NP-MRD: Showing NP-Card for Gymnastatin E (NP0076609)

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Record Information

Version

2.0

Created at

2022-04-28 21:48:05 UTC

Updated at

2022-04-28 21:48:05 UTC

NP-MRD ID

NP0076609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gymnastatin E

Description

(2E,4E,6R)-N-[(1'beta,2R,6'beta)-4,5-Dihydro-4'-chloro-5beta,5'alpha-dihydroxy-7'-oxaspiro[furan-2(3H),2'-bicyclo[4.1.0]Hept[3]en]-4alpha-yl]-4,6-dimethyl-2,4-dodecadienamide belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Gymnastatin E is found in Gymnascella dankaliensis. Based on a literature review very few articles have been published on (2E,4E,6R)-N-[(1'beta,2R,6'beta)-4,5-Dihydro-4'-chloro-5beta,5'alpha-dihydroxy-7'-oxaspiro[furan-2(3H),2'-bicyclo[4.1.0]Hept[3]en]-4alpha-yl]-4,6-dimethyl-2,4-dodecadienamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223482D          

 30 32  0  0  1  0            999 V2000
   -8.9579    8.0864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4730    8.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6525    8.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3170    7.9140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8019    7.2465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6224    7.3328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2868    6.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7649    8.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0113    8.1915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0975    7.3710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9045    7.1995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4844    6.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968    8.6040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823    7.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7244    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    8.6040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2955    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8479    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    9.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    9.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8086    9.5075    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -9.7784    8.1727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  7  1  1  0  0  0
  4  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
  4 11  1  1  0  0  0
 10 12  1  1  0  0  0
  9 13  1  6  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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 27  1  6  0  0  0
 18 28  1  0  0  0  0
  2 29  1  0  0  0  0
  1 30  1  1  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    7.0297    2.9855    2.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3959    2.1438    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4859    0.9015    1.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8133    0.0113   -0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9494   -1.2132   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098   -0.8522   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -2.0808   -0.1464 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7881   -2.8920    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2107   -1.6211   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172   -1.9761   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747   -2.8265   -2.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377   -1.5218   -1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7947   -1.8126   -2.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847   -1.3252   -2.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280   -1.6578   -3.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358   -0.5242   -1.2085 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1023   -0.0830   -1.2622 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8483   -0.4525    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8382    0.6465    0.1790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2256    0.1555   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2260    0.9785    0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8535    0.4534   -0.2636 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.9463    2.3228    0.7004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5203    3.2416   -0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9594    2.1339    1.8331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6666    2.5903    1.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8949    1.1790    1.5960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4723    1.6230   -0.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2450    1.4187   -1.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2582    1.9266   -2.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5646    2.6546    3.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2584    4.0607    2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292    2.9366    2.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2813    2.6936    0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4434    1.7476    1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4432    1.2975    1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6569    0.3977    2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6522    0.5467   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9023   -0.2624    0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -1.9207   -0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1872   -1.7345    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427   -0.2787   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220   -0.2245    0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9206   -2.7219   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3339   -2.2732    1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -3.1618    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3301   -3.8365    0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -1.0100    0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -3.8001   -1.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3925   -3.0323   -3.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9533   -2.3158   -2.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -0.9065   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4609   -2.4281   -3.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1878   -0.2049   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803   -0.4612   -2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3892   -1.3964   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1616   -0.5965    0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3047   -0.8303   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9038    2.7288    1.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9531    4.1156   -0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4342    2.0929    2.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5046    0.5394    2.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3933    1.8919   -0.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1680    1.8197   -2.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 28  1  6
 28 29  1  0
 29 30  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 29 17  1  0
 27 25  1  0
 27 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  6
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
 11 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 13 53  1  0
 16 54  1  0
 17 55  1  6
 18 56  1  0
 18 57  1  0
 29 63  1  1
 30 64  1  0
 20 58  1  0
 23 59  1  1
 24 60  1  0
 25 61  1  1
 27 62  1  1
M  END


  Mrv1652304282223482D          

 30 32  0  0  1  0            999 V2000
   -8.9579    8.0864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4730    8.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6525    8.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3170    7.9140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8019    7.2465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6224    7.3328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2868    6.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7649    8.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0113    8.1915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0975    7.3710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9045    7.1995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4844    6.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968    8.6040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5823    7.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7244    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    8.6040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2955    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8479    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    8.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769    8.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    9.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    9.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8086    9.5075    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -9.7784    8.1727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  7  1  1  0  0  0
  4  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
  4 11  1  1  0  0  0
 10 12  1  1  0  0  0
  9 13  1  6  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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 27  1  6  0  0  0
 18 28  1  0  0  0  0
  2 29  1  0  0  0  0
  1 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC[C@@H](C)\C=C(/C)\C=C\C(=O)N[C@H]1C[C@@]2(O[C@@H]1O)C=C(Cl)[C@H](O)[C@@H]1O[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C23H34ClNO5/c1-4-5-6-7-8-14(2)11-15(3)9-10-18(26)25-17-13-23(30-22(17)28)12-16(24)19(27)20-21(23)29-20/h9-12,14,17,19-22,27-28H,4-8,13H2,1-3H3,(H,25,26)/b10-9+,15-11+/t14-,17+,19+,20+,21+,22+,23+/m1/s1

> <INCHI_KEY>
XKJXLFLLICSWJK-MECFWYRWSA-N

> <FORMULA>
C23H34ClNO5

> <MOLECULAR_WEIGHT>
439.98

> <EXACT_MASS>
439.2125509

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.370986354542964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6R)-N-[(1S,2R,4'S,5R,5'S,6S)-4-chloro-5,5'-dihydroxy-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienamide

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.4450145453333323

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.75511650141209

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.747685528548136

> <JCHEM_PKA_STRONGEST_BASIC>
-0.18124472898452904

> <JCHEM_POLAR_SURFACE_AREA>
91.32000000000001

> <JCHEM_REFRACTIVITY>
118.082

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6R)-N-[(1S,2R,4'S,5R,5'S,6S)-4-chloro-5,5'-dihydroxy-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0     -16.721  15.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.816  16.341   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.285  16.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.658  14.773   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -14.564  13.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -16.095  13.688   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -15.469  12.281   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -12.628  15.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -11.221  15.291   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.382  13.759   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -12.888  13.439   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0     -10.238  12.729   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -9.887  16.061   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -8.554  15.291   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.554  13.751   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -7.220  16.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.886  15.291   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.553  16.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.219  15.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.885  16.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.552  15.291   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.782  16.061   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.116  15.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.449  16.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.783  15.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.117  16.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.885  17.601   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.553  17.601   0.000  0.00  0.00           C+0
HETATM   29 Cl   UNK     0     -16.443  17.747   0.000  0.00  0.00          Cl+0
HETATM   30  O   UNK     0     -18.253  15.256   0.000  0.00  0.00           O+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8   11                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    5                                                       
CONECT    8    4    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   20                                                            
CONECT   28   18                                                            
CONECT   29    2                                                            
CONECT   30    1                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
(2E,4E,6R)-N-[(1'b,2R,6'b)-4,5-Dihydro-4'-chloro-5b,5'a-dihydroxy-7'-oxaspiro[furan-2(3H),2'-bicyclo[4.1.0]hept[3]en]-4a-yl]-4,6-dimethyl-2,4-dodecadienamide	Generator
(2E,4E,6R)-N-[(1'Β,2R,6'β)-4,5-dihydro-4'-chloro-5β,5'α-dihydroxy-7'-oxaspiro[furan-2(3H),2'-bicyclo[4.1.0]hept[3]en]-4α-yl]-4,6-dimethyl-2,4-dodecadienamide	Generator

Chemical Formula

C₂₃H₃₄ClNO₅

Average Mass

439.9800 Da

Monoisotopic Mass

439.21255 Da

IUPAC Name

(2E,4E,6R)-N-[(1S,2R,4'S,5R,5'S,6S)-4-chloro-5,5'-dihydroxy-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienamide

Traditional Name

(2E,4E,6R)-N-[(1S,2R,4'S,5R,5'S,6S)-4-chloro-5,5'-dihydroxy-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienamide

CAS Registry Number

Not Available

SMILES

CCCCCC[C@@H](C)\C=C(/C)\C=C\C(=O)N[C@H]1C[C@@]2(O[C@@H]1O)C=C(Cl)[C@H](O)[C@@H]1O[C@H]21

InChI Identifier

InChI=1S/C23H34ClNO5/c1-4-5-6-7-8-14(2)11-15(3)9-10-18(26)25-17-13-23(30-22(17)28)12-16(24)19(27)20-21(23)29-20/h9-12,14,17,19-22,27-28H,4-8,13H2,1-3H3,(H,25,26)/b10-9+,15-11+/t14-,17+,19+,20+,21+,22+,23+/m1/s1

InChI Key

XKJXLFLLICSWJK-MECFWYRWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gymnoascus dankaliensis	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Oxolane
Carboxamide group
Chlorohydrin
Halohydrin
Hemiacetal
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl chloride
Vinyl halide
Hydrocarbon derivative
Alcohol
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
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	3.65	ALOGPS
logP	3.45	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-0.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	91.32 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.08 m³·mol⁻¹	ChemAxon
Polarizability	48.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10282830

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21672331

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gymnastatin E (NP0076609)

MOL for NP0076609 (Gymnastatin E)

3D MOL for NP0076609 (Gymnastatin E)

3D SDF for NP0076609 (Gymnastatin E)

3D-SDF for NP0076609 (Gymnastatin E)

PDB for NP0076609 (Gymnastatin E)

3D PDB for NP0076609 (Gymnastatin E)

SMILES for NP0076609 (Gymnastatin E)

INCHI for NP0076609 (Gymnastatin E)

Structure for NP0076609 (Gymnastatin E)

3D Structure for NP0076609 (Gymnastatin E)