NP-MRD: Showing NP-Card for [(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate (NP0204797)

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Record Information

Version

2.0

Created at

2022-09-05 00:33:32 UTC

Updated at

2022-09-05 00:33:32 UTC

NP-MRD ID

NP0204797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate

Description

[(1S,2S,4S,5R,6S,7S,9R,12R)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-6-yl]methyl acetate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). Based on a literature review very few articles have been published on [(1S,2S,4S,5R,6S,7S,9R,12R)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-6-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202332D          

 32 34  0  0  1  0            999 V2000
    4.6708   -2.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947   -1.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2644   -2.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488   -0.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726   -0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    0.1195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4112   -0.6432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8162   -1.3619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3962   -2.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713   -2.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8012   -2.7908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5568   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1157   -1.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500    0.1616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8099    0.4997    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2262   -0.2126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4150    0.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7071    1.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9577    1.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554    1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377    0.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585    1.5568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2312    1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    2.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7894    1.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9539    0.6490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582    0.0461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0068   -0.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8287   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3019   -0.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1774   -1.5212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    2.9480    1.6872    3.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9262    0.7341    3.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.1241    3.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3950    0.6788    1.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3989   -0.3037    1.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0109   -0.1425    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5398    1.2445   -0.1831 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4268    2.0519    0.9882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    3.2469    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    4.0885    2.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268    3.6256   -0.0550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    1.3076   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4248    2.4005   -0.8433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8743    0.1382   -0.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3103   -0.8806    0.3239 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1178   -1.9647    0.5009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0123   -1.1518   -0.3715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2367   -0.9744   -1.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -0.5548   -1.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854   -1.5746   -2.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4772    0.5403   -3.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796   -2.5830   -0.2346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7367   -3.1359    1.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5187   -3.2975   -1.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7539   -2.8317   -0.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509   -1.7423   -0.7793 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6905   -1.9338    0.2647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2148   -0.3400   -0.7994 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2835    0.5167   -0.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8105    1.4228   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9294    2.3324   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2816    1.4445   -2.5283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7737    1.8821    4.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786    2.6751    3.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9852    1.3005    3.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8959   -1.2674    1.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -0.1625    2.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293    1.7793   -0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2824    3.4531    3.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    4.7038    2.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916    4.7675    2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9133    0.3575   -0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190   -0.3414    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6736   -1.8558    1.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9807   -2.2062   -3.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836   -2.1591   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3024   -1.0433   -2.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    1.1292   -2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5676    1.1505   -2.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407    0.0593   -4.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -4.0237    1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -2.4082    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -3.5651    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -4.0627   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1952   -3.7185   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608   -3.2185   -1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3999   -1.8161   -1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8904   -2.8867    0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9307   -0.1220   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8663    2.6184    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8793    3.2517   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8640    1.8042   -1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  1
  6 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28 26  1  0
 26 27  1  0
 26 25  1  0
 25 22  1  0
 22 23  1  0
 22 24  1  6
 22 17  1  0
 17 18  1  6
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 14  1  0
 14 15  1  0
 15 16  1  0
 14 12  1  0
 12 13  2  0
 12  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 17  6  1  0
 15 17  1  0
  7  6  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  5 37  1  0
 28 59  1  6
 31 60  1  0
 31 61  1  0
 31 62  1  0
 26 57  1  6
 27 58  1  0
 25 55  1  0
 25 56  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 14 42  1  1
 15 43  1  1
 16 44  1  0
  7 38  1  6
 10 39  1  0
 10 40  1  0
 10 41  1  0
M  END


  Mrv1652309052202332D          

 32 34  0  0  1  0            999 V2000
    4.6708   -2.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947   -1.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2644   -2.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7488   -0.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9726   -0.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    0.1195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4112   -0.6432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8162   -1.3619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3962   -2.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713   -2.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8012   -2.7908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5568   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1157   -1.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500    0.1616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8099    0.4997    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2262   -0.2126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4150    0.9000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7071    1.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9577    1.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554    1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377    0.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9585    1.5568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2312    1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    2.3468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7894    1.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9539    0.6490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582    0.0461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0068   -0.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8287   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3019   -0.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1774   -1.5212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0204797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]12[C@@H](OC(C)=O)[C@@H](O)C[C@](C)(O)[C@]11OC(C)(C)[C@@H]([C@H]1O)C(=O)[C@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O11/c1-9(22)29-8-20-16(30-10(2)23)12(25)7-19(6,28)21(20)15(27)13(18(4,5)32-21)14(26)17(20)31-11(3)24/h12-13,15-17,25,27-28H,7-8H2,1-6H3/t12-,13+,15+,16-,17+,19-,20-,21-/m0/s1

> <INCHI_KEY>
HISDFVSSTMLDOG-DKWBATPYSA-N

> <FORMULA>
C21H30O11

> <MOLECULAR_WEIGHT>
458.46

> <EXACT_MASS>
458.178811786

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.090216701570185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2S,4S,5R,6S,7S,9R,12R)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

> <JCHEM_LOGP>
-2.0149235253333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.232857009073875

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.413517458800634

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2163406181651926

> <JCHEM_POLAR_SURFACE_AREA>
165.89

> <JCHEM_REFRACTIVITY>
103.25170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S,4S,5R,6S,7S,9R,12R)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.719  -3.852   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.270  -3.330   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.094  -4.324   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.998  -1.815   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.549  -1.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.277   0.223   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.501  -1.201   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.257  -2.542   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.473  -3.868   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.933  -3.852   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.229  -5.209   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.906  -1.128   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.083  -2.429   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.147   0.302   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.378   0.933   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.156  -0.397   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.508   1.680   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.187   2.716   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.788   1.877   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.850   3.099   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.257   1.709   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.522   2.906   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.165   3.633   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.966   4.381   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.074   2.762   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.714   1.353   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.247   1.211   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.829   0.086   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.479  -1.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.014  -1.444   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.897  -0.182   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.664  -2.840   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17   28                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6   18   22                                             
CONECT   18   17   19                                                       
CONECT   19   18   14   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
[(1S,2S,4S,5R,6S,7S,9R,12R)-5,7-Bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0,]dodecan-6-yl]methyl acetic acid	Generator

Chemical Formula

C₂₁H₃₀O₁₁

Average Mass

458.4600 Da

Monoisotopic Mass

458.17881 Da

IUPAC Name

[(1S,2S,4S,5R,6S,7S,9R,12R)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

Traditional Name

[(1S,2S,4S,5R,6S,7S,9R,12R)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]12[C@@H](OC(C)=O)[C@@H](O)C[C@](C)(O)[C@]11OC(C)(C)[C@@H]([C@H]1O)C(=O)[C@H]2OC(C)=O

InChI Identifier

InChI=1S/C21H30O11/c1-9(22)29-8-20-16(30-10(2)23)12(25)7-19(6,28)21(20)15(27)13(18(4,5)32-21)14(26)17(20)31-11(3)24/h12-13,15-17,25,27-28H,7-8H2,1-6H3/t12-,13+,15+,16-,17+,19-,20-,21-/m0/s1

InChI Key

HISDFVSSTMLDOG-DKWBATPYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Tricarboxylic acid or derivatives
Oxepane
Alpha-acyloxy ketone
Cyclitol or derivatives
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-2	ChemAxon
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.25 m³·mol⁻¹	ChemAxon
Polarizability	44.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

9103845

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10928601

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate (NP0204797)

MOL for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D MOL for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D SDF for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D-SDF for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

PDB for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D PDB for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

SMILES for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

INCHI for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

Structure for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D Structure for NP0204797 ([(1s,2s,4s,5r,6s,7s,9r,12r)-5,7-bis(acetyloxy)-2,4,12-trihydroxy-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)