NP-MRD: Showing NP-Card for (2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate (NP0190195)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 06:49:04 UTC

Updated at

2022-09-04 06:49:04 UTC

NP-MRD ID

NP0190195

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate

Description

(2R,4aS,8S,8aR)-8-{[(6,8-dimethoxy-2-oxo-2H-chromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-decahydronaphthalen-2-yl acetate belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). (2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate is found in Anthemis cretica. Based on a literature review very few articles have been published on (2R,4aS,8S,8aR)-8-{[(6,8-dimethoxy-2-oxo-2H-chromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-decahydronaphthalen-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208492D          

 36 39  0  0  1  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -2.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   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  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    0.1296   -0.7896   -3.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1418    0.2030   -2.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4653    1.5546   -2.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5542    2.1418   -1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3151    1.0061   -1.1838 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6758    1.4288   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7160    0.9957   -1.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8146    2.9334   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394    0.7504    0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6446    1.3872    1.3680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6521   -0.6708    0.7084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7098   -0.9354    2.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256   -1.8634    2.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6819   -2.1360    4.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3957   -2.4553    1.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2600   -0.9704    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5169    0.3041   -0.1384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3129    1.0712    1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367   -0.0041   -0.7307 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3576   -1.3201   -0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344   -1.7212   -0.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -1.2749   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2490   -1.6021    1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3843   -2.3169    1.9839 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -2.6515    3.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710   -1.2023    1.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3689   -0.4930    0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6071   -0.1000    1.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4474    0.6087    0.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0415    0.9031   -0.7546 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8156    1.5540   -1.5135 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8570    0.5086   -1.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0227   -0.1656   -0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7653   -0.5703   -0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318   -0.1788   -2.2208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236    1.0892   -2.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3600   -1.7728   -2.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1297   -0.6534   -4.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8327    1.4916   -3.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303    2.1998   -2.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711    2.6653   -2.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1464    2.8607   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4579    0.2492   -2.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8004   -0.0861   -1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948    1.4831   -2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6806    1.4982   -1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7145    3.1295   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9177    3.4265   -0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0393    3.3464   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950   -1.2754    0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7543   -1.8335    4.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -3.2475    4.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5675   -1.6651    4.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420   -1.6017   -0.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7233   -1.5752    0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221    0.8107    1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077    0.8016    1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647    2.1853    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5729    0.7836   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676   -1.2845    0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937   -2.1222   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431   -3.1888    3.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0494   -1.7356    3.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6474   -3.3009    3.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7928   -1.4374    2.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9045   -0.3455    2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4297    0.9502    0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    0.9720   -3.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444    1.8141   -2.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572    1.4397   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  2  0
  9 11  1  0
 11 16  1  0
 16 17  1  0
 17 18  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 22 34  1  0
 34 35  1  0
 35 36  1  0
 34 33  2  0
 33 32  1  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 29 28  2  0
 28 27  1  0
 27 26  2  0
 26 23  1  0
 17 19  1  0
 27 33  1  0
 17  5  1  0
 25 62  1  0
 25 63  1  0
 25 64  1  0
 20 60  1  0
 20 61  1  0
 19 59  1  1
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  6
  7 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
 11 50  1  6
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 14 51  1  0
 14 52  1  0
 14 53  1  0
 36 68  1  0
 36 69  1  0
 36 70  1  0
 29 67  1  0
 28 66  1  0
 26 65  1  0
M  END


  Mrv1652309042208492D          

 36 39  0  0  1  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401   -3.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -2.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   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  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190195

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC[C@H]2C(=C)CC[C@@H]3C(C)(C)C(=O)[C@@H](C[C@@]23C)OC(C)=O)C(OC)=C2OC(=O)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O8/c1-15-8-10-21-27(3,4)26(31)20(35-16(2)29)13-28(21,5)18(15)14-34-24-19(32-6)12-17-9-11-22(30)36-23(17)25(24)33-7/h9,11-12,18,20-21H,1,8,10,13-14H2,2-7H3/t18-,20+,21+,28-/m0/s1

> <INCHI_KEY>
VOGMGSXTNFUXDC-HGXKVACJSA-N

> <FORMULA>
C28H34O8

> <MOLECULAR_WEIGHT>
498.572

> <EXACT_MASS>
498.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.77481867738013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aS,8S,8aR)-8-{[(6,8-dimethoxy-2-oxo-2H-chromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-decahydronaphthalen-2-yl acetate

> <JCHEM_LOGP>
4.153341456666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.354076000695198

> <JCHEM_PKA_STRONGEST_BASIC>
-4.475932427846416

> <JCHEM_POLAR_SURFACE_AREA>
97.36000000000001

> <JCHEM_REFRACTIVITY>
132.34199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aS,8S,8aR)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.861  -6.067   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.851  -4.353   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17                                                       
CONECT   17   16    5   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   22   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2R,4AS,8S,8ar)-8-{[(6,8-dimethoxy-2-oxo-2H-chromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-decahydronaphthalen-2-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₄O₈

Average Mass

498.5720 Da

Monoisotopic Mass

498.22537 Da

IUPAC Name

(2R,4aS,8S,8aR)-8-{[(6,8-dimethoxy-2-oxo-2H-chromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-decahydronaphthalen-2-yl acetate

Traditional Name

(2R,4aS,8S,8aR)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(OC[C@H]2C(=C)CC[C@@H]3C(C)(C)C(=O)[C@@H](C[C@@]23C)OC(C)=O)C(OC)=C2OC(=O)C=CC2=C1

InChI Identifier

InChI=1S/C28H34O8/c1-15-8-10-21-27(3,4)26(31)20(35-16(2)29)13-28(21,5)18(15)14-34-24-19(32-6)12-17-9-11-22(30)36-23(17)25(24)33-7/h9,11-12,18,20-21H,1,8,10,13-14H2,2-7H3/t18-,20+,21+,28-/m0/s1

InChI Key

VOGMGSXTNFUXDC-HGXKVACJSA-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
Anthemis cretica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Alpha-acyloxy ketone
Benzenoid
Pyran
Heteroaromatic compound
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Ether
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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	4.15	ChemAxon
pKa (Strongest Acidic)	17.35	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.34 m³·mol⁻¹	ChemAxon
Polarizability	52.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162914093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate (NP0190195)

MOL for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

3D MOL for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

3D SDF for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

3D-SDF for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

PDB for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

3D PDB for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

SMILES for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

INCHI for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

Structure for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)

3D Structure for NP0190195 ((2r,4as,8s,8ar)-8-{[(6,8-dimethoxy-2-oxochromen-7-yl)oxy]methyl}-4,4,8a-trimethyl-7-methylidene-3-oxo-hexahydronaphthalen-2-yl acetate)