2588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0135    0.8348    3.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4212   -0.5790    1.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8649   -0.4850    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6184   -0.1667   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480   -0.7606    0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
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 29 72  1  0  0  0  0
 31 73  1  0  0  0  0
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M  END

     RDKit          3D

 75 75  0  0  0  0  0  0  0  0999 V2000
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 28 30  1  0
 30 31  1  0
 30 22  2  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  1
  4 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  6
 12 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 15 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 18 60  1  0
 18 61  1  0
 18 62  1  0
 19 63  1  0
 19 64  1  0
 20 65  1  1
 21 66  1  0
 21 67  1  0
 21 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 29 72  1  0
 31 73  1  0
 31 74  1  0
 31 75  1  0
M  END

  Mrv1652306242118253D          

 75 75  0  0  0  0            999 V2000
   -8.7405   -1.9646    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9348   -0.7317    1.3760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8101   -0.4148    2.2588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0135    0.8348    3.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4212   -0.5790    1.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8649   -0.4850    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6184   -0.1667   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480   -0.7606    0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6477    0.4561    0.0843 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1761    0.3987   -0.0483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5379   -0.5672   -0.9952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8412   -1.9898   -0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564   -0.3089   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746    0.0239   -1.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1815    0.1451   -3.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    0.2090   -1.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124    0.5577   -2.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    0.8132   -3.6911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5465    0.6716   -1.8073 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7894    0.2791   -0.3987 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4688   -1.1918   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2256    0.5544   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0477    0.9871   -0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3109    1.2574   -0.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0228    1.6743   -1.7665 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8420    1.0883    0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2667    1.3746    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0158    0.6336    1.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5114    0.4472    2.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6687    0.3539    1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.1176    2.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5341   -2.7205    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7517   -2.4087    0.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9249   -1.8244   -0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3804    0.1281    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8279   -0.9719    2.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9257   -1.2433    3.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2115    1.7277    2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1262    0.9350    3.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6625   -0.8231    2.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7570   -1.0654   -1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9516    0.4860   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3406   -1.5951   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9831   -1.1460    1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8446    1.2908    0.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694    1.4559   -0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9538   -0.3188   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -2.5983   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -2.1298    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.4485   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.4077    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -0.4813   -3.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -0.3566   -4.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.1457   -3.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    0.0745   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926    1.4383   -4.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913   -0.0647   -4.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693    1.5135   -3.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9196    1.6738   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0862   -0.0859   -2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1796    0.8508    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230   -1.7818   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9088   -1.6537   -0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8736   -1.3210    0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4086    2.1584    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7739    0.4583    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8105    1.6267   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0049    0.1230    3.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.2062    2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732    0.2487    3.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060    0.3730    2.1990 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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  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
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 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
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 30 31  1  0  0  0  0
 30 22  2  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
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 21 68  1  0  0  0  0
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 29 72  1  0  0  0  0
 31 73  1  0  0  0  0
 31 74  1  0  0  0  0
 31 75  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)OC(=C1C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C(=C(/[H])\C(=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C(=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O3/c1-10-18(2)14-19(3)12-11-13-20(4)15-21(5)16-22(6)17-23(7)27-24(8)26(29)25(9)28(30)31-27/h14-16,18,20,23,29H,10-13,17H2,1-9H3/b19-14+,21-15+,22-16+/t18-,20-,23+/m0/s1

> <INCHI_KEY>
ZPFTUJZLXSKBKE-NZDFSFLRSA-N

> <FORMULA>
C28H44O3

> <MOLECULAR_WEIGHT>
428.657

> <EXACT_MASS>
428.329045277

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.764519222321084

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3,5-dimethyl-6-[(2R,4E,6E,8S,12E,14S)-4,6,8,12,14-pentamethylhexadeca-4,6,12-trien-2-yl]-2H-pyran-2-one

> <ALOGPS_LOGP>
7.23

> <JCHEM_LOGP>
8.073238314666668

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.729695233765193

> <JCHEM_PKA_STRONGEST_BASIC>
-5.978831304752959

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
136.54760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3,5-dimethyl-6-[(2R,4E,6E,8S,12E,14S)-4,6,8,12,14-pentamethylhexadeca-4,6,12-trien-2-yl]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 75 75  0  0  0  0  0  0  0  0999 V2000
   -8.7405   -1.9646    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9348   -0.7317    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8101   -0.4148    2.2588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0135    0.8348    3.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4212   -0.5790    1.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8649   -0.4850    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6184   -0.1667   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1761    0.3987   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5379   -0.5672   -0.9952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8412   -1.9898   -0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564   -0.3089   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1815    0.1451   -3.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0228    1.6743   -1.7665 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8420    1.0883    0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2667    1.3746    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9538   -0.3188   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -2.5983   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -2.1298    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.4485   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.4077    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -0.4813   -3.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -0.3566   -4.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.1457   -3.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    0.0745   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926    1.4383   -4.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913   -0.0647   -4.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693    1.5135   -3.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9196    1.6738   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0862   -0.0859   -2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1796    0.8508    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230   -1.7818   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9088   -1.6537   -0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8736   -1.3210    0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4086    2.1584    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7739    0.4583    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8105    1.6267   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0049    0.1230    3.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.2062    2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732    0.2487    3.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060    0.3730    2.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 22  2  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  1
  4 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  6
 12 52  1  0
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 15 56  1  0
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 15 58  1  0
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 18 61  1  0
 18 62  1  0
 19 63  1  0
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 20 65  1  1
 21 66  1  0
 21 67  1  0
 21 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 29 72  1  0
 31 73  1  0
 31 74  1  0
 31 75  1  0
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      -8.741  -1.965   0.575  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.935  -0.732   1.376  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.810  -0.415   2.259  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.014   0.835   3.135  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.421  -0.579   1.885  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.865  -0.485   0.706  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.618  -0.167  -0.511  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.348  -0.761   0.570  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.648   0.456   0.084  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.176   0.399  -0.048  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.538  -0.567  -0.995  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.841  -1.990  -0.594  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.056  -0.309  -0.886  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.775   0.024  -1.866  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.182   0.145  -3.188  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.158   0.209  -1.476  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.112   0.558  -2.278  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.875   0.813  -3.691  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.547   0.672  -1.807  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.789   0.279  -0.399  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.469  -1.192  -0.136  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.226   0.554  -0.039  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.048   0.987  -0.974  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.311   1.257  -0.784  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.023   1.674  -1.767  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.842   1.088   0.462  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.267   1.375   0.751  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.016   0.634   1.484  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.511   0.447   2.758  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.669   0.354   1.249  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.726  -0.118   2.271  0.00  0.00           C+0
HETATM   32  H   UNK     0      -9.534  -2.720   0.875  0.00  0.00           H+0
HETATM   33  H   UNK     0      -7.752  -2.409   0.814  0.00  0.00           H+0
HETATM   34  H   UNK     0      -8.925  -1.824  -0.509  0.00  0.00           H+0
HETATM   35  H   UNK     0      -9.380   0.128   0.806  0.00  0.00           H+0
HETATM   36  H   UNK     0      -9.828  -0.972   2.078  0.00  0.00           H+0
HETATM   37  H   UNK     0      -7.926  -1.243   3.112  0.00  0.00           H+0
HETATM   38  H   UNK     0      -8.889   0.700   3.804  0.00  0.00           H+0
HETATM   39  H   UNK     0      -8.211   1.728   2.519  0.00  0.00           H+0
HETATM   40  H   UNK     0      -7.126   0.935   3.791  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.662  -0.823   2.708  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.757  -1.065  -1.192  0.00  0.00           H+0
HETATM   43  H   UNK     0      -7.508   0.445  -0.397  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.952   0.486  -1.177  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.341  -1.595  -0.193  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.983  -1.146   1.526  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.113   0.865  -0.860  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.845   1.291   0.850  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.769   1.456  -0.231  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.786   0.227   1.017  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.954  -0.319  -1.985  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.871  -2.598  -0.622  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.190  -2.130   0.430  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.563  -2.449  -1.295  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.388  -0.408   0.126  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.773  -0.481  -3.297  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.778  -0.357  -4.017  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.191   1.146  -3.467  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.442   0.075  -0.394  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.793   1.438  -4.039  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.991  -0.065  -4.367  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.069   1.514  -3.951  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.920   1.674  -2.050  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.086  -0.086  -2.452  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.180   0.851   0.335  0.00  0.00           H+0
HETATM   66  H   UNK     0       5.423  -1.782  -0.098  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.909  -1.654  -0.974  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.874  -1.321   0.776  0.00  0.00           H+0
HETATM   69  H   UNK     0      10.409   2.158   1.514  0.00  0.00           H+0
HETATM   70  H   UNK     0      10.774   0.458   1.154  0.00  0.00           H+0
HETATM   71  H   UNK     0      10.810   1.627  -0.177  0.00  0.00           H+0
HETATM   72  H   UNK     0       8.005   0.123   3.538  0.00  0.00           H+0
HETATM   73  H   UNK     0       5.665  -1.206   2.364  0.00  0.00           H+0
HETATM   74  H   UNK     0       6.073   0.249   3.284  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.706   0.373   2.199  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   35   36                                             
CONECT    3    2    4    5   37                                             
CONECT    4    3   38   39   40                                             
CONECT    5    3    6   41                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   42   43   44                                             
CONECT    8    6    9   45   46                                             
CONECT    9    8   10   47   48                                             
CONECT   10    9   11   49   50                                             
CONECT   11   10   12   13   51                                             
CONECT   12   11   52   53   54                                             
CONECT   13   11   14   55                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   56   57   58                                             
CONECT   16   14   17   59                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   60   61   62                                             
CONECT   19   17   20   63   64                                             
CONECT   20   19   21   22   65                                             
CONECT   21   20   66   67   68                                             
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26   69   70   71                                             
CONECT   28   26   29   30                                                  
CONECT   29   28   72                                                       
CONECT   30   28   31   22                                                  
CONECT   31   30   73   74   75                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    7                                                            
CONECT   43    7                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   10                                                            
CONECT   51   11                                                            
CONECT   52   12                                                            
CONECT   53   12                                                            
CONECT   54   12                                                            
CONECT   55   13                                                            
CONECT   56   15                                                            
CONECT   57   15                                                            
CONECT   58   15                                                            
CONECT   59   16                                                            
CONECT   60   18                                                            
CONECT   61   18                                                            
CONECT   62   18                                                            
CONECT   63   19                                                            
CONECT   64   19                                                            
CONECT   65   20                                                            
CONECT   66   21                                                            
CONECT   67   21                                                            
CONECT   68   21                                                            
CONECT   69   27                                                            
CONECT   70   27                                                            
CONECT   71   27                                                            
CONECT   72   29                                                            
CONECT   73   31                                                            
CONECT   74   31                                                            
CONECT   75   31                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  150    0
END

RDKit          3D

75 75  0  0  0  0  0  0  0  0999 V2000
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   -8.9348   -0.7317    1.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8101   -0.4148    2.2588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.0135    0.8348    3.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6184   -0.1667   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6477    0.4561    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8412   -1.9898   -0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0564   -0.3089   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2667    1.3746    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7258   -0.1176    2.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2115    1.7277    2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1262    0.9350    3.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9538   -0.3188   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -2.5983   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -2.1298    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634   -2.4485   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.4077    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7728   -0.4813   -3.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -0.3566   -4.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.1457   -3.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425    0.0745   -0.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926    1.4383   -4.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9913   -0.0647   -4.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693    1.5135   -3.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9196    1.6738   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0862   -0.0859   -2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1796    0.8508    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4230   -1.7818   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9088   -1.6537   -0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8736   -1.3210    0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4086    2.1584    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7739    0.4583    1.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8105    1.6267   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0049    0.1230    3.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.2062    2.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732    0.2487    3.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060    0.3730    2.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
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  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  1
  4 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
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 31 75  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3,5-Dimethyl-4-hydroxy-6-(1,3,5,7,11,13-hexamethyl-3,5,11-pentadecatrienyl)pyran-2-one	MeSH

Chemical Formula

C₂₈H₄₄O₃

Average Mass

428.6570 Da

Monoisotopic Mass

428.32905 Da

IUPAC Name

4-hydroxy-3,5-dimethyl-6-[(2R,4E,6E,8S,12E,14S)-4,6,8,12,14-pentamethylhexadeca-4,6,12-trien-2-yl]-2H-pyran-2-one

Traditional Name

4-hydroxy-3,5-dimethyl-6-[(2R,4E,6E,8S,12E,14S)-4,6,8,12,14-pentamethylhexadeca-4,6,12-trien-2-yl]pyran-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)\C=C(/C)CCCC(C)\C=C(/C)\C=C(/C)CC(C)C1=C(C)C(O)=C(C)C(=O)O1

InChI Identifier

InChI=1S/C28H44O3/c1-10-18(2)14-19(3)12-11-13-20(4)15-21(5)16-22(6)17-23(7)27-24(8)26(29)25(9)28(30)31-27/h14-16,18,20,23,29H,10-13,17H2,1-9H3/b19-14+,21-15+,22-16+

InChI Key

ZPFTUJZLXSKBKE-NZDFSFLRSA-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
Alternaria solani	NPAtlas	16356847

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.23	ALOGPS
logP	8.07	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	7.73	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	136.55 m³·mol⁻¹	ChemAxon
Polarizability	54.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020320

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21375531

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57467994

PDB ID

Not Available

ChEBI ID

156318

Good Scents ID

Not Available

References

General References

Fujii I, Yoshida N, Shimomaki S, Oikawa H, Ebizuka Y: An iterative type I polyketide synthase PKSN catalyzes synthesis of the decaketide alternapyrone with regio-specific octa-methylation. Chem Biol. 2005 Dec;12(12):1301-9. doi: 10.1016/j.chembiol.2005.09.015. [PubMed:16356847 ]
Gagunashvili AN, Davidsson SP, Jonsson ZO, Andresson OS: Cloning and heterologous transcription of a polyketide synthase gene from the lichen Solorina crocea. Mycol Res. 2009 Mar;113(Pt 3):354-63. doi: 10.1016/j.mycres.2008.11.011. Epub 2008 Dec 6. [PubMed:19100326 ]
Noar RD, Daub ME: Bioinformatics Prediction of Polyketide Synthase Gene Clusters from Mycosphaerella fijiensis. PLoS One. 2016 Jul 7;11(7):e0158471. doi: 10.1371/journal.pone.0158471. eCollection 2016. [PubMed:27388157 ]

Showing NP-Card for Alternapyrone (NP0006147)

MOL for NP0006147 (Alternapyrone)

3D MOL for NP0006147 (Alternapyrone)

3D SDF for NP0006147 (Alternapyrone)

3D-SDF for NP0006147 (Alternapyrone)

PDB for NP0006147 (Alternapyrone)

3D PDB for NP0006147 (Alternapyrone)

SMILES for NP0006147 (Alternapyrone)

INCHI for NP0006147 (Alternapyrone)

Structure for NP0006147 (Alternapyrone)

3D Structure for NP0006147 (Alternapyrone)