NP-MRD: Showing NP-Card for (1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate (NP0155657)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 12:45:34 UTC

Updated at

2022-09-02 12:45:34 UTC

NP-MRD ID

NP0155657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate

Description

Dichotellide C belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate is found in Dichotella gemmacea. Based on a literature review very few articles have been published on Dichotellide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214452D          

 38 42  0  0  1  0            999 V2000
    0.1858   -1.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3851   -0.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    0.1101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0356   -0.1122    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    0.9304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5719    1.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590    2.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990    2.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561    2.0786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2799    2.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281    1.2420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0771    0.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.2489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0476   -0.4147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1993   -1.2257    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    0.0364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4369   -0.4350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3673   -1.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0444   -1.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206   -1.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9351    0.8591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4791    0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7575    0.9245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2253    0.2449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0477    0.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4023    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5155   -0.3693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1121    1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443    2.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    2.2835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0770    2.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    3.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4673    1.5386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6080    1.6735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4645    2.4859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891    2.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0106    3.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    3.5802    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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  6  0  0  0
 33 30  1  1  0  0  0
 21 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 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
M  END

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
   -2.8811    3.2962   -2.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239    2.2301   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7156    0.8833   -2.1940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2838    0.9558   -3.0589 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9159    0.0128   -0.9841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2278    0.4452   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771    0.7639    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9126    1.4993    1.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0144    0.0238    1.3032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5116    0.6763    2.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    0.1482    0.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5265    1.4281    0.3995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210    2.2719   -0.6116 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0913    2.0622   -1.1548 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0199    3.9620   -1.5223 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    1.2296   -0.1766 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9794    2.0588    0.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818    2.6449    1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1782    3.5254    1.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1709    2.3914    2.2729 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -0.1339   -0.6523 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1958   -0.1280   -2.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -0.6342   -0.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1695   -0.2392    0.8412 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4352    0.3452    0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1062    0.7845    2.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0626    0.5180   -0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -2.1453   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7270   -2.9129   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172   -2.3069   -1.2157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4923   -2.6129   -2.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823   -3.3163   -1.0887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2576   -1.1851   -0.1857 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0178   -0.9181    0.4455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7346   -2.1718    0.4194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498   -2.9544    1.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7036   -4.2287    1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4970   -2.5686    2.6585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5941    4.2785   -1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5993    3.2097   -3.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272    0.5379   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -1.0547   -1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3395   -1.0179    1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    0.8914    2.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0181    1.6538    2.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109    0.0541    3.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389    3.3228   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0471    1.6167   -2.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2842    1.1416    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7799    4.5707    1.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5858    3.2516    2.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9998    3.4474    1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2237   -0.3115   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148    0.8118   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661   -0.9224   -2.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3437   -0.3169   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4103    0.8055    2.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5452    1.7830    1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9764    0.1021    2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194   -2.4203   -0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -2.5208    0.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591   -3.9301   -0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0925   -3.2112   -2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4354   -2.1177   -2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -3.2099   -3.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8488   -1.7189    0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097   -0.7888    1.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1219   -4.5757    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096   -4.0895    0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0024   -4.9732    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  2 13  1  0
 13 12  1  0
 11 12  1  6
 11 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 34 33  1  0
 33 30  1  0
 30 31  1  0
 31 32  1  0
 30 29  1  0
 29 28  1  0
 28 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 21  1  0
 21 22  1  6
 21 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 14  1  0
 14 15  1  0
 11  9  1  0
 21 33  1  0
 11  5  1  0
 30 32  1  1
 14 13  1  0
 10 44  1  0
 10 45  1  0
 10 46  1  0
  9 43  1  1
  5 42  1  6
  3 41  1  6
  1 39  1  0
  1 40  1  0
 13 47  1  1
 34 67  1  1
 37 68  1  0
 37 69  1  0
 37 70  1  0
 33 66  1  1
 31 64  1  0
 31 65  1  0
 29 62  1  0
 29 63  1  0
 28 60  1  0
 28 61  1  0
 23 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 16 49  1  1
 19 50  1  0
 19 51  1  0
 19 52  1  0
 14 48  1  6
M  END


  Mrv1652309022214452D          

 38 42  0  0  1  0            999 V2000
    0.1858   -1.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3851   -0.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    0.1101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0356   -0.1122    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    0.9304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5719    1.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590    2.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4990    2.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6561    2.0786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2799    2.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281    1.2420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0771    0.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.2489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0476   -0.4147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1993   -1.2257    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.7598    0.0364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4369   -0.4350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3673   -1.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0444   -1.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206   -1.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9351    0.8591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4791    0.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7575    0.9245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2253    0.2449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0477    0.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4023    1.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5155   -0.3693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1121    1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443    2.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    2.2835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0770    2.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    3.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4673    1.5386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6080    1.6735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4645    2.4859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891    2.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0106    3.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    3.5802    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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  6  0  0  0
 33 30  1  1  0  0  0
 21 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 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
M  END
> <DATABASE_ID>
NP0155657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H]3O[C@@]12[C@@H](OC(C)=O)[C@H]1[C@@]2(CO2)CC[C@H](OC(C)=O)[C@]1(C)[C@@H](OC(C)=O)[C@@H]3I

> <INCHI_IDENTIFIER>
InChI=1S/C26H32ClIO10/c1-10-16(27)20-26(11(2)23(32)37-20)22(36-14(5)31)19-24(6,21(35-13(4)30)17(28)18(10)38-26)15(34-12(3)29)7-8-25(19)9-33-25/h11,15-22H,1,7-9H2,2-6H3/t11-,15-,16-,17+,18+,19+,20-,21-,22-,24-,25-,26-/m0/s1

> <INCHI_KEY>
PYAMRIBFBUHYBG-GYVJCAKNSA-N

> <FORMULA>
C26H32ClIO10

> <MOLECULAR_WEIGHT>
666.89

> <EXACT_MASS>
666.07287

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.177414082518574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'S,3'S,7'S,8'R,9'R,10'R,11'R,13'S,14'R,17'R)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadecane]-9'-yl acetate

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
2.261851339666667

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9335962293948943

> <JCHEM_POLAR_SURFACE_AREA>
126.96000000000001

> <JCHEM_REFRACTIVITY>
136.8896

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,3'S,7'S,8'R,9'R,10'R,11'R,13'S,14'R,17'R)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadecane]-9'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.347  -2.347   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.719  -0.852   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.450   0.206   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -1.933  -0.210   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       0.006   1.737   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.067   2.850   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.297   4.186   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.931   5.589   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.225   3.880   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.522   5.251   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.546   2.318   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.010   0.983   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.253  -0.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.822  -0.774   0.000  0.00  0.00           C+0
HETATM   15  I   UNK     0       4.105  -2.288   0.000  0.00  0.00           I+0
HETATM   16  C   UNK     0       5.152   0.068   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.416  -0.812   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.286  -2.346   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.550  -3.226   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.892  -3.001   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.479   1.604   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.494   0.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.014   1.726   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.887   0.457   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.422   0.579   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.084   1.970   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.296  -0.689   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.676   3.116   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.803   4.385   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.268   4.263   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.877   4.925   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.145   5.798   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.606   2.872   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.002   3.124   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.734   4.640   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.286   5.167   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.020   5.982   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.019   6.683   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12   34                                             
CONECT   12   11   13                                                       
CONECT   13   12    2   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   23   33                                             
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30   32                                                       
CONECT   32   31   30                                                       
CONECT   33   30   21   34                                                  
CONECT   34   33   11   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂ClIO₁₀

Average Mass

666.8900 Da

Monoisotopic Mass

666.07287 Da

IUPAC Name

(1'R,2R,2'S,3'S,7'S,8'R,9'R,10'R,11'R,13'S,14'R,17'R)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0^{1,14}.0^{3,8}]octadecane]-9'-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H]3O[C@@]12[C@@H](OC(C)=O)[C@H]1[C@@]2(CO2)CC[C@H](OC(C)=O)[C@]1(C)[C@@H](OC(C)=O)[C@@H]3I

InChI Identifier

InChI=1S/C26H32ClIO10/c1-10-16(27)20-26(11(2)23(32)37-20)22(36-14(5)31)19-24(6,21(35-13(4)30)17(28)18(10)38-26)15(34-12(3)29)7-8-25(19)9-33-25/h11,15-22H,1,7-9H2,2-6H3/t11-,15-,16-,17+,18+,19+,20-,21-,22-,24-,25-,26-/m0/s1

InChI Key

PYAMRIBFBUHYBG-GYVJCAKNSA-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 tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Furopyran
Gamma butyrolactone
Pyran
Oxane
Furan
Tetrahydrofuran
Carboxylic acid ester
Lactone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Alkyl iodide
Hydrocarbon derivative
Organic oxide
Alkyl halide
Alkyl chloride
Organic oxygen compound
Carbonyl group
Organohalogen compound
Organochloride
Organoiodide
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
logP	3.6	ALOGPS
logP	2.26	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	126.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.89 m³·mol⁻¹	ChemAxon
Polarizability	57.18 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

27026428

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52916783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate (NP0155657)

MOL for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D MOL for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D SDF for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D-SDF for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

PDB for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D PDB for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

SMILES for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

INCHI for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

Structure for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)

3D Structure for NP0155657 ((1'r,2r,2's,3's,7's,8'r,9'r,10'r,11'r,13's,14'r,17'r)-2',7'-bis(acetyloxy)-13'-chloro-10'-iodo-8',17'-dimethyl-12'-methylidene-16'-oxo-15',18'-dioxaspiro[oxirane-2,4'-tetracyclo[9.6.1.0¹,¹⁴.0³,⁸]octadecan]-9'-yl acetate)