NP-MRD: Showing NP-Card for methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate (NP0235775)

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Record Information

Version

2.0

Created at

2022-09-06 18:30:19 UTC

Updated at

2022-09-06 18:30:19 UTC

NP-MRD ID

NP0235775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate

Description

Sarcodictyin D belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on Sarcodictyin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220302D          

 40 43  0  0  1  0            999 V2000
    2.6229   -2.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229   -1.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1940   -1.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930    0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    0.8793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1780    1.7043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6930    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084    2.6267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9084    3.4517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229    3.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229    4.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3374    3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    3.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7663    3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200    3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0720    3.1742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925    3.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595    2.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8525    2.6312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238    2.3718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6389    3.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238    0.2119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6389   -0.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938    1.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924    2.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924    2.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    0.8793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3214    0.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7503    0.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924    0.4668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8924   -0.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069   -0.7707    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  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  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
  8 29  1  1  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
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   -2.0200    0.3276    0.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6835    0.9622    0.4208 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2666    0.1142   -0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670   -0.7266    0.4460 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5114   -0.5884    0.1647 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078   -0.1304    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1525    0.2121    2.1111 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8707   -0.0673    0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1995   -0.4415   -0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7376   -3.1376   -1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789   -2.4709    0.0027 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2748   -3.5444    0.6047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6949   -1.9991    0.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6293    2.3072   -0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7633    2.8091   -0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6816    3.0628   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0179    2.5806    0.0203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8585    2.3446   -1.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0104    3.0374   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7656    2.6348   -2.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505    3.9485   -0.6019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0130    1.4178    0.9353 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8342    1.7898    2.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757    0.5761    3.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7493    2.8819    2.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5305   -4.5849   -1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8348   -3.7956   -3.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1539   -5.3442   -2.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479    0.2897   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -0.3286    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078    0.9662    1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.7344   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -0.5016   -1.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6918    0.2961    1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4426   -0.8139   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6755    0.4413    0.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2959    0.0791    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0001   -0.6880   -3.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2136   -2.7139   -1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9535    2.7243   -1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449    2.2690    0.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
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 17 18  1  0
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 18 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  1  1
 22 28  1  0
 28 26  1  0
 26 27  1  1
 26 25  1  0
 25 24  2  0
  8 29  1  0
 29 30  1  0
 29 31  2  0
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 32 33  1  0
 33 34  1  0
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 37 38  1  0
 38 39  1  0
 38 40  1  0
 26  5  1  0
 37  7  1  0
 21 16  1  0
 24 22  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  7 45  1  1
  8 46  1  1
  9 47  1  0
  9 48  1  0
 10 49  1  1
 14 50  1  0
 15 51  1  0
 17 52  1  0
 19 53  1  0
 19 54  1  0
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 20 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 27 62  1  0
 25 61  1  0
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 30 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 32 67  1  1
 35 68  1  0
 35 69  1  0
 35 70  1  0
 37 71  1  1
 38 72  1  0
 39 73  1  0
 39 74  1  0
 39 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
M  END


  Mrv1652309062220302D          

 40 43  0  0  1  0            999 V2000
    2.6229   -2.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229   -1.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1940   -1.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084   -0.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930    0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    0.8793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1780    1.7043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6930    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084    2.6267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9084    3.4517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229    3.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229    4.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3374    3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    3.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7663    3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200    3.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0720    3.1742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8925    3.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595    2.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8525    2.6312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238    2.3718    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6389    3.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6389    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238    0.2119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6389   -0.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8924    2.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6069    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069    0.8793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3214    0.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0359    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7503    0.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924    0.4668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8924   -0.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6069   -0.7707    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  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  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
  8 29  1  1  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C/[C@H]2[C@@H](C[C@H](OC(=O)\C=C\C3=CN(C)C=N3)[C@@]3(C)O[C@]\1(O)C=C3)C(C)=C[C@@H](OC(C)=O)[C@@H]2C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H38N2O8/c1-17(2)27-22-13-23(28(35)37-7)30(36)11-10-29(5,40-30)25(14-21(22)18(3)12-24(27)38-19(4)33)39-26(34)9-8-20-15-32(6)16-31-20/h8-13,15-17,21-22,24-25,27,36H,14H2,1-7H3/b9-8+,23-13-/t21-,22-,24+,25-,27+,29-,30+/m0/s1

> <INCHI_KEY>
DTXPJIMFCRPUBR-NIEYPKSZSA-N

> <FORMULA>
C30H38N2O8

> <MOLECULAR_WEIGHT>
554.64

> <EXACT_MASS>
554.262816192

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
58.85166201115402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2E,4S,5R,6S,9R,11S,12S)-6-(acetyloxy)-1-hydroxy-8,12-dimethyl-11-{[(2E)-3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-2,7,13-triene-2-carboxylate

> <JCHEM_LOGP>
3.968624549333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.79763289764684

> <JCHEM_PKA_STRONGEST_BASIC>
5.9466623877263265

> <JCHEM_POLAR_SURFACE_AREA>
126.18

> <JCHEM_REFRACTIVITY>
149.00130000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2E,4S,5R,6S,9R,11S,12S)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2E)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-2,7,13-triene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.896  -3.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.896  -2.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.562  -1.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.229  -2.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.562  -0.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.027   0.396   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.932   1.641   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.932   3.181   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.027   4.427   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.562   4.903   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.562   6.443   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.896   7.213   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.896   8.753   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.230   6.443   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.563   7.213   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.897   6.443   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.304   7.070   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      11.334   5.925   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      12.866   6.086   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.564   4.591   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       9.058   4.912   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.098   4.427   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.193   5.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.193   3.181   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.193   1.641   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.098   0.396   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.193  -0.850   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.602   2.411   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.266   3.951   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.266   5.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.600   3.181   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.600   1.641   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.933   0.871   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.267   1.641   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.267   3.181   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.601   0.871   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.266   0.871   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.266  -0.669   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.932  -1.439   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.600  -1.439   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   16                                                       
CONECT   22   10   23   24   28                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   22                                                       
CONECT   29    8   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32    7   38                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈N₂O₈

Average Mass

554.6400 Da

Monoisotopic Mass

554.26282 Da

IUPAC Name

methyl (1R,2E,4S,5R,6S,9R,11S,12S)-6-(acetyloxy)-1-hydroxy-8,12-dimethyl-11-{[(2E)-3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-2,7,13-triene-2-carboxylate

Traditional Name

methyl (1R,2E,4S,5R,6S,9R,11S,12S)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2E)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-2,7,13-triene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C/[C@H]2[C@@H](C[C@H](OC(=O)\C=C\C3=CN(C)C=N3)[C@@]3(C)O[C@]\1(O)C=C3)C(C)=C[C@@H](OC(C)=O)[C@@H]2C(C)C

InChI Identifier

InChI=1S/C30H38N2O8/c1-17(2)27-22-13-23(28(35)37-7)30(36)11-10-29(5,40-30)25(14-21(22)18(3)12-24(27)38-19(4)33)39-26(34)9-8-20-15-32(6)16-31-20/h8-13,15-17,21-22,24-25,27,36H,14H2,1-7H3/b9-8+,23-13-/t21-,22-,24+,25-,27+,29-,30+/m0/s1

InChI Key

DTXPJIMFCRPUBR-NIEYPKSZSA-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
N-substituted imidazole
Azole
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Dihydrofuran
Imidazole
Carboxylic acid ester
Hemiacetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.97	ChemAxon
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	5.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	126.18 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	149 m³·mol⁻¹	ChemAxon
Polarizability	58.85 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

8091306

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9915657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate (NP0235775)

MOL for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D MOL for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D SDF for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D-SDF for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

PDB for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D PDB for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

SMILES for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

INCHI for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

Structure for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D Structure for NP0235775 (methyl (1r,2e,4s,5r,6s,9r,11s,12s)-6-(acetyloxy)-1-hydroxy-5-isopropyl-8,12-dimethyl-11-{[(2e)-3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)