NP-MRD: Showing NP-Card for Nodulisporic acid F (NP0005512)

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Record Information

Version

2.0

Created at

2020-12-09 02:44:34 UTC

Updated at

2021-07-15 16:52:13 UTC

NP-MRD ID

NP0005512

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nodulisporic acid F

Provided By

NPAtlas

Description

Nodulisporic acid F is found in Nodulisporium sp., Nodulisporium sp.MF5954 and Nodulisporium sp.MF6518. Nodulisporic acid F was first documented in 2004 (PMID: 15387649). Based on a literature review very few articles have been published on (2E)-5-[(1S,12S,15R,16S,17S,20S)-17-hydroxy-1,16,20-trimethyl-3-azapentacyclo[10.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Icosa-2(10),4,6,8-tetraen-16-yl]-2-methylpent-2-enoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118193D          

 69 73  0  0  0  0            999 V2000
   -6.0296    1.4788   -1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8525    0.8171   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -0.1576    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363   -0.5594   -0.9599 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7017   -0.3300   -1.0114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7572   -0.9313   -0.0106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0095   -2.4546   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -0.4502    1.3320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6626   -1.5375    2.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    0.0297    2.2137 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0358    0.7517    1.4027 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6735   -0.2543    0.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2702   -1.3200    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724   -0.6223   -0.5313 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0412   -1.6713   -1.5425 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1431   -0.9865   -2.3820 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1880   -0.6617   -1.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4558   -0.0226   -1.8983 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0686    0.3052   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    0.5221    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687    0.8117    1.5777 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8923    0.7826    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553    0.9920    2.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2617    0.8886    1.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687    0.5800    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5433    0.3694   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.4736    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967    0.3576   -0.3626 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4388    1.6394   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6624    1.2121    1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306    0.6620    2.2388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6022    2.2181    0.9520 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9166   -0.6006    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701   -0.0591   -1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909   -1.6525   -1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    0.7754   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173   -0.6137   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7580   -2.7888    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959   -2.7062   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1062   -3.0320    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8544    0.3550    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440   -1.2191    2.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -0.8250    2.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5344    1.5278    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    1.2754    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519   -1.5546    1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -2.2737    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -1.0043    2.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840    0.3194   -1.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008   -1.9488   -2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -2.5387   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -0.1888   -3.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -1.7815   -3.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5210   -1.6378   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025   -0.7375   -2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3330    0.8878   -2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    1.0253    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7441    1.2362    3.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1101    1.0502    2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5775    0.4921    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781    0.1235   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4037    2.1931   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    1.5639   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    2.3514   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3189    3.2027    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
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  2 30  1  0  0  0  0
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 14  6  1  0  0  0  0
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  1 33  1  0  0  0  0
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  3 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
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  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
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 13 50  1  0  0  0  0
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 18 60  1  0  0  0  0
 21 61  1  0  0  0  0
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 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
 29 68  1  0  0  0  0
 32 69  1  0  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
   -6.0296    1.4788   -1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8525    0.8171   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -0.1576    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363   -0.5594   -0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017   -0.3300   -1.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0909   -0.4502    1.3320 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0412   -1.6713   -1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -0.9865   -2.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880   -0.6617   -1.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4558   -0.0226   -1.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    0.3052   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    0.5221    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687    0.8117    1.5777 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8923    0.7826    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553    0.9920    2.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2617    0.8886    1.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687    0.5800    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5433    0.3694   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.4736    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118193D          

 69 73  0  0  0  0            999 V2000
   -6.0296    1.4788   -1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8525    0.8171   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -0.1576    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363   -0.5594   -0.9599 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7017   -0.3300   -1.0114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7572   -0.9313   -0.0106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0095   -2.4546   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -0.4502    1.3320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6626   -1.5375    2.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    0.0297    2.2137 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0358    0.7517    1.4027 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6735   -0.2543    0.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2702   -1.3200    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724   -0.6223   -0.5313 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0412   -1.6713   -1.5425 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1431   -0.9865   -2.3820 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1880   -0.6617   -1.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4558   -0.0226   -1.8983 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0686    0.3052   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    0.5221    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687    0.8117    1.5777 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8923    0.7826    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553    0.9920    2.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2617    0.8886    1.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687    0.5800    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5433    0.3694   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.4736    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967    0.3576   -0.3626 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4388    1.6394   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6624    1.2121    1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306    0.6620    2.2388 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5882   -0.8250    2.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3890    0.7324    2.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344    1.5278    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    1.2754    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519   -1.5546    1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -2.2737    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -1.0043    2.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840    0.3194   -1.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008   -1.9488   -2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -2.5387   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -0.1888   -3.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -1.7815   -3.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5210   -1.6378   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025   -0.7375   -2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3330    0.8878   -2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    1.0253    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7441    1.2362    3.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1101    1.0502    2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5775    0.4921    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781    0.1235   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4037    2.1931   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    1.5639   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    2.3514   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3189    3.2027    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
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 19 20  2  0  0  0  0
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 22 23  2  0  0  0  0
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  2 30  1  0  0  0  0
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 14  6  1  0  0  0  0
 28 17  1  0  0  0  0
 28 12  1  0  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  3 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  7 41  1  0  0  0  0
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 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
 29 68  1  0  0  0  0
 32 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005512

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C(/[H])C([H])([H])C([H])([H])[C@]1(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]1([H])C([H])([H])C3=C(N([H])C4=C([H])C([H])=C([H])C([H])=C34)[C@]21C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H37NO3/c1-17(25(31)32)8-7-14-26(2)22-12-11-18-16-20-19-9-5-6-10-21(19)29-24(20)28(18,4)27(22,3)15-13-23(26)30/h5-6,8-10,18,22-23,29-30H,7,11-16H2,1-4H3,(H,31,32)/b17-8+/t18-,22-,23-,26-,27-,28+/m0/s1

> <INCHI_KEY>
FYZYVTHTMPXJHJ-UOOBVZAFSA-N

> <FORMULA>
C28H37NO3

> <MOLECULAR_WEIGHT>
435.608

> <EXACT_MASS>
435.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.58856407552629

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-5-[(1S,12S,15R,16S,17S,20S)-17-hydroxy-1,16,20-trimethyl-3-azapentacyclo[10.8.0.0^{2,10}.0^{4,9}.0^{15,20}]icosa-2(10),4,6,8-tetraen-16-yl]-2-methylpent-2-enoic acid

> <ALOGPS_LOGP>
6.11

> <JCHEM_LOGP>
5.806349977

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.859192772254413

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.77314416895048

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6570606753642675

> <JCHEM_POLAR_SURFACE_AREA>
73.32

> <JCHEM_REFRACTIVITY>
127.90639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.75e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-[(1S,12S,15R,16S,17S,20S)-17-hydroxy-1,16,20-trimethyl-3-azapentacyclo[10.8.0.0^{2,10}.0^{4,9}.0^{15,20}]icosa-2(10),4,6,8-tetraen-16-yl]-2-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
   -6.0296    1.4788   -1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8525    0.8171   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -0.1576    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1363   -0.5594   -0.9599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017   -0.3300   -1.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572   -0.9313   -0.0106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0095   -2.4546   -0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909   -0.4502    1.3320 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6626   -1.5375    2.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    0.0297    2.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0358    0.7517    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -0.2543    0.4459 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2702   -1.3200    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724   -0.6223   -0.5313 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0412   -1.6713   -1.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -0.9865   -2.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880   -0.6617   -1.4065 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4558   -0.0226   -1.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    0.3052   -0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    0.5221    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687    0.8117    1.5777 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8923    0.7826    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9553    0.9920    2.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2617    0.8886    1.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5687    0.5800    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5433    0.3694   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.4736    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967    0.3576   -0.3626 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4388    1.6394   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6624    1.2121    1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306    0.6620    2.2388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6022    2.2181    0.9520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6791    2.3646   -1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5060    0.8451   -2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0519    1.9088   -1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9166   -0.6006    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701   -0.0591   -1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909   -1.6525   -1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    0.7754   -0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173   -0.6137   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7580   -2.7888    0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3959   -2.7062   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1062   -3.0320    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8544    0.3550    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2440   -1.2191    2.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -0.8250    2.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3890    0.7324    2.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344    1.5278    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    1.2754    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519   -1.5546    1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -2.2737    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -1.0043    2.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840    0.3194   -1.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008   -1.9488   -2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5503   -2.5387   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -0.1888   -3.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -1.7815   -3.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5210   -1.6378   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025   -0.7375   -2.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3330    0.8878   -2.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    1.0253    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7441    1.2362    3.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1101    1.0502    2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5775    0.4921    0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7781    0.1235   -1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4037    2.1931   -1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    1.5639   -1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    2.3514   -0.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3189    3.2027    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  6  5  1  6
  6  7  1  0
  6  8  1  0
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  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
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 17 18  1  0
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 19 20  2  0
 20 21  1  0
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 22 23  2  0
 23 24  1  0
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 14  6  1  0
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 29 67  1  0
 29 68  1  0
 32 69  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      -6.030   1.479  -1.318  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.853   0.817  -0.016  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.950  -0.158   0.164  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.136  -0.559  -0.960  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.702  -0.330  -1.011  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.757  -0.931  -0.011  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.010  -2.455  -0.151  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.091  -0.450   1.332  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.663  -1.538   2.058  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.974   0.030   2.214  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.036   0.752   1.403  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.674  -0.254   0.446  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.270  -1.320   1.290  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.372  -0.622  -0.531  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.041  -1.671  -1.543  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.143  -0.987  -2.382  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.188  -0.662  -1.407  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.456  -0.023  -1.898  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.069   0.305  -0.551  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.050   0.522   0.359  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.569   0.812   1.578  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.892   0.783   1.456  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.955   0.992   2.337  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.262   0.889   1.903  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.569   0.580   0.606  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.543   0.369  -0.280  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.240   0.474   0.157  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.797   0.358  -0.363  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.439   1.639  -1.027  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.662   1.212   1.115  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.531   0.662   2.239  0.00  0.00           O+0
HETATM   32  O   UNK     0      -7.602   2.218   0.952  0.00  0.00           O+0
HETATM   33  H   UNK     0      -6.679   2.365  -1.173  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.506   0.845  -2.078  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.052   1.909  -1.688  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.917  -0.601   1.141  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.570  -0.059  -1.897  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.391  -1.653  -1.201  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.456   0.775  -0.987  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.317  -0.614  -2.052  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.758  -2.789   0.600  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.396  -2.706  -1.159  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.106  -3.032   0.008  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.854   0.355   1.365  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.244  -1.219   2.769  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.588  -0.825   2.792  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.389   0.732   2.964  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.534   1.528   0.811  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.751   1.275   2.032  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.352  -1.555   1.047  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.756  -2.274   1.310  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.379  -1.004   2.374  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.484   0.319  -1.158  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.801  -1.949  -2.170  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.550  -2.539  -1.075  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.746  -0.189  -3.003  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.516  -1.782  -3.057  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.521  -1.638  -0.953  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.103  -0.738  -2.440  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.333   0.888  -2.477  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.089   1.025   2.476  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.744   1.236   3.364  0.00  0.00           H+0
HETATM   63  H   UNK     0       8.110   1.050   2.583  0.00  0.00           H+0
HETATM   64  H   UNK     0       8.578   0.492   0.237  0.00  0.00           H+0
HETATM   65  H   UNK     0       6.778   0.124  -1.314  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.404   2.193  -1.233  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.928   1.564  -1.985  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.864   2.351  -0.401  0.00  0.00           H+0
HETATM   69  H   UNK     0      -7.319   3.203   0.961  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3   30                                                  
CONECT    3    2    4   36                                                  
CONECT    4    3    5   37   38                                             
CONECT    5    4    6   39   40                                             
CONECT    6    5    7    8   14                                             
CONECT    7    6   41   42   43                                             
CONECT    8    6    9   10   44                                             
CONECT    9    8   45                                                       
CONECT   10    8   11   46   47                                             
CONECT   11   10   12   48   49                                             
CONECT   12   11   13   14   28                                             
CONECT   13   12   50   51   52                                             
CONECT   14   12   15    6   53                                             
CONECT   15   14   16   54   55                                             
CONECT   16   15   17   56   57                                             
CONECT   17   16   18   28   58                                             
CONECT   18   17   19   59   60                                             
CONECT   19   18   20   27                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   61                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   62                                                  
CONECT   24   23   25   63                                                  
CONECT   25   24   26   64                                                  
CONECT   26   25   27   65                                                  
CONECT   27   26   19   22                                                  
CONECT   28   20   29   17   12                                             
CONECT   29   28   66   67   68                                             
CONECT   30    2   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   69                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   16                                                            
CONECT   58   17                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   21                                                            
CONECT   62   23                                                            
CONECT   63   24                                                            
CONECT   64   25                                                            
CONECT   65   26                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
CONECT   68   29                                                            
CONECT   69   32                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  146    0
END

RDKit          3D

69 73  0  0  0  0  0  0  0  0999 V2000
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 18 59  1  0
 18 60  1  0
 21 61  1  0
 23 62  1  0
 24 63  1  0
 25 64  1  0
 26 65  1  0
 29 66  1  0
 29 67  1  0
 29 68  1  0
 32 69  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E)-5-[(1S,12S,15R,16S,17S,20S)-17-Hydroxy-1,16,20-trimethyl-3-azapentacyclo[10.8.0.0,.0,.0,]icosa-2(10),4,6,8-tetraen-16-yl]-2-methylpent-2-enoate	Generator
Nodulispate F	Generator
Nodulispic acid F	Generator

Chemical Formula

C₂₈H₃₇NO₃

Average Mass

435.6080 Da

Monoisotopic Mass

435.27734 Da

IUPAC Name

(2E)-5-[(1S,12S,15R,16S,17S,20S)-17-hydroxy-1,16,20-trimethyl-3-azapentacyclo[10.8.0.0^{2,10}.0^{4,9}.0^{15,20}]icosa-2(10),4,6,8-tetraen-16-yl]-2-methylpent-2-enoic acid

Traditional Name

(2E)-5-[(1S,12S,15R,16S,17S,20S)-17-hydroxy-1,16,20-trimethyl-3-azapentacyclo[10.8.0.0^{2,10}.0^{4,9}.0^{15,20}]icosa-2(10),4,6,8-tetraen-16-yl]-2-methylpent-2-enoic acid

CAS Registry Number

Not Available

SMILES

C\C(=C/CC[C@]1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@H]1CC3=C(NC4=CC=CC=C34)[C@]21C)C(O)=O

InChI Identifier

InChI=1S/C28H37NO3/c1-17(25(31)32)8-7-14-26(2)22-12-11-18-16-20-19-9-5-6-10-21(19)29-24(20)28(18,4)27(22,3)15-13-23(26)30/h5-6,8-10,18,22-23,29-30H,7,11-16H2,1-4H3,(H,31,32)/b17-8+/t18-,22-,23-,26-,27-,28+/m0/s1

InChI Key

FYZYVTHTMPXJHJ-UOOBVZAFSA-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
Nodulisporium sp.	NPAtlas	15387649
Nodulisporium sp.MF5954	-	KNApSAcK
Nodulisporium sp.MF6518	-	KNApSAcK

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	6.11	ALOGPS
logP	5.81	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-0.66	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.91 m³·mol⁻¹	ChemAxon
Polarizability	51.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009237

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9456981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11281984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh SB, Ondeyka JG, Jayasuriya H, Zink DL, Ha SN, Dahl-Roshak A, Greene J, Kim JA, Smith MM, Shoop W, Tkacz JS: Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships. J Nat Prod. 2004 Sep;67(9):1496-506. doi: 10.1021/np0498455. [PubMed:15387649 ]

Showing NP-Card for Nodulisporic acid F (NP0005512)

MOL for NP0005512 (Nodulisporic acid F)

3D MOL for NP0005512 (Nodulisporic acid F)

3D SDF for NP0005512 (Nodulisporic acid F)

3D-SDF for NP0005512 (Nodulisporic acid F)

PDB for NP0005512 (Nodulisporic acid F)

3D PDB for NP0005512 (Nodulisporic acid F)

SMILES for NP0005512 (Nodulisporic acid F)

INCHI for NP0005512 (Nodulisporic acid F)

Structure for NP0005512 (Nodulisporic acid F)

3D Structure for NP0005512 (Nodulisporic acid F)