NP-MRD: Showing NP-Card for pyrrolizilactone (NP0042757)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-21 00:20:17 UTC

Updated at

2021-06-30 00:18:02 UTC

NP-MRD ID

NP0042757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pyrrolizilactone

Provided By

JEOL Database JEOL Logo

Description

Pyrrolizilactone belongs to the class of organic compounds known as pyrrolizidinones. Pyrrolizidinones are compounds containing a pyrrolizidine moiety which bears a ketone. Pyrrolizidine is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. pyrrolizilactone is found in fungal strain RKB3564. pyrrolizilactone was first documented in 2013 (PMID: 24166831). Based on a literature review very few articles have been published on Pyrrolizilactone (PMID: 23715039).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102203D          

 63 67  0  0  0  0            999 V2000
   -3.0009   -2.4279   -3.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -1.8890   -2.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -2.6727   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -2.2703   -0.1156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5964   -2.8472    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.9543    1.0093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2619   -2.3987    1.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9943   -3.1264    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804   -0.9044    1.4708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4833   -0.1504    0.3297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4781    1.3448    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0467   -0.7103    0.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4062    0.0056   -1.1929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1310   -0.0055   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311   -0.5976   -1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    0.8342   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1267    2.2051   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    3.1343   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    2.2147   -0.9663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298    3.3664   -0.8951 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6584    2.7945   -0.3849 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3221    1.3972    0.1503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7698    1.3757    1.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    1.8726    2.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.7107    1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1842    0.2781    0.2938 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1182    0.9928   -0.6468 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4359    0.3117   -1.8295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9539   -0.4772   -2.5716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9670    0.5395   -3.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167   -1.9199   -4.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.2847   -4.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199   -3.5002   -3.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9190   -3.6932   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -3.9387    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -2.4398    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171   -2.6515   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -4.0362    0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -2.8429    1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -2.5563    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0123   -2.7393    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -4.1983    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -3.0049    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1947   -0.5076    1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6454   -0.7303    2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.2793   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.9678   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    1.6694    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    1.5604    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.4807    0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    1.0791   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    0.9357    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103    4.1029   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261    3.8137   -1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563    2.7040   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177    3.4480    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598    0.6975    0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8142    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.0202   -2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.4790   -3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039    0.5450   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115    0.3211   -4.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526    1.5537   -3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
 13 29  1  0  0  0  0
 12 10  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 27  1  0  0  0  0
  4  6  1  0  0  0  0
 22 23  1  0  0  0  0
  6  7  1  0  0  0  0
 26 25  1  0  0  0  0
 23 25  1  0  0  0  0
  7  9  1  0  0  0  0
 23 24  2  0  0  0  0
  9 10  1  0  0  0  0
 17 18  2  0  0  0  0
 12  4  1  0  0  0  0
 16 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2  3  2  0  0  0  0
 26 58  1  1  0  0  0
 27 26  1  0  0  0  0
 27 28  1  6  0  0  0
 26 16  1  0  0  0  0
 16 52  1  1  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 17 19  1  0  0  0  0
  7  8  1  0  0  0  0
 27 19  1  0  0  0  0
  4  5  1  6  0  0  0
  2 29  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
 29 30  1  0  0  0  0
 13 14  1  0  0  0  0
  3 34  1  0  0  0  0
 13 51  1  1  0  0  0
 29 60  1  6  0  0  0
 12 50  1  1  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
  7 40  1  6  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
 10 46  1  6  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 21 55  1  0  0  0  0
 21 56  1  0  0  0  0
 22 57  1  1  0  0  0
 28 59  1  0  0  0  0
 11 47  1  0  0  0  0
 11 48  1  0  0  0  0
 11 49  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  5 37  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 30 61  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
   -3.0009   -2.4279   -3.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -1.8890   -2.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -2.6727   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -2.2703   -0.1156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5964   -2.8472    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.9543    1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2619   -2.3987    1.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9943   -3.1264    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804   -0.9044    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833   -0.1504    0.3297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4781    1.3448    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0467   -0.7103    0.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4062    0.0056   -1.1929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1310   -0.0055   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311   -0.5976   -1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    0.8342   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1267    2.2051   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    3.1343   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    2.2147   -0.9663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298    3.3664   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    2.7945   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3221    1.3972    0.1503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7698    1.3757    1.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    1.8726    2.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.7107    1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1842    0.2781    0.2938 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1182    0.9928   -0.6468 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4359    0.3117   -1.8295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9539   -0.4772   -2.5716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9670    0.5395   -3.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167   -1.9199   -4.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.2847   -4.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199   -3.5002   -3.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9190   -3.6932   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -3.9387    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -2.4398    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171   -2.6515   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -4.0362    0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -2.8429    1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -2.5563    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0123   -2.7393    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -4.1983    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -3.0049    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1947   -0.5076    1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6454   -0.7303    2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.2793   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.9678   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    1.6694    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    1.5604    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.4807    0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    1.0791   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    0.9357    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103    4.1029   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261    3.8137   -1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563    2.7040   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177    3.4480    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598    0.6975    0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8142    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.0202   -2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.4790   -3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039    0.5450   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115    0.3211   -4.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526    1.5537   -3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 29  1  0
 12 10  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 27  1  0
  4  6  1  0
 22 23  1  0
  6  7  1  0
 26 25  1  0
 23 25  1  0
  7  9  1  0
 23 24  2  0
  9 10  1  0
 17 18  2  0
 12  4  1  0
 16 14  1  0
 14 15  2  0
  2  3  2  0
 26 58  1  1
 27 26  1  0
 27 28  1  6
 26 16  1  0
 16 52  1  1
 16 17  1  0
 10 11  1  0
 17 19  1  0
  7  8  1  0
 27 19  1  0
  4  5  1  6
  2 29  1  0
  2  1  1  0
  3  4  1  0
 29 30  1  0
 13 14  1  0
  3 34  1  0
 13 51  1  1
 29 60  1  6
 12 50  1  1
  6 38  1  0
  6 39  1  0
  7 40  1  6
  9 44  1  0
  9 45  1  0
 10 46  1  6
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  1
 28 59  1  0
 11 47  1  0
 11 48  1  0
 11 49  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
M  END


  Mrv1652306212102203D          

 63 67  0  0  0  0            999 V2000
   -3.0009   -2.4279   -3.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -1.8890   -2.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -2.6727   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -2.2703   -0.1156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5964   -2.8472    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.9543    1.0093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2619   -2.3987    1.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9943   -3.1264    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804   -0.9044    1.4708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4833   -0.1504    0.3297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4781    1.3448    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0467   -0.7103    0.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4062    0.0056   -1.1929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1310   -0.0055   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311   -0.5976   -1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    0.8342   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1267    2.2051   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    3.1343   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    2.2147   -0.9663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298    3.3664   -0.8951 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6584    2.7945   -0.3849 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3221    1.3972    0.1503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7698    1.3757    1.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    1.8726    2.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.7107    1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1842    0.2781    0.2938 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1182    0.9928   -0.6468 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4359    0.3117   -1.8295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9539   -0.4772   -2.5716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9670    0.5395   -3.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167   -1.9199   -4.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.2847   -4.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199   -3.5002   -3.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9190   -3.6932   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -3.9387    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -2.4398    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171   -2.6515   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -4.0362    0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -2.8429    1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -2.5563    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0123   -2.7393    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -4.1983    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -3.0049    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1947   -0.5076    1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6454   -0.7303    2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.2793   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.9678   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    1.6694    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    1.5604    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.4807    0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    1.0791   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    0.9357    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103    4.1029   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261    3.8137   -1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563    2.7040   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177    3.4480    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598    0.6975    0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8142    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.0202   -2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.4790   -3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039    0.5450   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115    0.3211   -4.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526    1.5537   -3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0  0  0  0
 13 29  1  0  0  0  0
 12 10  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 27  1  0  0  0  0
  4  6  1  0  0  0  0
 22 23  1  0  0  0  0
  6  7  1  0  0  0  0
 26 25  1  0  0  0  0
 23 25  1  0  0  0  0
  7  9  1  0  0  0  0
 23 24  2  0  0  0  0
  9 10  1  0  0  0  0
 17 18  2  0  0  0  0
 12  4  1  0  0  0  0
 16 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2  3  2  0  0  0  0
 26 58  1  1  0  0  0
 27 26  1  0  0  0  0
 27 28  1  6  0  0  0
 26 16  1  0  0  0  0
 16 52  1  1  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 17 19  1  0  0  0  0
  7  8  1  0  0  0  0
 27 19  1  0  0  0  0
  4  5  1  6  0  0  0
  2 29  1  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
 29 30  1  0  0  0  0
 13 14  1  0  0  0  0
  3 34  1  0  0  0  0
 13 51  1  1  0  0  0
 29 60  1  6  0  0  0
 12 50  1  1  0  0  0
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
  7 40  1  6  0  0  0
  9 44  1  0  0  0  0
  9 45  1  0  0  0  0
 10 46  1  6  0  0  0
 20 53  1  0  0  0  0
 20 54  1  0  0  0  0
 21 55  1  0  0  0  0
 21 56  1  0  0  0  0
 22 57  1  1  0  0  0
 28 59  1  0  0  0  0
 11 47  1  0  0  0  0
 11 48  1  0  0  0  0
 11 49  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  5 37  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 30 61  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12N3C(=O)[C@@]([H])(C(=O)[C@@]4([H])[C@@]([H])(C(=C([H])[C@]5(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]45[H])C([H])([H])[H])C([H])([H])[H])[C@]1([H])OC(=O)[C@]2([H])C([H])([H])C3([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H33NO5/c1-11-8-12(2)18-16(14(4)13(3)10-23(18,5)9-11)19(26)17-20-24(29)15(22(28)30-20)6-7-25(24)21(17)27/h10-12,14-18,20,29H,6-9H2,1-5H3/t11-,12+,14+,15-,16-,17-,18+,20-,23-,24+/m0/s1

> <INCHI_KEY>
JBKBXMQKJLCRKG-BLRGGNKRSA-N

> <FORMULA>
C24H33NO5

> <MOLECULAR_WEIGHT>
415.53

> <EXACT_MASS>
415.235873167

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.06162087817977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S,7R,10R)-3-[(1S,2S,4aR,6S,8R,8aR)-2,3,4a,6,8-pentamethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-10-hydroxy-5-oxa-1-azatricyclo[5.2.1.0^{4,10}]decane-2,6-dione

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.263874474999998

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.17786371154153

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.67763862603902

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2508168262901345

> <JCHEM_POLAR_SURFACE_AREA>
83.91000000000001

> <JCHEM_REFRACTIVITY>
110.69579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S,7R,10R)-3-[(1S,2S,4aR,6S,8R,8aR)-2,3,4a,6,8-pentamethyl-2,5,6,7,8,8a-hexahydro-1H-naphthalene-1-carbonyl]-10-hydroxy-5-oxa-1-azatricyclo[5.2.1.0^{4,10}]decane-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
   -3.0009   -2.4279   -3.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -1.8890   -2.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -2.6727   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -2.2703   -0.1156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5964   -2.8472    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.9543    1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2619   -2.3987    1.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9943   -3.1264    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804   -0.9044    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833   -0.1504    0.3297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4781    1.3448    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0467   -0.7103    0.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4062    0.0056   -1.1929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1310   -0.0055   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311   -0.5976   -1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    0.8342   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1267    2.2051   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    3.1343   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    2.2147   -0.9663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298    3.3664   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    2.7945   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3221    1.3972    0.1503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7698    1.3757    1.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    1.8726    2.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.7107    1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1842    0.2781    0.2938 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1182    0.9928   -0.6468 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4359    0.3117   -1.8295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9539   -0.4772   -2.5716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9670    0.5395   -3.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167   -1.9199   -4.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.2847   -4.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199   -3.5002   -3.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9190   -3.6932   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -3.9387    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -2.4398    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171   -2.6515   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -4.0362    0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -2.8429    1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -2.5563    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0123   -2.7393    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -4.1983    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -3.0049    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1947   -0.5076    1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6454   -0.7303    2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.2793   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.9678   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    1.6694    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    1.5604    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.4807    0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    1.0791   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    0.9357    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103    4.1029   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261    3.8137   -1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563    2.7040   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177    3.4480    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598    0.6975    0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8142    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.0202   -2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.4790   -3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039    0.5450   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115    0.3211   -4.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526    1.5537   -3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 29  1  0
 12 10  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 27  1  0
  4  6  1  0
 22 23  1  0
  6  7  1  0
 26 25  1  0
 23 25  1  0
  7  9  1  0
 23 24  2  0
  9 10  1  0
 17 18  2  0
 12  4  1  0
 16 14  1  0
 14 15  2  0
  2  3  2  0
 26 58  1  1
 27 26  1  0
 27 28  1  6
 26 16  1  0
 16 52  1  1
 16 17  1  0
 10 11  1  0
 17 19  1  0
  7  8  1  0
 27 19  1  0
  4  5  1  6
  2 29  1  0
  2  1  1  0
  3  4  1  0
 29 30  1  0
 13 14  1  0
  3 34  1  0
 13 51  1  1
 29 60  1  6
 12 50  1  1
  6 38  1  0
  6 39  1  0
  7 40  1  6
  9 44  1  0
  9 45  1  0
 10 46  1  6
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  1
 28 59  1  0
 11 47  1  0
 11 48  1  0
 11 49  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.001  -2.428  -3.896  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.524  -1.889  -2.571  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.547  -2.673  -1.477  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.027  -2.270  -0.116  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.596  -2.847   0.006  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.850  -2.954   1.009  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.262  -2.399   1.180  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.994  -3.126   2.308  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.180  -0.904   1.471  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.483  -0.150   0.330  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.478   1.345   0.682  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.047  -0.710   0.040  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.406   0.006  -1.193  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.131  -0.006  -1.143  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.831  -0.598  -1.970  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.800   0.834  -0.078  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.127   2.205  -0.620  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.342   3.134  -0.701  0.00  0.00           O+0
HETATM   19  N   UNK     0       2.463   2.215  -0.966  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.330   3.366  -0.895  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.658   2.795  -0.385  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.322   1.397   0.150  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.770   1.376   1.548  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.309   1.873   2.524  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.572   0.711   1.607  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.184   0.278   0.294  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.118   0.993  -0.647  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.436   0.312  -1.829  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.954  -0.477  -2.572  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.967   0.540  -3.130  0.00  0.00           C+0
HETATM   31  H   UNK     0      -3.917  -1.920  -4.212  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.234  -2.285  -4.664  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.220  -3.500  -3.850  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.919  -3.693  -1.569  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.618  -3.939   0.120  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.078  -2.440   0.882  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.017  -2.652  -0.876  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.912  -4.036   0.826  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.311  -2.843   1.961  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.832  -2.556   0.256  0.00  0.00           H+0
HETATM   41  H   UNK     0      -6.012  -2.739   2.422  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.066  -4.198   2.095  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.476  -3.005   3.265  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.195  -0.508   1.607  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.645  -0.730   2.414  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.109  -0.279  -0.560  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.230   1.968  -0.181  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.468   1.669   1.022  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.761   1.560   1.481  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.452  -0.481   0.933  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.612   1.079  -1.126  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.175   0.936   0.812  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.910   4.103  -0.203  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.426   3.814  -1.888  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.356   2.704  -1.226  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.118   3.448   0.363  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.160   0.698   0.079  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.247  -0.814   0.250  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.595   0.020  -2.242  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.129  -0.479  -3.296  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.904   0.545  -2.567  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.212   0.321  -4.175  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.553   1.554  -3.112  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3   29    1                                                  
CONECT    3    2    4   34                                                  
CONECT    4    6   12    5    3                                             
CONECT    5    4   35   36   37                                             
CONECT    6    4    7   38   39                                             
CONECT    7    6    9    8   40                                             
CONECT    8    7   41   42   43                                             
CONECT    9    7   10   44   45                                             
CONECT   10   12    9   11   46                                             
CONECT   11   10   47   48   49                                             
CONECT   12   13   10    4   50                                             
CONECT   13   12   29   14   51                                             
CONECT   14   16   15   13                                                  
CONECT   15   14                                                            
CONECT   16   14   26   52   17                                             
CONECT   17   18   16   19                                                  
CONECT   18   17                                                            
CONECT   19   20   17   27                                                  
CONECT   20   19   21   53   54                                             
CONECT   21   20   22   55   56                                             
CONECT   22   21   27   23   57                                             
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   26   23                                                       
CONECT   26   25   58   27   16                                             
CONECT   27   22   26   28   19                                             
CONECT   28   27   59                                                       
CONECT   29   13    2   30   60                                             
CONECT   30   29   61   62   63                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   16                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   26                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  134    0
END

RDKit          3D

63 67  0  0  0  0  0  0  0  0999 V2000
   -3.0009   -2.4279   -3.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -1.8890   -2.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5473   -2.6727   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -2.2703   -0.1156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5964   -2.8472    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498   -2.9543    1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2619   -2.3987    1.1802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9943   -3.1264    2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804   -0.9044    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4833   -0.1504    0.3297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4781    1.3448    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0467   -0.7103    0.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4062    0.0056   -1.1929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1310   -0.0055   -1.1430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311   -0.5976   -1.9696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    0.8342   -0.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1267    2.2051   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    3.1343   -0.7006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4630    2.2147   -0.9663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298    3.3664   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    2.7945   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3221    1.3972    0.1503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7698    1.3757    1.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    1.8726    2.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.7107    1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1842    0.2781    0.2938 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1182    0.9928   -0.6468 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4359    0.3117   -1.8295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9539   -0.4772   -2.5716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9670    0.5395   -3.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167   -1.9199   -4.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.2847   -4.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199   -3.5002   -3.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9190   -3.6932   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181   -3.9387    0.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0783   -2.4398    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0171   -2.6515   -0.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116   -4.0362    0.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -2.8429    1.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -2.5563    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0123   -2.7393    2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661   -4.1983    2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4765   -3.0049    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1947   -0.5076    1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6454   -0.7303    2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1086   -0.2793   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.9678   -0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4680    1.6694    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    1.5604    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517   -0.4807    0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120    1.0791   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753    0.9357    0.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103    4.1029   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261    3.8137   -1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3563    2.7040   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177    3.4480    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598    0.6975    0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8142    0.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953    0.0202   -2.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.4790   -3.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039    0.5450   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2115    0.3211   -4.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5526    1.5537   -3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 29  1  0
 12 10  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 27  1  0
  4  6  1  0
 22 23  1  0
  6  7  1  0
 26 25  1  0
 23 25  1  0
  7  9  1  0
 23 24  2  0
  9 10  1  0
 17 18  2  0
 12  4  1  0
 16 14  1  0
 14 15  2  0
  2  3  2  0
 26 58  1  1
 27 26  1  0
 27 28  1  6
 26 16  1  0
 16 52  1  1
 16 17  1  0
 10 11  1  0
 17 19  1  0
  7  8  1  0
 27 19  1  0
  4  5  1  6
  2 29  1  0
  2  1  1  0
  3  4  1  0
 29 30  1  0
 13 14  1  0
  3 34  1  0
 13 51  1  1
 29 60  1  6
 12 50  1  1
  6 38  1  0
  6 39  1  0
  7 40  1  6
  9 44  1  0
  9 45  1  0
 10 46  1  6
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  1
 28 59  1  0
 11 47  1  0
 11 48  1  0
 11 49  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  5 35  1  0
  5 36  1  0
  5 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₃NO₅

Average Mass

415.5300 Da

Monoisotopic Mass

415.23587 Da

IUPAC Name

(3R,4S,7R,10R)-3-[(1S,2S,4aR,6S,8R,8aR)-2,3,4a,6,8-pentamethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-10-hydroxy-5-oxa-1-azatricyclo[5.2.1.0^{4,10}]decane-2,6-dione

Traditional Name

(3R,4S,7R,10R)-3-[(1S,2S,4aR,6S,8R,8aR)-2,3,4a,6,8-pentamethyl-2,5,6,7,8,8a-hexahydro-1H-naphthalene-1-carbonyl]-10-hydroxy-5-oxa-1-azatricyclo[5.2.1.0^{4,10}]decane-2,6-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12N3C(=O)[C@@]([H])(C(=O)[C@@]4([H])[C@@]([H])(C(=C([H])[C@]5(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]45[H])C([H])([H])[H])C([H])([H])[H])[C@]1([H])OC(=O)[C@]2([H])C([H])([H])C3([H])[H]

InChI Identifier

InChI=1S/C24H33NO5/c1-11-8-12(2)18-16(14(4)13(3)10-23(18,5)9-11)19(26)17-20-24(29)15(22(28)30-20)6-7-25(24)21(17)27/h10-12,14-18,20,29H,6-9H2,1-5H3/t11-,12+,14+,15-,16-,17-,18+,20-,23-,24+/m0/s1

InChI Key

JBKBXMQKJLCRKG-BLRGGNKRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
fungal strain RKB3564	JEOL database	Nogawa, T., et. al, J. Antibiotics, 66, 621 (2013)

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	3.19	ALOGPS
logP	3.26	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.7 m³·mol⁻¹	ChemAxon
Polarizability	45.06 Å³	ChemAxon
Number of Rings	5	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72707242

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Futamura Y, Kawatani M, Muroi M, Aono H, Nogawa T, Osada H: Identification of a molecular target of a novel fungal metabolite, pyrrolizilactone, by phenotypic profiling systems. Chembiochem. 2013 Dec 16;14(18):2456-63. doi: 10.1002/cbic.201300499. Epub 2013 Oct 25. [PubMed:24166831 ]
Nogawa T, Kawatani M, Uramoto M, Okano A, Aono H, Futamura Y, Koshino H, Takahashi S, Osada H: Pyrrolizilactone, a new pyrrolizidinone metabolite produced by a fungus. J Antibiot (Tokyo). 2013 Oct;66(10):621-3. doi: 10.1038/ja.2013.55. Epub 2013 May 29. [PubMed:23715039 ]
Nogawa, T., et al. (2013). Nogawa, T., et. al, J. Antibiotics, 66, 621 (2013). J. Antibiotics.

Showing NP-Card for pyrrolizilactone (NP0042757)

MOL for NP0042757 (pyrrolizilactone)

3D MOL for NP0042757 (pyrrolizilactone)

3D SDF for NP0042757 (pyrrolizilactone)

3D-SDF for NP0042757 (pyrrolizilactone)

PDB for NP0042757 (pyrrolizilactone)

3D PDB for NP0042757 (pyrrolizilactone)

SMILES for NP0042757 (pyrrolizilactone)

INCHI for NP0042757 (pyrrolizilactone)

Structure for NP0042757 (pyrrolizilactone)

3D Structure for NP0042757 (pyrrolizilactone)