NP-MRD: Showing NP-Card for (1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate (NP0262342)

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Record Information

Version

2.0

Created at

2022-09-08 05:05:40 UTC

Updated at

2022-09-08 05:05:40 UTC

NP-MRD ID

NP0262342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate

Description

(1'S,2S,3R,3aS,4R,5'S,5aS,6'S,7'R,8'S,9'S,9aS,9bS)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-1,2,3a,4,5,5a,8,9,9a,9b-decahydro-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]Dodecan]-3'-en-5'-yl benzoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate is found in Ruptiliocarpon caracolito. Based on a literature review very few articles have been published on (1'S,2S,3R,3aS,4R,5'S,5aS,6'S,7'R,8'S,9'S,9aS,9bS)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-1,2,3a,4,5,5a,8,9,9a,9b-decahydro-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]Dodecan]-3'-en-5'-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082207052D          

 56 62  0  0  1  0            999 V2000
    7.7379   -1.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9931   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1047   -0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5027   -0.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2065    0.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7132   -0.3201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1655    0.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1112    0.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217    0.0047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8981    0.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9259    0.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946   -0.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860    1.2835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341   -0.7987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7361   -1.3628    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1883   -2.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856   -2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670   -2.0071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4672   -2.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4116   -1.1969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7563   -1.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881   -2.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644   -0.5831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0223   -0.9297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8062   -1.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739   -2.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957   -0.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345   -1.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -0.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8706    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318    0.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -0.0644    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6625    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    0.7757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5205    1.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2071    2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    2.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2518    2.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417    1.3351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0260    2.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433    3.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891    4.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0329    3.7454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640    1.0588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0457    1.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5187    0.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534   -0.3459    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2487   -0.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    0.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811    1.3353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -1.1235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1276   -1.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9172   -1.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489   -2.0342    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 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
 28 33  1  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  6  0  0  0
 46 48  1  0  0  0  0
 49 48  1  6  0  0  0
 34 49  1  0  0  0  0
 20 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 46 51  1  0  0  0  0
 51 52  2  0  0  0  0
 15 53  1  0  0  0  0
  6 53  1  0  0  0  0
 53 54  1  1  0  0  0
 54 55  1  0  0  0  0
  3 55  1  0  0  0  0
 55 56  2  0  0  0  0
M  END

     RDKit          3D

110116  0  0  0  0  0  0  0  0999 V2000
    6.0426    4.0293    0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7076    2.8323   -0.0708 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0109    1.7625   -0.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273    0.9242    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4342    1.0001    1.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052   -0.2023   -0.4531 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8811   -0.9766   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981   -1.0942    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4827   -1.3988    0.2099 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2239   -2.2222    1.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0775   -3.5664    1.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7994   -4.1878    2.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1982   -4.1847    0.2921 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -0.2353   -0.3023 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6150   -0.1906   -1.6925 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0393   -1.5028   -2.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.1905   -2.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4029   -0.5311   -1.8519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6374   -0.7301   -2.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858    0.1539   -0.5568 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2644    1.6047   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563    2.7008   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9994    2.0596   -0.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2035    1.1572   -0.8205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3067    2.0677   -0.5563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4382    2.1408   -1.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5451    1.3686   -2.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5341    3.0578   -1.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4918    3.9310    0.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5501    4.7966    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6635    4.8282   -0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7112    3.9492   -1.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6604    3.0934   -1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620    0.4272    0.4580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0274    1.5029    1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9211   -0.5653    0.8147 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0087   -1.5868   -0.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -1.8281   -0.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2745   -2.9170   -1.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1863   -1.1098   -0.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448   -1.1635    2.1987 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2966   -2.4509    2.1413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2690   -2.8351    3.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231   -4.1626    2.9394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6339   -2.0529    3.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -1.4934    2.2890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7704   -2.0886    3.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -0.3447    1.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286   -0.2363    0.4443 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.1309   -3.6700    1.2033 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587    0.5109   -1.5141 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7019    0.9094   -2.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2420    3.8365    1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5571    4.5337   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4006    1.1652    2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8422    0.0807    2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0614    1.8242    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9032   -2.0399   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9514   -0.9024   -2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8832   -0.6070   -0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4522   -2.1339    0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393   -0.7411    1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4729   -2.2323   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -4.8510    2.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6579   -4.9013    2.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -3.4804    3.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2990    0.6379    0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.2111   -2.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4006   -1.1422   -3.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823   -2.0295   -1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512   -0.3242   -3.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2896    1.1961   -2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188   -1.5830   -1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682   -1.3589   -2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7759    3.6990   -0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7570    2.8843   -1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984    2.5965    0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421    3.1222   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353    0.6435   -1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0262342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)[C@@]2(C)C[C@@H](OC(C)=O)[C@H]3[C@@](C)(C[C@H](C)[C@]33C(C)=C[C@H](OC(=O)C4=CC=CC=C4)[C@@]4(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]5(C)C[C@]34OC5=O)[C@@H]2CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C44H54O12/c1-22-17-32(55-37(49)28-15-13-12-14-16-28)42(10)36(54-27(6)47)35(53-26(5)46)41(9)21-43(42,56-38(41)50)44(22)23(2)19-40(8)31-18-29(48)33(51-11)24(3)39(31,7)20-30(34(40)44)52-25(4)45/h12-17,23,30-32,34-36H,18-21H2,1-11H3/t23-,30+,31+,32-,34-,35+,36-,39+,40-,41-,42-,43+,44+/m0/s1

> <INCHI_KEY>
BFXFFTRLJXJGTQ-KNNHLRTBSA-N

> <FORMULA>
C44H54O12

> <MOLECULAR_WEIGHT>
774.904

> <EXACT_MASS>
774.361527179

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
82.99870546260269

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2S,3R,3aS,4R,5'S,5aS,6'S,7'R,8'S,9'S,9aS,9bS)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-1,2,3a,4,5,5a,8,9,9a,9b-decahydro-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0^{1,6}]dodecan]-3'-en-5'-yl benzoate

> <JCHEM_LOGP>
5.128013405666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.880969513735948

> <JCHEM_POLAR_SURFACE_AREA>
157.8

> <JCHEM_REFRACTIVITY>
201.20460000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,3R,3aS,4R,5'S,5aS,6'S,7'R,8'S,9'S,9aS,9bS)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1H-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0^{1,6}]dodecan]-3'-en-5'-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      14.444  -1.942   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.054  -1.154   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.395  -1.204   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.272  -0.151   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.586   0.845   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.798  -0.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.642   0.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.674   0.456   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.200   0.009   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.410   1.186   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.595   0.987   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.350  -0.837   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.587   2.396   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.850  -1.491   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.974  -2.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.818  -3.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.320  -3.938   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.792  -3.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.605  -5.376   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.502  -2.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.278  -3.198   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.591  -4.694   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.843  -2.617   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.614  -1.088   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.042  -1.735   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.505  -2.329   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.818  -3.901   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.792  -1.300   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.171  -1.986   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.454  -1.134   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.358   0.403   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.979   1.088   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.696   0.237   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.833  -0.120   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.237   0.371   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.417   1.448   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.972   2.651   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.387   3.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.905   4.249   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.470   5.400   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.624   2.492   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.782   4.368   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.374   5.993   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.713   7.469   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.662   6.991   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       5.160   1.976   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.685   3.672   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.701   0.671   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.393  -0.646   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       6.064  -0.489   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       6.505   1.082   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       7.618   2.493   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       8.448  -2.097   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.572  -3.150   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      11.045  -2.704   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      12.225  -3.797   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   55                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   53                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   20                                                  
CONECT   15   14   16   17   53                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21   49                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   24   35   36   49                                             
CONECT   35   34                                                            
CONECT   36   34   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   47   48   51                                             
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   34   20   50                                             
CONECT   50   49   51                                                       
CONECT   51   50   46   52                                                  
CONECT   52   51                                                            
CONECT   53   15    6   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54    3   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Value	Source
(1's,2S,3R,3AS,4R,5's,5as,6's,7'r,8's,9's,9as,9BS)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-1,2,3a,4,5,5a,8,9,9a,9b-decahydro-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0,]dodecan]-3'-en-5'-yl benzoic acid	Generator

Chemical Formula

C₄₄H₅₄O₁₂

Average Mass

774.9040 Da

Monoisotopic Mass

774.36153 Da

IUPAC Name

Traditional Name

(1'S,2S,3R,3aS,4R,5'S,5aS,6'S,7'R,8'S,9'S,9aS,9bS)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1H-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0^{1,6}]dodecan]-3'-en-5'-yl benzoate

CAS Registry Number

Not Available

SMILES

COC1=C(C)[C@@]2(C)C[C@@H](OC(C)=O)[C@H]3[C@@](C)(C[C@H](C)[C@]33C(C)=C[C@H](OC(=O)C4=CC=CC=C4)[C@@]4(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]5(C)C[C@]34OC5=O)[C@@H]2CC1=O

InChI Identifier

InChI=1S/C44H54O12/c1-22-17-32(55-37(49)28-15-13-12-14-16-28)42(10)36(54-27(6)47)35(53-26(5)46)41(9)21-43(42,56-38(41)50)44(22)23(2)19-40(8)31-18-29(48)33(51-11)24(3)39(31,7)20-30(34(40)44)52-25(4)45/h12-17,23,30-32,34-36H,18-21H2,1-11H3/t23-,30+,31+,32-,34-,35+,36-,39+,40-,41-,42-,43+,44+/m0/s1

InChI Key

BFXFFTRLJXJGTQ-KNNHLRTBSA-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
Ruptiliocarpon caracolito	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Clerodane diterpenoid
Diterpene lactone
Diterpenoid
Pentacarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Caprolactone
Cyclohexenone
Oxepane
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Cyclic ketone
Lactone
Ketone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	5.13	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	157.8 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	201.2 m³·mol⁻¹	ChemAxon
Polarizability	83 Å³	ChemAxon
Number of Rings	7	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

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

162884337

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate (NP0262342)

MOL for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

3D MOL for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

3D SDF for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

3D-SDF for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

PDB for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

3D PDB for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

SMILES for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

INCHI for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

Structure for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)

3D Structure for NP0262342 ((1's,2s,3r,3as,4r,5's,5as,6's,7'r,8's,9's,9as,9bs)-4,7',8'-tris(acetyloxy)-7-methoxy-2,3',5a,6,6',9',9b-heptamethyl-8,10'-dioxo-2,3a,4,5,9,9a-hexahydro-1h-11'-oxaspiro[cyclopenta[a]naphthalene-3,2'-tricyclo[7.2.1.0¹,⁶]dodecan]-3'-en-5'-yl benzoate)