NP-MRD: Showing NP-Card for Lolitriol (NP0001821)

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Record Information

Version

2.0

Created at

2020-10-21 16:45:33 UTC

Updated at

2021-07-15 16:45:22 UTC

NP-MRD ID

NP0001821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lolitriol

Provided By

NPAtlas

Description

(2S,3R,6S,8S,9R,12S,13S,16S,22R,26R)-9,13-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,11,24-trioxa-32-azanonacyclo[16.14.0.0²,¹⁶.0³,¹³.0⁶,¹².0¹⁰,¹².0¹⁹,³¹.0²⁰,²⁸.0²²,²⁶]Dotriaconta-1(18),19(31),20(28),29-tetraen-27-one belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Lolitriol is found in Epichloe festucae Fg1, Epichloe festucae Fl1, Lolium perenne, Lolium perenne L. , Neotyphodium, Neotyphodium coenophialum e822, Neotyphodium coenophialum Tf28, Neotyphodium festucae Frc7, Neotyphodium funkii e4096, Neotyphodium lolii AR1, Neotyphodium lolii Lp14, Neotyphodium lolii Lp19, Neotyphodium siegelii e915, Neotyphodium tembladerae e1169 and Neotyphodium tembladerae e4055. It was first documented in 1998 (PMID: 10554283). Based on a literature review very few articles have been published on (2S,3R,6S,8S,9R,12S,13S,16S,22R,26R)-9,13-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,11,24-trioxa-32-azanonacyclo[16.14.0.0²,¹⁶.0³,¹³.0⁶,¹².0¹⁰,¹².0¹⁹,³¹.0²⁰,²⁸.0²²,²⁶]Dotriaconta-1(18),19(31),20(28),29-tetraen-27-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652307012117063D          

 94102  0  0  0  0            999 V2000
    3.0543   -4.2437    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3894   -4.5037   -0.4710 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0067   -5.7113    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -4.8393   -1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -3.2902   -0.4361 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6553   -2.2589   -1.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -0.9797   -0.6137 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6770    0.0851   -1.5711 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7290    1.1240   -1.0593 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7243    0.4846   -0.1183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0145   -0.6771   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363    1.4211    0.3234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1106    2.7480    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5707    1.6135   -0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    1.7587   -2.0245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.9116   -2.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427    2.1085   -3.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065    2.2554   -3.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6974    2.2059   -2.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450    2.0056   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    1.8595   -1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6587    1.6676   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.5025    1.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8523    0.6786    1.3728 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5710    0.4534    2.6301 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7636   -0.4345    2.2504 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5290    0.0964    1.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1248    1.3028    1.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.8231    0.7786 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7411   -0.7246    1.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562   -1.9253    1.6421 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8404   -2.9897    0.9119 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2128   -2.6869    0.8920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    1.9368    0.2331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9703    1.2269   -0.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7743    2.2825   -0.8950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1438    2.3735   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8155    2.5862   -3.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1087    1.6435   -0.8066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1928    2.7013   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3052    0.4579   -1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029    1.2471    0.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9152    0.9990    1.0042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8584   -0.4626    1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6346    1.8119    2.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -4.0092   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678   -5.1306    0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -3.4006    0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9025   -5.7551    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0668   -5.8688   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4485   -6.6078   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -5.6956   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1779   -3.5676   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2025   -1.0508   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882   -0.4269   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5699    0.6592   -1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464    1.8228   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    1.6740   -1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244   -0.8831   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0008   -1.5758   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -0.4382   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705    3.4858    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623    3.1573    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    2.8115    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956    1.7647   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290    2.1507   -4.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759    2.4091   -4.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738    0.8611    1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    2.4795    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -0.3209    0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.3246    3.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425   -0.1810    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -1.4888    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588   -0.3186    3.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110    1.1367    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -2.1975    2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7587   -3.9166    1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7575   -3.4849    1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8763    2.9774    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509    1.3191    0.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7671    0.3841   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7652    3.2440   -0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1374    3.1263   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0559    3.4496   -0.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1654    2.2041   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8374   -0.4674   -1.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3846    0.2059   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8302    0.6014   -2.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7614   -0.9972    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7522   -0.5815    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9280   -0.9181    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1090    1.2061    2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1765    2.7904    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6399    2.0382    2.7024 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
  2  4  1  6  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
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 21 16  1  0  0  0  0
 37 19  1  0  0  0  0
  1 46  1  0  0  0  0
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M  END

     RDKit          3D

 94102  0  0  0  0  0  0  0  0999 V2000
    3.0543   -4.2437    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3894   -4.5037   -0.4710 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0067   -5.7113    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -4.8393   -1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -3.2902   -0.4361 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6553   -2.2589   -1.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -0.9797   -0.6137 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6770    0.0851   -1.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290    1.1240   -1.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    0.4846   -0.1183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0145   -0.6771   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363    1.4211    0.3234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1106    2.7480    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5707    1.6135   -0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    1.7587   -2.0245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.9116   -2.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427    2.1085   -3.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065    2.2554   -3.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6974    2.2059   -2.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450    2.0056   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    1.8595   -1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6587    1.6676   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.5025    1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.6786    1.3728 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5710    0.4534    2.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636   -0.4345    2.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5290    0.0964    1.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1248    1.3028    1.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.8231    0.7786 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7411   -0.7246    1.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562   -1.9253    1.6421 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8404   -2.9897    0.9119 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2128   -2.6869    0.8920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    1.9368    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9703    1.2269   -0.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7743    2.2825   -0.8950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1438    2.3735   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8155    2.5862   -3.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1087    1.6435   -0.8066 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652307012117063D          

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  4 52  1  0  0  0  0
  5 53  1  6  0  0  0
  7 54  1  1  0  0  0
  8 55  1  0  0  0  0
  8 56  1  0  0  0  0
  9 57  1  0  0  0  0
  9 58  1  0  0  0  0
 11 59  1  0  0  0  0
 11 60  1  0  0  0  0
 11 61  1  0  0  0  0
 13 62  1  0  0  0  0
 13 63  1  0  0  0  0
 13 64  1  0  0  0  0
 15 65  1  0  0  0  0
 17 66  1  0  0  0  0
 18 67  1  0  0  0  0
 23 68  1  0  0  0  0
 23 69  1  0  0  0  0
 24 70  1  6  0  0  0
 25 71  1  0  0  0  0
 25 72  1  0  0  0  0
 26 73  1  0  0  0  0
 26 74  1  0  0  0  0
 28 75  1  0  0  0  0
 31 76  1  1  0  0  0
 32 77  1  1  0  0  0
 33 78  1  0  0  0  0
 34 79  1  0  0  0  0
 34 80  1  0  0  0  0
 35 81  1  6  0  0  0
 36 82  1  1  0  0  0
 40 83  1  0  0  0  0
 40 84  1  0  0  0  0
 40 85  1  0  0  0  0
 41 86  1  0  0  0  0
 41 87  1  0  0  0  0
 41 88  1  0  0  0  0
 44 89  1  0  0  0  0
 44 90  1  0  0  0  0
 44 91  1  0  0  0  0
 45 92  1  0  0  0  0
 45 93  1  0  0  0  0
 45 94  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@]2([H])O[C@@]22[C@@]([H])(O[C@]1([H])C(O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]1(C([H])([H])[H])[C@]3(C4=C(C5=C6C(=C([H])C([H])=C5N4[H])C(=O)[C@]4([H])[C@@]([H])(C6([H])[H])C(OC4(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[C@]3([H])C([H])([H])C([H])([H])[C@@]21O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C37H49NO7/c1-31(2,41)29-27(40)30-37(44-30)23(43-29)12-13-34(7)35(8)17(11-14-36(34,37)42)15-20-24-19-16-21-25(33(5,6)45-32(21,3)4)26(39)18(19)9-10-22(24)38-28(20)35/h9-10,17,21,23,25,27,29-30,38,40-42H,11-16H2,1-8H3/t17-,21+,23-,25-,27+,29-,30+,34+,35+,36-,37-/m0/s1

> <INCHI_KEY>
GIHSQRKLXKCZNX-JDTQUMMESA-N

> <FORMULA>
C37H49NO7

> <MOLECULAR_WEIGHT>
619.799

> <EXACT_MASS>
619.350902922

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
70.08530460319962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,6S,8S,9R,10R,12S,13S,16S,22R,26R)-9,13-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,11,24-trioxa-32-azanonacyclo[16.14.0.0^{2,16}.0^{3,13}.0^{6,12}.0^{10,12}.0^{19,31}.0^{20,28}.0^{22,26}]dotriaconta-1(18),19,28,30-tetraen-27-one

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
3.707196830000001

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.34606037236006

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.764101471901661

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1321415241569808

> <JCHEM_POLAR_SURFACE_AREA>
124.54

> <JCHEM_REFRACTIVITY>
167.82679999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,6S,8S,9R,10R,12S,13S,16S,22R,26R)-9,13-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,11,24-trioxa-32-azanonacyclo[16.14.0.0^{2,16}.0^{3,13}.0^{6,12}.0^{10,12}.0^{19,31}.0^{20,28}.0^{22,26}]dotriaconta-1(18),19,28,30-tetraen-27-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 94102  0  0  0  0  0  0  0  0999 V2000
    3.0543   -4.2437    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3894   -4.5037   -0.4710 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0067   -5.7113    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -4.8393   -1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -3.2902   -0.4361 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6553   -2.2589   -1.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -0.9797   -0.6137 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6770    0.0851   -1.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290    1.1240   -1.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    0.4846   -0.1183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0145   -0.6771   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363    1.4211    0.3234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1106    2.7480    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5707    1.6135   -0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    1.7587   -2.0245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.9116   -2.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427    2.1085   -3.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065    2.2554   -3.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6974    2.2059   -2.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450    2.0056   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6587    1.6676   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.5025    1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.6786    1.3728 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5710    0.4534    2.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636   -0.4345    2.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5290    0.0964    1.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1248    1.3028    1.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.8231    0.7786 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7411   -0.7246    1.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8404   -2.9897    0.9119 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2128   -2.6869    0.8920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    1.9368    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9703    1.2269   -0.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7743    2.2825   -0.8950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1438    2.3735   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8155    2.5862   -3.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1087    1.6435   -0.8066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1928    2.7013   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3052    0.4579   -1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029    1.2471    0.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9152    0.9990    1.0042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8584   -0.4626    1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6346    1.8119    2.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -4.0092   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1968   -3.4006    0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9025   -5.7551    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0668   -5.8688   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6303   -5.6956   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1779   -3.5676   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2025   -1.0508   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5699    0.6592   -1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464    1.8228   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    1.6740   -1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244   -0.8831   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0008   -1.5758   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -0.4382   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705    3.4858    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623    3.1573    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    2.8115    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956    1.7647   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290    2.1507   -4.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759    2.4091   -4.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2592    2.4795    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -0.3209    0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.3246    3.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425   -0.1810    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -1.4888    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588   -0.3186    3.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110    1.1367    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -2.1975    2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7587   -3.9166    1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7575   -3.4849    1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8763    2.9774    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509    1.3191    0.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7671    0.3841   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7652    3.2440   -0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1374    3.1263   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0559    3.4496   -0.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1654    2.2041   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8374   -0.4674   -1.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7614   -0.9972    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7522   -0.5815    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9280   -0.9181    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1090    1.2061    2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1765    2.7904    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6399    2.0382    2.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  1
 12 14  1  0
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 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
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 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 29 30  1  1
 30 31  1  0
 31 32  1  0
 32 33  1  0
 20 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 36 39  1  0
 39 40  1  6
 39 41  1  0
 39 42  1  0
 42 43  1  0
 43 44  1  1
 43 45  1  0
 32  5  1  0
 43 35  1  0
 29  7  1  0
 27 10  1  0
 31 29  1  0
 24 12  1  0
 22 14  2  0
 21 16  1  0
 37 19  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  3 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  5 53  1  6
  7 54  1  1
  8 55  1  0
  8 56  1  0
  9 57  1  0
  9 58  1  0
 11 59  1  0
 11 60  1  0
 11 61  1  0
 13 62  1  0
 13 63  1  0
 13 64  1  0
 15 65  1  0
 17 66  1  0
 18 67  1  0
 23 68  1  0
 23 69  1  0
 24 70  1  6
 25 71  1  0
 25 72  1  0
 26 73  1  0
 26 74  1  0
 28 75  1  0
 31 76  1  1
 32 77  1  1
 33 78  1  0
 34 79  1  0
 34 80  1  0
 35 81  1  6
 36 82  1  1
 40 83  1  0
 40 84  1  0
 40 85  1  0
 41 86  1  0
 41 87  1  0
 41 88  1  0
 44 89  1  0
 44 90  1  0
 44 91  1  0
 45 92  1  0
 45 93  1  0
 45 94  1  0
M  END

HEADER    PROTEIN                                 01-JUL-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-JUL-21         0                                  
HETATM    1  C   UNK     0       3.054  -4.244   0.186  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.389  -4.504  -0.471  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.007  -5.711   0.148  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.106  -4.839  -1.816  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.297  -3.290  -0.436  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.655  -2.259  -1.054  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.072  -0.980  -0.614  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.677   0.085  -1.571  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.729   1.124  -1.059  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.724   0.485  -0.118  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.014  -0.677  -0.794  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.636   1.421   0.323  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.111   2.748   0.802  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.571   1.613  -0.713  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.393   1.759  -2.025  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.909   1.912  -2.281  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.643   2.108  -3.448  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.006   2.255  -3.460  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.697   2.206  -2.253  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.945   2.006  -1.084  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.586   1.859  -1.066  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.659   1.668  -0.037  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.406   1.502   1.420  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.852   0.679   1.373  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.571   0.453   2.630  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.764  -0.435   2.250  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.529   0.096   1.074  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.125   1.303   1.529  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.667  -0.823   0.779  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.741  -0.725   1.802  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.056  -1.925   1.642  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.840  -2.990   0.912  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.213  -2.687   0.892  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.680   1.937   0.233  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.970   1.227  -0.111  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.774   2.283  -0.895  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.144   2.373  -2.206  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.816   2.586  -3.239  0.00  0.00           O+0
HETATM   39  C   UNK     0      -7.109   1.644  -0.807  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.193   2.701  -1.015  0.00  0.00           C+0
HETATM   41  C   UNK     0      -7.305   0.458  -1.682  0.00  0.00           C+0
HETATM   42  O   UNK     0      -7.203   1.247   0.529  0.00  0.00           O+0
HETATM   43  C   UNK     0      -5.915   0.999   1.004  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.858  -0.463   1.408  0.00  0.00           C+0
HETATM   45  C   UNK     0      -5.635   1.812   2.245  0.00  0.00           C+0
HETATM   46  H   UNK     0       2.265  -4.009  -0.564  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.768  -5.131   0.784  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.197  -3.401   0.892  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.902  -5.755   1.269  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.067  -5.869  -0.161  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.449  -6.608  -0.227  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.630  -5.696  -1.869  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.178  -3.568  -1.087  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.202  -1.051  -0.653  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.288  -0.427  -2.502  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.570   0.659  -1.967  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.346   1.823  -0.421  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.293   1.674  -1.888  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.424  -0.883  -1.821  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.001  -1.576  -0.179  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.931  -0.438  -1.017  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.270   3.486   0.624  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.962   3.157   0.249  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.322   2.812   1.877  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.096   1.765  -2.803  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.129   2.151  -4.407  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.576   2.409  -4.372  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.174   0.861   1.876  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.259   2.479   1.923  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.543  -0.321   0.972  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.873   1.325   3.202  0.00  0.00           H+0
HETATM   72  H   UNK     0       0.943  -0.181   3.294  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.468  -1.489   2.174  0.00  0.00           H+0
HETATM   74  H   UNK     0       3.459  -0.319   3.137  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.711   1.137   2.301  0.00  0.00           H+0
HETATM   76  H   UNK     0       4.461  -2.197   2.537  0.00  0.00           H+0
HETATM   77  H   UNK     0       5.759  -3.917   1.547  0.00  0.00           H+0
HETATM   78  H   UNK     0       7.758  -3.485   1.108  0.00  0.00           H+0
HETATM   79  H   UNK     0      -3.876   2.977   0.520  0.00  0.00           H+0
HETATM   80  H   UNK     0      -3.151   1.319   0.955  0.00  0.00           H+0
HETATM   81  H   UNK     0      -4.767   0.384  -0.769  0.00  0.00           H+0
HETATM   82  H   UNK     0      -5.765   3.244  -0.332  0.00  0.00           H+0
HETATM   83  H   UNK     0      -8.137   3.126  -2.036  0.00  0.00           H+0
HETATM   84  H   UNK     0      -8.056   3.450  -0.212  0.00  0.00           H+0
HETATM   85  H   UNK     0      -9.165   2.204  -0.815  0.00  0.00           H+0
HETATM   86  H   UNK     0      -6.837  -0.467  -1.238  0.00  0.00           H+0
HETATM   87  H   UNK     0      -8.385   0.206  -1.778  0.00  0.00           H+0
HETATM   88  H   UNK     0      -6.830   0.601  -2.647  0.00  0.00           H+0
HETATM   89  H   UNK     0      -6.761  -0.997   1.093  0.00  0.00           H+0
HETATM   90  H   UNK     0      -5.752  -0.582   2.528  0.00  0.00           H+0
HETATM   91  H   UNK     0      -4.928  -0.918   1.000  0.00  0.00           H+0
HETATM   92  H   UNK     0      -5.109   1.206   2.996  0.00  0.00           H+0
HETATM   93  H   UNK     0      -5.176   2.790   2.059  0.00  0.00           H+0
HETATM   94  H   UNK     0      -6.640   2.038   2.702  0.00  0.00           H+0
CONECT    1    2   46   47   48                                             
CONECT    2    1    3    4    5                                             
CONECT    3    2   49   50   51                                             
CONECT    4    2   52                                                       
CONECT    5    2    6   32   53                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   29   54                                             
CONECT    8    7    9   55   56                                             
CONECT    9    8   10   57   58                                             
CONECT   10    9   11   12   27                                             
CONECT   11   10   59   60   61                                             
CONECT   12   10   13   14   24                                             
CONECT   13   12   62   63   64                                             
CONECT   14   12   15   22                                                  
CONECT   15   14   16   65                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   66                                                  
CONECT   18   17   19   67                                                  
CONECT   19   18   20   37                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   22   16                                                  
CONECT   22   21   23   14                                                  
CONECT   23   22   24   68   69                                             
CONECT   24   23   25   12   70                                             
CONECT   25   24   26   71   72                                             
CONECT   26   25   27   73   74                                             
CONECT   27   26   28   29   10                                             
CONECT   28   27   75                                                       
CONECT   29   27   30    7   31                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   29   76                                             
CONECT   32   31   33    5   77                                             
CONECT   33   32   78                                                       
CONECT   34   20   35   79   80                                             
CONECT   35   34   36   43   81                                             
CONECT   36   35   37   39   82                                             
CONECT   37   36   38   19                                                  
CONECT   38   37                                                            
CONECT   39   36   40   41   42                                             
CONECT   40   39   83   84   85                                             
CONECT   41   39   86   87   88                                             
CONECT   42   39   43                                                       
CONECT   43   42   44   45   35                                             
CONECT   44   43   89   90   91                                             
CONECT   45   43   92   93   94                                             
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    3                                                            
CONECT   50    3                                                            
CONECT   51    3                                                            
CONECT   52    4                                                            
CONECT   53    5                                                            
CONECT   54    7                                                            
CONECT   55    8                                                            
CONECT   56    8                                                            
CONECT   57    9                                                            
CONECT   58    9                                                            
CONECT   59   11                                                            
CONECT   60   11                                                            
CONECT   61   11                                                            
CONECT   62   13                                                            
CONECT   63   13                                                            
CONECT   64   13                                                            
CONECT   65   15                                                            
CONECT   66   17                                                            
CONECT   67   18                                                            
CONECT   68   23                                                            
CONECT   69   23                                                            
CONECT   70   24                                                            
CONECT   71   25                                                            
CONECT   72   25                                                            
CONECT   73   26                                                            
CONECT   74   26                                                            
CONECT   75   28                                                            
CONECT   76   31                                                            
CONECT   77   32                                                            
CONECT   78   33                                                            
CONECT   79   34                                                            
CONECT   80   34                                                            
CONECT   81   35                                                            
CONECT   82   36                                                            
CONECT   83   40                                                            
CONECT   84   40                                                            
CONECT   85   40                                                            
CONECT   86   41                                                            
CONECT   87   41                                                            
CONECT   88   41                                                            
CONECT   89   44                                                            
CONECT   90   44                                                            
CONECT   91   44                                                            
CONECT   92   45                                                            
CONECT   93   45                                                            
CONECT   94   45                                                            
MASTER        0    0    0    0    0    0    0    0   94    0  204    0
END

RDKit          3D

94102  0  0  0  0  0  0  0  0999 V2000
    3.0543   -4.2437    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3894   -4.5037   -0.4710 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0067   -5.7113    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -4.8393   -1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -3.2902   -0.4361 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6553   -2.2589   -1.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0723   -0.9797   -0.6137 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6770    0.0851   -1.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290    1.1240   -1.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    0.4846   -0.1183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0145   -0.6771   -0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363    1.4211    0.3234 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1106    2.7480    0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5707    1.6135   -0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3927    1.7587   -2.0245 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    1.9116   -2.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427    2.1085   -3.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0065    2.2554   -3.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6974    2.2059   -2.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450    2.0056   -1.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    1.8595   -1.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6587    1.6676   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    1.5025    1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8523    0.6786    1.3728 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5710    0.4534    2.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636   -0.4345    2.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5290    0.0964    1.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1248    1.3028    1.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.8231    0.7786 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7411   -0.7246    1.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562   -1.9253    1.6421 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8404   -2.9897    0.9119 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2128   -2.6869    0.8920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    1.9368    0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9703    1.2269   -0.1109 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7743    2.2825   -0.8950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1438    2.3735   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8155    2.5862   -3.2393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1087    1.6435   -0.8066 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1928    2.7013   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3052    0.4579   -1.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029    1.2471    0.5294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9152    0.9990    1.0042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8584   -0.4626    1.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6346    1.8119    2.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -4.0092   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678   -5.1306    0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -3.4006    0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9025   -5.7551    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0668   -5.8688   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4485   -6.6078   -0.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6303   -5.6956   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1779   -3.5676   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2025   -1.0508   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2882   -0.4269   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5699    0.6592   -1.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464    1.8228   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2926    1.6740   -1.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244   -0.8831   -1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0008   -1.5758   -0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -0.4382   -1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2705    3.4858    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9623    3.1573    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    2.8115    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956    1.7647   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290    2.1507   -4.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759    2.4091   -4.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738    0.8611    1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    2.4795    1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -0.3209    0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.3246    3.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425   -0.1810    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -1.4888    2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588   -0.3186    3.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110    1.1367    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -2.1975    2.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7587   -3.9166    1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7575   -3.4849    1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8763    2.9774    0.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1509    1.3191    0.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7671    0.3841   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7652    3.2440   -0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1374    3.1263   -2.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0559    3.4496   -0.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1654    2.2041   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8374   -0.4674   -1.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3846    0.2059   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8302    0.6014   -2.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7614   -0.9972    1.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7522   -0.5815    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9280   -0.9181    1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1090    1.2061    2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1765    2.7904    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6399    2.0382    2.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  5  6  1  0
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M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₇H₄₉NO₇

Average Mass

619.7990 Da

Monoisotopic Mass

619.35090 Da

IUPAC Name

(2S,3R,6S,8S,9R,10R,12S,13S,16S,22R,26R)-9,13-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,11,24-trioxa-32-azanonacyclo[16.14.0.0^{2,16}.0^{3,13}.0^{6,12}.0^{10,12}.0^{19,31}.0^{20,28}.0^{22,26}]dotriaconta-1(18),19,28,30-tetraen-27-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@H](CC5=C4NC4=C5C5=C(C=C4)C(=O)[C@@H]4[C@@H](C5)C(C)(C)OC4(C)C)CC[C@@]3(O)[C@]22OC2[C@@H]1O

InChI Identifier

InChI=1S/C37H49NO7/c1-31(2,41)29-27(40)30-37(44-30)23(43-29)12-13-34(7)35(8)17(11-14-36(34,37)42)15-20-24-19-16-21-25(33(5,6)45-32(21,3)4)26(39)18(19)9-10-22(24)38-28(20)35/h9-10,17,21,23,25,27,29-30,38,40-42H,11-16H2,1-8H3/t17-,21+,23-,25-,27+,29-,30?,34+,35+,36-,37-/m0/s1

InChI Key

GIHSQRKLXKCZNX-JDTQUMMESA-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
Epichloe festucae Fg1	Fungi	KNApSAcK
Epichloe festucae Fl1	Fungi	KNApSAcK
Lolium perenne	LOTUS Database	35616633
Lolium perenne L.	Plant	KNApSAcK
Neotyphodium	NPAtlas	10554283
Neotyphodium coenophialum e822	-	KNApSAcK
Neotyphodium coenophialum Tf28	-	KNApSAcK
Neotyphodium festucae Frc7	-	KNApSAcK
Neotyphodium funkii e4096	-	KNApSAcK
Neotyphodium lolii AR1	-	KNApSAcK
Neotyphodium lolii Lp14	-	KNApSAcK
Neotyphodium lolii Lp19	-	KNApSAcK
Neotyphodium siegelii e915	-	KNApSAcK
Neotyphodium tembladerae e1169	-	KNApSAcK
Neotyphodium tembladerae e4055	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthofuran
Naphthalene
Tetralin
3-alkylindole
Indole
Indole or derivatives
Aryl ketone
Aryl alkyl ketone
1,4-dioxepane
Dioxepane
Benzenoid
Pyran
Oxane
Monosaccharide
Cyclic alcohol
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Pyrrole
Secondary alcohol
Ketone
Azacycle
Oxacycle
Dialkyl ether
Oxirane
Ether
Organic nitrogen compound
Alcohol
Organooxygen compound
Organic oxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.63	ALOGPS
logP	3.71	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.54 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	167.83 m³·mol⁻¹	ChemAxon
Polarizability	70.09 Å³	ChemAxon
Number of Rings	9	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

NPA016492

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439807

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587684

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Munday-Finch SC, Wilkins AL, Miles CO: Isolation of Lolicine A, Lolicine B, Lolitriol, and Lolitrem N from Lolium perenne Infected with Neotyphodium lolii and Evidence for the Natural Occurrence of 31-Epilolitrem N and 31-Epilolitrem F. J Agric Food Chem. 1998 Feb 16;46(2):590-598. doi: 10.1021/jf9706787. [PubMed:10554283 ]

Showing NP-Card for Lolitriol (NP0001821)

MOL for NP0001821 (Lolitriol)

3D MOL for NP0001821 (Lolitriol)

3D SDF for NP0001821 (Lolitriol)

3D-SDF for NP0001821 (Lolitriol)

PDB for NP0001821 (Lolitriol)

3D PDB for NP0001821 (Lolitriol)

SMILES for NP0001821 (Lolitriol)

INCHI for NP0001821 (Lolitriol)

Structure for NP0001821 (Lolitriol)

3D Structure for NP0001821 (Lolitriol)