NP-MRD: Showing NP-Card for (+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one (NP0059876)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 05:02:00 UTC

Updated at

2022-04-28 05:02:00 UTC

NP-MRD ID

NP0059876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one

Description

(9S)-9-(2-hydroperoxypropan-2-yl)-5,14-dihydroxy-16-methoxy-15-(3-methylbut-1-en-1-yl)-8,19-dioxatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-1(11),2(7),3,5,13(18),14,16-heptaen-12-one belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom). (+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one is found in Artocarpus champeden. Based on a literature review very few articles have been published on (9S)-9-(2-hydroperoxypropan-2-yl)-5,14-dihydroxy-16-methoxy-15-(3-methylbut-1-en-1-yl)-8,19-dioxatetracyclo[9.8.0.0²,⁷.0¹³,¹⁸]Nonadeca-1(11),2(7),3,5,13(18),14,16-heptaen-12-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207022D          

 34 37  0  0  1  0            999 V2000
    5.4769   -0.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1339   -0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126   -0.1131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8343   -0.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774   -1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3418   -2.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047   -2.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969   -2.4392    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3623   -1.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787   -1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338   -0.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653    0.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102    0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    0.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974   -3.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979   -3.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -3.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -4.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048   -4.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6121    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4334    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7765   -0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -1.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5978   -0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9408   -1.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7621   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2404   -0.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1052   -2.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7329    0.9973    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  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
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  1  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  1 26  2  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    4.1201    3.0343   -1.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.8245   -1.2584 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1104    1.1883   -0.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8874    1.7545   -0.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7354    1.1317   -0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    1.7007   -0.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5180    1.1327   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863   -0.0494    0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712   -0.6506    0.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -1.7061    1.2894 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -0.0469    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1208   -0.6471    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2660   -1.8025    1.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2580   -0.0010   -0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.4895    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0083   -1.5787    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -1.9513    0.8093 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7983   -1.9348    2.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3209   -0.9205    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -0.8568    0.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7490   -0.9289    0.0552 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7235   -2.0108    0.3881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1193   -3.3860    0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8048   -1.9900   -0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643   -1.8247    1.5891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5869   -1.7689    2.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4816    0.2966   -0.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0456    1.5282   -0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0810    2.3631   -0.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127    3.6111   -1.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8341    4.4812   -1.8024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    3.9615   -1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    3.1344   -1.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193    1.8858   -0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790    3.7700   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5614    2.8416   -2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797    3.5315   -2.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7635    2.6735   -1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -2.4009    1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4642    0.0901   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889   -2.2216    1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5882   -2.9466    0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0087   -0.9043    2.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9482   -2.3938    2.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6912   -2.5537    2.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1151   -0.8528   -0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4101   -1.2270    0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2418    0.0620    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -1.8702    1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -0.3598    1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325   -1.1586   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615   -3.5185    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6072   -3.6455   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9517   -4.1168    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1880   -0.9477   -0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3205   -2.1773   -1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5808   -2.7327   -0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8454   -0.9578    3.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1037    2.0490   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1977    5.1262   -1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2741    4.9478   -1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056    3.4100   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7 34  1  0
 34 28  2  0
 28 27  1  0
 27 21  1  0
 21 20  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  1
 25 26  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
  4  3  1  0
 33 34  1  0
  5 11  1  0
 20  8  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 13 39  1  0
  4 38  1  0
 21 51  1  6
 20 49  1  0
 20 50  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 26 58  1  0
 29 59  1  0
 31 60  1  0
 32 61  1  0
 33 62  1  0
M  END


  Mrv1652304282207022D          

 34 37  0  0  1  0            999 V2000
    5.4769   -0.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1339   -0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126   -0.1131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8343   -0.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774   -1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3418   -2.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047   -2.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9969   -2.4392    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3623   -1.9121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787   -1.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338   -0.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1653    0.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102    0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    0.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974   -3.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979   -3.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969   -3.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -4.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048   -4.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6121    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4334    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7765   -0.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -1.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5978   -0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9408   -1.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7621   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2404   -0.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1052   -2.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116    1.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7329    0.9973    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  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
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  1  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  1 26  2  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(\C=C\C(C)C)C(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[C@@H](C3)C(C)(C)OO)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O8/c1-13(2)6-8-15-18(31-5)12-20-22(23(15)28)24(29)17-11-21(26(3,4)34-30)32-19-10-14(27)7-9-16(19)25(17)33-20/h6-10,12-13,21,27-28,30H,11H2,1-5H3/b8-6+/t21-/m0/s1

> <INCHI_KEY>
UYYZSBJGWJNBMX-PVHVJQTOSA-N

> <FORMULA>
C26H28O8

> <MOLECULAR_WEIGHT>
468.502

> <EXACT_MASS>
468.178417862

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.918347272421755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S)-9-(2-hydroperoxypropan-2-yl)-5,14-dihydroxy-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
4.988006482666666

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.769299705764265

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.281158569692792

> <JCHEM_PKA_STRONGEST_BASIC>
-4.23904657664118

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
127.364

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-9-(2-hydroperoxypropan-2-yl)-5,14-dihydroxy-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      10.224  -1.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.583  -0.357   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.050  -0.211   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.157  -1.466   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.798  -2.867   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.331  -3.012   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.971  -4.413   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.102  -4.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.594  -4.553   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.410  -3.569   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.440  -2.029   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.663  -1.093   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.464   0.434   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.042   1.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.819   0.089   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.018  -1.438   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.397   0.680   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.222  -6.047   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.716  -6.420   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.727  -5.675   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.849  -7.542   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.369  -7.966   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.476   0.898   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.009   0.752   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.649  -0.648   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.757  -1.903   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.397  -3.303   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.182  -0.794   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.823  -2.194   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.356  -2.340   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.249  -1.085   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.996  -3.740   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.902   2.007   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.435   1.862   0.000  0.00  0.00           C+0
CONECT    1    2    6   26                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15                                                            
CONECT   18    9   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21                                                            
CONECT   23    2   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25    1   27                                                  
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   24   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₈

Average Mass

468.5020 Da

Monoisotopic Mass

468.17842 Da

IUPAC Name

(9S)-9-(2-hydroperoxypropan-2-yl)-5,14-dihydroxy-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

Traditional Name

(9S)-9-(2-hydroperoxypropan-2-yl)-5,14-dihydroxy-16-methoxy-15-[(1E)-3-methylbut-1-en-1-yl]-8,19-dioxatetracyclo[9.8.0.0^{2,7}.0^{13,18}]nonadeca-1(11),2(7),3,5,13,15,17-heptaen-12-one

CAS Registry Number

Not Available

SMILES

COC1=C(\C=C\C(C)C)C(O)=C2C(=O)C3=C(OC2=C1)C1=C(O[C@@H](C3)C(C)(C)OO)C=C(O)C=C1

InChI Identifier

InChI=1S/C26H28O8/c1-13(2)6-8-15-18(31-5)12-20-22(23(15)28)24(29)17-11-21(26(3,4)34-30)32-19-10-14(27)7-9-16(19)25(17)33-20/h6-10,12-13,21,27-28,30H,11H2,1-5H3/b8-6+/t21-/m0/s1

InChI Key

UYYZSBJGWJNBMX-PVHVJQTOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Artocarpus champeden	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Not Available

Direct Parent

Benzoxepines

Alternative Parents

Substituents

Chromone
Benzoxepine
1-benzopyran
Benzopyran
Styrene
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Hydroperoxide
Alkyl hydroperoxide
Oxacycle
Peroxol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.4	ALOGPS
logP	4.99	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	7.28	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.36 m³·mol⁻¹	ChemAxon
Polarizability	49.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

162903223

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one (NP0059876)

MOL for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

3D MOL for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

3D SDF for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

3D-SDF for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

PDB for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

3D PDB for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

SMILES for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

INCHI for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

Structure for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)

3D Structure for NP0059876 ((+)-6,7-Dihydro-6-(1-hydroperoxy-1-methylethyl)-3,9-dihydroxy-11-methoxy-10-[(1E)-3-methyl-1-butenyl]-8H-[1]benzopyrano[3,2-d][1]benzoxepin-8-one)