NP-MRD: Showing NP-Card for 9,15-dihydroxy presilphiperfolan-4-oic acid (NP0039907)

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Record Information

Version

2.0

Created at

2021-06-20 22:12:35 UTC

Updated at

2021-06-30 00:13:30 UTC

NP-MRD ID

NP0039907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,15-dihydroxy presilphiperfolan-4-oic acid

Provided By

JEOL Database JEOL Logo

Description

9,15-dihydroxy presilphiperfolan-4-oic acid is found in Xylaria sp. 9,15-dihydroxy presilphiperfolan-4-oic acid was first documented in 2010 (Silva, G. H., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100123D          

 43 45  0  0  0  0            999 V2000
    0.8757    2.2290   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351    1.4788    0.3630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8337    1.2257    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5022    2.2598    1.2574 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8953    1.9692    0.6476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3478    3.1387   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    3.1083   -1.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    4.2986    0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866    1.5663    1.5454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7900    0.4214    0.7547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5859   -0.3938    0.3233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6432    0.6936   -0.1508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2438    0.1824    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0344   -0.8531   -0.9584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0420   -1.9875   -0.8869 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5420   -1.5384   -0.7044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2642   -2.6477   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.2336   -2.0655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6017   -1.0145   -1.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.4062   -1.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.6640   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    3.2050   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    0.7041    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.6105    0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    2.1689    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    3.3252    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    1.8817    2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    4.9449   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    2.3826    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.1868    2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785   -0.1441    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.8333   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8423    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711    0.9015   -1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.3630    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0076   -0.3946   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.2866   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -2.6338   -1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -2.6309   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081   -2.4256   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.0995   -2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -0.3658   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -0.7637   -2.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
  5  4  1  0  0  0  0
 16 15  1  0  0  0  0
 14 15  1  0  0  0  0
  4  2  1  0  0  0  0
  5  6  1  6  0  0  0
  2 13  1  0  0  0  0
  2  1  1  6  0  0  0
 13 12  1  0  0  0  0
 16 18  1  0  0  0  0
 12 11  1  0  0  0  0
 13 35  1  1  0  0  0
 11 10  1  0  0  0  0
  2  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11 33  1  1  0  0  0
  9  5  1  0  0  0  0
 16 17  1  1  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
 11 16  1  0  0  0  0
  6  7  2  0  0  0  0
 18 19  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
 12 34  1  6  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 17 40  1  0  0  0  0
  8 28  1  0  0  0  0
 19 43  1  0  0  0  0
M  END

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    0.8757    2.2290   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351    1.4788    0.3630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8337    1.2257    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5022    2.2598    1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.9692    0.6476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3478    3.1387   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    3.1083   -1.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    4.2986    0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866    1.5663    1.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900    0.4214    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5859   -0.3938    0.3233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6432    0.6936   -0.1508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2438    0.1824    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0344   -0.8531   -0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420   -1.9875   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420   -1.5384   -0.7044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2642   -2.6477   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.2336   -2.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6017   -1.0145   -1.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.4062   -1.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.6640   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    3.2050   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    0.7041    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.6105    0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    2.1689    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    3.3252    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    1.8817    2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    4.9449   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    2.3826    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.1868    2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785   -0.1441    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.8333   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8423    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711    0.9015   -1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.3630    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0076   -0.3946   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.2866   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -2.6338   -1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -2.6309   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081   -2.4256   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.0995   -2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -0.3658   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -0.7637   -2.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  4  1  0
 16 15  1  0
 14 15  1  0
  4  2  1  0
  5  6  1  6
  2 13  1  0
  2  1  1  6
 13 12  1  0
 16 18  1  0
 12 11  1  0
 13 35  1  1
 11 10  1  0
  2  3  1  0
 10  9  1  0
 11 33  1  1
  9  5  1  0
 16 17  1  1
  5 12  1  0
  6  8  1  0
 11 16  1  0
  6  7  2  0
 18 19  1  0
  4 26  1  0
  4 27  1  0
 12 34  1  6
 10 31  1  0
 10 32  1  0
  9 29  1  0
  9 30  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 18 41  1  0
 18 42  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 17 40  1  0
  8 28  1  0
 19 43  1  0
M  END


  Mrv1652306212100123D          

 43 45  0  0  0  0            999 V2000
    0.8757    2.2290   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351    1.4788    0.3630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8337    1.2257    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5022    2.2598    1.2574 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8953    1.9692    0.6476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3478    3.1387   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    3.1083   -1.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    4.2986    0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866    1.5663    1.5454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7900    0.4214    0.7547 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5859   -0.3938    0.3233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6432    0.6936   -0.1508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2438    0.1824    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0344   -0.8531   -0.9584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0420   -1.9875   -0.8869 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5420   -1.5384   -0.7044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2642   -2.6477   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.2336   -2.0655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6017   -1.0145   -1.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.4062   -1.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.6640   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    3.2050   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    0.7041    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.6105    0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    2.1689    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    3.3252    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    1.8817    2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    4.9449   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    2.3826    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.1868    2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785   -0.1441    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.8333   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8423    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711    0.9015   -1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.3630    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0076   -0.3946   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.2866   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -2.6338   -1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -2.6309   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081   -2.4256   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.0995   -2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -0.3658   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -0.7637   -2.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
  5  4  1  0  0  0  0
 16 15  1  0  0  0  0
 14 15  1  0  0  0  0
  4  2  1  0  0  0  0
  5  6  1  6  0  0  0
  2 13  1  0  0  0  0
  2  1  1  6  0  0  0
 13 12  1  0  0  0  0
 16 18  1  0  0  0  0
 12 11  1  0  0  0  0
 13 35  1  1  0  0  0
 11 10  1  0  0  0  0
  2  3  1  0  0  0  0
 10  9  1  0  0  0  0
 11 33  1  1  0  0  0
  9  5  1  0  0  0  0
 16 17  1  1  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
 11 16  1  0  0  0  0
  6  7  2  0  0  0  0
 18 19  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
 12 34  1  6  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 17 40  1  0  0  0  0
  8 28  1  0  0  0  0
 19 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039907

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]12C([H])([H])C([H])([H])[C@]3([H])[C@]1([H])[C@@]([H])(C([H])([H])C([H])([H])[C@]3(O[H])C([H])([H])O[H])C(C([H])([H])[H])(C([H])([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4/c1-13(2)7-14(12(17)18)5-3-10-11(14)9(13)4-6-15(10,19)8-16/h9-11,16,19H,3-8H2,1-2H3,(H,17,18)/t9-,10-,11+,14-,15+/m1/s1

> <INCHI_KEY>
DFHURQMGOXKZSE-ZNLHFFCSSA-N

> <FORMULA>
C15H24O4

> <MOLECULAR_WEIGHT>
268.353

> <EXACT_MASS>
268.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
28.967138653800635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,7R,8R,11S)-8-hydroxy-8-(hydroxymethyl)-2,2-dimethyltricyclo[5.3.1.0^{4,11}]undecane-4-carboxylic acid

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
1.3363130749999992

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.69304893671907

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5045720162102745

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0755526782353764

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
69.78739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,7R,8R,11S)-8-hydroxy-8-(hydroxymethyl)-2,2-dimethyltricyclo[5.3.1.0^{4,11}]undecane-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    0.8757    2.2290   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351    1.4788    0.3630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8337    1.2257    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5022    2.2598    1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.9692    0.6476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3478    3.1387   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    3.1083   -1.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    4.2986    0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866    1.5663    1.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900    0.4214    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5859   -0.3938    0.3233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6432    0.6936   -0.1508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2438    0.1824    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0344   -0.8531   -0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420   -1.9875   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420   -1.5384   -0.7044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2642   -2.6477   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.2336   -2.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6017   -1.0145   -1.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.4062   -1.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.6640   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    3.2050   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    0.7041    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.6105    0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    2.1689    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    3.3252    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    1.8817    2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    4.9449   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    2.3826    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.1868    2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785   -0.1441    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.8333   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8423    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711    0.9015   -1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.3630    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0076   -0.3946   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.2866   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -2.6338   -1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -2.6309   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081   -2.4256   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.0995   -2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -0.3658   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -0.7637   -2.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  4  1  0
 16 15  1  0
 14 15  1  0
  4  2  1  0
  5  6  1  6
  2 13  1  0
  2  1  1  6
 13 12  1  0
 16 18  1  0
 12 11  1  0
 13 35  1  1
 11 10  1  0
  2  3  1  0
 10  9  1  0
 11 33  1  1
  9  5  1  0
 16 17  1  1
  5 12  1  0
  6  8  1  0
 11 16  1  0
  6  7  2  0
 18 19  1  0
  4 26  1  0
  4 27  1  0
 12 34  1  6
 10 31  1  0
 10 32  1  0
  9 29  1  0
  9 30  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 18 41  1  0
 18 42  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 17 40  1  0
  8 28  1  0
 19 43  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.876   2.229  -0.932  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.535   1.479   0.363  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.834   1.226   1.137  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.502   2.260   1.257  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.895   1.969   0.648  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.348   3.139  -0.223  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.660   3.108  -1.401  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.423   4.299   0.462  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.087   1.566   1.545  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.790   0.421   0.755  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.586  -0.394   0.323  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.643   0.694  -0.151  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.244   0.182   0.131  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.034  -0.853  -0.958  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.042  -1.988  -0.887  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.542  -1.538  -0.704  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.264  -2.648  -0.142  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.201  -1.234  -2.066  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.602  -1.014  -1.873  0.00  0.00           O+0
HETATM   20  H   UNK     0       0.003   2.406  -1.566  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.599   1.664  -1.531  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.321   3.205  -0.709  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.645   0.704   2.082  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.527   0.611   0.553  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.337   2.169   1.377  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.251   3.325   1.296  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.467   1.882   2.287  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.745   4.945  -0.201  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.789   2.383   1.742  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.734   1.187   2.512  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.479  -0.144   1.389  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.343   0.833  -0.095  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.230  -0.842   1.266  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.771   0.902  -1.218  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.212  -0.363   1.087  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.008  -0.395  -1.954  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.032  -1.287  -0.829  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.947  -2.634  -1.768  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.780  -2.631  -0.035  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.208  -2.426  -0.279  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.110  -2.099  -2.731  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.769  -0.366  -2.569  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.966  -0.764  -2.741  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    4   13    1    3                                             
CONECT    3    2   23   24   25                                             
CONECT    4    5    2   26   27                                             
CONECT    5    4    6    9   12                                             
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8    6   28                                                       
CONECT    9   10    5   29   30                                             
CONECT   10   11    9   31   32                                             
CONECT   11   12   10   33   16                                             
CONECT   12   13   11    5   34                                             
CONECT   13   14    2   12   35                                             
CONECT   14   13   15   36   37                                             
CONECT   15   16   14   38   39                                             
CONECT   16   15   18   17   11                                             
CONECT   17   16   40                                                       
CONECT   18   16   19   41   42                                             
CONECT   19   18   43                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
    0.8757    2.2290   -0.9321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351    1.4788    0.3630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8337    1.2257    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5022    2.2598    1.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    1.9692    0.6476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3478    3.1387   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    3.1083   -1.4014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4234    4.2986    0.4615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866    1.5663    1.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900    0.4214    0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5859   -0.3938    0.3233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6432    0.6936   -0.1508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2438    0.1824    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0344   -0.8531   -0.9584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420   -1.9875   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420   -1.5384   -0.7044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2642   -2.6477   -0.1423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2013   -1.2336   -2.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6017   -1.0145   -1.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.4062   -1.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991    1.6640   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3211    3.2050   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    0.7041    2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5268    0.6105    0.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3369    2.1689    1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514    3.3252    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670    1.8817    2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7452    4.9449   -0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    2.3826    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    1.1868    2.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785   -0.1441    1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3434    0.8333   -0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -0.8423    1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7711    0.9015   -1.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119   -0.3630    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0076   -0.3946   -1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -1.2866   -0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -2.6338   -1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7796   -2.6309   -0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2081   -2.4256   -0.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102   -2.0995   -2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -0.3658   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9657   -0.7637   -2.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  4  1  0
 16 15  1  0
 14 15  1  0
  4  2  1  0
  5  6  1  6
  2 13  1  0
  2  1  1  6
 13 12  1  0
 16 18  1  0
 12 11  1  0
 13 35  1  1
 11 10  1  0
  2  3  1  0
 10  9  1  0
 11 33  1  1
  9  5  1  0
 16 17  1  1
  5 12  1  0
  6  8  1  0
 11 16  1  0
  6  7  2  0
 18 19  1  0
  4 26  1  0
  4 27  1  0
 12 34  1  6
 10 31  1  0
 10 32  1  0
  9 29  1  0
  9 30  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 18 41  1  0
 18 42  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 17 40  1  0
  8 28  1  0
 19 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₄

Average Mass

268.3530 Da

Monoisotopic Mass

268.16746 Da

IUPAC Name

(1R,4R,7R,8R,11S)-8-hydroxy-8-(hydroxymethyl)-2,2-dimethyltricyclo[5.3.1.0^{4,11}]undecane-4-carboxylic acid

Traditional Name

(1R,4R,7R,8R,11S)-8-hydroxy-8-(hydroxymethyl)-2,2-dimethyltricyclo[5.3.1.0^{4,11}]undecane-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]12C([H])([H])C([H])([H])[C@]3([H])[C@]1([H])[C@@]([H])(C([H])([H])C([H])([H])[C@]3(O[H])C([H])([H])O[H])C(C([H])([H])[H])(C([H])([H])[H])C2([H])[H]

InChI Identifier

InChI=1S/C15H24O4/c1-13(2)7-14(12(17)18)5-3-10-11(14)9(13)4-6-15(10,19)8-16/h9-11,16,19H,3-8H2,1-2H3,(H,17,18)/t9-,10-,11+,14-,15+/m1/s1

InChI Key

DFHURQMGOXKZSE-ZNLHFFCSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylaria sp.	JEOL database	Silva, G. H., et al, Phytochem. Lett. 3, 164 (2010)

Chemical Taxonomy

Classification

Not classified

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	0.72	ALOGPS
logP	1.34	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.5	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.79 m³·mol⁻¹	ChemAxon
Polarizability	28.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Silva, G. H., et al. (2010). Silva, G. H., et al, Phytochem. Lett. 3, 164 (2010). Phytochem..

Showing NP-Card for 9,15-dihydroxy presilphiperfolan-4-oic acid (NP0039907)

MOL for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

3D MOL for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

3D SDF for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

3D-SDF for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

PDB for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

3D PDB for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

SMILES for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

INCHI for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

Structure for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)

3D Structure for NP0039907 (9,15-dihydroxy presilphiperfolan-4-oic acid)