NP-MRD: Showing NP-Card for (2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate (NP0267862)

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Record Information

Version

2.0

Created at

2022-09-08 12:47:07 UTC

Updated at

2022-09-08 12:47:07 UTC

NP-MRD ID

NP0267862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate

Description

Maculansin A belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate is found in Leptosphaeria maculans. (2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate was first documented in 2008 (PMID: 18977007). Based on a literature review very few articles have been published on Maculansin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214472D          

 34 33  0  0  1  0            999 V2000
    5.0996   -0.2546    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.5051   -0.8266    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.9107   -1.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088   -2.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143   -2.7715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9015   -2.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0996   -3.2291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5051   -3.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1180   -4.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254   -3.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162   -4.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -3.4579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4867   -2.8859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904   -4.2588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4959   -4.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830   -4.4876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4775   -3.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2701   -4.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6665   -2.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6573   -3.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0812   -5.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8738   -5.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4683   -4.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0720   -6.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -6.5469    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    9.6573   -6.7757    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    7.4775   -6.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6849   -6.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6757   -7.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1180   -1.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199   -0.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5235   -1.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  3  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  CHG  4   1  -1   2   1  27   1  28  -1
M  END

     RDKit          3D

 62 61  0  0  0  0  0  0  0  0999 V2000
    2.8846   -3.3120    2.3558 C   0  0  0  0  0  3  0  0  0  0  0  0
    3.0329   -2.6928    1.3895 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.2328   -1.9545    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737   -0.5814    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9295    0.1169   -0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7357    1.3213    1.2786 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7807    2.0811    2.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    3.4444    2.2145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976    4.3293    1.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    5.7959    1.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7159    3.8900    0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726    1.6095    1.7747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1071    2.9718    1.6091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7496    0.7163    1.4118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3857   -0.5953    1.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4975    0.9990    0.1738 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7487    0.6486   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388   -0.7580   -1.1404 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -1.4161   -2.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1158   -2.9042   -2.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -0.7092   -3.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360    0.3291    0.0541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524    0.9758   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8414    2.2340   -0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199    0.2931   -0.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3665    1.0270   -0.3843 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.3291    1.6615   -0.5264 C   0  0  0  0  0  3  0  0  0  0  0  0
   -5.2867   -1.0080   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6122   -1.7074   -0.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540   -1.8106   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8142   -2.5029   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0390   -1.7488   -2.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2582   -3.9302   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9201    1.7325    0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    1.6669    3.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7568    1.8162    1.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5020    6.0888    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429    6.3623    1.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    5.9759    2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4533    1.5194    2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208    3.2303    0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5131    0.8577    2.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -1.0048    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995    2.1247    0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4395    0.9350   -1.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.1494   -1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964   -3.1399   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3106   -3.2031   -3.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4220   -3.3944   -1.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4277   -0.9425   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7340   -2.4840    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6980   -2.1955   -1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5489   -1.6568    0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3462   -1.7061   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3331   -2.9070   -0.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585   -2.3941   -2.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7149   -0.8622   -1.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908   -1.4346   -2.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7668   -4.2250   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3665   -4.6111   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9553   -4.0995    0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  1  0
  2  1  3  0
  3 32  2  3
 32 33  1  0
 32 34  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 17 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  3  0
 26 29  2  3
 29 30  1  0
 29 31  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
  8 36  1  0
  8 37  1  0
  7 35  1  6
 33 57  1  0
 33 58  1  0
 33 59  1  0
 34 60  1  0
 34 61  1  0
 34 62  1  0
 13 41  1  1
 14 42  1  0
 15 43  1  1
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 30 51  1  0
 30 52  1  0
 30 53  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
M  CHG  4   1  -1   2   1  27   1  28  -1
M  END


  Mrv1652309082214472D          

 34 33  0  0  1  0            999 V2000
    5.0996   -0.2546    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.5051   -0.8266    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.9107   -1.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088   -2.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5143   -2.7715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9015   -2.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0996   -3.2291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5051   -3.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1180   -4.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254   -3.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162   -4.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922   -3.4579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4867   -2.8859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904   -4.2588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4959   -4.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830   -4.4876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4775   -3.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2701   -4.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6665   -2.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6573   -3.8012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0812   -5.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8738   -5.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4683   -4.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0720   -6.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -6.5469    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    9.6573   -6.7757    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    7.4775   -6.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6849   -6.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6757   -7.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1180   -1.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199   -0.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5235   -1.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 20 22  2  0  0  0  0
 17 23  1  1  0  0  0
 23 24  1  0  0  0  0
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 24 26  1  0  0  0  0
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 27 28  3  0  0  0  0
 26 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  3 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  CHG  4   1  -1   2   1  27   1  28  -1
M  END
> <DATABASE_ID>
NP0267862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@H](OC(=O)C([N+]#[C-])=C(C)C)[C@@H](O)[C@H](O)[C@@H](COC(C)=O)OC(=O)C([N+]#[C-])=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O10/c1-11(2)17(23-7)21(29)33-15(9-31-13(5)25)19(27)20(28)16(10-32-14(6)26)34-22(30)18(24-8)12(3)4/h15-16,19-20,27-28H,9-10H2,1-6H3/t15-,16-,19-,20-/m1/s1

> <INCHI_KEY>
XQBSOXRYXYNGRH-XNFNUYLZSA-N

> <FORMULA>
C22H28N2O10

> <MOLECULAR_WEIGHT>
480.47

> <EXACT_MASS>
480.17439511

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.32844963100946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate

> <JCHEM_LOGP>
-3.703849454418557

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.15971920016533

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.739322329251973

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6558719688415398

> <JCHEM_POLAR_SURFACE_AREA>
154.38

> <JCHEM_REFRACTIVITY>
134.65140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.519  -0.475   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       8.410  -1.543   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       7.300  -2.611   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.670  -4.106   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.560  -5.173   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.149  -4.533   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.519  -6.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.410  -7.096   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.930  -6.668   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.820  -7.736   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.341  -7.309   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.190  -9.231   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.999  -6.455   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.109  -5.387   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.369  -7.950   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.259  -9.018   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.848  -8.377   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.958  -7.309   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.438  -7.736   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.547  -6.668   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.177  -5.173   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.027  -7.096   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.218  -9.872   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.698 -10.299   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.808  -9.231   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.068 -11.794   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      16.547 -12.221   0.000  0.00  0.00           N+1
HETATM   28  C   UNK     0      18.027 -12.648   0.000  0.00  0.00           C-1
HETATM   29  C   UNK     0      13.958 -12.862   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.478 -12.435   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.328 -14.357   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.820  -2.184   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.450  -0.689   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.711  -3.251   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    3   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈N₂O₁₀

Average Mass

480.4700 Da

Monoisotopic Mass

480.17440 Da

IUPAC Name

(2R,3S,4S,5R)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate

Traditional Name

(2R,3S,4S,5R)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@H](OC(=O)C([N+]#[C-])=C(C)C)[C@@H](O)[C@H](O)[C@@H](COC(C)=O)OC(=O)C([N+]#[C-])=C(C)C

InChI Identifier

InChI=1S/C22H28N2O10/c1-11(2)17(23-7)21(29)33-15(9-31-13(5)25)19(27)20(28)16(10-32-14(6)26)34-22(30)18(24-8)12(3)4/h15-16,19-20,27-28H,9-10H2,1-6H3/t15-,16-,19-,20-/m1/s1

InChI Key

XQBSOXRYXYNGRH-XNFNUYLZSA-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
Leptosphaeria maculans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Alpha-amino acid or derivatives
Fatty acid ester
Monosaccharide
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Organic isocyanide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-3.7	ChemAxon
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.38 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	134.65 m³·mol⁻¹	ChemAxon
Polarizability	47.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034047

Chemspider ID

28285797

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25180954

PDB ID

Not Available

ChEBI ID

188585

Good Scents ID

Not Available

References

General References

Pedras MS, Yu Y: Structure and biological activity of maculansin A, a phytotoxin from the phytopathogenic fungus Leptosphaeria maculans. Phytochemistry. 2008 Dec;69(17):2966-71. doi: 10.1016/j.phytochem.2008.09.015. Epub 2008 Oct 30. [PubMed:18977007 ]
LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate (NP0267862)

MOL for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

3D MOL for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

3D SDF for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

3D-SDF for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

PDB for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

3D PDB for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

SMILES for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

INCHI for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

Structure for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)

3D Structure for NP0267862 ((2r,3s,4s,5r)-1,6-bis(acetyloxy)-3,4-dihydroxy-5-[(2-isocyano-3-methylbut-2-enoyl)oxy]hexan-2-yl 2-isocyano-3-methylbut-2-enoate)