NP-MRD: Showing NP-Card for (5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide (NP0146333)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 01:43:02 UTC

Updated at

2022-09-02 01:43:02 UTC

NP-MRD ID

NP0146333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

Description

(5S,10R)-7,9-dibromo-N-(4-{[(5R,10R)-7,9-dibromo-10-hydroxy-8-methoxy-2-azaspiro[4.5]Deca-2,6,8-trien-3-yl]formamido}-3-oxobutyl)-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-carboxamide belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms. (5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide is found in Aplysina cavernicola. Based on a literature review very few articles have been published on (5S,10R)-7,9-dibromo-N-(4-{[(5R,10R)-7,9-dibromo-10-hydroxy-8-methoxy-2-azaspiro[4.5]Deca-2,6,8-trien-3-yl]formamido}-3-oxobutyl)-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]Deca-2,6,8-triene-3-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203432D          

 41 44  0  0  1  0            999 V2000
   -5.5327   -5.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478   -5.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2273   -5.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424   -4.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0780   -3.9167    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -4.7566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4370   -4.0891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5864   -5.5102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0713   -6.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8918   -6.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3767   -6.7589    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0343   -4.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2807   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662   -3.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483   -5.2327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -3.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206   -4.8202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -6.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1496   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2358   -3.9997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428   -3.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4553   -4.5427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9402   -3.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7607   -3.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2456   -3.2940    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.0962   -4.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -4.8014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4016   -4.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6113   -5.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9469   -6.1363    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.7908   -5.2963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3059   -5.9638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9033   -5.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669   -6.0532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739   -6.2247    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  6  0  0  0
 28 39  1  0  0  0  0
 25 39  1  0  0  0  0
 13 40  2  0  0  0  0
 40 41  1  0  0  0  0
  8 41  1  1  0  0  0
M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
   11.5224    0.6119   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3353    1.3139   -0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1236    0.9828    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9111   -0.0665    0.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3031   -1.2909    1.2297 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.5580   -0.4671    1.2295 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1930   -1.5388    0.3520 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5021    0.5429    1.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7547    1.6163    0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9235    1.8465   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2821    3.2512   -1.5441 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.1677   -0.1135    1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2616    1.0139    1.6163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214    1.0387    1.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1943    2.0691    1.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3676   -0.0512    0.4214 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150   -1.1155   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193   -0.6001   -1.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1146    0.1893   -1.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558    1.2606   -0.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750   -0.3865   -1.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0649   -0.4693   -0.8387 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3780   -1.0041   -1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6711   -1.3141   -2.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3418   -1.2206    0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2488   -1.0321    1.3088 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5266   -1.4357    1.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5219   -1.0618    0.8573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8375   -1.6027    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9322   -0.8789    1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6528   -1.6584    1.1302 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -8.8111    0.5804    0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9505    1.3905    0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4034    1.9067   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6597    1.1847    0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6169    3.1283    0.7591 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -6.3943    0.4325    0.6904 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7813    0.6743   -0.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7182   -1.7681   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9874    1.7280    2.2953 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3014    1.2424    2.4486 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3001    1.2248   -0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9734    0.5337    0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4610   -0.4023   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5817   -0.9378    2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2409   -1.6670    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9233    2.2648   -0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505   -0.9575    1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474   -0.2283    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1384    0.4421    0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -1.7218    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6219   -1.8723   -0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -1.4973   -2.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483    0.0217   -2.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6936    0.3478   -2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -1.3267   -2.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7667   -0.1364    0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6413   -0.8229    2.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4528   -2.5116    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9770   -2.7014    1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6394    1.0350   -0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5544    2.4412   -0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2430    2.5930   -0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6641    0.8334    1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4183    0.4703   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650   -2.8401   -0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0480   -1.5137   -1.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 32  1  0
 32 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  2  0
 25 39  1  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 40  2  0
 40 41  1  0
  8 41  1  1
  8 12  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
 28 29  1  1
 29 30  2  0
 30 31  1  0
 30 32  1  0
 39 28  1  0
 12 13  1  0
  6  8  1  0
 34 61  1  0
 34 62  1  0
 34 63  1  0
 37 64  1  1
 38 65  1  0
 27 58  1  0
 27 59  1  0
 39 66  1  0
 39 67  1  0
 22 57  1  0
 21 55  1  0
 21 56  1  0
 18 53  1  0
 18 54  1  0
 17 51  1  0
 17 52  1  0
 16 50  1  0
 12 48  1  0
 12 49  1  0
  9 47  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  6 45  1  1
  7 46  1  0
 29 60  1  0
M  END


  Mrv1652309022203432D          

 41 44  0  0  1  0            999 V2000
   -5.5327   -5.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478   -5.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2273   -5.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424   -4.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0780   -3.9167    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -4.7566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4370   -4.0891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5864   -5.5102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0713   -6.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8918   -6.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3767   -6.7589    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0343   -4.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2807   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5662   -3.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483   -5.2327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917   -3.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206   -4.8202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -5.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -6.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1496   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2358   -3.9997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428   -3.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4553   -4.5427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9402   -3.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7607   -3.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2456   -3.2940    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.0962   -4.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -4.8014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4016   -4.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6113   -5.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9469   -6.1363    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.7908   -5.2963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3059   -5.9638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9033   -5.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669   -6.0532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739   -6.2247    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  6  0  0  0
 28 39  1  0  0  0  0
 25 39  1  0  0  0  0
 13 40  2  0  0  0  0
 40 41  1  0  0  0  0
  8 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0146333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Br)[C@H](O)[C@@]2(CN=C(C2)C(=O)NCC(=O)CCNC(=O)C2=NO[C@@]3(C2)C=C(Br)C(OC)=C(Br)[C@@H]3O)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C25H26Br4N4O8/c1-39-18-12(26)5-24(20(35)16(18)28)7-14(32-10-24)22(37)31-9-11(34)3-4-30-23(38)15-8-25(41-33-15)6-13(27)19(40-2)17(29)21(25)36/h5-6,20-21,35-36H,3-4,7-10H2,1-2H3,(H,30,38)(H,31,37)/t20-,21-,24-,25+/m0/s1

> <INCHI_KEY>
WHMSDQSUQQPCBG-WIHVIGOGSA-N

> <FORMULA>
C25H26Br4N4O8

> <MOLECULAR_WEIGHT>
830.119

> <EXACT_MASS>
825.848416

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
66.33625533782721

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,10R)-7,9-dibromo-N-(4-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
0.040447477333333925

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.539361759505287

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.991373899999903

> <JCHEM_PKA_STRONGEST_BASIC>
1.9265398107644391

> <JCHEM_POLAR_SURFACE_AREA>
168.13999999999996

> <JCHEM_REFRACTIVITY>
165.56609999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,10R)-7,9-dibromo-N-(4-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

> <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     -10.328 -11.049   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.423  -9.803   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.891  -9.964   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.986  -8.718   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0      -7.612  -7.311   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0      -5.454  -8.879   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.549  -7.633   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.828 -10.286   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.733 -11.532   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.265 -11.371   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0      -8.170 -12.617   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0      -3.797  -9.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.391  -9.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.057  -8.998   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.057  -7.458   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       0.277  -9.768   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       1.610  -8.998   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.944  -9.768   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.278  -8.998   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.278  -7.458   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.612  -9.768   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.945  -8.998   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.279  -9.768   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.279 -11.308   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.613  -8.998   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       9.774  -7.466   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      11.280  -7.146   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.050  -8.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.955  -7.234   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.487  -7.395   0.000  0.00  0.00           C+0
HETATM   31 Br   UNK     0      15.392  -6.149   0.000  0.00  0.00          Br+0
HETATM   32  C   UNK     0      15.113  -8.802   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.645  -8.963   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      17.550  -7.717   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.208 -10.047   0.000  0.00  0.00           C+0
HETATM   36 Br   UNK     0      14.834 -11.454   0.000  0.00  0.00          Br+0
HETATM   37  C   UNK     0      12.676  -9.887   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.771 -11.132   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      11.019  -9.624   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      -2.552 -11.299   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0      -4.058 -11.619   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12   41                                             
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   40                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   39                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   37   39                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   28   38                                                  
CONECT   38   37                                                            
CONECT   39   28   25                                                       
CONECT   40   13   41                                                       
CONECT   41   40    8                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆Br₄N₄O₈

Average Mass

830.1190 Da

Monoisotopic Mass

825.84842 Da

IUPAC Name

(5R,10R)-7,9-dibromo-N-(4-{[(5S,10R)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=C(Br)[C@H](O)[C@@]2(CN=C(C2)C(=O)NCC(=O)CCNC(=O)C2=NO[C@@]3(C2)C=C(Br)C(OC)=C(Br)[C@@H]3O)C=C1Br

InChI Identifier

InChI=1S/C25H26Br4N4O8/c1-39-18-12(26)5-24(20(35)16(18)28)7-14(32-10-24)22(37)31-9-11(34)3-4-30-23(38)15-8-25(41-33-15)6-13(27)19(40-2)17(29)21(25)36/h5-6,20-21,35-36H,3-4,7-10H2,1-2H3,(H,30,38)(H,31,37)/t20-,21-,24-,25+/m0/s1

InChI Key

WHMSDQSUQQPCBG-WIHVIGOGSA-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

Species Name	Source	Reference
Aplysina cavernicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Isoxazolines

Direct Parent

Isoxazolines

Alternative Parents

Substituents

Isoxazoline
Pyrroline
Bromohydrin
Carboxamide group
Halohydrin
Ketimine
Ketone
Oxime ether
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Bromoalkene
Haloalkene
Organic 1,3-dipolar compound
Vinyl bromide
Vinyl halide
Propargyl-type 1,3-dipolar organic compound
Organobromide
Organohalogen compound
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Imine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.62	ALOGPS
logP	0.04	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	11.99	ChemAxon
pKa (Strongest Basic)	1.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	168.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	165.57 m³·mol⁻¹	ChemAxon
Polarizability	66.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162893198

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide (NP0146333)

MOL for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D MOL for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D SDF for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D-SDF for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

PDB for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D PDB for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

SMILES for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

INCHI for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

Structure for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)

3D Structure for NP0146333 ((5r,10r)-7,9-dibromo-n-(4-{[(5s,10r)-7,9-dibromo-10-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,6,8-trien-3-yl]formamido}-2-oxobutyl)-10-hydroxy-8-methoxy-2-azaspiro[4.5]deca-2,6,8-triene-3-carboxamide)