NP-MRD: Showing NP-Card for Cis-Fumagillin (NP0003511)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 00:44:18 UTC

Updated at

2021-07-15 16:46:36 UTC

NP-MRD ID

NP0003511

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cis-Fumagillin

Provided By

NPAtlas

Description

(3S,4S,5S,6R)-5-methoxy-4-[(3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]Octan-6-yl 10-methyl (2Z,4E,6E,8E)-deca-2,4,6,8-tetraenedioate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Cis-Fumagillin is found in Penicillium and Penicillium janczewskii sp. F2757. Cis-Fumagillin was first documented in 2000 (PMID: 11079802). Based on a literature review very few articles have been published on (3S,4S,5S,6R)-5-methoxy-4-[(3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]Octan-6-yl 10-methyl (2Z,4E,6E,8E)-deca-2,4,6,8-tetraenedioate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 70 72  0  0  0  0            999 V2000
    4.0996    2.2193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.8276    1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.4376    2.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7854    1.3301    3.4677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1192   -0.9666    2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -1.8991    2.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -2.9680    1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672   -2.8290   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180   -2.7978   -1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -1.8028   -2.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -1.1375   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.0442   -3.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590    0.6683   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9023   -2.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.0666   -1.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230    0.3522   -0.0129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1758   -0.8304    0.7821 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0611   -1.7920    0.7545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0951   -1.3470   -0.0334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9870   -2.3115   -0.6630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8967   -1.7394   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    0.1088    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0914    0.4922    1.3382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1782    0.4647    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.0470    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.3540    1.4631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0127    2.1317    0.4951 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7330    1.6371   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753    0.5741   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0178    0.4240   -2.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6475   -0.5641   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    0.9327   -0.3399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3181    1.4339   -1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6041    2.8313   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    2.6176    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    2.3606    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    2.7612    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559   -1.2284    3.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -2.6703    3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261   -4.0213    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7251   -1.4977    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -3.6679   -2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -1.0045   -1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.5312   -4.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722    0.4241   -4.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228    1.2935    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -1.4684    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.5460    1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -2.7794    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -2.1413    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -3.3787   -0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -2.0532   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.2953   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.5151    3.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214    1.1533    3.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231    0.9216    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289    1.7461    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    3.0744    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791    2.6907    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964    2.3884   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2528   -2.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0650    0.0207   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0780    1.4330   -2.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8533   -1.3403   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8553   -0.2416    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884   -1.1292   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    1.8223    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    3.2992   -2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    3.2755   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    2.9821   -1.1405 H   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 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  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  3  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 16  1  0  0  0  0
 19 21  1  6  0  0  0
 26 23  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6 39  1  0  0  0  0
  7 40  1  0  0  0  0
  8 41  1  0  0  0  0
  9 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  0  0  0  0
 12 45  1  0  0  0  0
 16 46  1  1  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 20 51  1  0  0  0  0
 20 52  1  0  0  0  0
 22 53  1  6  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 24 56  1  0  0  0  0
 26 57  1  1  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 28 60  1  0  0  0  0
 30 61  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 31 64  1  0  0  0  0
 31 65  1  0  0  0  0
 31 66  1  0  0  0  0
 32 67  1  1  0  0  0
 34 68  1  0  0  0  0
 34 69  1  0  0  0  0
 34 70  1  0  0  0  0
M  END

     RDKit          3D

 70 72  0  0  0  0  0  0  0  0999 V2000
    4.0996    2.2193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.8276    1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.4376    2.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7854    1.3301    3.4677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1192   -0.9666    2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -1.8991    2.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -2.9680    1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672   -2.8290   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180   -2.7978   -1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -1.8028   -2.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -1.1375   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.0442   -3.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590    0.6683   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9023   -2.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.0666   -1.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230    0.3522   -0.0129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1758   -0.8304    0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611   -1.7920    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951   -1.3470   -0.0334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9870   -2.3115   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -1.7394   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    0.1088    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0914    0.4922    1.3382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1782    0.4647    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.0470    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.3540    1.4631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0127    2.1317    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7330    1.6371   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753    0.5741   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0178    0.4240   -2.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6475   -0.5641   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    0.9327   -0.3399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3181    1.4339   -1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6041    2.8313   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    2.6176    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    2.3606    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    2.7612    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559   -1.2284    3.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -2.6703    3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261   -4.0213    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7251   -1.4977    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -3.6679   -2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -1.0045   -1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.5312   -4.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722    0.4241   -4.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228    1.2935    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -1.4684    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.5460    1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -2.7794    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -2.1413    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -3.3787   -0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -2.0532   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.2953   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.5151    3.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214    1.1533    3.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231    0.9216    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289    1.7461    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    3.0744    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791    2.6907    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964    2.3884   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2528   -2.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0650    0.0207   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0780    1.4330   -2.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8533   -1.3403   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8553   -0.2416    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884   -1.1292   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    1.8223    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    3.2992   -2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    3.2755   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    2.9821   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
  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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 22 32  1  0
 32 33  1  0
 33 34  1  0
 32 16  1  0
 19 21  1  6
 26 23  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 22 53  1  6
 24 54  1  0
 24 55  1  0
 24 56  1  0
 26 57  1  1
 27 58  1  0
 27 59  1  0
 28 60  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 31 66  1  0
 32 67  1  1
 34 68  1  0
 34 69  1  0
 34 70  1  0
M  END


  Mrv1652306242117483D          

 70 72  0  0  0  0            999 V2000
    4.0996    2.2193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.8276    1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.4376    2.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7854    1.3301    3.4677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1192   -0.9666    2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -1.8991    2.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -2.9680    1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672   -2.8290   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180   -2.7978   -1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -1.8028   -2.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -1.1375   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.0442   -3.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590    0.6683   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9023   -2.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.0666   -1.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230    0.3522   -0.0129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1758   -0.8304    0.7821 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0611   -1.7920    0.7545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0951   -1.3470   -0.0334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9870   -2.3115   -0.6630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8967   -1.7394   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    0.1088    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0914    0.4922    1.3382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1782    0.4647    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.0470    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.3540    1.4631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0127    2.1317    0.4951 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7330    1.6371   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753    0.5741   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0178    0.4240   -2.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6475   -0.5641   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    0.9327   -0.3399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3181    1.4339   -1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6041    2.8313   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    2.6176    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    2.3606    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    2.7612    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559   -1.2284    3.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -2.6703    3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261   -4.0213    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7251   -1.4977    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -3.6679   -2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -1.0045   -1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.5312   -4.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722    0.4241   -4.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228    1.2935    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -1.4684    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.5460    1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -2.7794    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -2.1413    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -3.3787   -0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -2.0532   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.2953   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.5151    3.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214    1.1533    3.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231    0.9216    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289    1.7461    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    3.0744    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791    2.6907    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964    2.3884   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2528   -2.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0650    0.0207   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0780    1.4330   -2.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8533   -1.3403   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8553   -0.2416    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884   -1.1292   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    1.8223    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    3.2992   -2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    3.2755   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    2.9821   -1.1405 H   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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 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  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  3  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 16  1  0  0  0  0
 19 21  1  6  0  0  0
 26 23  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6 39  1  0  0  0  0
  7 40  1  0  0  0  0
  8 41  1  0  0  0  0
  9 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  0  0  0  0
 12 45  1  0  0  0  0
 16 46  1  1  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 20 51  1  0  0  0  0
 20 52  1  0  0  0  0
 22 53  1  6  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 24 56  1  0  0  0  0
 26 57  1  1  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
 28 60  1  0  0  0  0
 30 61  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 31 64  1  0  0  0  0
 31 65  1  0  0  0  0
 31 66  1  0  0  0  0
 32 67  1  1  0  0  0
 34 68  1  0  0  0  0
 34 69  1  0  0  0  0
 34 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003511

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(\C(\[H])=C(/[H])\C(\[H])=C(\[H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@]2(OC2([H])[H])[C@]([H])([C@]1([H])OC([H])([H])[H])[C@@]1(O[C@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])=C(\[H])/C(/[H])=C(\[H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O7/c1-19(2)14-15-21-26(3,34-21)25-24(31-5)20(16-17-27(25)18-32-27)33-23(29)13-11-9-7-6-8-10-12-22(28)30-4/h6-14,20-21,24-25H,15-18H2,1-5H3/b8-6+,9-7+,12-10-,13-11-/t20-,21-,24-,25-,26-,27-/m1/s1

> <INCHI_KEY>
NWHKXUNHXNCFFG-ZAXOMQPBSA-N

> <FORMULA>
C27H36O7

> <MOLECULAR_WEIGHT>
472.578

> <EXACT_MASS>
472.246103499

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.83768557674101

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5S,6R)-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl 10-methyl (2Z,4E,6E,8E)-deca-2,4,6,8-tetraenedioate

> <ALOGPS_LOGP>
5.59

> <JCHEM_LOGP>
4.427882393666666

> <ALOGPS_LOGS>
-5.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7142131524317636

> <JCHEM_POLAR_SURFACE_AREA>
86.89000000000001

> <JCHEM_REFRACTIVITY>
133.1439

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5S,6R)-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl 10-methyl (2Z,4E,6E,8E)-deca-2,4,6,8-tetraenedioate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 72  0  0  0  0  0  0  0  0999 V2000
    4.0996    2.2193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.8276    1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.4376    2.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7854    1.3301    3.4677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1192   -0.9666    2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -1.8991    2.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -2.9680    1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672   -2.8290   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180   -2.7978   -1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -1.8028   -2.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -1.1375   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.0442   -3.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590    0.6683   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9023   -2.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.0666   -1.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230    0.3522   -0.0129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1758   -0.8304    0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611   -1.7920    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951   -1.3470   -0.0334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9870   -2.3115   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -1.7394   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    0.1088    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0914    0.4922    1.3382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1782    0.4647    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.0470    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.3540    1.4631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0127    2.1317    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7330    1.6371   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753    0.5741   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0178    0.4240   -2.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6475   -0.5641   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    0.9327   -0.3399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3181    1.4339   -1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6041    2.8313   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    2.6176    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    2.3606    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    2.7612    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559   -1.2284    3.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -2.6703    3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261   -4.0213    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7251   -1.4977    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -3.6679   -2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -1.0045   -1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.5312   -4.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722    0.4241   -4.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228    1.2935    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -1.4684    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.5460    1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -2.7794    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -2.1413    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -3.3787   -0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -2.0532   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.2953   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.5151    3.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214    1.1533    3.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231    0.9216    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289    1.7461    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    3.0744    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791    2.6907    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964    2.3884   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2528   -2.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0650    0.0207   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0780    1.4330   -2.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8533   -1.3403   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8553   -0.2416    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884   -1.1292   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    1.8223    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    3.2992   -2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    3.2755   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    2.9821   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
  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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 22 32  1  0
 32 33  1  0
 33 34  1  0
 32 16  1  0
 19 21  1  6
 26 23  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 22 53  1  6
 24 54  1  0
 24 55  1  0
 24 56  1  0
 26 57  1  1
 27 58  1  0
 27 59  1  0
 28 60  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 31 66  1  0
 32 67  1  1
 34 68  1  0
 34 69  1  0
 34 70  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.100   2.219   0.957  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.150   0.828   1.285  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.000   0.438   2.635  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.785   1.330   3.468  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.119  -0.967   2.975  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.268  -1.899   2.107  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.436  -2.968   1.289  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.367  -2.829  -0.018  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.318  -2.798  -1.370  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.914  -1.803  -2.101  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644  -1.137  -3.226  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.955  -0.044  -3.329  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.259   0.668  -2.283  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.038   1.902  -2.461  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.816   0.067  -1.216  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.123   0.352  -0.013  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.176  -0.830   0.782  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.061  -1.792   0.755  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.095  -1.347  -0.033  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.987  -2.312  -0.663  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.897  -1.739  -1.462  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.451   0.109   0.054  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.091   0.492   1.338  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.178   0.465   2.587  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.361  -0.047   1.548  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.264   1.354   1.463  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.013   2.132   0.495  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.733   1.637  -0.659  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.375   0.574  -0.935  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.018   0.424  -2.307  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.648  -0.564  -0.034  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.261   0.933  -0.340  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.318   1.434  -1.599  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.604   2.831  -1.569  0.00  0.00           C+0
HETATM   35  H   UNK     0       5.133   2.618   0.987  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.627   2.361   0.002  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.595   2.761   1.809  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.956  -1.228   3.975  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.731  -2.670   3.216  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.626  -4.021   1.421  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.725  -1.498   0.173  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.561  -3.668  -2.035  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.523  -1.004  -1.195  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.089  -1.531  -4.226  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.872   0.424  -4.352  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.623   1.294   0.364  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.087  -1.468   0.462  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.433  -0.546   1.857  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.411  -2.779   0.304  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.238  -2.141   1.785  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.901  -3.379  -0.414  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.933  -2.053  -1.196  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.228   0.295  -0.767  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.269  -0.515   3.033  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.721   1.153   3.345  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.223   0.922   2.438  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.429   1.746   2.545  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.413   3.074   0.261  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.879   2.691   1.093  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.696   2.388  -1.537  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.435  -0.253  -2.926  0.00  0.00           H+0
HETATM   62  H   UNK     0      -7.065   0.021  -2.168  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.078   1.433  -2.745  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.853  -1.340  -0.125  0.00  0.00           H+0
HETATM   65  H   UNK     0      -5.855  -0.242   0.987  0.00  0.00           H+0
HETATM   66  H   UNK     0      -6.588  -1.129  -0.370  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.368   1.822   0.370  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.555   3.299  -2.549  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.108   3.276  -0.802  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.608   2.982  -1.141  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   38                                                  
CONECT    6    5    7   39                                                  
CONECT    7    6    8   40                                                  
CONECT    8    7    9   41                                                  
CONECT    9    8   10   42                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10   12   44                                                  
CONECT   12   11   13   45                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   32   46                                             
CONECT   17   16   18   47   48                                             
CONECT   18   17   19   49   50                                             
CONECT   19   18   20   22   21                                             
CONECT   20   19   21   51   52                                             
CONECT   21   20   19                                                       
CONECT   22   19   23   32   53                                             
CONECT   23   22   24   25   26                                             
CONECT   24   23   54   55   56                                             
CONECT   25   23   26                                                       
CONECT   26   25   27   23   57                                             
CONECT   27   26   28   58   59                                             
CONECT   28   27   29   60                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   61   62   63                                             
CONECT   31   29   64   65   66                                             
CONECT   32   22   33   16   67                                             
CONECT   33   32   34                                                       
CONECT   34   33   68   69   70                                             
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   22                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   31                                                            
CONECT   66   31                                                            
CONECT   67   32                                                            
CONECT   68   34                                                            
CONECT   69   34                                                            
CONECT   70   34                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  144    0
END

RDKit          3D

70 72  0  0  0  0  0  0  0  0999 V2000
    4.0996    2.2193    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.8276    1.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.4376    2.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7854    1.3301    3.4677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1192   -0.9666    2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -1.8991    2.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -2.9680    1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3672   -2.8290   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3180   -2.7978   -1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140   -1.8028   -2.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -1.1375   -3.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.0442   -3.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590    0.6683   -2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0377    1.9023   -2.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8164    0.0666   -1.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230    0.3522   -0.0129 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1758   -0.8304    0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611   -1.7920    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951   -1.3470   -0.0334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9870   -2.3115   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -1.7394   -1.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508    0.1088    0.0544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0914    0.4922    1.3382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1782    0.4647    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3610   -0.0470    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2637    1.3540    1.4631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0127    2.1317    0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7330    1.6371   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753    0.5741   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0178    0.4240   -2.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6475   -0.5641   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    0.9327   -0.3399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3181    1.4339   -1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6041    2.8313   -1.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    2.6176    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270    2.3606    0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5951    2.7612    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559   -1.2284    3.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -2.6703    3.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6261   -4.0213    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7251   -1.4977    0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -3.6679   -2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -1.0045   -1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.5312   -4.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8722    0.4241   -4.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228    1.2935    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -1.4684    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.5460    1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113   -2.7794    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -2.1413    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -3.3787   -0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -2.0532   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278    0.2953   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.5151    3.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214    1.1533    3.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2231    0.9216    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289    1.7461    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    3.0744    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8791    2.6907    1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6964    2.3884   -1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2528   -2.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0650    0.0207   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0780    1.4330   -2.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8533   -1.3403   -0.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8553   -0.2416    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884   -1.1292   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    1.8223    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    3.2992   -2.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1079    3.2755   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    2.9821   -1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
  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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
 22 32  1  0
 32 33  1  0
 33 34  1  0
 32 16  1  0
 19 21  1  6
 26 23  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 16 46  1  1
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 20 51  1  0
 20 52  1  0
 22 53  1  6
 24 54  1  0
 24 55  1  0
 24 56  1  0
 26 57  1  1
 27 58  1  0
 27 59  1  0
 28 60  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 31 66  1  0
 32 67  1  1
 34 68  1  0
 34 69  1  0
 34 70  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3S,4S,5S,6R)-5-Methoxy-4-[(3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl 10-methyl (2Z,4E,6E,8E)-deca-2,4,6,8-tetraenedioic acid	Generator

Chemical Formula

C₂₇H₃₆O₇

Average Mass

472.5780 Da

Monoisotopic Mass

472.24610 Da

IUPAC Name

(3S,4S,5S,6R)-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl 10-methyl (2Z,4E,6E,8E)-deca-2,4,6,8-tetraenedioate

Traditional Name

(3S,4S,5S,6R)-5-methoxy-4-[(2S,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl 10-methyl (2Z,4E,6E,8E)-deca-2,4,6,8-tetraenedioate

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](CC[C@@]2(CO2)[C@H]1C1(C)O[C@@H]1CC=C(C)C)OC(=O)\C=C/C=C/C=C/C=C/C(=O)OC

InChI Identifier

InChI=1S/C27H36O7/c1-19(2)14-15-21-26(3,34-21)25-24(31-5)20(16-17-27(25)18-32-27)33-23(29)13-11-9-7-6-8-10-12-22(28)30-4/h6-14,20-21,24-25H,15-18H2,1-5H3/b8-6+,9-7+,12-10+,13-11-/t20-,21-,24-,25-,26?,27-/m1/s1

InChI Key

NWHKXUNHXNCFFG-ZAXOMQPBSA-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
Penicillium	NPAtlas	11079802
Penicillium janczewskii sp. F2757	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.59	ALOGPS
logP	4.43	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.89 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	133.14 m³·mol⁻¹	ChemAxon
Polarizability	50.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA007024

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78440975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585076

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kwon JY, Jeong HW, Kim HK, Kang KH, Chang YH, Bae KS, Choi JD, Lee UC, Son KH, Kwon BM: cis-fumagillin, a new methionine aminopeptidase (type 2) inhibitor produced by Penicillium sp. F2757. J Antibiot (Tokyo). 2000 Aug;53(8):799-806. doi: 10.7164/antibiotics.53.799. [PubMed:11079802 ]

Showing NP-Card for Cis-Fumagillin (NP0003511)

MOL for NP0003511 (Cis-Fumagillin)

3D MOL for NP0003511 (Cis-Fumagillin)

3D SDF for NP0003511 (Cis-Fumagillin)

3D-SDF for NP0003511 (Cis-Fumagillin)

PDB for NP0003511 (Cis-Fumagillin)

3D PDB for NP0003511 (Cis-Fumagillin)

SMILES for NP0003511 (Cis-Fumagillin)

INCHI for NP0003511 (Cis-Fumagillin)

Structure for NP0003511 (Cis-Fumagillin)

3D Structure for NP0003511 (Cis-Fumagillin)