NP-MRD: Showing NP-Card for Integramycin (NP0004121)

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Record Information

Version

2.0

Created at

2020-12-09 01:37:00 UTC

Updated at

2021-07-15 16:48:17 UTC

NP-MRD ID

NP0004121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Integramycin

Provided By

NPAtlas

Description

4-{[(1R,2S,4aR,7R,8R,8aR)-2-{[(2R,3S,5S,6R,8S,9S)-8-(3,5-dihydroxyphenyl)-3,5,9-trimethyl-1,7-dioxaspiro[5.5]Undecan-2-yl]methyl}-7-hydroxy-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-2,5-dihydroxy-3,4-dihydro-2H-pyrrol-3-one belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. Integramycin is found in Actinoplanes sp. Integramycin was first documented in 2002 (PMID: 11922798). Based on a literature review very few articles have been published on 4-{[(1R,2S,4aR,7R,8R,8aR)-2-{[(2R,3S,5S,6R,8S,9S)-8-(3,5-dihydroxyphenyl)-3,5,9-trimethyl-1,7-dioxaspiro[5.5]Undecan-2-yl]methyl}-7-hydroxy-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-2,5-dihydroxy-3,4-dihydro-2H-pyrrol-3-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652307012117503D          

 95100  0  0  0  0            999 V2000
   -1.0408   -3.0041   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791   -2.2098    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347   -2.8328    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -1.9569    1.5332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0869   -2.6858    2.1026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2108   -2.9394    1.1516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6704   -1.5992    0.6174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0440   -0.8162    1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276   -1.0194   -0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2259   -1.9231   -1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3464   -0.7436    0.7232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2062   -0.1625   -0.0879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1467    1.3015    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    1.7116    1.4481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2445    2.2242   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865    3.6704   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268    4.2930    0.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3406    4.2807   -1.8841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354    3.3246   -2.9319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6703    3.3607   -3.1601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4379    2.0499   -2.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    1.0540   -2.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790   -0.7791    0.4043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7880   -0.0136   -0.1909 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6195   -0.3495    0.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3881    0.5651   -0.6031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667    0.7137   -0.1543 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3716    1.6693   -1.1079 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8112    0.9888   -2.3606 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2954   -0.3999   -2.1108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3203   -1.4457   -2.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -0.6864   -0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6446   -0.0607   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5743    0.6368   -0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6675    1.2065   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5900    1.9067   -0.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8369    1.0856    1.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830    0.3787    1.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792    0.2702    3.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969   -0.1922    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.4352    0.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593    1.4762    1.1718 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8560    2.8026    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598    0.5797    2.1285 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9729   -0.4604    1.5511 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5457   -1.8416    1.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -3.9253   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -2.4733   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -3.4259   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4672   -2.0910    2.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0630   -3.3381    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5304   -1.7758   -0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3417   -1.3556    2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8608   -0.0516   -0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7363   -2.8660   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2291   -2.2197   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -1.4681   -2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6795    0.0109    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2799   -0.3682   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    2.2738    1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6274    5.2597   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6315    3.4918   -3.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    4.2208   -2.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105   -0.5337    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619    1.0697    0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9194   -0.0244   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -1.3254   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    2.2300   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    2.4416   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9053    0.9075   -3.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272    1.6271   -2.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455   -0.6052   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352   -0.9439   -2.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.8294   -3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2398   -2.3212   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6474   -1.8001   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4793    0.7583   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4421    2.9107   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6893    1.5270    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6711    0.9961    3.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843   -0.7347    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112    1.7068    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2309    2.8464    0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    3.6450    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    2.9532    1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638    0.1106    2.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280    1.2559    2.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -0.4088    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -1.7427    2.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.4483    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8576   -2.4436    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
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 27 26  1  6  0  0  0
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 23  2  1  0  0  0  0
 45 25  1  0  0  0  0
 11  4  1  0  0  0  0
 21 15  1  0  0  0  0
 41 27  1  0  0  0  0
 40 33  1  0  0  0  0
  1 47  1  0  0  0  0
  1 48  1  0  0  0  0
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M  END

     RDKit          3D

 95100  0  0  0  0  0  0  0  0999 V2000
   -1.0408   -3.0041   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791   -2.2098    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347   -2.8328    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -1.9569    1.5332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0869   -2.6858    2.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2108   -2.9394    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6704   -1.5992    0.6174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0440   -0.8162    1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276   -1.0194   -0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2259   -1.9231   -1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3464   -0.7436    0.7232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2062   -0.1625   -0.0879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1467    1.3015    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    1.7116    1.4481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2445    2.2242   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865    3.6704   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268    4.2930    0.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3406    4.2807   -1.8841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354    3.3246   -2.9319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6703    3.3607   -3.1601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4379    2.0499   -2.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    1.0540   -2.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790   -0.7791    0.4043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7880   -0.0136   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -0.3495    0.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3881    0.5651   -0.6031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667    0.7137   -0.1543 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3716    1.6693   -1.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112    0.9888   -2.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954   -0.3999   -2.1108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3203   -1.4457   -2.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -0.6864   -0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6446   -0.0607   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5743    0.6368   -0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6675    1.2065   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5900    1.9067   -0.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8369    1.0856    1.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830    0.3787    1.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792    0.2702    3.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969   -0.1922    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.4352    0.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593    1.4762    1.1718 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8560    2.8026    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652307012117503D          

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 10 59  1  0  0  0  0
 10 60  1  0  0  0  0
 10 61  1  0  0  0  0
 11 62  1  1  0  0  0
 12 63  1  6  0  0  0
 14 64  1  0  0  0  0
 18 65  1  0  0  0  0
 19 66  1  6  0  0  0
 20 67  1  0  0  0  0
 23 68  1  1  0  0  0
 24 69  1  0  0  0  0
 24 70  1  0  0  0  0
 25 71  1  6  0  0  0
 28 72  1  0  0  0  0
 28 73  1  0  0  0  0
 29 74  1  0  0  0  0
 29 75  1  0  0  0  0
 30 76  1  6  0  0  0
 31 77  1  0  0  0  0
 31 78  1  0  0  0  0
 31 79  1  0  0  0  0
 32 80  1  6  0  0  0
 34 81  1  0  0  0  0
 36 82  1  0  0  0  0
 37 83  1  0  0  0  0
 39 84  1  0  0  0  0
 40 85  1  0  0  0  0
 42 86  1  1  0  0  0
 43 87  1  0  0  0  0
 43 88  1  0  0  0  0
 43 89  1  0  0  0  0
 44 90  1  0  0  0  0
 44 91  1  0  0  0  0
 45 92  1  1  0  0  0
 46 93  1  0  0  0  0
 46 94  1  0  0  0  0
 46 95  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C(=C1/C(=O)N([H])[C@@]([H])(O[H])C1=O)[C@@]1([H])[C@@]([H])(C(=C([H])[C@]2([H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(C([H])([H])[H])[C@]12[H])C([H])([H])[H])C([H])([H])[C@@]1([H])O[C@]2(O[C@]([H])(C3=C([H])C(O[H])=C([H])C(O[H])=C3[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C2([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C36H49NO9/c1-16-8-9-36(46-33(16)22-12-23(38)14-24(39)13-22)19(4)10-18(3)27(45-36)15-25-17(2)11-21-6-7-26(40)20(5)28(21)29(25)31(41)30-32(42)35(44)37-34(30)43/h11-14,16,18-21,25-29,33,35,38-41,44H,6-10,15H2,1-5H3,(H,37,43)/b31-30-/t16-,18-,19-,20-,21-,25+,26+,27+,28-,29-,33-,35-,36+/m0/s1

> <INCHI_KEY>
GAMYHMPHACRYMO-MHAWJCPTSA-N

> <FORMULA>
C36H49NO9

> <MOLECULAR_WEIGHT>
639.786

> <EXACT_MASS>
639.340732162

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
68.5652650864781

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z,5S)-3-{[(1R,2S,4aR,7R,8R,8aR)-2-{[(2R,3S,5S,6R,8S,9S)-8-(3,5-dihydroxyphenyl)-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-7-hydroxy-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-hydroxypyrrolidine-2,4-dione

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
4.518404782666665

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.064711648721845

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.510063471474878

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9980541170260174

> <JCHEM_POLAR_SURFACE_AREA>
165.78

> <JCHEM_REFRACTIVITY>
172.6023

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5S)-3-{[(1R,2S,4aR,7R,8R,8aR)-2-{[(2R,3S,5S,6R,8S,9S)-8-(3,5-dihydroxyphenyl)-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-7-hydroxy-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-hydroxypyrrolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 95100  0  0  0  0  0  0  0  0999 V2000
   -1.0408   -3.0041   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791   -2.2098    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347   -2.8328    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -1.9569    1.5332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0869   -2.6858    2.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2108   -2.9394    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6704   -1.5992    0.6174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0440   -0.8162    1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276   -1.0194   -0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2259   -1.9231   -1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3464   -0.7436    0.7232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2062   -0.1625   -0.0879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1467    1.3015    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    1.7116    1.4481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2445    2.2242   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865    3.6704   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268    4.2930    0.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3406    4.2807   -1.8841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354    3.3246   -2.9319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6703    3.3607   -3.1601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4379    2.0499   -2.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    1.0540   -2.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790   -0.7791    0.4043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7880   -0.0136   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -0.3495    0.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3881    0.5651   -0.6031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667    0.7137   -0.1543 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3716    1.6693   -1.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112    0.9888   -2.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954   -0.3999   -2.1108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3203   -1.4457   -2.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -0.6864   -0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6446   -0.0607   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5743    0.6368   -0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6675    1.2065   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5900    1.9067   -0.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8369    1.0856    1.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830    0.3787    1.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792    0.2702    3.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969   -0.1922    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.4352    0.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593    1.4762    1.1718 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8560    2.8026    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598    0.5797    2.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.4604    1.5511 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5457   -1.8416    1.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -3.9253   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -2.4733   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -3.4259   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7038   -3.6305    2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9449   -3.6576    0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0630   -3.3381    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5304   -1.7758   -0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3417   -1.3556    2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8608   -0.0516   -0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7363   -2.8660   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2291   -2.2197   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -1.4681   -2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6795    0.0109    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2799   -0.3682   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    2.2738    1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6274    5.2597   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6315    3.4918   -3.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    4.2208   -2.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105   -0.5337    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619    1.0697    0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9194   -0.0244   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -1.3254   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    2.2300   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    2.4416   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9053    0.9075   -3.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272    1.6271   -2.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455   -0.6052   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352   -0.9439   -2.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.8294   -3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2398   -2.3212   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4793    0.7583   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4421    2.9107   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6893    1.5270    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6711    0.9961    3.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843   -0.7347    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112    1.7068    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2309    2.8464    0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    3.6450    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    2.9532    1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638    0.1106    2.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280    1.2559    2.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -0.4088    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -1.7427    2.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.4483    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8576   -2.4436    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
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  9 10  1  0
  9 11  1  0
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 12 13  1  0
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 15 16  1  0
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 19 21  1  0
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 12 23  1  0
 23 24  1  0
 24 25  1  0
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 30 31  1  0
 30 32  1  0
 32 33  1  0
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 34 35  1  0
 35 36  1  0
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 37 38  1  0
 38 39  1  0
 38 40  2  0
 32 41  1  0
 27 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 45 46  1  0
 23  2  1  0
 45 25  1  0
 11  4  1  0
 21 15  1  0
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  1 47  1  0
  1 48  1  0
  1 49  1  0
  3 50  1  0
  4 51  1  1
  5 52  1  0
  5 53  1  0
  6 54  1  0
  6 55  1  0
  7 56  1  6
  8 57  1  0
  9 58  1  6
 10 59  1  0
 10 60  1  0
 10 61  1  0
 11 62  1  1
 12 63  1  6
 14 64  1  0
 18 65  1  0
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 20 67  1  0
 23 68  1  1
 24 69  1  0
 24 70  1  0
 25 71  1  6
 28 72  1  0
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 30 76  1  6
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 31 79  1  0
 32 80  1  6
 34 81  1  0
 36 82  1  0
 37 83  1  0
 39 84  1  0
 40 85  1  0
 42 86  1  1
 43 87  1  0
 43 88  1  0
 43 89  1  0
 44 90  1  0
 44 91  1  0
 45 92  1  1
 46 93  1  0
 46 94  1  0
 46 95  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      -1.041  -3.004  -0.710  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.979  -2.210   0.132  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.035  -2.833   0.713  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.914  -1.957   1.533  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.087  -2.686   2.103  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.211  -2.939   1.152  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.670  -1.599   0.617  0.00  0.00           C+0
HETATM    8  O   UNK     0      -7.044  -0.816   1.700  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.528  -1.019  -0.170  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.226  -1.923  -1.325  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.346  -0.744   0.723  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.206  -0.163  -0.088  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.147   1.302   0.113  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.964   1.712   1.448  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.244   2.224  -0.802  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.187   3.670  -0.614  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.027   4.293   0.487  0.00  0.00           O+0
HETATM   18  N   UNK     0      -3.341   4.281  -1.884  0.00  0.00           N+0
HETATM   19  C   UNK     0      -3.035   3.325  -2.932  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.670   3.361  -3.160  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.438   2.050  -2.235  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.859   1.054  -2.866  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.879  -0.779   0.404  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.788  -0.014  -0.191  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.620  -0.350   0.116  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.388   0.565  -0.603  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   0.714  -0.154  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.372   1.669  -1.108  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.811   0.989  -2.361  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.295  -0.400  -2.111  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.320  -1.446  -2.662  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.461  -0.686  -0.665  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.645  -0.061  -0.023  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.574   0.637  -0.756  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.668   1.206  -0.107  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.590   1.907  -0.883  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.837   1.086   1.254  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.883   0.379   1.954  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.079   0.270   3.341  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.797  -0.192   1.339  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.351  -0.435   0.092  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.559   1.476   1.172  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.856   2.803   0.984  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.860   0.580   2.128  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.973  -0.460   1.551  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.546  -1.842   1.900  0.00  0.00           C+0
HETATM   47  H   UNK     0      -1.576  -3.925  -1.115  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.743  -2.473  -1.646  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.189  -3.426  -0.145  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.178  -3.884   0.560  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.366  -1.545   2.433  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.467  -2.091   2.982  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.704  -3.631   2.557  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.945  -3.658   0.378  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.063  -3.338   1.757  0.00  0.00           H+0
HETATM   56  H   UNK     0      -7.530  -1.776  -0.043  0.00  0.00           H+0
HETATM   57  H   UNK     0      -7.342  -1.356   2.478  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.861  -0.052  -0.574  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.736  -2.866  -1.063  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.229  -2.220  -1.754  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.679  -1.468  -2.149  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.680   0.011   1.468  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.280  -0.368  -1.158  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.617   2.274   1.945  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.627   5.260  -2.030  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.632   3.492  -3.833  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.303   4.221  -2.864  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.911  -0.534   1.497  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.962   1.070   0.065  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.919  -0.024  -1.313  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.864  -1.325  -0.356  0.00  0.00           H+0
HETATM   72  H   UNK     0       4.172   2.230  -0.577  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.598   2.442  -1.372  0.00  0.00           H+0
HETATM   74  H   UNK     0       2.905   0.908  -3.023  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.527   1.627  -2.902  0.00  0.00           H+0
HETATM   76  H   UNK     0       5.245  -0.605  -2.655  0.00  0.00           H+0
HETATM   77  H   UNK     0       2.335  -0.944  -2.839  0.00  0.00           H+0
HETATM   78  H   UNK     0       3.642  -1.829  -3.652  0.00  0.00           H+0
HETATM   79  H   UNK     0       3.240  -2.321  -1.990  0.00  0.00           H+0
HETATM   80  H   UNK     0       4.647  -1.800  -0.578  0.00  0.00           H+0
HETATM   81  H   UNK     0       6.479   0.758  -1.845  0.00  0.00           H+0
HETATM   82  H   UNK     0       8.442   2.911  -1.028  0.00  0.00           H+0
HETATM   83  H   UNK     0       8.689   1.527   1.776  0.00  0.00           H+0
HETATM   84  H   UNK     0       6.671   0.996   3.918  0.00  0.00           H+0
HETATM   85  H   UNK     0       5.084  -0.735   1.947  0.00  0.00           H+0
HETATM   86  H   UNK     0       3.611   1.707   1.469  0.00  0.00           H+0
HETATM   87  H   UNK     0       1.231   2.846   0.087  0.00  0.00           H+0
HETATM   88  H   UNK     0       2.581   3.645   0.959  0.00  0.00           H+0
HETATM   89  H   UNK     0       1.245   2.953   1.921  0.00  0.00           H+0
HETATM   90  H   UNK     0       2.664   0.111   2.772  0.00  0.00           H+0
HETATM   91  H   UNK     0       1.328   1.256   2.864  0.00  0.00           H+0
HETATM   92  H   UNK     0       0.007  -0.409   2.136  0.00  0.00           H+0
HETATM   93  H   UNK     0       2.486  -1.743   2.491  0.00  0.00           H+0
HETATM   94  H   UNK     0       1.700  -2.448   0.972  0.00  0.00           H+0
HETATM   95  H   UNK     0       0.858  -2.444   2.528  0.00  0.00           H+0
CONECT    1    2   47   48   49                                             
CONECT    2    1    3   23                                                  
CONECT    3    2    4   50                                                  
CONECT    4    3    5   11   51                                             
CONECT    5    4    6   52   53                                             
CONECT    6    5    7   54   55                                             
CONECT    7    6    8    9   56                                             
CONECT    8    7   57                                                       
CONECT    9    7   10   11   58                                             
CONECT   10    9   59   60   61                                             
CONECT   11    9   12    4   62                                             
CONECT   12   11   13   23   63                                             
CONECT   13   12   14   15                                                  
CONECT   14   13   64                                                       
CONECT   15   13   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   65                                                  
CONECT   19   18   20   21   66                                             
CONECT   20   19   67                                                       
CONECT   21   19   22   15                                                  
CONECT   22   21                                                            
CONECT   23   12   24    2   68                                             
CONECT   24   23   25   69   70                                             
CONECT   25   24   26   45   71                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   42   41                                             
CONECT   28   27   29   72   73                                             
CONECT   29   28   30   74   75                                             
CONECT   30   29   31   32   76                                             
CONECT   31   30   77   78   79                                             
CONECT   32   30   33   41   80                                             
CONECT   33   32   34   40                                                  
CONECT   34   33   35   81                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   82                                                       
CONECT   37   35   38   83                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38   84                                                       
CONECT   40   38   33   85                                                  
CONECT   41   32   27                                                       
CONECT   42   27   43   44   86                                             
CONECT   43   42   87   88   89                                             
CONECT   44   42   45   90   91                                             
CONECT   45   44   46   25   92                                             
CONECT   46   45   93   94   95                                             
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    1                                                            
CONECT   50    3                                                            
CONECT   51    4                                                            
CONECT   52    5                                                            
CONECT   53    5                                                            
CONECT   54    6                                                            
CONECT   55    6                                                            
CONECT   56    7                                                            
CONECT   57    8                                                            
CONECT   58    9                                                            
CONECT   59   10                                                            
CONECT   60   10                                                            
CONECT   61   10                                                            
CONECT   62   11                                                            
CONECT   63   12                                                            
CONECT   64   14                                                            
CONECT   65   18                                                            
CONECT   66   19                                                            
CONECT   67   20                                                            
CONECT   68   23                                                            
CONECT   69   24                                                            
CONECT   70   24                                                            
CONECT   71   25                                                            
CONECT   72   28                                                            
CONECT   73   28                                                            
CONECT   74   29                                                            
CONECT   75   29                                                            
CONECT   76   30                                                            
CONECT   77   31                                                            
CONECT   78   31                                                            
CONECT   79   31                                                            
CONECT   80   32                                                            
CONECT   81   34                                                            
CONECT   82   36                                                            
CONECT   83   37                                                            
CONECT   84   39                                                            
CONECT   85   40                                                            
CONECT   86   42                                                            
CONECT   87   43                                                            
CONECT   88   43                                                            
CONECT   89   43                                                            
CONECT   90   44                                                            
CONECT   91   44                                                            
CONECT   92   45                                                            
CONECT   93   46                                                            
CONECT   94   46                                                            
CONECT   95   46                                                            
MASTER        0    0    0    0    0    0    0    0   95    0  200    0
END

RDKit          3D

95100  0  0  0  0  0  0  0  0999 V2000
   -1.0408   -3.0041   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791   -2.2098    0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347   -2.8328    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9142   -1.9569    1.5332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0869   -2.6858    2.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2108   -2.9394    1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6704   -1.5992    0.6174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0440   -0.8162    1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5276   -1.0194   -0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2259   -1.9231   -1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3464   -0.7436    0.7232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2062   -0.1625   -0.0879 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1467    1.3015    0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    1.7116    1.4481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2445    2.2242   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1865    3.6704   -0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268    4.2930    0.4867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3406    4.2807   -1.8841 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354    3.3246   -2.9319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6703    3.3607   -3.1601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4379    2.0499   -2.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8591    1.0540   -2.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790   -0.7791    0.4043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7880   -0.0136   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -0.3495    0.1158 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3881    0.5651   -0.6031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667    0.7137   -0.1543 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3716    1.6693   -1.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112    0.9888   -2.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2954   -0.3999   -2.1108 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3203   -1.4457   -2.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -0.6864   -0.6647 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6446   -0.0607   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5743    0.6368   -0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6675    1.2065   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5900    1.9067   -0.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8369    1.0856    1.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830    0.3787    1.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792    0.2702    3.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969   -0.1922    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.4352    0.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593    1.4762    1.1718 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8560    2.8026    0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598    0.5797    2.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -0.4604    1.5511 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5457   -1.8416    1.9002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5760   -3.9253   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -2.4733   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894   -3.4259   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -3.8836    0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664   -1.5447    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4672   -2.0910    2.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038   -3.6305    2.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9449   -3.6576    0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0630   -3.3381    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5304   -1.7758   -0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3417   -1.3556    2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8608   -0.0516   -0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7363   -2.8660   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2291   -2.2197   -1.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6788   -1.4681   -2.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6795    0.0109    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2799   -0.3682   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    2.2738    1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6274    5.2597   -2.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6315    3.4918   -3.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    4.2208   -2.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105   -0.5337    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619    1.0697    0.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9194   -0.0244   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -1.3254   -0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1722    2.2300   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    2.4416   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9053    0.9075   -3.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5272    1.6271   -2.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455   -0.6052   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352   -0.9439   -2.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.8294   -3.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2398   -2.3212   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6474   -1.8001   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4793    0.7583   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4421    2.9107   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6893    1.5270    1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6711    0.9961    3.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843   -0.7347    1.9471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112    1.7068    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2309    2.8464    0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    3.6450    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447    2.9532    1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638    0.1106    2.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3280    1.2559    2.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -0.4088    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -1.7427    2.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000   -2.4483    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8576   -2.4436    2.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 12 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 27 26  1  6
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 32 41  1  0
 27 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 45 46  1  0
 23  2  1  0
 45 25  1  0
 11  4  1  0
 21 15  1  0
 41 27  1  0
 40 33  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  3 50  1  0
  4 51  1  1
  5 52  1  0
  5 53  1  0
  6 54  1  0
  6 55  1  0
  7 56  1  6
  8 57  1  0
  9 58  1  6
 10 59  1  0
 10 60  1  0
 10 61  1  0
 11 62  1  1
 12 63  1  6
 14 64  1  0
 18 65  1  0
 19 66  1  6
 20 67  1  0
 23 68  1  1
 24 69  1  0
 24 70  1  0
 25 71  1  6
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  6
 31 77  1  0
 31 78  1  0
 31 79  1  0
 32 80  1  6
 34 81  1  0
 36 82  1  0
 37 83  1  0
 39 84  1  0
 40 85  1  0
 42 86  1  1
 43 87  1  0
 43 88  1  0
 43 89  1  0
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 44 91  1  0
 45 92  1  1
 46 93  1  0
 46 94  1  0
 46 95  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₆H₄₉NO₉

Average Mass

639.7860 Da

Monoisotopic Mass

639.34073 Da

IUPAC Name

(3Z,5S)-3-{[(1R,2S,4aR,7R,8R,8aR)-2-{[(2R,3S,5S,6R,8S,9S)-8-(3,5-dihydroxyphenyl)-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]methyl}-7-hydroxy-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-hydroxypyrrolidine-2,4-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@]2(O[C@H](C[C@H]3[C@@H]([C@H]4[C@@H](C)[C@H](O)CC[C@H]4C=C3C)C(O)=C3C(=O)NC(O)C3=O)[C@@H](C)C[C@@H]2C)O[C@@H]1C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C36H49NO9/c1-16-8-9-36(46-33(16)22-12-23(38)14-24(39)13-22)19(4)10-18(3)27(45-36)15-25-17(2)11-21-6-7-26(40)20(5)28(21)29(25)31(41)30-32(42)35(44)37-34(30)43/h11-14,16,18-21,25-29,33,35,38-41,44H,6-10,15H2,1-5H3,(H,37,43)/t16-,18-,19-,20-,21-,25+,26+,27+,28-,29-,33-,35?,36+/m0/s1

InChI Key

GAMYHMPHACRYMO-MHAWJCPTSA-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
Actinoplanes sp.	NPAtlas	11922798

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
3-pyrrolidone
2-pyrrolidone
Pyrrolidone
Oxane
Monocyclic benzene moiety
Vinylogous acid
Pyrrolidine
Cyclic alcohol
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Ketone
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Enol
Carboxylic acid derivative
Alkanolamine
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	3.22	ALOGPS
logP	4.52	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	165.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	172.6 m³·mol⁻¹	ChemAxon
Polarizability	68.57 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA014542

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54687418

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh SB, Zink DL, Heimbach B, Genilloud O, Teran A, Silverman KC, Lingham RB, Felock P, Hazuda DJ: Structure, stereochemistry, and biological activity of integramycin, a novel hexacyclic natural product produced by Actinoplanes sp. that inhibits HIV-1 integrase. Org Lett. 2002 Apr 4;4(7):1123-6. doi: 10.1021/ol025539b. [PubMed:11922798 ]

Showing NP-Card for Integramycin (NP0004121)

MOL for NP0004121 (Integramycin)

3D MOL for NP0004121 (Integramycin)

3D SDF for NP0004121 (Integramycin)

3D-SDF for NP0004121 (Integramycin)

PDB for NP0004121 (Integramycin)

3D PDB for NP0004121 (Integramycin)

SMILES for NP0004121 (Integramycin)

INCHI for NP0004121 (Integramycin)

Structure for NP0004121 (Integramycin)

3D Structure for NP0004121 (Integramycin)