NP-MRD: Showing NP-Card for (1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate (NP0297965)

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Record Information

Version

2.0

Created at

2022-09-10 08:47:27 UTC

Updated at

2022-09-10 08:47:27 UTC

NP-MRD ID

NP0297965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate

Description

(1'S,2S,2'R,3'R,5'S,7'R,8'R,9'R,12'R,13'S,14'S,17'S)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]Octadecane]-9'-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate is found in Dichotella gemmacea. Based on a literature review very few articles have been published on (1'S,2S,2'R,3'R,5'S,7'R,8'R,9'R,12'R,13'S,14'S,17'S)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]Octadecane]-9'-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102210472D          

 42 46  0  0  1  0            999 V2000
    4.7914   -1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4916   -0.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073    0.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6761   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    0.5061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8920    1.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5922    1.9187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1079    2.5626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9234    2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4391    3.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232    1.6693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7766    2.0433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3860    2.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    2.8789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4822    3.2090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744    4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105    4.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305    4.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411    3.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762    3.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    3.1129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1824    3.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6431    4.5385    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.6994    2.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5816    1.6187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3594    0.7871    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1977   -0.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561    0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -0.1012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8334    1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336    1.9518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.9344    3.2888    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    1.3019    0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159    0.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609    1.3994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5607    0.6308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4361   -0.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921    0.3310    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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
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  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  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
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 22 23  1  0  0  0  0
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 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
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 31 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  6  0  0  0
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 34 35  1  1  0  0  0
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 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 34 39  1  0  0  0  0
 12 39  1  0  0  0  0
 39 40  1  1  0  0  0
  5 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 42  1  6  0  0  0
M  END

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
    1.9956    4.8805    1.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878    3.9778    0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3256    4.4289   -0.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5496    1.8025   -0.4633 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2155    0.5667    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3151   -0.5735    0.3882 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0210   -0.7554    1.7260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5230   -1.7186    2.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627   -1.8792    3.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3348   -2.4888    1.9965 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8470   -0.9680   -1.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5331   -2.0213   -0.1221 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.4295    2.2330    0.2723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1354    2.7173    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8595    2.2967   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4473    3.3648   -0.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3147    1.0130   -0.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2220    0.1071   -0.2223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2872   -0.8866    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7319   -0.6743    1.9217 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9384    0.7155   -1.1498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4330    0.2531   -2.3285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343    0.7613   -3.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337   -0.0797   -4.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7478    2.0066   -3.5335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270    0.4893   -0.6874 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4057    1.4356   -1.3779 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.8092    2.6535   -1.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0313    0.2817   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371    0.8629    1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102210472D          

 42 46  0  0  1  0            999 V2000
    4.7914   -1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4916   -0.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0073    0.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6761   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    0.5061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8920    1.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5922    1.9187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1079    2.5626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9234    2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4391    3.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232    1.6693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7766    2.0433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3860    2.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    2.8789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4822    3.2090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744    4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105    4.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305    4.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411    3.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762    3.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    3.1129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1824    3.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6431    4.5385    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.6994    2.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5816    1.6187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3594    0.7871    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1977   -0.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561    0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -0.1012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8334    1.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2336    1.9518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2534    2.8231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9344    3.2888    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4045    1.2565    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3019    0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4391   -0.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159    0.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609    1.3994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5607    0.6308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4361   -0.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921    0.3310    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
  5  4  1  6  0  0  0
  5  6  1  0  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  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  6  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  6  0  0  0
 25 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 34 39  1  0  0  0  0
 12 39  1  0  0  0  0
 39 40  1  1  0  0  0
  5 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0297965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)O[C@@H]2[C@H](Cl)[C@@]3(CI)CC[C@@H](OC(C)=O)[C@]4(C)[C@@H](C[C@H](OC(C)=O)[C@@]5(CO5)[C@H]4[C@@H](OC(C)=O)[C@@]12O3)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36ClIO12/c1-12-24(35)41-23-21(29)26(10-30)8-7-17(37-13(2)31)25(6)18(38-14(3)32)9-19(39-15(4)33)27(11-36-27)20(25)22(40-16(5)34)28(12,23)42-26/h12,17-23H,7-11H2,1-6H3/t12-,17-,18-,19+,20+,21+,22-,23-,25-,26+,27+,28+/m1/s1

> <INCHI_KEY>
LJVXOXNEMVDEAL-XRFJESQOSA-N

> <FORMULA>
C28H36ClIO12

> <MOLECULAR_WEIGHT>
726.94

> <EXACT_MASS>
726.094

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
63.599369393847994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2S,2'R,3'R,5'S,7'R,8'R,9'R,12'R,13'S,14'S,17'S)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0^{1,14}.0^{3,8}]octadecane]-9'-yl acetate

> <JCHEM_LOGP>
1.752836207666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.943581624446655

> <JCHEM_POLAR_SURFACE_AREA>
153.26000000000002

> <JCHEM_REFRACTIVITY>
148.13389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,3'R,5'S,7'R,8'R,9'R,12'R,13'S,14'S,17'S)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0^{1,14}.0^{3,8}]octadecane]-9'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.944  -2.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.384  -0.723   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.347   0.479   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.862  -0.490   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.302   0.945   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.265   2.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.705   3.581   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.668   4.784   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.190   4.551   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.153   5.753   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.750   3.116   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.183   3.814   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.321   4.852   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.089   5.374   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.500   5.990   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.672   7.521   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.433   8.435   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.084   8.137   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.997   6.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.382   6.669   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.017   5.811   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.340   7.194   0.000  0.00  0.00           C+0
HETATM   23  I   UNK     0       1.200   8.472   0.000  0.00  0.00           I+0
HETATM   24  O   UNK     0       1.305   4.437   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.086   3.022   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.671   1.469   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.369  -0.041   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.851   1.192   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.534  -0.189   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.556   2.571   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.436   3.643   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.473   5.270   0.000  0.00  0.00           C+0
HETATM   33 Cl   UNK     0      -1.744   6.139   0.000  0.00  0.00          Cl+0
HETATM   34  C   UNK     0       2.622   2.345   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.430   0.817   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.011   0.219   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.820  -1.309   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.216   1.149   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.220   2.612   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.780   1.177   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.547  -0.345   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.345   0.618   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   40                                                  
CONECT    6    5    7                                                       
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   39                                             
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24   32                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   31   34                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   21   33                                                  
CONECT   33   32                                                            
CONECT   34   25   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   34   12   40                                                  
CONECT   40   39    5   41   42                                             
CONECT   41   40   42                                                       
CONECT   42   41   40                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1's,2S,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-Tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0,.0,]octadecane]-9'-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₆ClIO₁₂

Average Mass

726.9400 Da

Monoisotopic Mass

726.09400 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)O[C@@H]2[C@H](Cl)[C@@]3(CI)CC[C@@H](OC(C)=O)[C@]4(C)[C@@H](C[C@H](OC(C)=O)[C@@]5(CO5)[C@H]4[C@@H](OC(C)=O)[C@@]12O3)OC(C)=O

InChI Identifier

InChI=1S/C28H36ClIO12/c1-12-24(35)41-23-21(29)26(10-30)8-7-17(37-13(2)31)25(6)18(38-14(3)32)9-19(39-15(4)33)27(11-36-27)20(25)22(40-16(5)34)28(12,23)42-26/h12,17-23H,7-11H2,1-6H3/t12-,17-,18-,19+,20+,21+,22-,23-,25-,26+,27+,28+/m1/s1

InChI Key

LJVXOXNEMVDEAL-XRFJESQOSA-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
Pentacarboxylic acid or derivatives
Furofuran
Gamma butyrolactone
Monosaccharide
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Organoheterocyclic compound
Oxirane
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Alkyl chloride
Organic oxide
Organic oxygen compound
Organohalogen compound
Organochloride
Carbonyl group
Alkyl iodide
Alkyl halide
Organoiodide
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	1.75	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	153.26 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	148.13 m³·mol⁻¹	ChemAxon
Polarizability	63.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

163072074

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,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate (NP0297965)

MOL for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D MOL for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D SDF for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D-SDF for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

PDB for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D PDB for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

SMILES for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

INCHI for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

Structure for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D Structure for NP0297965 ((1's,2s,2'r,3'r,5's,7'r,8'r,9'r,12'r,13's,14's,17's)-2',5',7'-tris(acetyloxy)-13'-chloro-12'-(iodomethyl)-8',17'-dimethyl-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[10.5.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)