NP-MRD: Showing NP-Card for trichinenlide F (NP0043750)

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Record Information

Version

1.0

Created at

2021-06-21 01:04:21 UTC

Updated at

2021-06-30 00:19:37 UTC

NP-MRD ID

NP0043750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trichinenlide F

Provided By

JEOL Database JEOL Logo

Description

(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]Octadecan-17-yl pyridine-3-carboxylate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. trichinenlide F is found in Trichilia sinensis. It was first documented in 2013 (Xu, J. -B., et al.). Based on a literature review very few articles have been published on (1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0²,⁴.0⁴,¹³.0⁵,¹⁰]Octadecan-17-yl pyridine-3-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212103043D          

 81 87  0  0  0  0            999 V2000
   -0.6514   -5.5161    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -4.7927    1.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -3.7160    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -3.3671   -0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -3.0174    0.4862 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7694   -1.4676    0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5473   -0.7850    1.8467 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3811   -1.4540    2.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841   -0.9229    2.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    0.7512    1.6425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2151    0.8990    1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    1.7749    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    2.4090    3.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2779    1.8885    1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9251    0.9512    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2523    1.1632    0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8927    2.2979    1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3035    3.2122    1.9465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079    2.9874    2.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9518    1.4375    0.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2629    2.7794    0.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083    0.6206    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    1.0842    0.3186 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -0.7851   -0.3999 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2647   -1.5652   -0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039   -0.4969   -1.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2081   -1.7331   -2.7364 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8817   -1.2878   -4.1597 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5735   -0.4526   -4.2641 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8136    0.6680   -5.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172   -1.3867   -4.6988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6076   -1.8244   -6.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -3.0141   -6.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2936   -2.9876   -8.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2794   -0.2738   -2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418   -0.5014   -2.2045 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1881    0.2479   -2.9153 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3478    0.5009   -1.9648 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8359    1.8575   -2.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    1.4973   -0.8231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4517   -4.8718    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -6.3446    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -5.9285    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -3.3402    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624   -3.4147   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383   -1.2578   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5249   -1.5262    2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1299   -0.8814    3.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6715   -0.4113    2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -1.9704    2.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180    1.2670    2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175    0.0568    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7719    0.4611    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9264    2.5070    0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639    3.7475    2.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    3.0509    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -1.0142   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.7275    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085   -2.5411   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.0016   -2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849   -2.3879   -2.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -2.3259   -2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -2.1735   -4.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -0.7048   -4.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    1.3884   -4.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    1.2220   -5.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    0.2696   -6.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -2.3129   -4.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4873   -3.7981   -6.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -3.6531   -8.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6848   -1.5292   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    1.2325   -3.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    1.9892   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 44  1  0  0  0  0
 29 31  1  0  0  0  0
 41 40  1  0  0  0  0
 40 38  1  0  0  0  0
 38 37  1  0  0  0  0
 37 31  1  0  0  0  0
 11 12  1  0  0  0  0
 31 32  1  0  0  0  0
  6  5  1  0  0  0  0
 29 30  1  6  0  0  0
 12 13  2  0  0  0  0
 41 80  1  6  0  0  0
  5  3  1  0  0  0  0
  7  8  1  1  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
 22 23  2  0  0  0  0
  6 50  1  6  0  0  0
 10 11  1  0  0  0  0
 38 39  2  0  0  0  0
 32 36  2  0  0  0  0
 26 42  1  0  0  0  0
  6 24  1  0  0  0  0
  7 10  1  0  0  0  0
 36 35  1  0  0  0  0
 35 34  1  0  0  0  0
 34 33  2  0  0  0  0
 33 32  1  0  0  0  0
 10 20  1  0  0  0  0
  3  4  2  0  0  0  0
 26 27  1  0  0  0  0
  3  2  1  0  0  0  0
 42 41  1  0  0  0  0
  2  1  1  0  0  0  0
 29 28  1  0  0  0  0
 24 25  1  6  0  0  0
 28 27  1  0  0  0  0
 20 21  1  1  0  0  0
 29 41  1  0  0  0  0
 42 43  1  6  0  0  0
 44 43  1  0  0  0  0
 20 22  1  0  0  0  0
 14 15  2  0  0  0  0
 22 24  1  0  0  0  0
 15 16  1  0  0  0  0
 24 26  1  0  0  0  0
 16 17  2  0  0  0  0
 12 14  1  0  0  0  0
 17 18  1  0  0  0  0
 20 44  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 10 57  1  1  0  0  0
 44 81  1  1  0  0  0
  5 48  1  0  0  0  0
  5 49  1  0  0  0  0
 26 66  1  6  0  0  0
 28 69  1  0  0  0  0
 28 70  1  0  0  0  0
 27 67  1  0  0  0  0
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 40 78  1  0  0  0  0
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 31 74  1  1  0  0  0
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  8 51  1  0  0  0  0
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M  END

     RDKit          3D

 81 87  0  0  0  0  0  0  0  0999 V2000
   -0.6514   -5.5161    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -4.7927    1.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -3.7160    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -3.3671   -0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -3.0174    0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -1.4676    0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5473   -0.7850    1.8467 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3811   -1.4540    2.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841   -0.9229    2.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    0.7512    1.6425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2151    0.8990    1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    1.7749    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    2.4090    3.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2779    1.8885    1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9251    0.9512    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2523    1.1632    0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8927    2.2979    1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3035    3.2122    1.9465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079    2.9874    2.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9518    1.4375    0.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2629    2.7794    0.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083    0.6206    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    1.0842    0.3186 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -0.7851   -0.3999 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2647   -1.5652   -0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039   -0.4969   -1.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2081   -1.7331   -2.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8817   -1.2878   -4.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5735   -0.4526   -4.2641 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8136    0.6680   -5.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172   -1.3867   -4.6988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6076   -1.8244   -6.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -3.0141   -6.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2936   -2.9876   -8.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916   -1.8729   -8.3644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -1.1817   -7.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882   -0.7726   -4.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1499   -0.5027   -3.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2794   -0.2738   -2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3478    0.5009   -1.9648 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8359    1.8575   -2.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    1.4973   -0.8231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4517   -4.8718    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -6.3446    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0535   -1.9704    2.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180    1.2670    2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175    0.0568    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7719    0.4611    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9264    2.5070    0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639    3.7475    2.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    3.0509    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -1.0142   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.7275    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085   -2.5411   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.0016   -2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849   -2.3879   -2.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -2.3259   -2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -2.1735   -4.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -0.7048   -4.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    1.3884   -4.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    1.2220   -5.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    0.2696   -6.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -2.3129   -4.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4873   -3.7981   -6.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -3.6531   -8.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -0.2655   -7.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075    0.0146   -1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848   -1.5292   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    1.2325   -3.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    1.9892   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 44  1  0
 29 31  1  0
 41 40  1  0
 40 38  1  0
 38 37  1  0
 37 31  1  0
 11 12  1  0
 31 32  1  0
  6  5  1  0
 29 30  1  6
 12 13  2  0
 41 80  1  6
  5  3  1  0
  7  8  1  1
  6  7  1  0
  7  9  1  0
 22 23  2  0
  6 50  1  6
 10 11  1  0
 38 39  2  0
 32 36  2  0
 26 42  1  0
  6 24  1  0
  7 10  1  0
 36 35  1  0
 35 34  1  0
 34 33  2  0
 33 32  1  0
 10 20  1  0
  3  4  2  0
 26 27  1  0
  3  2  1  0
 42 41  1  0
  2  1  1  0
 29 28  1  0
 24 25  1  6
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 20 21  1  1
 29 41  1  0
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 14 15  2  0
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 15 16  1  0
 24 26  1  0
 16 17  2  0
 12 14  1  0
 17 18  1  0
 20 44  1  0
 18 19  2  0
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 10 57  1  1
 44 81  1  1
  5 48  1  0
  5 49  1  0
 26 66  1  6
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 27 67  1  0
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 40 78  1  0
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 30 72  1  0
 30 73  1  0
  8 51  1  0
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  9 54  1  0
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 33 75  1  0
  1 45  1  0
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 25 63  1  0
 25 64  1  0
 25 65  1  0
 21 62  1  0
 15 58  1  0
 16 59  1  0
 17 60  1  0
 19 61  1  0
M  END


  Mrv1652306212103043D          

 81 87  0  0  0  0            999 V2000
   -0.6514   -5.5161    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -4.7927    1.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -3.7160    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -3.3671   -0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -3.0174    0.4862 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7694   -1.4676    0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5473   -0.7850    1.8467 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3811   -1.4540    2.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841   -0.9229    2.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    0.7512    1.6425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2151    0.8990    1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    1.7749    2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    2.4090    3.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2779    1.8885    1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9251    0.9512    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2523    1.1632    0.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8927    2.2979    1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3035    3.2122    1.9465 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0079    2.9874    2.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9518    1.4375    0.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2629    2.7794    0.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2083    0.6206    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    1.0842    0.3186 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317   -0.7851   -0.3999 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2647   -1.5652   -0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039   -0.4969   -1.8842 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2081   -1.7331   -2.7364 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8817   -1.2878   -4.1597 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5735   -0.4526   -4.2641 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8136    0.6680   -5.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172   -1.3867   -4.6988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6076   -1.8244   -6.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -3.0141   -6.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2936   -2.9876   -8.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9916   -1.8729   -8.3644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -1.1817   -7.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8882   -0.7726   -4.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1499   -0.5027   -3.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2794   -0.2738   -2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418   -0.5014   -2.2045 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1881    0.2479   -2.9153 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3478    0.5009   -1.9648 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8359    1.8575   -2.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    1.4973   -0.8231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4517   -4.8718    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -6.3446    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -5.9285    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -3.3402    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624   -3.4147   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383   -1.2578   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5249   -1.5262    2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -2.4630    2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299   -0.8814    3.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739   -0.4919    3.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0535   -1.9704    2.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180    1.2670    2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175    0.0568    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7719    0.4611    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9264    2.5070    0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639    3.7475    2.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    3.0509    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -1.0142   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.7275    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085   -2.5411   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.0016   -2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849   -2.3879   -2.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -2.3259   -2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -2.1735   -4.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -0.7048   -4.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    1.3884   -4.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    1.2220   -5.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    0.2696   -6.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -2.3129   -4.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4873   -3.7981   -6.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -3.6531   -8.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -0.2655   -7.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075    0.0146   -1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848   -1.5292   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    1.2325   -3.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    1.9892   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 44  1  0  0  0  0
 29 31  1  0  0  0  0
 41 40  1  0  0  0  0
 40 38  1  0  0  0  0
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 37 31  1  0  0  0  0
 11 12  1  0  0  0  0
 31 32  1  0  0  0  0
  6  5  1  0  0  0  0
 29 30  1  6  0  0  0
 12 13  2  0  0  0  0
 41 80  1  6  0  0  0
  5  3  1  0  0  0  0
  7  8  1  1  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
 22 23  2  0  0  0  0
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 10 11  1  0  0  0  0
 38 39  2  0  0  0  0
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 26 42  1  0  0  0  0
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 10 20  1  0  0  0  0
  3  4  2  0  0  0  0
 26 27  1  0  0  0  0
  3  2  1  0  0  0  0
 42 41  1  0  0  0  0
  2  1  1  0  0  0  0
 29 28  1  0  0  0  0
 24 25  1  6  0  0  0
 28 27  1  0  0  0  0
 20 21  1  1  0  0  0
 29 41  1  0  0  0  0
 42 43  1  6  0  0  0
 44 43  1  0  0  0  0
 20 22  1  0  0  0  0
 14 15  2  0  0  0  0
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 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 10 57  1  1  0  0  0
 44 81  1  1  0  0  0
  5 48  1  0  0  0  0
  5 49  1  0  0  0  0
 26 66  1  6  0  0  0
 28 69  1  0  0  0  0
 28 70  1  0  0  0  0
 27 67  1  0  0  0  0
 27 68  1  0  0  0  0
 40 78  1  0  0  0  0
 40 79  1  0  0  0  0
 31 74  1  1  0  0  0
 30 71  1  0  0  0  0
 30 72  1  0  0  0  0
 30 73  1  0  0  0  0
  8 51  1  0  0  0  0
  8 52  1  0  0  0  0
  8 53  1  0  0  0  0
  9 54  1  0  0  0  0
  9 55  1  0  0  0  0
  9 56  1  0  0  0  0
 36 77  1  0  0  0  0
 34 76  1  0  0  0  0
 33 75  1  0  0  0  0
  1 45  1  0  0  0  0
  1 46  1  0  0  0  0
  1 47  1  0  0  0  0
 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 25 65  1  0  0  0  0
 21 62  1  0  0  0  0
 15 58  1  0  0  0  0
 16 59  1  0  0  0  0
 17 60  1  0  0  0  0
 19 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C(=O)[C@@](C([H])([H])[H])([C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])OC(=O)C1=C([H])C([H])=C([H])N=C1[H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@@]3([H])[C@]11O[C@]21[H])C1=C([H])OC([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C33H37NO10/c1-29(2)20(13-22(35)40-5)31(4)19-8-10-30(3)21(14-23(36)42-24(30)18-9-12-41-16-18)33(19)28(44-33)32(39,26(31)38)27(29)43-25(37)17-7-6-11-34-15-17/h6-7,9,11-12,15-16,19-21,24,27-28,39H,8,10,13-14H2,1-5H3/t19-,20+,21-,24+,27+,28-,30-,31-,32+,33-/m1/s1

> <INCHI_KEY>
ZVNCTUYWKIENQR-DTEKRUFUSA-N

> <FORMULA>
C33H37NO10

> <MOLECULAR_WEIGHT>
607.656

> <EXACT_MASS>
607.241746395

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
61.328292997169115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl pyridine-3-carboxylate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.255991474666666

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.110768298047017

> <JCHEM_PKA_STRONGEST_BASIC>
3.2396158799522894

> <JCHEM_POLAR_SURFACE_AREA>
151.46

> <JCHEM_REFRACTIVITY>
150.21650000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 81 87  0  0  0  0  0  0  0  0999 V2000
   -0.6514   -5.5161    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -4.7927    1.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -3.7160    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4253   -3.3671   -0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -3.0174    0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -1.4676    0.4364 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5473   -0.7850    1.8467 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3811   -1.4540    2.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7841   -0.9229    2.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209    0.7512    1.6425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2151    0.8990    1.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6076   -1.8244   -6.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -3.0141   -6.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2936   -2.9876   -8.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8882   -0.7726   -4.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1499   -0.5027   -3.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2794   -0.2738   -2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418   -0.5014   -2.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1881    0.2479   -2.9153 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3478    0.5009   -1.9648 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8359    1.8575   -2.0137 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    1.4973   -0.8231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4517   -4.8718    1.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -6.3446    2.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -5.9285    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -3.3402    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624   -3.4147   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383   -1.2578   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5249   -1.5262    2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -2.4630    2.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299   -0.8814    3.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739   -0.4919    3.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715   -0.4113    2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0535   -1.9704    2.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180    1.2670    2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4175    0.0568    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7719    0.4611    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9264    2.5070    0.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639    3.7475    2.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    3.0509    0.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -1.0142   -0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -1.7275    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2085   -2.5411   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.0016   -2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849   -2.3879   -2.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -2.3259   -2.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396   -2.1735   -4.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7335   -0.7048   -4.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556    1.3884   -4.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    1.2220   -5.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    0.2696   -6.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5752   -2.3129   -4.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4873   -3.7981   -6.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641   -3.6531   -8.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584   -0.2655   -7.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075    0.0146   -1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848   -1.5292   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366    1.2325   -3.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1711    1.9892   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
 42 44  1  0
 29 31  1  0
 41 40  1  0
 40 38  1  0
 38 37  1  0
 37 31  1  0
 11 12  1  0
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  6  5  1  0
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 42 41  1  0
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 29 28  1  0
 24 25  1  6
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 27 67  1  0
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 40 78  1  0
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 31 74  1  1
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 30 72  1  0
 30 73  1  0
  8 51  1  0
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 17 60  1  0
 19 61  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      -0.651  -5.516   1.412  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.578  -4.793   1.335  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.539  -3.716   0.507  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.425  -3.367  -0.160  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.883  -3.017   0.486  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.769  -1.468   0.436  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.547  -0.785   1.847  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.381  -1.454   2.619  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.784  -0.923   2.773  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.221   0.751   1.643  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.215   0.899   1.450  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.864   1.775   2.260  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.380   2.409   3.180  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.278   1.889   1.848  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.925   0.951   1.040  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.252   1.163   0.672  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.893   2.298   1.144  0.00  0.00           C+0
HETATM   18  N   UNK     0      -4.303   3.212   1.946  0.00  0.00           N+0
HETATM   19  C   UNK     0      -3.008   2.987   2.281  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.952   1.438   0.443  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.263   2.779   0.807  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.208   0.621   0.165  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.338   1.084   0.319  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.932  -0.785  -0.400  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.265  -1.565  -0.361  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.504  -0.497  -1.884  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.208  -1.733  -2.736  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.882  -1.288  -4.160  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.574  -0.453  -4.264  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.814   0.668  -5.307  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.617  -1.387  -4.699  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.608  -1.824  -6.139  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.041  -3.014  -6.686  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.294  -2.988  -8.037  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.992  -1.873  -8.364  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.192  -1.182  -7.215  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.888  -0.773  -4.396  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.150  -0.503  -3.095  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.279  -0.274  -2.681  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.942  -0.501  -2.204  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.188   0.248  -2.915  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.348   0.501  -1.965  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.836   1.857  -2.014  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.126   1.497  -0.823  0.00  0.00           C+0
HETATM   45  H   UNK     0      -1.452  -4.872   1.790  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.514  -6.345   2.113  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.914  -5.928   0.433  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.486  -3.340   1.340  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.362  -3.415  -0.413  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.838  -1.258  -0.102  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.525  -1.526   2.009  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.642  -2.463   2.954  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.130  -0.881   3.520  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.574  -0.492   3.760  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.672  -0.411   2.398  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.054  -1.970   2.938  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.518   1.267   2.565  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.418   0.057   0.693  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.772   0.461   0.027  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.926   2.507   0.882  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.564   3.748   2.920  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.011   3.051   0.241  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.062  -1.014  -0.875  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.603  -1.728   0.667  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.208  -2.541  -0.849  0.00  0.00           H+0
HETATM   66  H   UNK     0       3.364  -0.002  -2.363  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.085  -2.388  -2.773  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.384  -2.326  -2.332  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.840  -2.174  -4.801  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.733  -0.705  -4.536  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.556   1.388  -4.943  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.108   1.222  -5.518  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.196   0.270  -6.253  0.00  0.00           H+0
HETATM   74  H   UNK     0      -0.575  -2.313  -4.106  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.487  -3.798  -6.161  0.00  0.00           H+0
HETATM   76  H   UNK     0      -0.064  -3.653  -8.858  0.00  0.00           H+0
HETATM   77  H   UNK     0      -1.758  -0.266  -7.316  0.00  0.00           H+0
HETATM   78  H   UNK     0      -1.208   0.015  -1.278  0.00  0.00           H+0
HETATM   79  H   UNK     0      -0.685  -1.529  -1.944  0.00  0.00           H+0
HETATM   80  H   UNK     0      -0.237   1.232  -3.168  0.00  0.00           H+0
HETATM   81  H   UNK     0       0.171   1.989  -0.691  0.00  0.00           H+0
CONECT    1    2   45   46   47                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3   48   49                                             
CONECT    6    5    7   50   24                                             
CONECT    7    8    6    9   10                                             
CONECT    8    7   51   52   53                                             
CONECT    9    7   54   55   56                                             
CONECT   10   11    7   20   57                                             
CONECT   11   12   10                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   15   12   19                                                  
CONECT   15   14   16   58                                                  
CONECT   16   15   17   59                                                  
CONECT   17   16   18   60                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   61                                                  
CONECT   20   10   21   22   44                                             
CONECT   21   20   62                                                       
CONECT   22   23   20   24                                                  
CONECT   23   22                                                            
CONECT   24    6   25   22   26                                             
CONECT   25   24   63   64   65                                             
CONECT   26   42   27   24   66                                             
CONECT   27   26   28   67   68                                             
CONECT   28   29   27   69   70                                             
CONECT   29   31   30   28   41                                             
CONECT   30   29   71   72   73                                             
CONECT   31   29   37   32   74                                             
CONECT   32   31   36   33                                                  
CONECT   33   34   32   75                                                  
CONECT   34   35   33   76                                                  
CONECT   35   36   34                                                       
CONECT   36   32   35   77                                                  
CONECT   37   38   31                                                       
CONECT   38   40   37   39                                                  
CONECT   39   38                                                            
CONECT   40   41   38   78   79                                             
CONECT   41   40   80   42   29                                             
CONECT   42   44   26   41   43                                             
CONECT   43   42   44                                                       
CONECT   44   42   43   20   81                                             
CONECT   45    1                                                            
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    5                                                            
CONECT   49    5                                                            
CONECT   50    6                                                            
CONECT   51    8                                                            
CONECT   52    8                                                            
CONECT   53    8                                                            
CONECT   54    9                                                            
CONECT   55    9                                                            
CONECT   56    9                                                            
CONECT   57   10                                                            
CONECT   58   15                                                            
CONECT   59   16                                                            
CONECT   60   17                                                            
CONECT   61   19                                                            
CONECT   62   21                                                            
CONECT   63   25                                                            
CONECT   64   25                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   27                                                            
CONECT   68   27                                                            
CONECT   69   28                                                            
CONECT   70   28                                                            
CONECT   71   30                                                            
CONECT   72   30                                                            
CONECT   73   30                                                            
CONECT   74   31                                                            
CONECT   75   33                                                            
CONECT   76   34                                                            
CONECT   77   36                                                            
CONECT   78   40                                                            
CONECT   79   40                                                            
CONECT   80   41                                                            
CONECT   81   44                                                            
MASTER        0    0    0    0    0    0    0    0   81    0  174    0
END

RDKit          3D

81 87  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Value	Source
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(Furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0,.0,.0,]octadecan-17-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₃₃H₃₇NO₁₀

Average Mass

607.6560 Da

Monoisotopic Mass

607.24175 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12C(=O)[C@@](C([H])([H])[H])([C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])OC(=O)C1=C([H])C([H])=C([H])N=C1[H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[C@@]3([H])[C@]11O[C@]21[H])C1=C([H])OC([H])=C1[H]

InChI Identifier

InChI=1S/C33H37NO10/c1-29(2)20(13-22(35)40-5)31(4)19-8-10-30(3)21(14-23(36)42-24(30)18-9-12-41-16-18)33(19)28(44-33)32(39,26(31)38)27(29)43-25(37)17-7-6-11-34-15-17/h6-7,9,11-12,15-16,19-21,24,27-28,39H,8,10,13-14H2,1-5H3/t19-,20+,21-,24+,27+,28-,30-,31-,32+,33-/m1/s1

InChI Key

ZVNCTUYWKIENQR-DTEKRUFUSA-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
Trichilia sinensis	JEOL database	Xu, J. -B., et al, J. Nat. Prod. 76, 1872 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Mexicanolide
Limonoid skeleton
Naphthopyran
Naphthalene
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Tricarboxylic acid or derivatives
Delta valerolactone
Oxepane
Delta_valerolactone
Oxane
Pyran
Pyridine
Heteroaromatic compound
Cyclic alcohol
Furan
Tertiary alcohol
Methyl ester
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.41	ALOGPS
logP	3.26	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.46 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	150.22 m³·mol⁻¹	ChemAxon
Polarizability	61.33 Å³	ChemAxon
Number of Rings	7	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72702567

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu, J. -B., et al. (2013). Xu, J. -B., et al, J. Nat. Prod. 76, 1872 (2013). J. Nat. Prod..

Showing NP-Card for trichinenlide F (NP0043750)

MOL for NP0043750 (trichinenlide F)

3D MOL for NP0043750 (trichinenlide F)

3D SDF for NP0043750 (trichinenlide F)

3D-SDF for NP0043750 (trichinenlide F)

PDB for NP0043750 (trichinenlide F)

3D PDB for NP0043750 (trichinenlide F)

SMILES for NP0043750 (trichinenlide F)

INCHI for NP0043750 (trichinenlide F)

Structure for NP0043750 (trichinenlide F)

3D Structure for NP0043750 (trichinenlide F)