NP-MRD: Showing NP-Card for (10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (NP0296115)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 05:30:31 UTC

Updated at

2022-09-10 05:30:31 UTC

NP-MRD ID

NP0296115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

Description

CHEMBL1778163 belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one is found in Bursera tonkinensis, Diphylleia cymosa and Juniperus communis. CHEMBL1778163 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006282D          

 41 46  0  0  0  0            999 V2000
 9998.9187 9995.4369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2022 9999.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4837 9999.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0598 9999.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7734 9999.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.631310000.8081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.488110000.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.200810001.2198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.630210002.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.059110003.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.488110002.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9187 9997.9181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6313 9999.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9169 9999.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9169 9998.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6313 9998.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3458 9998.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3458 9999.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0577 9997.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0577 9995.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6311 9997.5026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6311 9995.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3456 9996.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3456 9997.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.772810001.2200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.772810002.0450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.058310002.4576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.343910002.0450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.343810001.2200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.058310000.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.5568 9997.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7722 9997.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7722 9996.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5568 9996.0101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.0417 9996.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1319 9997.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6471 9996.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1320 9996.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9166 9996.2650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9165 9997.0900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8770 9998.1296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
 18  4  1  0  0  0  0
 14  2  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 16  1  6  0  0  0
 19 24  2  0  0  0  0
 23 20  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 29 30  1  0  0  0  0
 28  9  1  6  0  0  0
 27 10  1  1  0  0  0
 26 11  1  6  0  0  0
 25  7  1  1  0  0  0
 29  6  1  1  0  0  0
 32 33  2  0  0  0  0
 31 32  1  0  0  0  0
 31 35  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 20 33  1  0  0  0  0
 32 19  1  0  0  0  0
 36 40  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 41  2  0  0  0  0
 21 40  1  0  0  0  0
 39 22  1  0  0  0  0
 39  1  1  6  0  0  0
 40 12  1  1  0  0  0
 13  6  1  0  0  0  0
M  END

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
   -0.4378   -0.1113    3.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2467   -0.4030    2.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941   -0.7349    1.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754   -0.7776    1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533   -1.1081   -0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972   -1.1829   -0.2605 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5583   -0.0643    0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9747    1.0997    0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805    2.0497    1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1194    1.8189    1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6863    0.6044    1.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9090   -0.3257    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4244   -1.6220   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9949   -1.4633   -1.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2979   -2.3405   -2.5369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2998   -1.8674   -3.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.0792   -2.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7032   -0.1892   -3.3611 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4390   -1.6570   -1.4564 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6274    2.9352    2.2428 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887    3.8009    2.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4785    3.2991    1.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5574   -1.3840   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8464   -1.3418   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -1.6307   -2.2490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0407   -1.9715   -3.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -1.0096    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8008   -0.9698    0.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    0.1702   -0.1163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3503    0.4026    1.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0372    1.5925    0.9289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9897    1.6638    2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229    1.6233    3.2803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8978    1.6465   -0.3180 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2748    2.4239   -1.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9741    0.2263   -0.8626 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4380   -0.6278    0.1367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5473   -0.1779   -1.2368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2106    0.4123   -2.4348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1844   -0.9991    3.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804    0.7060    3.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485    0.1434    4.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3648   -0.5536    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264   -2.0362    0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293    1.3240    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315    0.4048    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5254   -1.6910    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9782   -2.4684    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2002   -0.3994   -1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021   -3.4022   -2.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3088   -2.2071   -2.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3419   -2.7913   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8369    4.8489    2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4206    3.7809    3.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9318   -1.6826   -2.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4944   -2.9411   -3.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -2.0827   -4.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038   -1.1760   -3.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9933    1.0591   -0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3302    2.4551    0.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6229    0.7650    2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6218    2.5621    2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4277    0.8193    3.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9016    2.0369   -0.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6561    3.3400   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5793    0.1633   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4016   -1.5587   -0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5805   -1.2868   -1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5385    1.1376   -2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 31 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 27 24  1  0
 24 25  1  0
 25 26  1  0
 24 23  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 20  1  0
 20 21  1  0
 21 22  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 19 14  1  0
 23  5  1  0
 12  7  1  0
 13 14  1  0
 38 29  1  0
 22  9  1  0
 14 49  1  6
 15 50  1  0
 15 51  1  0
 19 52  1  6
  6 44  1  1
  4 43  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 29 59  1  6
 31 60  1  6
 32 61  1  0
 32 62  1  0
 33 63  1  0
 34 64  1  1
 35 65  1  0
 36 66  1  6
 37 67  1  0
 38 68  1  6
 39 69  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 23 55  1  0
  8 45  1  0
 21 53  1  0
 21 54  1  0
 11 46  1  0
 13 47  1  0
 13 48  1  0
M  END


  Mrv1652309272006282D          

 41 46  0  0  0  0            999 V2000
 9998.9187 9995.4369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2022 9999.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4837 9999.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0598 9999.9837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7734 9999.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.631310000.8081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.488110000.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.200810001.2198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.630210002.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.059110003.2812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.488110002.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9187 9997.9181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6313 9999.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9169 9999.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9169 9998.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6313 9998.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3458 9998.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3458 9999.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0577 9997.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0577 9995.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6311 9997.5026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6311 9995.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3456 9996.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3456 9997.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.772810001.2200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.772810002.0450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.058310002.4576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.343910002.0450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.343810001.2200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.058310000.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.5568 9997.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7722 9997.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7722 9996.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5568 9996.0101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.0417 9996.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1319 9997.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.6471 9996.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1320 9996.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9166 9996.2650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9165 9997.0900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8770 9998.1296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
 18  4  1  0  0  0  0
 14  2  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 16  1  6  0  0  0
 19 24  2  0  0  0  0
 23 20  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 29 30  1  0  0  0  0
 28  9  1  6  0  0  0
 27 10  1  1  0  0  0
 26 11  1  6  0  0  0
 25  7  1  1  0  0  0
 29  6  1  1  0  0  0
 32 33  2  0  0  0  0
 31 32  1  0  0  0  0
 31 35  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 20 33  1  0  0  0  0
 32 19  1  0  0  0  0
 36 40  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 41  2  0  0  0  0
 21 40  1  0  0  0  0
 39 22  1  0  0  0  0
 39  1  1  6  0  0  0
 40 12  1  1  0  0  0
 13  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(OC)=C1)C1=CC3=C(OCO3)C=C1C2

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O12/c1-33-17-5-12(6-18(34-2)25(17)39-27-24(31)23(30)22(29)19(8-28)38-27)20-14-7-16-15(36-10-37-16)4-11(14)3-13-9-35-26(32)21(13)20/h4-7,13,19-24,27-31H,3,8-10H2,1-2H3/t13-,19+,20+,21-,22+,23-,24+,27-/m0/s1

> <INCHI_KEY>
QMXNRLBPHJPLKV-QNRBAVQLSA-N

> <FORMULA>
C27H30O12

> <MOLECULAR_WEIGHT>
546.525

> <EXACT_MASS>
546.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.963438080956095

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11R,15R)-10-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
0.39809046000000037

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19599566885724

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199887080240053

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662076965

> <JCHEM_POLAR_SURFACE_AREA>
162.6

> <JCHEM_REFRACTIVITY>
130.15039999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15R)-10-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  H   UNK     0    8664.6488658.149   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0    8663.3118666.636   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8661.9708665.860   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8668.6458666.636   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8669.9778665.864   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8665.9788668.175   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8671.3118668.172   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8672.6418668.944   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8665.9768671.252   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8668.6448672.792   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8671.3118671.252   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0    8664.6488662.780   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0    8665.9788666.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6458665.865   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6458664.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.9788663.555   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3128664.325   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.3128665.865   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.6418662.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.6418658.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.9788662.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8665.9788658.925   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3128659.695   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.3128661.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.9768668.944   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.9768670.484   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8668.6428671.254   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8667.3098670.484   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8667.3088668.944   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8668.6428668.174   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8671.4398661.711   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0    8669.9758661.235   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8669.9758659.695   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0    8671.4398659.219   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0    8672.3458660.465   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8663.1808661.711   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0    8662.2758660.465   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0    8663.1808659.219   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0    8664.6448659.695   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8664.6448661.235   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0    8662.7048663.175   0.000  0.00  0.00           O+0
CONECT    1   39                                                            
CONECT    2    3   14                                                       
CONECT    3    2                                                            
CONECT    4    5   18                                                       
CONECT    5    4                                                            
CONECT    6   29   13                                                       
CONECT    7    8   25                                                       
CONECT    8    7                                                            
CONECT    9   28                                                            
CONECT   10   27                                                            
CONECT   11   26                                                            
CONECT   12   40                                                            
CONECT   13   14   18    6                                                  
CONECT   14   13   15    2                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13    4                                                  
CONECT   19   24   32                                                       
CONECT   20   23   33                                                       
CONECT   21   24   16   40                                                  
CONECT   22   23   39                                                       
CONECT   23   22   24   20                                                  
CONECT   24   21   23   19                                                  
CONECT   25   26   30    7                                                  
CONECT   26   25   27   11                                                  
CONECT   27   26   28   10                                                  
CONECT   28   27   29    9                                                  
CONECT   29   28   30    6                                                  
CONECT   30   25   29                                                       
CONECT   31   32   35                                                       
CONECT   32   33   31   19                                                  
CONECT   33   32   34   20                                                  
CONECT   34   33   35                                                       
CONECT   35   31   34                                                       
CONECT   36   40   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   39   37                                                       
CONECT   39   38   40   22    1                                             
CONECT   40   36   39   21   12                                             
CONECT   41   36                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Value	Source
(7R,8R,8'R)-4-Demethyldeoxypodophyllotoxin 4-O-beta-D-glucopyranoside	PhytoBank
(7R,8R,8’R)-4-Demethyldeoxypodophyllotoxin 4-O-β-D-glucopyranoside	PhytoBank
(7R,8R,8'R)-4-Demethyldeoxypodophyllotoxin 4-O-β-D-glucopyranoside	PhytoBank
4-Demethyldeoxypodophyllotoxin 4-O-beta-D-glucopyranoside	PhytoBank

Chemical Formula

C₂₇H₃₀O₁₂

Average Mass

546.5250 Da

Monoisotopic Mass

546.17373 Da

IUPAC Name

(10R,11R,15R)-10-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

Traditional Name

(10R,11R,15R)-10-(3,5-dimethoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

CAS Registry Number

Not Available

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(OC)=C1)C1=CC3=C(OCO3)C=C1C2

InChI Identifier

InChI=1S/C27H30O12/c1-33-17-5-12(6-18(34-2)25(17)39-27-24(31)23(30)22(29)19(8-28)38-27)20-14-7-16-15(36-10-37-16)4-11(14)3-13-9-35-26(32)21(13)20/h4-7,13,19-24,27-31H,3,8-10H2,1-2H3/t13-,19+,20+,21-,22+,23-,24+,27-/m0/s1

InChI Key

QMXNRLBPHJPLKV-QNRBAVQLSA-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
Bursera tonkinensis	LOTUS Database	35616633
Diphylleia cymosa	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Lignan lactone
1-aryltetralin lignan
Linear furanonaphthodioxole
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Naphthofuran
Hexose monosaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Tetralin
Benzodioxole
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
Alkyl aryl ether
Fatty acyl
Oxane
Monosaccharide
Gamma butyrolactone
Monocyclic benzene moiety
Benzenoid
Oxolane
Secondary alcohol
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	0.98	ALOGPS
logP	0.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	162.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.15 m³·mol⁻¹	ChemAxon
Polarizability	53.96 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

26339923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12311205

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one (NP0296115)

MOL for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D MOL for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D SDF for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D-SDF for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

PDB for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D PDB for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

SMILES for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

INCHI for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

Structure for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)

3D Structure for NP0296115 ((10r,11r,15r)-10-(3,5-dimethoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one)