NP-MRD: Showing NP-Card for (2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid (NP0149978)

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Record Information

Version

2.0

Created at

2022-09-02 05:57:30 UTC

Updated at

2022-09-02 05:57:30 UTC

NP-MRD ID

NP0149978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid

Description

Micropeptin MM850 belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Based on a literature review very few articles have been published on Micropeptin MM850.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207572D          

 61 64  0  0  1  0            999 V2000
   10.9003    0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1397    0.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4826    0.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5863   -0.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7220    0.4549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0151   -0.1066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8432   -0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3949   -1.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0226   -0.9993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6098   -1.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0219   -2.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8469   -2.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2590   -3.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8461   -3.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0211   -3.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6090   -3.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875   -0.2455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2837    0.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8796    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6073   -0.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7938    0.9781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1261    0.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120   -0.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9655   -0.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0513   -1.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3836   -1.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6301   -1.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443   -0.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    1.3141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9545    2.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6222    2.6192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    2.4705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5333    1.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    1.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3726    0.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4585    0.0090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   -0.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    3.2910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829    3.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6971    4.5962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5364    3.4397    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4506    4.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1183    4.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0324    5.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7923    4.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2041    3.9243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9576    3.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2129    4.3728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0434    2.7678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7111    3.2524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6253    4.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8718    4.4088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2930    4.5575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0465    4.2215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2071    5.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4536    5.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7969    2.4318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4646    2.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8827    1.6113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6362    1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3039    1.7600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 32 30  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  4  0  0  0
 39 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  4  0  0  0
 47 49  1  0  0  0  0
 49 50  1  6  0  0  0
 50 51  2  0  0  0  0
 51 52  1  4  0  0  0
 51 53  1  0  0  0  0
 53 54  1  1  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 49 57  1  0  0  0  0
 57 58  1  1  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
  5 60  1  0  0  0  0
 60 61  2  0  0  0  0
M  END

     RDKit          3D

123126  0  0  0  0  0  0  0  0999 V2000
    2.1268   -4.0832    3.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502   -3.5252    2.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -2.5191    2.5614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5032   -3.2778    3.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533   -1.8643    1.2894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3759   -2.8161    0.3755 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5785   -3.2426    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403   -4.5763    0.3577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6373   -2.2585   -0.0825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0147   -2.7295   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4777   -3.7205   -1.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350   -5.0545   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0715   -5.9771   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3695   -5.5172   -3.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2281   -4.1970   -3.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7966   -3.3088   -2.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488   -1.3578   -1.1622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -1.9526   -2.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206    0.0324   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551    0.6575   -1.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9739    0.9499   -0.1930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2970    1.3462   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1063    2.2479    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0250    1.7878    1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7894    2.6015    1.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6124    3.9714    1.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7025    4.4443    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560    3.6045   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    2.0694    0.2075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4277    3.0019   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257    3.7753   -1.4754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0108    3.1004   -0.0123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1410    3.8457    1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587    3.6967    1.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0232    2.2512    1.6829 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1403    1.9372    2.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927    0.9767    3.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8574    3.7994   -0.9205 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757    3.2813   -1.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5919    3.5595   -3.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    2.3646   -1.2734 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7236    3.0775   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4480    4.2177   -1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2439    3.7722   -2.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6615    5.4562   -1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3412    1.6272   -2.3315 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309    0.4034   -2.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7619    0.0442   -3.9320 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5680   -0.7295   -1.7607 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2467   -0.3376   -0.5519 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5358   -0.2906   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2846   -0.6322   -1.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2565    0.1090    0.7689 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0436    1.2476    0.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1657   -1.0236    1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1372   -1.3361    0.3327 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3449   -1.6165   -1.4679 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9152   -2.9395   -1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -1.0123   -0.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800   -1.0529    0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9575   -0.4474    1.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293   -4.8825    4.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1435   -4.5500    3.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -3.2949    4.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6424   -3.0335    1.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876   -4.3766    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0433   -1.7530    3.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -3.3619    4.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856   -4.3160    2.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429   -2.7411    3.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6380   -1.1374    1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3381   -4.9640    1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5849   -1.5920    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605   -1.8056   -0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -3.0517    0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1836   -7.0264   -1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7087   -6.2596   -3.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4805   -3.8874   -4.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2302    0.2915    0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9555    0.4651   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250    1.8209   -1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1713    0.7035    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5021    2.1986    2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2157    4.6352    2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5814    5.5134    0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395    4.0206   -0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    2.1125    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0275    4.9269    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5785    4.0374    2.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
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 37100  1  0
M  END


  Mrv1652309022207572D          

 61 64  0  0  1  0            999 V2000
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 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  2  0  0  0  0
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 50 51  2  0  0  0  0
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 51 53  1  0  0  0  0
 53 54  1  1  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 49 57  1  0  0  0  0
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 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
  5 60  1  0  0  0  0
 60 61  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0149978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1N=C(O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](CC2=CC=CC=C2)N2[C@@H](CC[C@H](N=C(O)[C@H](CC(C)C)N=C(O)[C@@H](N=C(O)[C@H](O)CO)[C@@H](C)OC1=O)C2=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C44H62N6O11/c1-8-26(4)36-44(59)61-27(5)37(48-40(55)34(52)24-51)41(56)46-31(21-25(2)3)38(53)45-30-19-20-35(60-7)50(42(30)57)33(23-29-17-13-10-14-18-29)43(58)49(6)32(39(54)47-36)22-28-15-11-9-12-16-28/h9-18,25-27,30-37,51-52H,8,19-24H2,1-7H3,(H,45,53)(H,46,56)(H,47,54)(H,48,55)/t26-,27+,30-,31-,32-,33-,34+,35+,36-,37-/m0/s1

> <INCHI_KEY>
JRYZCWOROGUEPY-ZDYYWPHCSA-N

> <FORMULA>
C44H62N6O11

> <MOLECULAR_WEIGHT>
851.011

> <EXACT_MASS>
850.44765684

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
89.03753608271951

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,5-dibenzyl-8-[(2S)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
5.020068739333334

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.593670805305085

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9486217735247715

> <JCHEM_PKA_STRONGEST_BASIC>
1.3374852920766993

> <JCHEM_POLAR_SURFACE_AREA>
246.96999999999994

> <JCHEM_REFRACTIVITY>
223.71050000000017

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,5-dibenzyl-8-[(2S)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      20.347   0.588   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.927   1.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.701   0.253   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.894  -1.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.281   0.849   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      14.961  -0.199   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      14.641  -1.705   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      15.670  -2.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.109  -1.865   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.338  -3.199   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.108  -4.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.648  -4.534   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.417  -5.868   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.646  -7.201   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.106  -7.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.337  -5.866   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      12.483  -0.458   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      13.596   0.606   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.975   0.294   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.467  -1.160   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.815   1.826   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.569   0.921   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.729  -0.610   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.136  -1.237   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.296  -2.769   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.049  -3.674   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.643  -3.047   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.483  -1.515   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       9.409   2.453   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       9.248   3.985   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.495   4.889   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.842   4.612   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.596   3.707   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.756   2.175   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.162   1.548   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.322   0.017   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.076  -0.888   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       7.682   6.143   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       8.928   7.048   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.768   8.579   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      10.335   6.421   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.174   7.952   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.421   8.857   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.261  10.389   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.018   8.716   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      11.581   7.325   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0      12.987   6.698   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      13.464   8.163   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      13.148   5.167   0.000  0.00  0.00           C+0
HETATM   50  N   UNK     0      14.394   6.071   0.000  0.00  0.00           N+0
HETATM   51  C   UNK     0      14.234   7.603   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      12.827   8.230   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      15.480   8.507   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      16.887   7.880   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      15.320  10.039   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      13.913  10.666   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      14.554   4.539   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      15.801   5.444   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      14.714   3.008   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      16.121   2.381   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      17.367   3.285   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   60                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    9   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   21   30   35                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   29   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   32   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   57                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55                                                            
CONECT   57   49   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59    5   61                                                  
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₆₂N₆O₁₁

Average Mass

851.0110 Da

Monoisotopic Mass

850.44766 Da

IUPAC Name

(2R)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2,5-dibenzyl-8-[(2S)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1N=C(O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](CC2=CC=CC=C2)N2[C@@H](CC[C@H](N=C(O)[C@H](CC(C)C)N=C(O)[C@@H](N=C(O)[C@H](O)CO)[C@@H](C)OC1=O)C2=O)OC

InChI Identifier

InChI=1S/C44H62N6O11/c1-8-26(4)36-44(59)61-27(5)37(48-40(55)34(52)24-51)41(56)46-31(21-25(2)3)38(53)45-30-19-20-35(60-7)50(42(30)57)33(23-29-17-13-10-14-18-29)43(58)49(6)32(39(54)47-36)22-28-15-11-9-12-16-28/h9-18,25-27,30-37,51-52H,8,19-24H2,1-7H3,(H,45,53)(H,46,56)(H,47,54)(H,48,55)/t26-,27+,30-,31-,32-,33-,34+,35+,36-,37-/m0/s1

InChI Key

JRYZCWOROGUEPY-ZDYYWPHCSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Alpha-amino acid ester
Macrolactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Delta-lactam
Piperidinone
Monocyclic benzene moiety
Monosaccharide
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Secondary alcohol
1,2-diol
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic oxide
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
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	2.68	ALOGPS
logP	5.02	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	1.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	246.97 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	223.71 m³·mol⁻¹	ChemAxon
Polarizability	89.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50923794

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid (NP0149978)

MOL for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

3D MOL for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

3D SDF for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

3D-SDF for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

PDB for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

3D PDB for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

SMILES for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

INCHI for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

Structure for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)

3D Structure for NP0149978 ((2r)-n-[(2s,5s,8s,11r,12s,15s,18s,21r)-2,5-dibenzyl-8-[(2s)-butan-2-yl]-6,13,16-trihydroxy-21-methoxy-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2,3-dihydroxypropanimidic acid)