NP-MRD: Showing NP-Card for 2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0184393)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 23:30:48 UTC

Updated at

2022-09-03 23:30:48 UTC

NP-MRD ID

NP0184393

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

Description

2-{[(3,4-Dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]Tridec-12-ene-1-carboxylic acid belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid is found in Sordaria araneosa. 2-{[(3,4-Dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]Tridec-12-ene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171511202D          

 35 39  0  0  0  0            999 V2000
   -0.2997   -5.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -4.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -3.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707   -3.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855   -2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1489   -2.4184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636   -2.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832   -1.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -1.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9162   -0.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -0.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4049   -0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055   -0.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467    1.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    0.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563   -0.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812   -0.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3311    1.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919    1.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216    2.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177    1.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    1.7266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368    2.4588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651    1.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967    2.2468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -3.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393   -3.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346   -4.7294    0.0000 O   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 10 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  2  0  0  0  0
  7 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 75 79  0  0  0  0  0  0  0  0999 V2000
    6.8504    1.2228   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6242    0.9321   -0.9142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8163    0.2415   -0.0424 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5825    1.0402    0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9916    2.4990    0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999    0.9342   -0.6924 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2052   -0.4049   -0.8889 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1151   -0.4020   -1.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0771   -0.9182   -1.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962   -0.1788   -0.2611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0279    1.2210   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    2.1428    0.2963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1872    3.3854   -0.3155 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6758    4.6189    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7013    3.3371   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    1.8071    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080    1.4291    0.8978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5699    0.0065    1.2261 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7523   -0.4948    1.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8980   -0.3266    1.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    0.0333    2.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -0.3390    1.1161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2819   -1.8280    1.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763   -2.1517    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8891   -3.5657    0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -4.0874   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1553   -3.9017    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -0.8857    0.1105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0473   -1.0263   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089   -0.7601   -2.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3241   -1.5427   -0.6525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -1.0146   -1.6210 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0863   -2.2206   -2.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048   -1.1241   -0.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6636   -1.5934   -1.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4109    0.2946   -0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7189    1.8435    0.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4412    1.8203   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3753    0.0947    0.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1425    0.7383    1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0880    3.1492    0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    2.6855   -0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4971    2.7354    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583   -0.9294    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0355   -2.0126   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6714   -1.0382   -2.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201    1.1770   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386    1.6349   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8797    2.4451    1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641    3.4014   -1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6079    4.7776    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2916    5.4992    0.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456    4.3881    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9688    3.7876    0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2659    3.7601   -0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8574    1.5046   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9288    1.6981    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    1.9417    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6051   -1.0418    2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460    0.9957    2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573   -0.7121    2.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7021    0.1342    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4786   -2.4656    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1019   -4.2412    0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598   -3.4441   -1.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5763   -5.0445   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9965   -4.3764   -1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0774   -4.9867    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2224   -3.3081    2.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0740   -3.8615    0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6447   -2.3102   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.2641   -2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2044   -2.2195   -3.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -1.8055    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8171   -2.5299   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24 28  1  0
 28 29  1  6
 29 31  1  0
 29 30  2  0
 18 19  1  1
 19 20  2  0
  7 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34  3  1  0
 22 10  1  0
 28 10  1  0
 17 12  1  0
 28 18  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  1
  4 40  1  1
  5 41  1  0
  5 42  1  0
  5 43  1  0
  7 44  1  1
  9 45  1  0
  9 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  1
 13 50  1  6
 14 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  1
 21 60  1  0
 21 61  1  0
 22 62  1  6
 23 63  1  0
 25 64  1  0
 26 65  1  0
 26 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 31 71  1  0
 19 59  1  0
 32 72  1  6
 33 73  1  0
 34 74  1  1
 35 75  1  0
M  END


  Mrv1533004171511202D          

 35 39  0  0  0  0            999 V2000
   -0.2997   -5.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -4.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0754   -3.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707   -3.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855   -2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1489   -2.4184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636   -2.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832   -1.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -1.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9162   -0.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -0.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4049   -0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0055   -0.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467    1.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    0.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563   -0.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812   -0.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3311    1.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919    1.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458    2.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216    2.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177    1.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868    1.7266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1368    2.4588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651    1.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967    2.2468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736   -3.4477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393   -3.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0346   -4.7294    0.0000 O   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 10 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  2  0  0  0  0
  7 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184393

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(C)OC(OCC23CC4C(C)CCC4C4(CC2C=C(C(C)C)C34C(O)=O)C=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O8/c1-13(2)19-8-16-9-25(11-28)18-7-6-14(3)17(18)10-26(16,27(19,25)24(31)32)12-34-23-21(30)20(29)22(33-5)15(4)35-23/h8,11,13-18,20-23,29-30H,6-7,9-10,12H2,1-5H3,(H,31,32)

> <INCHI_KEY>
OGGVRVMISBQNMQ-UHFFFAOYSA-N

> <FORMULA>
C27H40O8

> <MOLECULAR_WEIGHT>
492.609

> <EXACT_MASS>
492.272318248

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.32282222341812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.106303971333333

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.278874515867924

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.179115773290818

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6804000200793787

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
126.51859999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -0.559  -9.783   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.111  -8.345   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.141  -7.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.692  -5.711   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.213  -5.469   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.278  -4.514   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.799  -4.756   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.769  -3.560   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.170  -1.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.227  -0.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.577  -1.130   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.817  -0.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.356  -0.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.477  -1.373   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.894   1.189   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.687   2.147   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.404   1.295   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.783   0.880   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.785  -0.943   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.525  -0.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.341   0.975   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.618   2.161   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.358   3.614   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.459   5.034   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.720   4.554   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.967   1.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.206   3.014   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.829   3.223   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.122   4.590   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.362   2.678   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.354   4.194   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.350  -6.194   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.871  -6.436   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.380  -7.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.931  -8.828   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20   26                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   26   30                                             
CONECT   19   18   20                                                       
CONECT   20   19   10   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   10   18   27                                             
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   18   31                                                       
CONECT   31   30                                                            
CONECT   32    7   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0,.0,]tridec-12-ene-1-carboxylate	Generator
2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylate	Generator

Chemical Formula

C₂₇H₄₀O₈

Average Mass

492.6090 Da

Monoisotopic Mass

492.27232 Da

IUPAC Name

2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

Traditional Name

2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1C(C)OC(OCC23CC4C(C)CCC4C4(CC2C=C(C(C)C)C34C(O)=O)C=O)C(O)C1O

InChI Identifier

InChI=1S/C27H40O8/c1-13(2)19-8-16-9-25(11-28)18-7-6-14(3)17(18)10-26(16,27(19,25)24(31)32)12-34-23-21(30)20(29)22(33-5)15(4)35-23/h8,11,13-18,20-23,29-30H,6-7,9-10,12H2,1-5H3,(H,31,32)

InChI Key

OGGVRVMISBQNMQ-UHFFFAOYSA-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
Sordaria araneosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
1,2-diol
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Aldehyde
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
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	2.32	ALOGPS
logP	2.11	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.18	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.52 m³·mol⁻¹	ChemAxon
Polarizability	53.32 Å³	ChemAxon
Number of Rings	5	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

22219016

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0184393)

MOL for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D MOL for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D SDF for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D-SDF for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

PDB for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D PDB for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

SMILES for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

INCHI for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

Structure for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D Structure for NP0184393 (2-{[(3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl)oxy]methyl}-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)