NP-MRD: Showing NP-Card for (1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione (NP0304640)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 19:53:08 UTC

Updated at

2022-09-10 19:53:09 UTC

NP-MRD ID

NP0304640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione

Description

(1'S,2S,2'R,3'S,4E,5'R,7'R,8'S,9'S,12'R)-2',12'-dihydroxy-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-12'-(propan-2-yl)-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]Dodecane]-5,11'-dione belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. (1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione is found in Picrodendron baccatum. Based on a literature review very few articles have been published on (1'S,2S,2'R,3'S,4E,5'R,7'R,8'S,9'S,12'R)-2',12'-dihydroxy-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-12'-(propan-2-yl)-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]Dodecane]-5,11'-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221532D          

 41 46  0  0  1  0            999 V2000
    4.1995   -2.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8287   -1.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6394   -1.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8182   -2.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -2.8987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6052   -2.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2132   -2.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0001   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6081   -1.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1790   -3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9659   -3.3322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5709   -3.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7498   -4.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840   -3.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117   -0.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6511   -0.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5661    0.6256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3593    0.8524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    0.2485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955    1.4501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4529    2.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205    1.7329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3121    1.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9550    1.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4897    1.1496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9251    0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    0.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434   -0.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -0.6850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5251   -0.3881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5316   -1.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3386   -2.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729    0.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1827   -0.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3933    0.1991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8951    0.7996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312   -0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -1.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  3 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 18 35  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  1  0  0  0
 31 37  1  0  0  0  0
 27 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
M  END

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
    2.8838    3.3185   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671    2.3002    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669    0.9265    0.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6800    0.3555    0.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7761    0.6701   -0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6918    1.2887   -1.2747 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1165    0.1913    0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3224   -0.5005    1.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5579   -0.9445    1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7506   -1.6441    2.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6527   -0.6920    0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9246   -1.1345    1.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4352    0.0049   -0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5451    0.2562   -1.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2012    0.4457   -0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4063    0.1307   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0165    0.5580   -0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7538   -0.6490    0.0013 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0592   -1.6797   -0.5453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3879   -1.2947   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -2.0720   -0.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658   -0.8373    1.5063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7444   -2.3127    1.8196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7996   -1.4569    1.9378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8524   -1.3508    0.8301 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2298   -2.6950    0.5899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254   -0.6753    1.4095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4893    0.4235    2.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753    0.4371    3.5575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381    1.3704    1.3827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7460    1.2045    0.1418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8275    0.5042   -0.8735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0346    1.4982   -1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390    1.8679   -2.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858   -0.7216   -0.3591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2453   -1.7807   -1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8046    0.2316    0.5051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6905    0.9337    1.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6174   -0.3660   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6162   -1.3208    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4706    0.6992   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    3.3008   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4123    4.3334    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    3.4223    0.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6032   -0.6816    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9781    0.8989    1.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4701   -0.7020    1.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9621   -1.8259    3.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0878   -1.6441    2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231    0.7647   -1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0795    0.9930   -1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1846    1.4849    0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0712    0.5767   -1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1567   -0.3670    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1820   -1.4073    2.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9281   -2.9625    1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6580   -1.3739    1.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0742    2.1517   -0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    0.2354   -1.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2073    0.9709   -3.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6800    2.6425   -3.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165    2.1381   -2.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4476   -2.5381   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1848   -1.2562   -2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090   -2.3105   -1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865    0.3099    2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1606   -0.9402   -1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1129   -2.1293    0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2029   -1.7731   -0.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3343   -0.7391    0.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4235    0.8359   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7125    0.4217   -2.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9872    1.6816   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 32  1  0
 32 31  1  0
 31 30  1  0
 30 28  1  0
 28 29  2  0
 28 27  1  0
 27 37  1  0
 37 38  1  1
 37 39  1  0
 39 40  1  0
 39 41  1  0
 27 25  1  0
 25 26  1  6
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 18  1  0
 18 17  1  0
 17 16  1  0
 16  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  3  2  1  0
  2  1  1  0
 16 20  1  0
 20 21  2  0
 20 19  1  0
 18 35  1  0
 35 36  1  6
 35 32  1  0
 37 31  1  0
 35 25  1  0
 22 24  1  0
 18 19  1  6
 15  7  1  0
 34 60  1  0
 34 61  1  0
 34 62  1  0
 32 59  1  6
 31 58  1  6
 27 57  1  1
 38 66  1  0
 39 67  1  0
 40 68  1  0
 40 69  1  0
 40 70  1  0
 41 71  1  0
 41 72  1  0
 41 73  1  0
 26 56  1  0
 24 55  1  1
 22 54  1  1
 17 52  1  0
 17 53  1  0
  4 45  1  0
  4 46  1  0
  8 47  1  0
 10 48  1  0
 12 49  1  0
 14 50  1  0
 15 51  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
 36 63  1  0
 36 64  1  0
 36 65  1  0
M  END


  Mrv1652309102221532D          

 41 46  0  0  1  0            999 V2000
    4.1995   -2.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8287   -1.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6394   -1.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8182   -2.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2102   -2.8987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6052   -2.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2132   -2.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0001   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6081   -1.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1790   -3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9659   -3.3322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5709   -3.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7498   -4.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840   -3.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117   -0.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6511   -0.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5661    0.6256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3593    0.8524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696    0.2485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955    1.4501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4529    2.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205    1.7329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3121    1.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9550    1.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4897    1.1496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9251    0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0979    0.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434   -0.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -0.6850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5251   -0.3881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5316   -1.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3386   -2.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729    0.3989    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1827   -0.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3933    0.1991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8951    0.7996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312   -0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789    0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -1.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  3 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
 18 35  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  1  0  0  0
 31 37  1  0  0  0  0
 27 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H]2OC(=O)[C@@H]([C@]2(O)C(C)C)[C@]2(O)[C@H]3O[C@H]3[C@]3(C\C(=C(\CC(=O)C4=CC(O)=C(O)C(O)=C4)OC)C(=O)O3)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O13/c1-10(2)27(35)18-24(34)40-21(27)19(38-5)25(3)26(20-22(39-20)28(18,25)36)9-12(23(33)41-26)16(37-4)8-13(29)11-6-14(30)17(32)15(31)7-11/h6-7,10,18-22,30-32,35-36H,8-9H2,1-5H3/b16-12+/t18-,19+,20+,21-,22-,25-,26+,27+,28-/m0/s1

> <INCHI_KEY>
FVUBKLFJOPKGMQ-IVOUCQKHSA-N

> <FORMULA>
C28H32O13

> <MOLECULAR_WEIGHT>
576.551

> <EXACT_MASS>
576.18429109

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.18361223703031

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2S,2'R,3'S,4E,5'R,7'R,8'S,9'S,12'R)-2',12'-dihydroxy-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-12'-(propan-2-yl)-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-5,11'-dione

> <JCHEM_LOGP>
0.15857472133333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.284954610623688

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.390433749124385

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6713113420574244

> <JCHEM_POLAR_SURFACE_AREA>
201.80999999999997

> <JCHEM_REFRACTIVITY>
135.6463

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,3'S,4E,5'R,7'R,8'S,9'S,12'R)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-5,11'-dione

> <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       7.839  -4.864   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.120  -4.008   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.013  -2.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.527  -2.867   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.861  -4.370   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.726  -5.411   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.330  -4.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.465  -3.792   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.934  -4.254   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.069  -3.213   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.267  -5.758   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.736  -6.220   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.132  -6.798   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.466  -8.302   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.664  -6.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.048  -0.899   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.815  -0.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.657   1.168   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.137   1.591   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.997   0.314   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.583   0.464   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.712   2.707   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.445   4.224   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.265   3.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.316   2.022   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.649   3.627   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.781   2.146   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.727   1.023   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.183   1.455   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.948  -0.501   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.277  -1.279   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.714  -0.724   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.726  -2.564   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.365  -4.219   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.176   0.745   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.941  -0.870   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.601   0.372   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.538   1.492   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.605  -0.618   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.254   0.623   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.889  -2.348   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16    3   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22   35                                             
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22   24                                                       
CONECT   24   23   22   25                                                  
CONECT   25   24   26   27   35                                             
CONECT   26   25                                                            
CONECT   27   25   28   37                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   18   25   36                                             
CONECT   36   35                                                            
CONECT   37   31   27   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₁₃

Average Mass

576.5510 Da

Monoisotopic Mass

576.18429 Da

IUPAC Name

Traditional Name

(1'S,2S,2'R,3'S,4E,5'R,7'R,8'S,9'S,12'R)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0^{2,7}.0^{3,5}]dodecane]-5,11'-dione

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H]2OC(=O)[C@@H]([C@]2(O)C(C)C)[C@]2(O)[C@H]3O[C@H]3[C@]3(C\C(=C(\CC(=O)C4=CC(O)=C(O)C(O)=C4)OC)C(=O)O3)[C@]12C

InChI Identifier

InChI=1S/C28H32O13/c1-10(2)27(35)18-24(34)40-21(27)19(38-5)25(3)26(20-22(39-20)28(18,25)36)9-12(23(33)41-26)16(37-4)8-13(29)11-6-14(30)17(32)15(31)7-11/h6-7,10,18-22,30-32,35-36H,8-9H2,1-5H3/b16-12+/t18-,19+,20+,21-,22-,25-,26+,27+,28-/m0/s1

InChI Key

FVUBKLFJOPKGMQ-IVOUCQKHSA-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
Picrodendron baccatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Alkyl-phenylketone
Benzenetriol
Phenylketone
Pyrogallol derivative
Benzoyl
Caprolactone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxepane
Phenol
Benzenoid
Monocyclic benzene moiety
Oxane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Vinylogous ester
Cyclic alcohol
Carboxylic acid ester
Lactone
Ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Dialkyl ether
Oxirane
Ether
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.16	ChemAxon
pKa (Strongest Acidic)	7.39	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	201.81 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.65 m³·mol⁻¹	ChemAxon
Polarizability	55.18 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163190942

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's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione (NP0304640)

MOL for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

3D MOL for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

3D SDF for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

3D-SDF for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

PDB for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

3D PDB for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

SMILES for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

INCHI for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

Structure for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)

3D Structure for NP0304640 ((1's,2s,2'r,3's,4e,5'r,7'r,8's,9's,12'r)-2',12'-dihydroxy-12'-isopropyl-8'-methoxy-4-[1-methoxy-3-oxo-3-(3,4,5-trihydroxyphenyl)propylidene]-7'-methyl-4',10'-dioxaspiro[oxolane-2,6'-tetracyclo[7.2.1.0²,⁷.0³,⁵]dodecane]-5,11'-dione)