NP-MRD: Showing NP-Card for robustolide A (NP0025110)

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Record Information

Version

2.0

Created at

2021-06-19 17:18:47 UTC

Updated at

2021-06-29 23:49:50 UTC

NP-MRD ID

NP0025110

Secondary Accession Numbers

None

Natural Product Identification

Common Name

robustolide A

Provided By

JEOL Database JEOL Logo

Description

Umbraculolide C belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. robustolide A is found in Ellisella robusta (Ellisellidae). robustolide A was first documented in 2007 (Sung, P.-J., et al.). Based on a literature review very few articles have been published on Umbraculolide C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119183D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192119183D          

 71 73  0  0  0  0            999 V2000
    0.7334    3.9003    3.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    2.9900    2.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    3.0992    0.7264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2648    2.8232    0.2304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3363    1.7276   -0.8579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6860    2.4600   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368    2.9070   -2.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083    3.6334   -4.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271    2.7583   -2.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    0.5728   -0.6750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7750    1.1856   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -0.0950   -2.1110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3137   -0.5421   -2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0436   -0.3745   -3.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428   -0.8554   -4.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8041    0.1039   -4.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -1.3094   -2.1341 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1735   -2.3546   -1.0922 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0413   -1.6994    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -2.0656    1.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449   -0.6064    0.3043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135   -0.3289    1.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0443    0.8393    2.3179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6394    0.7270    3.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    1.9941    3.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -0.2513    4.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674   -0.3260    1.9207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7780    0.0540    0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6412   -1.7521    2.2942 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9929   -2.6740    1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -1.4993    3.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -2.3066    3.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.2443    3.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    0.5220    3.0959 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2610    1.9470    2.8321 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8293    1.9077    1.9296 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    4.6887    2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654    3.9004    4.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324    4.1259    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    2.4819    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    3.7686   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    2.6273    1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    1.2499   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    3.0010   -4.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    4.5649   -3.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6100    3.8677   -4.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    1.6180    0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873    0.4539   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    1.9821   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    0.6495   -2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.9173   -3.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495   -0.7252   -5.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0684   -0.2698   -3.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197   -1.7832   -3.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5841   -0.9843   -1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2248   -2.8376   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315   -3.1470   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6082   -2.8426    1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -1.6123    2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -1.0943   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.1782    2.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    2.6532    4.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7267    2.4979    3.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063    1.7530    4.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    0.1837    0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9177   -2.2535    2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256   -3.6488    1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -2.8515    0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8105   -2.2748    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563    0.5871    3.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    2.3154    3.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0  0  0  0
 19 20  2  3  0  0  0
 21 10  1  0  0  0  0
 12 13  1  0  0  0  0
 10  5  1  0  0  0  0
 35 36  1  0  0  0  0
  5  4  1  0  0  0  0
 27 28  1  6  0  0  0
  4  3  1  0  0  0  0
 34 33  1  0  0  0  0
 29 30  1  0  0  0  0
 34 35  1  0  0  0  0
 22 23  1  0  0  0  0
 17 18  1  0  0  0  0
  5  6  1  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  1  0  0  0
  2 35  1  0  0  0  0
 21 60  1  6  0  0  0
 17 12  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  2  3  0  0  0
  7  8  1  0  0  0  0
 34 27  1  0  0  0  0
  7  9  2  0  0  0  0
 18 19  1  0  0  0  0
 23 24  1  0  0  0  0
 19 21  1  0  0  0  0
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 10 12  1  0  0  0  0
 24 26  2  0  0  0  0
 27 22  1  0  0  0  0
 13 14  1  0  0  0  0
 27 29  1  0  0  0  0
 14 15  1  0  0  0  0
 29 31  1  0  0  0  0
 14 16  2  0  0  0  0
 31 33  1  0  0  0  0
 31 32  2  0  0  0  0
 17 54  1  0  0  0  0
 17 55  1  0  0  0  0
 18 56  1  0  0  0  0
 18 57  1  0  0  0  0
 12 50  1  6  0  0  0
 22 61  1  1  0  0  0
  5 43  1  6  0  0  0
  4 41  1  0  0  0  0
  4 42  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
 35 71  1  1  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
 34 70  1  1  0  0  0
 29 66  1  1  0  0  0
 20 58  1  0  0  0  0
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 28 65  1  0  0  0  0
 30 67  1  0  0  0  0
 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
 11 47  1  0  0  0  0
 11 48  1  0  0  0  0
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  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
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 25 62  1  0  0  0  0
 25 63  1  0  0  0  0
 25 64  1  0  0  0  0
 15 51  1  0  0  0  0
 15 52  1  0  0  0  0
 15 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025110

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H35ClO9/c1-12-8-10-18(33-15(4)28)25(7)19(34-16(5)29)11-9-13(2)21(27)23-26(32,14(3)24(31)36-23)22(20(12)25)35-17(6)30/h14,18-23,32H,1-2,8-11H2,3-7H3/t14-,18-,19-,20+,21-,22-,23-,25+,26+/m0/s1

> <INCHI_KEY>
LEXFNQLRCIGWON-OHKCJQIGSA-N

> <FORMULA>
C26H35ClO9

> <MOLECULAR_WEIGHT>
527.01

> <EXACT_MASS>
526.1969604

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.26357000839164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4R,7R,8S,12S,13R,14S)-2,14-bis(acetyloxy)-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadecan-12-yl acetate

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.3089299169999995

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.362780699030516

> <JCHEM_PKA_STRONGEST_BASIC>
-3.952319722244053

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000002

> <JCHEM_REFRACTIVITY>
126.4497

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4R,7R,8S,12S,13R,14S)-2,14-bis(acetyloxy)-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadecan-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 73  0  0  0  0  0  0  0  0999 V2000
    0.7334    3.9003    3.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    2.9900    2.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1627    3.0992    0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2648    2.8232    0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363    1.7276   -0.8579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6860    2.4600   -2.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3368    2.9070   -2.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083    3.6334   -4.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271    2.7583   -2.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    0.5728   -0.6750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7750    1.1856   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -0.0950   -2.1110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3137   -0.5421   -2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0436   -0.3745   -3.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428   -0.8554   -4.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8041    0.1039   -4.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -1.3094   -2.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735   -2.3546   -1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413   -1.6994    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -2.0656    1.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449   -0.6064    0.3043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135   -0.3289    1.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0443    0.8393    2.3179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6394    0.7270    3.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    1.9941    3.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -0.2513    4.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1674   -0.3260    1.9207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7780    0.0540    0.6883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6412   -1.7521    2.2942 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9929   -2.6740    1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -1.4993    3.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -2.3066    3.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.2443    3.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    0.5220    3.0959 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2610    1.9470    2.8321 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8293    1.9077    1.9296 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    4.6887    2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654    3.9004    4.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324    4.1259    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    2.4819    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    3.7686   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    2.6273    1.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    1.2499   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    3.0010   -4.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    4.5649   -3.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6100    3.8677   -4.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    1.6180    0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873    0.4539   -0.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661    1.9821   -0.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294    0.6495   -2.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -1.9173   -3.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495   -0.7252   -5.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0684   -0.2698   -3.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5197   -1.7832   -3.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5841   -0.9843   -1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2248   -2.8376   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315   -3.1470   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6082   -2.8426    1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -1.6123    2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -1.0943   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.1782    2.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    2.6532    4.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7267    2.4979    3.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063    1.7530    4.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    0.1837    0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9177   -2.2535    2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256   -3.6488    1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -2.8515    0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8105   -2.2748    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563    0.5871    3.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    2.3154    3.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 19 20  2  3
 21 10  1  0
 12 13  1  0
 10  5  1  0
 35 36  1  0
  5  4  1  0
 27 28  1  6
  4  3  1  0
 34 33  1  0
 29 30  1  0
 34 35  1  0
 22 23  1  0
 17 18  1  0
  5  6  1  0
  3  2  1  0
 10 11  1  1
  2 35  1  0
 21 60  1  6
 17 12  1  0
  6  7  1  0
  2  1  2  3
  7  8  1  0
 34 27  1  0
  7  9  2  0
 18 19  1  0
 23 24  1  0
 19 21  1  0
 24 25  1  0
 10 12  1  0
 24 26  2  0
 27 22  1  0
 13 14  1  0
 27 29  1  0
 14 15  1  0
 29 31  1  0
 14 16  2  0
 31 33  1  0
 31 32  2  0
 17 54  1  0
 17 55  1  0
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 12 50  1  6
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  5 43  1  6
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  3 39  1  0
  3 40  1  0
 35 71  1  1
  1 37  1  0
  1 38  1  0
 34 70  1  1
 29 66  1  1
 20 58  1  0
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 30 68  1  0
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 11 47  1  0
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  8 44  1  0
  8 45  1  0
  8 46  1  0
 25 62  1  0
 25 63  1  0
 25 64  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.733   3.900   3.031  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.329   2.990   2.235  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.163   3.099   0.726  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.265   2.823   0.230  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.336   1.728  -0.858  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.686   2.460  -2.076  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.337   2.907  -2.854  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.208   3.633  -4.045  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.527   2.758  -2.620  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.408   0.573  -0.675  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.775   1.186  -0.269  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.608  -0.095  -2.111  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.314  -0.542  -2.590  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.044  -0.375  -3.912  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.343  -0.855  -4.211  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.804   0.104  -4.741  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.549  -1.309  -2.134  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.174  -2.355  -1.092  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.041  -1.699   0.262  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.860  -2.066   1.263  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.945  -0.606   0.304  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.414  -0.329   1.764  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.044   0.839   2.318  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.639   0.727   3.538  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.348   1.994   3.906  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.565  -0.251   4.267  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.167  -0.326   1.921  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.778   0.054   0.688  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.641  -1.752   2.294  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.993  -2.674   1.135  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.830  -1.499   3.170  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.701  -2.307   3.447  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.782  -0.244   3.679  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.699   0.522   3.096  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.261   1.947   2.832  0.00  0.00           C+0
HETATM   36 Cl   UNK     0       3.829   1.908   1.930  0.00  0.00          Cl+0
HETATM   37  H   UNK     0       0.109   4.689   2.619  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.865   3.900   4.109  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.432   4.126   0.439  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.888   2.482   0.195  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.646   3.769  -0.183  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.928   2.627   1.065  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.633   1.250  -1.016  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.927   3.001  -4.573  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.681   4.565  -3.724  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.610   3.868  -4.732  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.765   1.618   0.732  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.587   0.454  -0.275  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.066   1.982  -0.963  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.029   0.650  -2.798  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.428  -1.917  -3.967  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.550  -0.725  -5.277  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.068  -0.270  -3.641  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.520  -1.783  -3.123  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.584  -0.984  -1.975  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.225  -2.838  -1.357  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.932  -3.147  -1.089  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.608  -2.843   1.122  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.846  -1.612   2.248  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.098  -1.094  -0.193  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.731  -1.178   2.373  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.664   2.653   4.445  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.727   2.498   3.013  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.206   1.753   4.539  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.741   0.184   0.810  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.918  -2.253   2.950  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.326  -3.649   1.509  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.129  -2.852   0.490  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.811  -2.275   0.525  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.956   0.587   3.896  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.588   2.315   3.813  0.00  0.00           H+0
CONECT    1    2   37   38                                                  
CONECT    2    3   35    1                                                  
CONECT    3    4    2   39   40                                             
CONECT    4    5    3   41   42                                             
CONECT    5   10    4    6   43                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   44   45   46                                             
CONECT    9    7                                                            
CONECT   10   21    5   11   12                                             
CONECT   11   10   47   48   49                                             
CONECT   12   13   17   10   50                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   51   52   53                                             
CONECT   16   14                                                            
CONECT   17   18   12   54   55                                             
CONECT   18   17   19   56   57                                             
CONECT   19   20   18   21                                                  
CONECT   20   19   58   59                                                  
CONECT   21   22   10   60   19                                             
CONECT   22   21   23   27   61                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   62   63   64                                             
CONECT   26   24                                                            
CONECT   27   28   34   22   29                                             
CONECT   28   27   65                                                       
CONECT   29   30   27   31   66                                             
CONECT   30   29   67   68   69                                             
CONECT   31   29   33   32                                                  
CONECT   32   31                                                            
CONECT   33   34   31                                                       
CONECT   34   33   35   27   70                                             
CONECT   35   36   34    2   71                                             
CONECT   36   35                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    4                                                            
CONECT   43    5                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47   11                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   15                                                            
CONECT   52   15                                                            
CONECT   53   15                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   18                                                            
CONECT   57   18                                                            
CONECT   58   20                                                            
CONECT   59   20                                                            
CONECT   60   21                                                            
CONECT   61   22                                                            
CONECT   62   25                                                            
CONECT   63   25                                                            
CONECT   64   25                                                            
CONECT   65   28                                                            
CONECT   66   29                                                            
CONECT   67   30                                                            
CONECT   68   30                                                            
CONECT   69   30                                                            
CONECT   70   34                                                            
CONECT   71   35                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  146    0
END

RDKit          3D

71 73  0  0  0  0  0  0  0  0999 V2000
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    1.3289    2.9900    2.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2648    2.8232    0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3368    2.9070   -2.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083    3.6334   -4.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271    2.7583   -2.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    0.5728   -0.6750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7750    1.1856   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080   -0.0950   -2.1110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3137   -0.5421   -2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0436   -0.3745   -3.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428   -0.8554   -4.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8041    0.1039   -4.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1735   -2.3546   -1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413   -1.6994    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -2.0656    1.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9449   -0.6064    0.3043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4135   -0.3289    1.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0443    0.8393    2.3179 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5653   -0.2513    4.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6412   -1.7521    2.2942 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9929   -2.6740    1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -1.4993    3.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -2.3066    3.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.2443    3.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    0.5220    3.0959 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2610    1.9470    2.8321 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8293    1.9077    1.9296 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    4.6887    2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654    3.9004    4.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324    4.1259    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    2.4819    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6456    3.7686   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9315   -3.1470   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6082   -2.8426    1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465   -1.6123    2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979   -1.0943   -0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.1782    2.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2063    1.7530    4.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407    0.1837    0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9177   -2.2535    2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256   -3.6488    1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -2.8515    0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8105   -2.2748    0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563    0.5871    3.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879    2.3154    3.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 19 20  2  3
 21 10  1  0
 12 13  1  0
 10  5  1  0
 35 36  1  0
  5  4  1  0
 27 28  1  6
  4  3  1  0
 34 33  1  0
 29 30  1  0
 34 35  1  0
 22 23  1  0
 17 18  1  0
  5  6  1  0
  3  2  1  0
 10 11  1  1
  2 35  1  0
 21 60  1  6
 17 12  1  0
  6  7  1  0
  2  1  2  3
  7  8  1  0
 34 27  1  0
  7  9  2  0
 18 19  1  0
 23 24  1  0
 19 21  1  0
 24 25  1  0
 10 12  1  0
 24 26  2  0
 27 22  1  0
 13 14  1  0
 27 29  1  0
 14 15  1  0
 29 31  1  0
 14 16  2  0
 31 33  1  0
 31 32  2  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 12 50  1  6
 22 61  1  1
  5 43  1  6
  4 41  1  0
  4 42  1  0
  3 39  1  0
  3 40  1  0
 35 71  1  1
  1 37  1  0
  1 38  1  0
 34 70  1  1
 29 66  1  1
 20 58  1  0
 20 59  1  0
 28 65  1  0
 30 67  1  0
 30 68  1  0
 30 69  1  0
 11 47  1  0
 11 48  1  0
 11 49  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
 25 62  1  0
 25 63  1  0
 25 64  1  0
 15 51  1  0
 15 52  1  0
 15 53  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₅ClO₉

Average Mass

527.0100 Da

Monoisotopic Mass

526.19696 Da

IUPAC Name

(1S,2S,3R,4R,7R,8S,12S,13R,14S)-2,14-bis(acetyloxy)-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadecan-12-yl acetate

Traditional Name

(1S,2S,3R,4R,7R,8S,12S,13R,14S)-2,14-bis(acetyloxy)-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadecan-12-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H35ClO9/c1-12-8-10-18(33-15(4)28)25(7)19(34-16(5)29)11-9-13(2)21(27)23-26(32,14(3)24(31)36-23)22(20(12)25)35-17(6)30/h14,18-23,32H,1-2,8-11H2,3-7H3/t14-,18-,19-,20+,21-,22-,23-,25+,26+/m0/s1

InChI Key

LEXFNQLRCIGWON-OHKCJQIGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃ at -35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ellisella robusta	JEOL database	Sung, P.-J., et al, Tetrahedron 63, 7582 (2007)

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
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Organohalogen compound
Organochloride
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	3.04	ALOGPS
logP	2.31	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.45 m³·mol⁻¹	ChemAxon
Polarizability	52.26 Å³	ChemAxon
Number of Rings	3	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

10214831

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21592662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sung, P.-J., et al. (2007). Sung, P.-J., et al, Tetrahedron 63, 7582 (2007). Tetrahedron.

Showing NP-Card for robustolide A (NP0025110)

MOL for NP0025110 (robustolide A)

3D MOL for NP0025110 (robustolide A)

3D SDF for NP0025110 (robustolide A)

3D-SDF for NP0025110 (robustolide A)

PDB for NP0025110 (robustolide A)

3D PDB for NP0025110 (robustolide A)

SMILES for NP0025110 (robustolide A)

INCHI for NP0025110 (robustolide A)

Structure for NP0025110 (robustolide A)

3D Structure for NP0025110 (robustolide A)