NP-MRD: Showing NP-Card for (1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione (NP0165572)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 00:45:18 UTC

Updated at

2022-09-03 00:45:18 UTC

NP-MRD ID

NP0165572

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione

Description

Lancifoldilactone G belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione is found in Schisandra lancifolia. Based on a literature review very few articles have been published on Lancifoldilactone G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202452D          

 39 46  0  0  1  0            999 V2000
    4.3002   -0.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    0.0580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9221   -0.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785    0.7131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1857    1.2716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6546    1.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    0.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    0.5051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3998    0.6094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    0.5403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4070    1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1158    2.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    2.0742    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6752    2.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5717    2.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338    3.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274    2.3085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0491    2.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259    1.4732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4021    1.3433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2103    0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    0.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1361    1.0147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    2.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875    0.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231   -0.0637    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -0.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3121   -1.2781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7817   -1.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758   -1.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123   -2.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411   -0.6943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1224   -1.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152   -0.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8522   -0.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035   -0.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 18  1  1  0  0  0
  4 20  1  0  0  0  0
 21 20  1  1  0  0  0
  9 21  1  0  0  0  0
 14 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 30 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  2  0  0  0  0
  9 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 75 82  0  0  0  0  0  0  0  0999 V2000
    5.4523    2.5709    0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0978    2.5084    1.4265 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1225    1.6478    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1781    0.3260    1.2887 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0965    0.4272    2.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2435    1.7519    2.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4605    2.2919    3.8160 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -0.0444    1.8724 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2016   -0.5728    0.7908 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5775    0.4641    0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806   -0.0871   -0.4051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1886   -0.5437   -1.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -0.2821   -2.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021   -1.3276   -1.4443 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6964   -2.6762   -2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5320   -1.1212   -1.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -1.2942   -2.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3452   -0.6547   -0.7240 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5968   -1.5426   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072   -0.8381    0.4597 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1478   -1.3726    0.0155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6799    0.9231   -0.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961    0.7854    0.6344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0450    0.6884    1.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4349    1.7227    2.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8430    2.1399    3.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7057    2.2568    2.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5437    2.0335    0.6820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7353    1.7753    0.0414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804    0.4304   -0.1674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0999    0.1949   -1.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1608   -0.0202    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2742    0.6447    0.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094   -0.2800    0.4029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2203   -1.4389   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1097   -2.1024    0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121   -1.2500    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -1.4177    1.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609   -2.2066    2.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0830    1.6880    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3486    2.5815   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0132    3.4756    1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451    3.5385    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    2.0968    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585    1.6972   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -1.6218   -1.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7679    0.0143   -2.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007    0.7456   -1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340   -0.3192   -3.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4274   -2.4829   -3.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5943   -3.3341   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9020   -3.1613   -1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6959    0.3507   -0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0840   -1.3331    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2142   -2.5832   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2550   -1.3350   -1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9870   -1.6178    1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0506   -2.4515    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302    0.9464   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2031    1.9359   -0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8421    3.3266    2.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5141    1.6188    2.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874    2.8673    0.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7326   -0.7282   -1.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1990    0.0077   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6505    1.0779   -2.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3378   -1.1122    0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1328    0.1256    1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0377    1.5804   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0055   -0.6841    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583   -1.1548   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317   -2.1745   -0.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042   -2.1324    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9314   -3.1340    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5405   -2.8245    2.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  1
  5  6  1  0
  6  7  2  0
  4  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  6
 12 13  1  0
 13 14  1  0
 14 15  1  6
 14 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  2  0
 11 22  1  0
 22 23  1  0
 23 24  1  1
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
 30 32  1  0
 32 33  1  0
 30 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
  6  2  1  0
 21  9  1  0
 28 23  1  0
 20  4  1  0
 34 23  1  0
 38  9  1  0
 37 11  1  0
 16 14  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  1
  3 44  1  0
  3 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 15 50  1  0
 15 51  1  0
 15 52  1  0
 21 58  1  6
 20 57  1  1
 18 53  1  6
 19 54  1  0
 19 55  1  0
 19 56  1  0
 22 59  1  0
 22 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  6
 31 64  1  0
 31 65  1  0
 31 66  1  0
 32 67  1  0
 32 68  1  0
 33 69  1  0
 34 70  1  1
 35 71  1  0
 35 72  1  0
 36 73  1  0
 36 74  1  0
 39 75  1  0
M  END


  Mrv1652309032202452D          

 39 46  0  0  1  0            999 V2000
    4.3002   -0.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    0.0580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9221   -0.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5785    0.7131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1857    1.2716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6546    1.2104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    0.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    0.5051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3998    0.6094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    0.5403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4070    1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1158    2.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    2.0742    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6752    2.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5717    2.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338    3.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3274    2.3085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0491    2.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259    1.4732    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4021    1.3433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2103    0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    0.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1361    1.0147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    2.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875    0.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231   -0.0637    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -0.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3121   -1.2781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7817   -1.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758   -1.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123   -2.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411   -0.6943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1224   -1.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0152   -0.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8522   -0.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035   -0.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 18  1  1  0  0  0
  4 20  1  0  0  0  0
 21 20  1  1  0  0  0
  9 21  1  0  0  0  0
 14 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 30 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  2  0  0  0  0
  9 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165572

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@]2(OC1=O)O[C@@]13O[C@]4(CC[C@]5(C)[C@H]1[C@H]2[C@@H](C)C5=O)C[C@@]12OC(=O)C[C@@H]1O[C@](C)(CO)[C@H]2CCC4=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O10/c1-13-10-28(37-23(13)34)19-14(2)21(32)24(3)7-8-26-11-27-16(25(4,12-30)35-17(27)9-18(31)36-27)6-5-15(26)22(33)29(38-26,39-28)20(19)24/h13-14,16-17,19-20,30,33H,5-12H2,1-4H3/t13-,14+,16+,17-,19+,20+,24+,25+,26+,27-,28+,29-/m0/s1

> <INCHI_KEY>
LTHLIQFAHGGQPW-YEJHDGNSSA-N

> <FORMULA>
C29H36O10

> <MOLECULAR_WEIGHT>
544.597

> <EXACT_MASS>
544.230847359

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.86006673243026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4'S,7S,9S,10R,15S,17S,18R,19R,21R,25R)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1^{15,18}.0^{1,13}.0^{3,7}.0^{3,10}.0^{21,25}]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
2.023611819666666

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.35899923855889

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.636360169513308

> <JCHEM_PKA_STRONGEST_BASIC>
-3.078309282953404

> <JCHEM_POLAR_SURFACE_AREA>
137.82

> <JCHEM_REFRACTIVITY>
132.2426

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4'S,7S,9S,10R,15S,17S,18R,19R,21R,25R)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1^{15,18}.0^{1,13}.0^{3,7}.0^{3,10}.0^{21,25}]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.027  -1.025   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.984   0.108   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.455  -0.069   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.813   1.331   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.947   2.374   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.288   1.618   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.689   2.259   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.671   0.275   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.202   0.943   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.746   1.138   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.631   1.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.760   2.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.216   3.942   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.810   3.872   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.260   5.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.934   4.970   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.676   6.489   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.344   4.309   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.692   5.055   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.155   2.750   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.617   2.508   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.259   1.151   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.671   0.266   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.987   1.894   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.493   2.307   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.044   3.745   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.323   1.014   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.270  -0.119   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.639  -1.627   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.316  -2.386   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.192  -3.652   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.128  -3.366   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.383  -4.885   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.250  -1.296   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.095  -2.321   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.639  -1.913   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.028  -0.515   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.591  -0.558   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.433  -1.847   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8   20                                             
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   21   38                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   22   37                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    4   21                                                  
CONECT   21   20    9   14                                                  
CONECT   22   11   23                                                       
CONECT   23   22   24   28   34                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32   34                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   30   23   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   11   38                                                  
CONECT   38   37    9   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₀

Average Mass

544.5970 Da

Monoisotopic Mass

544.23085 Da

IUPAC Name

(1R,3S,4'S,7S,9S,10R,15S,17S,18R,19R,21R,25R)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1^{15,18}.0^{1,13}.0^{3,7}.0^{3,10}.0^{21,25}]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@]2(OC1=O)O[C@@]13O[C@]4(CC[C@]5(C)[C@H]1[C@H]2[C@@H](C)C5=O)C[C@@]12OC(=O)C[C@@H]1O[C@](C)(CO)[C@H]2CCC4=C3O

InChI Identifier

InChI=1S/C29H36O10/c1-13-10-28(37-23(13)34)19-14(2)21(32)24(3)7-8-26-11-27-16(25(4,12-30)35-17(27)9-18(31)36-27)6-5-15(26)22(33)29(38-26,39-28)20(19)24/h13-14,16-17,19-20,30,33H,5-12H2,1-4H3/t13-,14+,16+,17-,19+,20+,24+,25+,26+,27-,28+,29-/m0/s1

InChI Key

LTHLIQFAHGGQPW-YEJHDGNSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Schisandra lancifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Ketal
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Dihydrofuran
Oxolane
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Enol
Acetal
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Primary 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	1.61	ALOGPS
logP	2.02	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	137.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.24 m³·mol⁻¹	ChemAxon
Polarizability	55.86 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

4443082

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5279322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione (NP0165572)

MOL for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

3D MOL for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

3D SDF for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

3D-SDF for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

PDB for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

3D PDB for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

SMILES for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

INCHI for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

Structure for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)

3D Structure for NP0165572 ((1r,3s,4's,7s,9s,10r,15s,17s,18r,19r,21r,25r)-14-hydroxy-9-(hydroxymethyl)-4',9,19,21-tetramethyl-4,8,16,24-tetraoxaspiro[heptacyclo[13.8.1.1¹⁵,¹⁸.0¹,¹³.0³,⁷.0³,¹⁰.0²¹,²⁵]pentacosane-17,2'-oxolan]-13-ene-5,5',20-trione)