NP-MRD: Showing NP-Card for ukulactone A (NP0040604)

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Record Information

Version

2.0

Created at

2021-06-20 22:43:30 UTC

Updated at

2021-06-30 00:14:36 UTC

NP-MRD ID

NP0040604

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ukulactone A

Provided By

JEOL Database JEOL Logo

Description

(1S,4S,6R,7S)-7-[(1E,3E,5E,7E,9E)-10-[(2S,5R,6R)-5-hydroxy-3,5,6-trimethyl-5,6-dihydro-2H-pyran-2-yl]-2-methylundeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]Heptane-3,5-dione belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. ukulactone A is found in Penicillium sp. FKI-3389. ukulactone A was first documented in 2011 (Mori, M., et al.). Based on a literature review very few articles have been published on (1S,4S,6R,7S)-7-[(1E,3E,5E,7E,9E)-10-[(2S,5R,6R)-5-hydroxy-3,5,6-trimethyl-5,6-dihydro-2H-pyran-2-yl]-2-methylundeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]Heptane-3,5-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100433D          

 72 74  0  0  0  0            999 V2000
   -6.8484   -2.9885    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -1.9189   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1425   -2.0807   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1287   -1.0614   -0.6855 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.3604   -1.7446   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5435   -0.3204    0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4319   -0.1285   -1.7164 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.2623    1.0949   -2.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2128    0.3686   -1.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2256   -0.6623   -0.9558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1043   -0.0441   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    0.5745    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363   -0.0723   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6563    0.4757    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308    0.3716   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.9215    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    0.8151   -0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604    1.3670    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    1.2576   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.7871    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    2.4285    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    1.6460   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1835    2.1392   -0.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8347    1.1548    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430    3.6336    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7749    3.8225    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2506    3.0391   -0.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4181    2.9387   -1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375    2.3722   -1.4859 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3495    1.2010   -2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2671    3.5236   -2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0992    3.7007   -3.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373    4.4247   -1.0192 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2264    5.8533   -1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1853   -3.2598   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3661   -3.9006    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2386   -2.6489    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5439   -2.9629    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1370   -1.0150   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1128   -2.3178   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8192   -2.4276   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7710    0.2221    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1852   -0.6766   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1970    0.8162   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6950    1.7365   -2.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4934    1.7094   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8563   -0.9315   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056    0.8983    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1670    1.4514    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1131   -0.1425    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -0.5497   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.9957    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -0.1428   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860    1.4398    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1120    0.2966   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    1.8881    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742    0.7340   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    3.3878    1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520    2.6082    2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491    1.7784    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6737    1.1032   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.1511    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8103    0.1310    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805    1.3865    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480    3.9360    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4465    0.7761   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8729    0.4065   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999    1.5100   -3.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    4.3790   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974    6.4262   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361    6.3440   -1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3047    5.9098   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  6  0  0  0
  3  2  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 20 21  1  0  0  0  0
  4  7  1  0  0  0  0
 23 25  1  0  0  0  0
 14 15  2  0  0  0  0
 23 24  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  1  0  0  0  0
 15 16  1  0  0  0  0
 25 26  1  0  0  0  0
  9 10  1  0  0  0  0
 26 27  1  0  0  0  0
 27 29  1  0  0  0  0
 16 17  2  0  0  0  0
 29 31  1  0  0  0  0
 10  2  1  0  0  0  0
 25 33  1  0  0  0  0
 33 31  1  0  0  0  0
 17 18  1  0  0  0  0
 23 29  1  0  0  0  0
 27 28  2  0  0  0  0
 18 19  2  0  0  0  0
 31 32  2  0  0  0  0
 10 11  1  0  0  0  0
 29 30  1  6  0  0  0
 19 20  1  0  0  0  0
 33 34  1  0  0  0  0
  3  4  1  0  0  0  0
  7  8  1  0  0  0  0
 20 22  2  0  0  0  0
  4  6  1  1  0  0  0
 11 13  2  0  0  0  0
  4  5  1  0  0  0  0
  3 38  1  0  0  0  0
  7 43  1  6  0  0  0
 10 47  1  6  0  0  0
 13 51  1  0  0  0  0
 14 52  1  0  0  0  0
 15 53  1  0  0  0  0
 16 54  1  0  0  0  0
 17 55  1  0  0  0  0
 18 56  1  0  0  0  0
 19 57  1  0  0  0  0
 22 61  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 21 60  1  0  0  0  0
 25 65  1  1  0  0  0
 24 62  1  0  0  0  0
 24 63  1  0  0  0  0
 24 64  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
 33 69  1  1  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 30 68  1  0  0  0  0
 34 70  1  0  0  0  0
 34 71  1  0  0  0  0
 34 72  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
  8 46  1  0  0  0  0
  6 42  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
M  END

     RDKit          3D

 72 74  0  0  0  0  0  0  0  0999 V2000
   -6.8484   -2.9885    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -1.9189   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1425   -2.0807   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1287   -1.0614   -0.6855 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.3604   -1.7446   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5435   -0.3204    0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4319   -0.1285   -1.7164 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.2623    1.0949   -2.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2128    0.3686   -1.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2256   -0.6623   -0.9558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1043   -0.0441   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    0.5745    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363   -0.0723   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6563    0.4757    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308    0.3716   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.9215    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    0.8151   -0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604    1.3670    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    1.2576   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.7871    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    2.4285    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    1.6460   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1835    2.1392   -0.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8347    1.1548    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430    3.6336    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7749    3.8225    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2506    3.0391   -0.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4181    2.9387   -1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3495    1.2010   -2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2671    3.5236   -2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0992    3.7007   -3.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373    4.4247   -1.0192 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2264    5.8533   -1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1853   -3.2598   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3661   -3.9006    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2386   -2.6489    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5439   -2.9629    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1370   -1.0150   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1128   -2.3178   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8192   -2.4276   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7710    0.2221    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1852   -0.6766   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1970    0.8162   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6950    1.7365   -2.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4934    1.7094   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8563   -0.9315   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056    0.8983    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1670    1.4514    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1131   -0.1425    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -0.5497   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.9957    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -0.1428   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860    1.4398    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4742    0.7340   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    3.3878    1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520    2.6082    2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491    1.7784    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6737    1.1032   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.1511    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8103    0.1310    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805    1.3865    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480    3.9360    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4465    0.7761   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8729    0.4065   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999    1.5100   -3.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    4.3790   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974    6.4262   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361    6.3440   -1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3047    5.9098   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  6
  3  2  2  0
 11 12  1  0
 13 14  1  0
 20 21  1  0
  4  7  1  0
 23 25  1  0
 14 15  2  0
 23 24  1  0
  7  9  1  0
  2  1  1  0
 15 16  1  0
 25 26  1  0
  9 10  1  0
 26 27  1  0
 27 29  1  0
 16 17  2  0
 29 31  1  0
 10  2  1  0
 25 33  1  0
 33 31  1  0
 17 18  1  0
 23 29  1  0
 27 28  2  0
 18 19  2  0
 31 32  2  0
 10 11  1  0
 29 30  1  6
 19 20  1  0
 33 34  1  0
  3  4  1  0
  7  8  1  0
 20 22  2  0
  4  6  1  1
 11 13  2  0
  4  5  1  0
  3 38  1  0
  7 43  1  6
 10 47  1  6
 13 51  1  0
 14 52  1  0
 15 53  1  0
 16 54  1  0
 17 55  1  0
 18 56  1  0
 19 57  1  0
 22 61  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 21 58  1  0
 21 59  1  0
 21 60  1  0
 25 65  1  1
 24 62  1  0
 24 63  1  0
 24 64  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 33 69  1  1
 30 66  1  0
 30 67  1  0
 30 68  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  6 42  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
M  END


  Mrv1652306212100433D          

 72 74  0  0  0  0            999 V2000
   -6.8484   -2.9885    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -1.9189   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1425   -2.0807   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1287   -1.0614   -0.6855 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.3604   -1.7446   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5435   -0.3204    0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4319   -0.1285   -1.7164 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.2623    1.0949   -2.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2128    0.3686   -1.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2256   -0.6623   -0.9558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1043   -0.0441   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    0.5745    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363   -0.0723   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6563    0.4757    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308    0.3716   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.9215    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    0.8151   -0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604    1.3670    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    1.2576   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.7871    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    2.4285    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    1.6460   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1835    2.1392   -0.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8347    1.1548    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430    3.6336    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7749    3.8225    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2506    3.0391   -0.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4181    2.9387   -1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375    2.3722   -1.4859 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3495    1.2010   -2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2671    3.5236   -2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0992    3.7007   -3.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373    4.4247   -1.0192 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2264    5.8533   -1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1853   -3.2598   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3661   -3.9006    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2386   -2.6489    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5439   -2.9629    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1370   -1.0150   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1128   -2.3178   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8192   -2.4276   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7710    0.2221    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1852   -0.6766   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1970    0.8162   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6950    1.7365   -2.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4934    1.7094   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8563   -0.9315   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056    0.8983    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1670    1.4514    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1131   -0.1425    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -0.5497   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.9957    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -0.1428   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860    1.4398    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1120    0.2966   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    1.8881    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742    0.7340   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    3.3878    1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520    2.6082    2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491    1.7784    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6737    1.1032   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.1511    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8103    0.1310    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805    1.3865    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480    3.9360    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4465    0.7761   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8729    0.4065   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999    1.5100   -3.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    4.3790   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974    6.4262   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361    6.3440   -1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3047    5.9098   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  6  0  0  0
  3  2  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 20 21  1  0  0  0  0
  4  7  1  0  0  0  0
 23 25  1  0  0  0  0
 14 15  2  0  0  0  0
 23 24  1  0  0  0  0
  7  9  1  0  0  0  0
  2  1  1  0  0  0  0
 15 16  1  0  0  0  0
 25 26  1  0  0  0  0
  9 10  1  0  0  0  0
 26 27  1  0  0  0  0
 27 29  1  0  0  0  0
 16 17  2  0  0  0  0
 29 31  1  0  0  0  0
 10  2  1  0  0  0  0
 25 33  1  0  0  0  0
 33 31  1  0  0  0  0
 17 18  1  0  0  0  0
 23 29  1  0  0  0  0
 27 28  2  0  0  0  0
 18 19  2  0  0  0  0
 31 32  2  0  0  0  0
 10 11  1  0  0  0  0
 29 30  1  6  0  0  0
 19 20  1  0  0  0  0
 33 34  1  0  0  0  0
  3  4  1  0  0  0  0
  7  8  1  0  0  0  0
 20 22  2  0  0  0  0
  4  6  1  1  0  0  0
 11 13  2  0  0  0  0
  4  5  1  0  0  0  0
  3 38  1  0  0  0  0
  7 43  1  6  0  0  0
 10 47  1  6  0  0  0
 13 51  1  0  0  0  0
 14 52  1  0  0  0  0
 15 53  1  0  0  0  0
 16 54  1  0  0  0  0
 17 55  1  0  0  0  0
 18 56  1  0  0  0  0
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 22 61  1  0  0  0  0
 12 48  1  0  0  0  0
 12 49  1  0  0  0  0
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 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 21 60  1  0  0  0  0
 25 65  1  1  0  0  0
 24 62  1  0  0  0  0
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 24 64  1  0  0  0  0
  1 35  1  0  0  0  0
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  1 37  1  0  0  0  0
 33 69  1  1  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 30 68  1  0  0  0  0
 34 70  1  0  0  0  0
 34 71  1  0  0  0  0
 34 72  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
  8 46  1  0  0  0  0
  6 42  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040604

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O5/c1-18(16-27(6)25-21(4)24(30)29(27,8)26(31)34-25)14-12-10-9-11-13-15-19(2)23-20(3)17-28(7,32)22(5)33-23/h9-17,21-23,25,32H,1-8H3/b10-9+,13-11+,14-12+,18-16+,19-15+/t21-,22+,23-,25-,27+,28+,29-/m0/s1

> <INCHI_KEY>
RHXSRISAJFLIHS-WQEIKUNISA-N

> <FORMULA>
C29H38O5

> <MOLECULAR_WEIGHT>
466.618

> <EXACT_MASS>
466.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.9223776833431

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,6R,7S)-7-[(1E,3E,5E,7E,9E)-10-[(2S,5R,6R)-5-hydroxy-3,5,6-trimethyl-5,6-dihydro-2H-pyran-2-yl]-2-methylundeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

> <ALOGPS_LOGP>
5.30

> <JCHEM_LOGP>
5.264730870999999

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.730911654796067

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.665224030270707

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3824675022254054

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
139.91080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6R,7S)-7-[(1E,3E,5E,7E,9E)-10-[(2S,5R,6R)-5-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]-2-methylundeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 74  0  0  0  0  0  0  0  0999 V2000
   -6.8484   -2.9885    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -1.9189   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1425   -2.0807   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1287   -1.0614   -0.6855 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.3604   -1.7446   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5435   -0.3204    0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4319   -0.1285   -1.7164 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.2623    1.0949   -2.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2128    0.3686   -1.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2256   -0.6623   -0.9558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1043   -0.0441   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    0.5745    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363   -0.0723   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6563    0.4757    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308    0.3716   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.9215    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    0.8151   -0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604    1.3670    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    1.2576   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.7871    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    2.4285    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    1.6460   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1835    2.1392   -0.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8347    1.1548    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430    3.6336    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7749    3.8225    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2506    3.0391   -0.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4181    2.9387   -1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375    2.3722   -1.4859 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3495    1.2010   -2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2671    3.5236   -2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0992    3.7007   -3.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373    4.4247   -1.0192 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2264    5.8533   -1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1853   -3.2598   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3661   -3.9006    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.5439   -2.9629    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1370   -1.0150   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1128   -2.3178   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8192   -2.4276   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7710    0.2221    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1852   -0.6766   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1970    0.8162   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6950    1.7365   -2.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4934    1.7094   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8563   -0.9315   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056    0.8983    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1670    1.4514    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1131   -0.1425    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -0.5497   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.9957    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -0.1428   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860    1.4398    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1120    0.2966   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    1.8881    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742    0.7340   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    3.3878    1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520    2.6082    2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491    1.7784    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6737    1.1032   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.1511    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8103    0.1310    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805    1.3865    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480    3.9360    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4465    0.7761   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8729    0.4065   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999    1.5100   -3.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    4.3790   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974    6.4262   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361    6.3440   -1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3047    5.9098   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  6
  3  2  2  0
 11 12  1  0
 13 14  1  0
 20 21  1  0
  4  7  1  0
 23 25  1  0
 14 15  2  0
 23 24  1  0
  7  9  1  0
  2  1  1  0
 15 16  1  0
 25 26  1  0
  9 10  1  0
 26 27  1  0
 27 29  1  0
 16 17  2  0
 29 31  1  0
 10  2  1  0
 25 33  1  0
 33 31  1  0
 17 18  1  0
 23 29  1  0
 27 28  2  0
 18 19  2  0
 31 32  2  0
 10 11  1  0
 29 30  1  6
 19 20  1  0
 33 34  1  0
  3  4  1  0
  7  8  1  0
 20 22  2  0
  4  6  1  1
 11 13  2  0
  4  5  1  0
  3 38  1  0
  7 43  1  6
 10 47  1  6
 13 51  1  0
 14 52  1  0
 15 53  1  0
 16 54  1  0
 17 55  1  0
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 22 61  1  0
 12 48  1  0
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 21 58  1  0
 21 59  1  0
 21 60  1  0
 25 65  1  1
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 24 63  1  0
 24 64  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 33 69  1  1
 30 66  1  0
 30 67  1  0
 30 68  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  6 42  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.848  -2.989   0.113  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.812  -1.919  -0.321  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.143  -2.081  -0.178  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.129  -1.061  -0.686  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.360  -1.745  -1.278  0.00  0.00           C+0
HETATM    6  O   UNK     0     -10.543  -0.320   0.463  0.00  0.00           O+0
HETATM    7  C   UNK     0      -9.432  -0.129  -1.716  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.262   1.095  -2.094  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.213   0.369  -1.136  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.226  -0.662  -0.956  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.104  -0.044  -0.128  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.538   0.575   1.179  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.836  -0.072  -0.593  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.656   0.476   0.043  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.431   0.372  -0.496  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.248   0.922   0.132  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.023   0.815  -0.405  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.160   1.367   0.222  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.386   1.258  -0.318  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.636   1.787   0.237  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.569   2.429   1.599  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.764   1.646  -0.493  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.184   2.139  -0.205  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.835   1.155   0.787  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.343   3.634   0.170  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.775   3.822   0.160  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.251   3.039  -0.872  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.418   2.939  -1.195  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.037   2.372  -1.486  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.349   1.201  -2.385  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.267   3.524  -2.121  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.099   3.701  -3.318  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.737   4.425  -1.019  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.226   5.853  -1.151  0.00  0.00           C+0
HETATM   35  H   UNK     0      -6.185  -3.260  -0.715  0.00  0.00           H+0
HETATM   36  H   UNK     0      -7.366  -3.901   0.429  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.239  -2.649   0.956  0.00  0.00           H+0
HETATM   38  H   UNK     0      -9.544  -2.963   0.314  0.00  0.00           H+0
HETATM   39  H   UNK     0     -12.137  -1.015  -1.531  0.00  0.00           H+0
HETATM   40  H   UNK     0     -11.113  -2.318  -2.178  0.00  0.00           H+0
HETATM   41  H   UNK     0     -11.819  -2.428  -0.553  0.00  0.00           H+0
HETATM   42  H   UNK     0      -9.771   0.222   0.711  0.00  0.00           H+0
HETATM   43  H   UNK     0      -9.185  -0.677  -2.636  0.00  0.00           H+0
HETATM   44  H   UNK     0     -11.197   0.816  -2.588  0.00  0.00           H+0
HETATM   45  H   UNK     0      -9.695   1.736  -2.778  0.00  0.00           H+0
HETATM   46  H   UNK     0     -10.493   1.709  -1.218  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.856  -0.932  -1.954  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.706   0.898   1.807  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.167   1.451   0.995  0.00  0.00           H+0
HETATM   50  H   UNK     0      -7.113  -0.143   1.773  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.655  -0.550  -1.557  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.776   0.996   0.988  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.293  -0.143  -1.445  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.386   1.440   1.078  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.112   0.297  -1.352  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.008   1.888   1.163  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.474   0.734  -1.270  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.044   3.388   1.547  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.552   2.608   2.036  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.049   1.778   2.311  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.674   1.103  -1.437  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.306   1.151   1.746  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.810   0.131   0.396  0.00  0.00           H+0
HETATM   64  H   UNK     0       7.880   1.387   1.011  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.948   3.936   1.141  0.00  0.00           H+0
HETATM   66  H   UNK     0       6.447   0.776  -2.833  0.00  0.00           H+0
HETATM   67  H   UNK     0       7.873   0.407  -1.843  0.00  0.00           H+0
HETATM   68  H   UNK     0       8.000   1.510  -3.211  0.00  0.00           H+0
HETATM   69  H   UNK     0       4.644   4.379  -1.007  0.00  0.00           H+0
HETATM   70  H   UNK     0       5.997   6.426  -0.247  0.00  0.00           H+0
HETATM   71  H   UNK     0       5.736   6.344  -1.999  0.00  0.00           H+0
HETATM   72  H   UNK     0       7.305   5.910  -1.333  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    3    1   10                                                  
CONECT    3    2    4   38                                                  
CONECT    4    7    3    6    5                                             
CONECT    5    4   39   40   41                                             
CONECT    6    4   42                                                       
CONECT    7    4    9    8   43                                             
CONECT    8    7   44   45   46                                             
CONECT    9    7   10                                                       
CONECT   10    9    2   11   47                                             
CONECT   11   12   10   13                                                  
CONECT   12   11   48   49   50                                             
CONECT   13   14   11   51                                                  
CONECT   14   13   15   52                                                  
CONECT   15   14   16   53                                                  
CONECT   16   15   17   54                                                  
CONECT   17   16   18   55                                                  
CONECT   18   17   19   56                                                  
CONECT   19   18   20   57                                                  
CONECT   20   21   19   22                                                  
CONECT   21   20   58   59   60                                             
CONECT   22   23   20   61                                                  
CONECT   23   22   25   24   29                                             
CONECT   24   23   62   63   64                                             
CONECT   25   23   26   33   65                                             
CONECT   26   25   27                                                       
CONECT   27   26   29   28                                                  
CONECT   28   27                                                            
CONECT   29   27   31   23   30                                             
CONECT   30   29   66   67   68                                             
CONECT   31   29   33   32                                                  
CONECT   32   31                                                            
CONECT   33   25   31   34   69                                             
CONECT   34   33   70   71   72                                             
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47   10                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   16                                                            
CONECT   55   17                                                            
CONECT   56   18                                                            
CONECT   57   19                                                            
CONECT   58   21                                                            
CONECT   59   21                                                            
CONECT   60   21                                                            
CONECT   61   22                                                            
CONECT   62   24                                                            
CONECT   63   24                                                            
CONECT   64   24                                                            
CONECT   65   25                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   30                                                            
CONECT   69   33                                                            
CONECT   70   34                                                            
CONECT   71   34                                                            
CONECT   72   34                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  148    0
END

RDKit          3D

72 74  0  0  0  0  0  0  0  0999 V2000
   -6.8484   -2.9885    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8121   -1.9189   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1425   -2.0807   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1287   -1.0614   -0.6855 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.3604   -1.7446   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5435   -0.3204    0.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4319   -0.1285   -1.7164 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.2623    1.0949   -2.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2128    0.3686   -1.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2256   -0.6623   -0.9558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1043   -0.0441   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5376    0.5745    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363   -0.0723   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6563    0.4757    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4308    0.3716   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482    0.9215    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    0.8151   -0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1604    1.3670    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    1.2576   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.7871    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    2.4285    1.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7642    1.6460   -0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1835    2.1392   -0.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8347    1.1548    0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3430    3.6336    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7749    3.8225    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2506    3.0391   -0.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4181    2.9387   -1.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375    2.3722   -1.4859 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3495    1.2010   -2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2671    3.5236   -2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0992    3.7007   -3.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373    4.4247   -1.0192 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2264    5.8533   -1.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1853   -3.2598   -0.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3661   -3.9006    0.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2386   -2.6489    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5439   -2.9629    0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1370   -1.0150   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1128   -2.3178   -2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8192   -2.4276   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7710    0.2221    0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1852   -0.6766   -2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1970    0.8162   -2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6950    1.7365   -2.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4934    1.7094   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8563   -0.9315   -1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7056    0.8983    1.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1670    1.4514    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1131   -0.1425    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548   -0.5497   -1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763    0.9957    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2932   -0.1428   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860    1.4398    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1120    0.2966   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    1.8881    1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742    0.7340   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439    3.3878    1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520    2.6082    2.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491    1.7784    2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6737    1.1032   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3057    1.1511    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8103    0.1310    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805    1.3865    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9480    3.9360    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4465    0.7761   -2.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8729    0.4065   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999    1.5100   -3.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    4.3790   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974    6.4262   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7361    6.3440   -1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3047    5.9098   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  6
  3  2  2  0
 11 12  1  0
 13 14  1  0
 20 21  1  0
  4  7  1  0
 23 25  1  0
 14 15  2  0
 23 24  1  0
  7  9  1  0
  2  1  1  0
 15 16  1  0
 25 26  1  0
  9 10  1  0
 26 27  1  0
 27 29  1  0
 16 17  2  0
 29 31  1  0
 10  2  1  0
 25 33  1  0
 33 31  1  0
 17 18  1  0
 23 29  1  0
 27 28  2  0
 18 19  2  0
 31 32  2  0
 10 11  1  0
 29 30  1  6
 19 20  1  0
 33 34  1  0
  3  4  1  0
  7  8  1  0
 20 22  2  0
  4  6  1  1
 11 13  2  0
  4  5  1  0
  3 38  1  0
  7 43  1  6
 10 47  1  6
 13 51  1  0
 14 52  1  0
 15 53  1  0
 16 54  1  0
 17 55  1  0
 18 56  1  0
 19 57  1  0
 22 61  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 21 58  1  0
 21 59  1  0
 21 60  1  0
 25 65  1  1
 24 62  1  0
 24 63  1  0
 24 64  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 33 69  1  1
 30 66  1  0
 30 67  1  0
 30 68  1  0
 34 70  1  0
 34 71  1  0
 34 72  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  6 42  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈O₅

Average Mass

466.6180 Da

Monoisotopic Mass

466.27192 Da

IUPAC Name

(1S,4S,6R,7S)-7-[(1E,3E,5E,7E,9E)-10-[(2S,5R,6R)-5-hydroxy-3,5,6-trimethyl-5,6-dihydro-2H-pyran-2-yl]-2-methylundeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

Traditional Name

(1S,4S,6R,7S)-7-[(1E,3E,5E,7E,9E)-10-[(2S,5R,6R)-5-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]-2-methylundeca-1,3,5,7,9-pentaen-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C([H])=C(C([H])([H])[H])[C@@]([H])(O[C@]1([H])C([H])([H])[H])C(=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(=C(/[H])[C@]1(C([H])([H])[H])[C@@]2([H])OC(=O)[C@@]1(C(=O)[C@]2([H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C29H38O5/c1-18(16-27(6)25-21(4)24(30)29(27,8)26(31)34-25)14-12-10-9-11-13-15-19(2)23-20(3)17-28(7,32)22(5)33-23/h9-17,21-23,25,32H,1-8H3/b10-9+,13-11+,14-12+,18-16+,19-15+/t21-,22+,23-,25-,27+,28+,29-/m0/s1

InChI Key

RHXSRISAJFLIHS-WQEIKUNISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium sp. FKI-3389	JEOL database	Mori, M., et al, Tetrahedron, 67, 6582 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	5.3	ALOGPS
logP	5.26	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.67	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.91 m³·mol⁻¹	ChemAxon
Polarizability	54.92 Å³	ChemAxon
Number of Rings	3	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

76823601

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54590540

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mori, M., et al. (2011). Mori, M., et al, Tetrahedron, 67, 6582 (2011). Tetrahedron.

Showing NP-Card for ukulactone A (NP0040604)

MOL for NP0040604 (ukulactone A)

3D MOL for NP0040604 (ukulactone A)

3D SDF for NP0040604 (ukulactone A)

3D-SDF for NP0040604 (ukulactone A)

PDB for NP0040604 (ukulactone A)

3D PDB for NP0040604 (ukulactone A)

SMILES for NP0040604 (ukulactone A)

INCHI for NP0040604 (ukulactone A)

Structure for NP0040604 (ukulactone A)

3D Structure for NP0040604 (ukulactone A)