NP-MRD: Showing NP-Card for (1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0326453)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 08:01:01 UTC

Updated at

2022-09-12 08:01:01 UTC

NP-MRD ID

NP0326453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

Description

Hydroxysordarin 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. (1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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. (1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid was first documented in 2005 (PMID: 16018317). Based on a literature review very few articles have been published on Hydroxysordarin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210012D          

 36 40  0  0  1  0            999 V2000
    1.2213   -5.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460   -4.6774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705   -3.8835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2953   -3.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5045   -3.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5198   -2.4983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0555   -1.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3195   -2.2958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5440   -1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -0.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -0.1167    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    3.4049   -0.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8610   -0.8233    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  1  0  0  0  0  0  0  0  0  0
    1.4907    0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7204    1.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    1.4611    0.0000 O   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  2  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
    0.1374    1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351    2.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    2.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.8377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4899    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    1.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -3.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2455   -4.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0210   -5.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 19 22  1  0  0  0  0
 23 22  1  6  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 19 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 76 80  0  0  0  0  0  0  0  0999 V2000
    4.6039    1.3737    2.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8380    0.9284    1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153    0.3997    0.5300 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2451   -1.0456    0.3623 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3560   -1.6646    1.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -1.1862   -0.2112 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8183   -2.2169   -1.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    0.1383   -0.8352 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3518   -0.1085   -1.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110    0.3173   -1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -0.1494   -0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8769   -1.6314   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058   -2.0788    0.7262 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0649   -3.4983    0.8008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7095   -4.0277   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0992   -3.4107    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -1.9347    2.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9162   -1.3667    0.7611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7351    0.1224    0.7585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9833    0.8233    1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0195    0.6372    0.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342    0.4149    1.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    0.4704    0.8511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4572    1.8881    0.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6036    1.9766   -0.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600    3.3041   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4349    3.6621   -0.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156    3.6336   -2.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294    0.5786   -0.5373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8955    0.3110   -1.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3518    1.2026   -2.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376   -0.9803   -2.1843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596    0.6633   -1.5874 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783    1.1040   -0.7722 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7801    1.0316   -1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611   -0.2703   -1.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2095    0.5570    3.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8660    1.6608    3.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1856    2.2813    2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7101    0.4539    0.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857   -1.5879   -0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2978   -1.7851    1.8380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1557   -1.4112    0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857   -2.3626   -1.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1248    0.8409   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    1.4510   -1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648    0.0298   -2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1577   -2.0352   -0.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4022   -1.9507   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9596   -1.9242    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226   -4.1333    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074   -3.8627   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7647   -5.1503   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7686   -3.7077   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638   -3.6278    2.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -4.0709    1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1626   -1.4473    2.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6201   -1.9112    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373   -1.7339   -0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9620    1.5248    1.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853    1.4028    2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5475   -0.2629    2.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919    0.1483    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    2.6120    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3923    4.0885   -0.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6705    4.7348   -0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4567    3.6376    0.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2204    3.0647   -0.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279    4.6674   -2.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4560    3.0140   -2.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1232    3.8264   -2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378   -1.2226   -3.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2769    2.1851   -0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6326    1.4328   -0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7506    1.6864   -2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5763   -0.5236   -2.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 34  1  0
 34 35  1  0
 35 36  1  0
 34 33  1  0
 33  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 25 29  1  0
 29 30  1  6
 30 32  1  0
 30 31  2  0
 19 20  1  1
 20 21  2  0
  8  6  1  0
  6  7  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
 23 11  1  0
 29 11  1  0
 18 13  1  0
 29 19  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  1
 34 73  1  1
 35 74  1  0
 35 75  1  0
 36 76  1  0
  8 45  1  1
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  1
 14 51  1  1
 15 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  6
 22 61  1  0
 22 62  1  0
 23 63  1  1
 24 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 32 72  1  0
 20 60  1  0
  6 43  1  1
  7 44  1  0
  4 41  1  6
  5 42  1  0
M  END


  Mrv1652309122210012D          

 36 40  0  0  1  0            999 V2000
    1.2213   -5.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460   -4.6774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705   -3.8835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2953   -3.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5045   -3.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5198   -2.4983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0555   -1.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3195   -2.2958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5440   -1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -0.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -0.1167    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    3.4049   -0.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8610   -0.8233    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  1  0  0  0  0  0  0  0  0  0
    1.4907    0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7204    1.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    1.4611    0.0000 O   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  2  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
    0.1374    1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351    2.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    2.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.8377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4899    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    1.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -3.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2455   -4.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0210   -5.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 19 22  1  0  0  0  0
 23 22  1  6  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 19 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326453

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](CO)O[C@@H](OC[C@@]23C[C@@H]4[C@H](C)CC[C@H]4[C@]4(C[C@@H]2C=C(C(C)C)[C@@]34C(O)=O)C=O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O9/c1-13(2)18-7-15-8-25(11-29)17-6-5-14(3)16(17)9-26(15,27(18,25)24(32)33)12-35-23-21(31)20(30)22(34-4)19(10-28)36-23/h7,11,13-17,19-23,28,30-31H,5-6,8-10,12H2,1-4H3,(H,32,33)/t14-,15+,16-,17-,19-,20+,21+,22-,23-,25+,26+,27+/m1/s1

> <INCHI_KEY>
TXOLGFOIEXLJBG-KXSYRKOWSA-N

> <FORMULA>
C27H40O9

> <MOLECULAR_WEIGHT>
508.608

> <EXACT_MASS>
508.267232868

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.64036907979589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,5R,8R,9S,11R)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_LOGP>
1.059394004666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.275504058962225

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.081359289169619

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9812923174205554

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
128.06229999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,8R,9S,11R)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.280  -9.835   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.206  -8.731   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.625  -7.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.551  -6.145   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.942  -6.523   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.970  -4.663   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.104  -3.560   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.463  -4.285   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.882  -2.804   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.808  -1.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.227  -0.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.577  -1.130   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.817  -0.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.356  -0.254   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.207  -1.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.894   1.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.687   2.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.404   1.295   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.783   0.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.211   2.359   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.707   2.727   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.785  -0.943   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.525  -0.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.341   0.975   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.618   2.161   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.257   3.658   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.372   4.719   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.221   4.093   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.967   1.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.781   2.871   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.261   3.297   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.056   4.230   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.537  -5.389   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.118  -6.871   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.192  -7.975   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.773  -9.457   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23   29                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   22   29                                             
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   19   11   30                                             
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    8   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Hydroxy-sordarin	MeSH

Chemical Formula

C₂₇H₄₀O₉

Average Mass

508.6080 Da

Monoisotopic Mass

508.26723 Da

IUPAC Name

(1R,2S,4R,5R,8R,9S,11R)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

Traditional Name

(1R,2S,4R,5R,8R,9S,11R)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](CO)O[C@@H](OC[C@@]23C[C@@H]4[C@H](C)CC[C@H]4[C@]4(C[C@@H]2C=C(C(C)C)[C@@]34C(O)=O)C=O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H40O9/c1-13(2)18-7-15-8-25(11-29)17-6-5-14(3)16(17)9-26(15,27(18,25)24(32)33)12-35-23-21(31)20(30)22(34-4)19(10-28)36-23/h7,11,13-17,19-23,28,30-31H,5-6,8-10,12H2,1-4H3,(H,32,33)/t14-,15+,16-,17-,19-,20+,21+,22-,23-,25+,26+,27+/m1/s1

InChI Key

TXOLGFOIEXLJBG-KXSYRKOWSA-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
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Aldehyde
Alcohol
Organooxygen compound
Organic oxide
Primary alcohol
Organic oxygen 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	1.06	ChemAxon
pKa (Strongest Acidic)	4.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.06 m³·mol⁻¹	ChemAxon
Polarizability	53.64 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015130

Chemspider ID

78438101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101171171

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Weber RW, Meffert A, Anke H, Sterner O: Production of sordarin and related metabolites by the coprophilous fungus Podospora pleiospora in submerged culture and in its natural substrate. Mycol Res. 2005 May;109(Pt 5):619-26. doi: 10.1017/s0953756205002765. [PubMed:16018317 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0326453)

MOL for NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-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 NP0326453 ((1r,2s,4r,5r,8r,9s,11r)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)