NP-MRD: Showing NP-Card for (1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione (NP0326053)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-12 07:16:43 UTC

Updated at

2022-09-12 07:16:43 UTC

NP-MRD ID

NP0326053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione

Description

Plukenetione C belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione is found in Hypericum sampsonii. It was first documented in 2010 (PMID: 20397228). Based on a literature review very few articles have been published on Plukenetione C (PMID: 29461053).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122209162D          

 40 44  0  0  1  0            999 V2000
    5.5454   -2.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8778   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6518   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4955   -0.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6381    0.7385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5991    1.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6096    2.5200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7541    2.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1489    1.9423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4646    2.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015    3.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585    3.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518    2.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    1.4404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    0.6698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1180   -0.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3071    0.3072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026    0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3309    1.0676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8538    0.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3138   -0.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1840    1.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1699    2.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1311    1.3160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0684    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8017    1.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4051    0.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289    0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6791    0.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3056   -0.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4817   -0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9600   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4507    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1920    0.2105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3729    2.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0927    2.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990    3.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 27 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  2  0  0  0  0
 27 38  1  0  0  0  0
  8 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
   -5.7192   -1.9608    0.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2808   -2.0372    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0494   -1.9617    2.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3385   -2.1846    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8885   -2.2800    0.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0383   -1.2834    0.0722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1748   -1.4048   -1.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6142   -0.2800   -2.2072 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8216   -0.2725   -2.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -1.0278   -1.4794 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0917   -0.9865   -1.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    0.1532   -2.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -2.2524   -2.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0473   -0.8849   -0.9356 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -1.9518   -0.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -1.4039    1.0543 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5931   -0.9257    1.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484   -0.3338    3.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5566   -2.0794    2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3074    0.0381    1.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110   -0.2465    0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408   -0.4588   -0.1412 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3921   -1.3842    0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -2.1960    1.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7443    0.8875   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4544    1.8565   -0.4921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563    1.1833   -0.2660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9313    2.4675    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2193    3.0252    0.7051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0720    3.2540    0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3890    2.9025    0.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958    3.7541    1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1458    4.9982    1.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210    5.3562    1.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8161    4.5154    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4190    0.1033    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1958    0.2164    1.3991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675    1.0721   -1.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6144    2.1614   -2.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556    0.9589   -1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4115   -2.1563    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8421   -0.9545    0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8636   -2.7335    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8281   -1.2838    3.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0806   -1.5641    3.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1902   -2.9393    3.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6603   -2.2515   -0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7253   -2.2025    1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995   -3.3353    0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -2.3403   -1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2530   -1.4752   -1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1328   -0.3686   -3.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2029    0.7669   -2.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -0.6454   -3.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3345   -2.0938   -1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2063    1.1356   -2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -0.0377   -3.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139    0.0907   -3.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5903   -3.0926   -2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3567   -2.0339   -3.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021   -2.4086   -3.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9547   -2.2317    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.7482    3.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4691   -0.9050    3.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743   -0.4197    3.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714   -2.8802    1.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5015   -2.4083    3.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081   -1.7929    1.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9867   -0.4301    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259    0.1877    1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1439    0.5515    0.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6860    1.9652    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4558    3.4758    0.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9270    5.6816    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669    6.3355    2.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949    4.8797    1.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752    2.8115   -2.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542    1.7058   -3.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1514    2.7829   -2.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960    0.5053   -2.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0859    1.9735   -2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783    0.2803   -1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 22  1  0
 22 21  1  1
 21 16  1  0
 16 15  1  0
 15 14  1  0
 14 11  1  0
 11 12  1  0
 11 13  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 22 23  1  0
 23 24  2  0
 22 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  1
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 27 36  1  0
 36 37  2  0
 27 38  1  0
 38 39  1  0
 38 40  1  0
 23  6  1  0
 35 30  1  0
 36  6  1  0
 38  8  1  0
 11 10  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  3 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  7 51  1  0
  8 52  1  6
  9 53  1  0
  9 54  1  0
 10 55  1  1
 21 70  1  0
 21 71  1  0
 16 62  1  1
 12 56  1  0
 12 57  1  0
 12 58  1  0
 13 59  1  0
 13 60  1  0
 13 61  1  0
 18 63  1  0
 18 64  1  0
 18 65  1  0
 19 66  1  0
 19 67  1  0
 19 68  1  0
 20 69  1  0
 31 72  1  0
 32 73  1  0
 33 74  1  0
 34 75  1  0
 35 76  1  0
 39 77  1  0
 39 78  1  0
 39 79  1  0
 40 80  1  0
 40 81  1  0
 40 82  1  0
M  END


  Mrv1652309122209162D          

 40 44  0  0  1  0            999 V2000
    5.5454   -2.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8778   -2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6518   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4955   -0.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6381    0.7385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5991    1.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6096    2.5200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7541    2.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1489    1.9423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4646    2.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015    3.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8585    3.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518    2.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    1.4404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    0.6698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1180   -0.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3071    0.3072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026    0.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3309    1.0676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8538    0.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3138   -0.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1840    1.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1699    2.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1311    1.3160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0684    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8017    1.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4051    0.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289    0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6791    0.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3056   -0.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4817   -0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9600   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4507    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1920    0.2105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3729    2.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0927    2.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3990    3.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 27 36  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  2  0  0  0  0
 27 38  1  0  0  0  0
  8 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@]12C[C@@H]3C[C@@H]4[C@](C[C@@H](OOC4(C)C)C(C)(C)O)(C1=O)C(=O)[C@](C(=O)C1=CC=CC=C1)(C2=O)C3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O7/c1-19(2)14-15-31-17-21-16-22-30(7,8)40-39-23(29(5,6)38)18-32(22,25(31)35)27(37)33(26(31)36,28(21,3)4)24(34)20-12-10-9-11-13-20/h9-14,21-23,38H,15-18H2,1-8H3/t21-,22-,23+,31-,32+,33-/m0/s1

> <INCHI_KEY>
XWHHFHMIFCAIHB-BELRDVMKSA-N

> <FORMULA>
C33H42O7

> <MOLECULAR_WEIGHT>
550.692

> <EXACT_MASS>
550.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.53810174533278

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,7R,9S,11R,13S)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1^{9,13}.0^{1,7}]hexadecane-12,14,15-trione

> <JCHEM_LOGP>
6.560868947999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.217760643444997

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1409514945571573

> <JCHEM_POLAR_SURFACE_AREA>
106.97

> <JCHEM_REFRACTIVITY>
150.79459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,7R,9S,11R,13S)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1^{9,13}.0^{1,7}]hexadecane-12,14,15-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.351  -4.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.105  -3.795   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.249  -5.118   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.683  -2.198   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.392  -0.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.658   1.378   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.585   3.131   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.605   4.704   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.008   4.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.878   3.626   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.601   4.585   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.043   6.175   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.469   5.794   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.083   4.204   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.651   2.689   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.289   1.250   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.087  -0.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.956  -1.214   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.666  -1.539   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.573   0.573   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.858   1.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.218   1.993   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.194   0.705   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.186  -0.592   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.810   2.275   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.784   4.012   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.578   2.457   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.328   2.698   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.697   3.711   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.956   1.249   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.494   1.331   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.334   0.041   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.637  -1.332   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.099  -1.415   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.125  -0.539   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.175   1.001   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.558   0.393   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.029   4.016   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.373   4.930   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.078   5.712   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23   36                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   38                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   16   22                                                       
CONECT   22   21   10   23   25                                             
CONECT   23   22    6   24                                                  
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   36   38                                             
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   27    6   37                                                  
CONECT   37   36                                                            
CONECT   38   27    8   39   40                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₇

Average Mass

550.6920 Da

Monoisotopic Mass

550.29305 Da

IUPAC Name

(1R,3R,7R,9S,11R,13S)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1^{9,13}.0^{1,7}]hexadecane-12,14,15-trione

Traditional Name

(1R,3R,7R,9S,11R,13S)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1^{9,13}.0^{1,7}]hexadecane-12,14,15-trione

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@]12C[C@@H]3C[C@@H]4[C@](C[C@@H](OOC4(C)C)C(C)(C)O)(C1=O)C(=O)[C@](C(=O)C1=CC=CC=C1)(C2=O)C3(C)C

InChI Identifier

InChI=1S/C33H42O7/c1-19(2)14-15-31-17-21-16-22-30(7,8)40-39-23(29(5,6)38)18-32(22,25(31)35)27(37)33(26(31)36,28(21,3)4)24(34)20-12-10-9-11-13-20/h9-14,21-23,38H,15-18H2,1-8H3/t21-,22-,23+,31-,32+,33-/m0/s1

InChI Key

XWHHFHMIFCAIHB-BELRDVMKSA-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
Hypericum sampsonii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aryl alkyl ketone
Benzoyl
Dioxepane
1,2-dioxepane
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Dialkyl peroxide
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
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	6.56	ChemAxon
pKa (Strongest Acidic)	14.22	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	150.79 m³·mol⁻¹	ChemAxon
Polarizability	59.54 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

C00046319

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

100932396

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang XW, Grossman RB, Xu G: Research Progress of Polycyclic Polyprenylated Acylphloroglucinols. Chem Rev. 2018 Apr 11;118(7):3508-3558. doi: 10.1021/acs.chemrev.7b00551. Epub 2018 Feb 20. [PubMed:29461053 ]
Xiao ZY, Zeng YH, Mu Q, Shiu WK, Gibbons S: Prenylated benzophenone peroxide derivatives from Hypericum sampsonii. Chem Biodivers. 2010 Apr;7(4):953-8. doi: 10.1002/cbdv.200900247. [PubMed:20397228 ]
LOTUS database [Link]

Showing NP-Card for (1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione (NP0326053)

MOL for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

3D MOL for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

3D SDF for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

3D-SDF for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

PDB for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

3D PDB for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

SMILES for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

INCHI for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

Structure for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)

3D Structure for NP0326053 ((1r,3r,7r,9s,11r,13s)-11-benzoyl-3-(2-hydroxypropan-2-yl)-6,6,10,10-tetramethyl-13-(3-methylbut-2-en-1-yl)-4,5-dioxatetracyclo[9.3.1.1⁹,¹³.0¹,⁷]hexadecane-12,14,15-trione)