NP-MRD: Showing NP-Card for (1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate (NP0306989)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 23:48:41 UTC

Updated at

2022-09-10 23:48:42 UTC

NP-MRD ID

NP0306989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate

Description

(1'S,2R,2'R,3'R,4'R,7'R,8'S,10'Z,12'S,13'R,14'R,15'R,16'R)-12',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]Heptadecan]-10'-en-2'-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate is found in Dichotella gemmacea. Based on a literature review very few articles have been published on (1'S,2R,2'R,3'R,4'R,7'R,8'S,10'Z,12'S,13'R,14'R,15'R,16'R)-12',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]Heptadecan]-10'-en-2'-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201482D          

 39 42  0  0  1  0            999 V2000
    4.8374   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3341    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7654    0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    0.7307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4849    0.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642   -0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -0.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.5554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6416    0.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052    2.2361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4824    2.5128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4594    3.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    3.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1391    4.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878    3.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2738    2.2798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9971    3.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7400    2.9605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3936    3.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5314    2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1850    3.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5544    1.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    1.6262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8002    0.8015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5916    0.5685    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3488    2.9801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4121    3.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0928    3.3366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262    3.0434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1698    3.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    2.3627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2375    2.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1189    3.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415    3.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3472    3.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165    1.6187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9504    0.9380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  1  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 12 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  1  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 10 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
   -2.2511    4.5617   -0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9494    3.3076   -1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    3.0633   -1.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    2.3790   -1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5115    1.7025   -0.3026 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5427    2.4815    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704    3.2481    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    4.0751    2.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928    3.2650    1.8440 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9218    0.2529   -0.4908 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1247    0.0398   -1.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -0.7678    0.1715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2889   -1.0363   -0.3287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7378   -2.3351   -0.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1745   -3.2778   -0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6231   -4.6176   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816   -2.9810   -2.1347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125   -0.1110    0.0818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2599    0.3947    1.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7201   -0.8610    0.1313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6696   -0.2938    1.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864   -0.6404   -1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2973   -1.3389   -1.6418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8148    0.4505   -1.7273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7074    0.9162   -0.9720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9111    2.2982   -0.5333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0948    2.5753    1.2022 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8121   -2.0576    0.2499 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0175   -3.0071   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2577   -3.2836    0.3024 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0293   -1.8890    1.1767 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6273   -1.1701    2.2640 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -1.1012    0.2334 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1933   -0.9537    0.8564 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3551   -1.4416    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6863   -1.3028    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651   -2.0373   -0.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3246    0.2197    0.1148 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2125    0.7286    1.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    5.4372   -0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1337    4.7446   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    3.5131   -2.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896    2.2643   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3651    1.8868    0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8201    5.0208    2.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353    4.2157    1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5383    3.4956    3.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002    0.5585   -2.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848   -0.9936   -2.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    0.4373   -2.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0121   -0.3679    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -0.9964   -1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7215   -5.2886   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2878   -5.0976   -1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0974   -4.6371    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0297   -0.2792    2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6355   -1.9448    0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2097   -0.0433    2.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4309   -1.0993    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2646    0.5576    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8890    0.9426   -1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9143    2.6577   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0283   -3.5428   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -3.1075   -1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715   -2.8573    1.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789   -1.5414    3.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020   -1.6437   -0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1763   -0.3418    0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6471   -1.2625    2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3473   -2.1414    0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9116    0.9773   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913    1.0222    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  5 10  1  0
 10 11  1  6
 10 38  1  0
 38 39  1  0
 38 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 33 31  1  0
 31 32  1  0
 31 28  1  0
 28 29  1  0
 29 30  1  0
 28 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 18  1  0
 18 19  1  1
 18 20  1  0
 18 25  1  0
 12 10  1  0
 28 30  1  1
 21 58  1  0
 21 59  1  0
 21 60  1  0
 20 57  1  1
 25 61  1  6
 26 62  1  6
  1 40  1  0
  1 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  1
  8 45  1  0
  8 46  1  0
  8 47  1  0
 11 48  1  0
 11 49  1  0
 11 50  1  0
 38 71  1  6
 39 72  1  0
 33 67  1  6
 36 68  1  0
 36 69  1  0
 36 70  1  0
 31 65  1  1
 32 66  1  0
 29 63  1  0
 29 64  1  0
 12 51  1  1
 13 52  1  6
 16 53  1  0
 16 54  1  0
 16 55  1  0
 19 56  1  0
M  END


  Mrv1652309112201482D          

 39 42  0  0  1  0            999 V2000
    4.8374   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3341    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7654    0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    0.7307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4849    0.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642   -0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587   -0.6342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    1.5554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6416    0.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052    2.2361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4824    2.5128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4594    3.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    3.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1391    4.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8878    3.3773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2738    2.2798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9971    3.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7400    2.9605    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3936    3.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5314    2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1850    3.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5544    1.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    1.6262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8002    0.8015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5916    0.5685    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3488    2.9801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4121    3.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0928    3.3366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262    3.0434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1698    3.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0601    2.3627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2375    2.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1189    3.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415    3.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3472    3.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165    1.6187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9504    0.9380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  1  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
 12 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  1  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 10 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0306989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)\C=C/[C@H](OC(C)=O)[C@@]3(C)[C@@H](O)[C@@H](OC(C)=O)[C@@H](O)[C@]4(CO4)[C@@H]3[C@@H](OC(C)=O)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C26H33ClO12/c1-10-7-8-15(36-12(3)28)24(6)18(25(9-35-25)20(32)17(19(24)31)37-13(4)29)22(38-14(5)30)26(34)11(2)23(33)39-21(26)16(10)27/h7-8,11,15-22,31-32,34H,1,9H2,2-6H3/b8-7-/t11-,15-,16-,17+,18+,19-,20+,21-,22+,24+,25-,26-/m0/s1

> <INCHI_KEY>
HTDHEUULGXFIKK-RPZGWZLCSA-N

> <FORMULA>
C26H33ClO12

> <MOLECULAR_WEIGHT>
572.99

> <EXACT_MASS>
572.1660542

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.207371024147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'R,3'R,4'R,7'R,8'S,10'Z,12'S,13'R,14'R,15'R,16'R)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecan]-10'-en-12'-yl acetate

> <JCHEM_LOGP>
-0.6242413849999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.904650321177751

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.225919056074211

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4361952932625393

> <JCHEM_POLAR_SURFACE_AREA>
178.42

> <JCHEM_REFRACTIVITY>
129.7437

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'R,3'R,4'R,7'R,8'S,10'Z,12'S,13'R,14'R,15'R,16'R)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0^{3,7}]heptadecan]-10'-en-12'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       9.030  -0.995   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.090   0.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.639  -0.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.162   0.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.223   1.364   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.772   0.847   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.494  -0.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.666  -1.665   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.043  -1.184   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.180   2.903   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.064   1.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.050   4.174   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.501   4.691   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.458   6.230   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.769   7.037   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.726   8.576   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.124   6.304   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.978   4.256   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.461   5.706   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.848   5.526   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.068   6.466   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.325   5.091   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.545   6.031   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.368   3.552   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.917   3.036   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.960   1.496   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0      10.438   1.061   0.000  0.00  0.00          Cl+0
HETATM   28  C   UNK     0       4.384   5.563   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.503   7.098   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.773   6.228   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.849   5.681   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.184   7.070   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.979   4.410   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.443   4.529   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.222   5.917   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.757   6.036   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.648   7.188   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.644   3.022   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.774   1.751   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   38                                             
CONECT   11   10                                                            
CONECT   12   10   13   28                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25    2   27                                                  
CONECT   27   26                                                            
CONECT   28   12   29   30   31                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   10   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1's,2R,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-12',15'-Bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0,]heptadecan]-10'-en-2'-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₃ClO₁₂

Average Mass

572.9900 Da

Monoisotopic Mass

572.16605 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)\C=C/[C@H](OC(C)=O)[C@@]3(C)[C@@H](O)[C@@H](OC(C)=O)[C@@H](O)[C@]4(CO4)[C@@H]3[C@@H](OC(C)=O)[C@]12O

InChI Identifier

InChI=1S/C26H33ClO12/c1-10-7-8-15(36-12(3)28)24(6)18(25(9-35-25)20(32)17(19(24)31)37-13(4)29)22(38-14(5)30)26(34)11(2)23(33)39-21(26)16(10)27/h7-8,11,15-22,31-32,34H,1,9H2,2-6H3/b8-7-/t11-,15-,16-,17+,18+,19-,20+,21-,22+,24+,25-,26-/m0/s1

InChI Key

HTDHEUULGXFIKK-RPZGWZLCSA-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
Dichotella gemmacea	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

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Tetracarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Oxirane
Alkyl chloride
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organohalogen compound
Organochloride
Carbonyl group
Alkyl halide
Organooxygen compound
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

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

162880413

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,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate (NP0306989)

MOL for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

3D MOL for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

3D SDF for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

3D-SDF for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

PDB for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

3D PDB for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

SMILES for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

INCHI for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

Structure for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)

3D Structure for NP0306989 ((1's,2r,2'r,3'r,4'r,7'r,8's,10'z,12's,13'r,14'r,15'r,16'r)-2',15'-bis(acetyloxy)-8'-chloro-3',14',16'-trihydroxy-4',13'-dimethyl-9'-methylidene-5'-oxo-6'-oxaspiro[oxirane-2,17'-tricyclo[11.4.0.0³,⁷]heptadecan]-10'-en-12'-yl acetate)