NP-MRD: Showing NP-Card for [1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid (NP0244845)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 05:43:54 UTC

Updated at

2022-09-07 05:43:54 UTC

NP-MRD ID

NP0244845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid

Description

{[14-(3,6-Dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-yl]oxy}phosphonic acid belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. [1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid is found in Locusta migratoria. {[14-(3,6-Dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-yl]oxy}phosphonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500272D          

 36 39  0  0  0  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -4.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -3.7114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -0.8691    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.3261   -0.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8218   -1.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2699   -0.5888    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 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
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END

     RDKit          3D

 81 84  0  0  0  0  0  0  0  0999 V2000
   -3.4347   -0.2567   -1.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883   -0.3833   -0.1683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6935   -0.9259    0.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4483   -1.0136    1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -0.6043    1.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640   -0.6288    0.3690 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6968   -1.9459   -0.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828    0.1253    0.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6113    0.4032    1.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8133    1.1660    0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5011    1.6540    1.7166 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2256    1.3672   -0.5808 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7213    1.1817   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0807   -0.2138   -0.3084 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2699   -0.2215    1.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8492   -0.5660    1.5158 P   0  0  0  0  0  5  0  0  0  0  0  0
    8.5808    0.7403    1.8089 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6937   -1.3914    0.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8245   -1.4253    2.9839 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0481   -1.2417   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685   -0.8669   -1.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5040    0.5013   -1.5909 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7116    1.1925   -2.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    0.5705   -1.2689 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1541   -0.1745   -2.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2978   -0.0157   -1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    0.0147   -0.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8770    1.3786    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0254   -1.4024    0.4401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8108   -2.5976   -0.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4522   -1.0080    0.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7149    0.2284    1.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1993    0.5856    1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7222    0.8236   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3210    1.8776    2.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9244   -0.3885    1.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2105   -1.2014   -2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410   -0.0836   -1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9789    0.6365   -2.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    0.5589    0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6132   -1.9215   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -2.0597    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0717   -0.3057    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093   -1.2622    2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0722    0.4368    2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878   -2.3421    0.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557    0.1012    2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995    2.4264   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1710    1.9114    0.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296    1.4662   -1.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0867   -0.4512   -0.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1497   -0.7046   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6812   -0.7568    3.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119   -1.6144    0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024   -2.1511   -0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852   -1.0405   -2.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2730   -1.6710   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377    2.2283   -2.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2086    0.6416   -3.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7979    1.1728   -3.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7588    1.6411   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662   -1.2562   -2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839    0.2227   -3.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8478   -0.8409   -2.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128    0.9797   -2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620    1.9718   -0.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0556    1.9503    0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889    1.3527    1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7000   -1.6052    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8121   -3.3890    0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465   -0.9243   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9900   -1.8480    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1056    1.0517    0.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4285    0.0635    2.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6944    1.3691    0.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0453    1.5125   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9487   -0.1033   -0.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5025    1.8854    2.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3049    1.8830    2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2060    2.7076    1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3942   -1.0280    2.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 14 15  1  0
 15 16  1  0
 16 18  1  0
 16 19  1  0
 16 17  2  0
 27  3  1  0
 27  6  1  0
 24  8  1  0
 22 12  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  1
 29 69  1  1
 30 70  1  0
 31 71  1  0
 31 72  1  0
 32 73  1  0
 32 74  1  0
 34 75  1  0
 34 76  1  0
 34 77  1  0
 35 78  1  0
 35 79  1  0
 35 80  1  0
 36 81  1  0
  3 41  1  6
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  7 46  1  0
  9 47  1  0
 12 48  1  6
 13 49  1  0
 13 50  1  0
 14 51  1  6
 20 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  1
 25 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
 18 52  1  0
 19 53  1  0
M  END


  Mrv1533004261500272D          

 36 39  0  0  0  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -4.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -3.7114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -0.8691    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.3261   -0.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8218   -1.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2699   -0.5888    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 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
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(O)CCC(C)(C)O)C1CCC2(O)C3=CC(=O)C4CC(CCC4(C)C3CCC12C)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H45O8P/c1-16(22(28)9-10-24(2,3)30)18-8-13-27(31)20-15-23(29)21-14-17(35-36(32,33)34)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28,30-31H,6-14H2,1-5H3,(H2,32,33,34)

> <INCHI_KEY>
GIUAFYXKULGOEW-UHFFFAOYSA-N

> <FORMULA>
C27H45O8P

> <MOLECULAR_WEIGHT>
528.623

> <EXACT_MASS>
528.285205407

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.59467050169599

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[14-(3,6-dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.6425458153333334

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.7859219927840435

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7595879499154057

> <JCHEM_PKA_STRONGEST_BASIC>
-2.627362688414686

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
136.9361

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[14-(3,6-dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.676  -4.226   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.104  -9.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.057  -8.818   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.375  -6.928   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   33  P   UNK     0      16.886  -1.622   0.000  0.00  0.00           P+0
HETATM   34  O   UNK     0      17.409  -0.174   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      18.334  -2.146   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      15.437  -1.099   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    2   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   16   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   11   14   31                                             
CONECT   31   30                                                            
CONECT   32   22   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
{[14-(3,6-dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0,.0,]heptadec-9-en-5-yl]oxy}phosphonate	Generator
{[14-(3,6-dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-yl]oxy}phosphonate	Generator

Chemical Formula

C₂₇H₄₅O₈P

Average Mass

528.6230 Da

Monoisotopic Mass

528.28521 Da

IUPAC Name

{[14-(3,6-dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-yl]oxy}phosphonic acid

Traditional Name

[14-(3,6-dihydroxy-6-methylheptan-2-yl)-11-hydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(C(O)CCC(C)(C)O)C1CCC2(O)C3=CC(=O)C4CC(CCC4(C)C3CCC12C)OP(O)(O)=O

InChI Identifier

InChI=1S/C27H45O8P/c1-16(22(28)9-10-24(2,3)30)18-8-13-27(31)20-15-23(29)21-14-17(35-36(32,33)34)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28,30-31H,6-14H2,1-5H3,(H2,32,33,34)

InChI Key

GIUAFYXKULGOEW-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
Locusta migratoria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholestane-skeleton
Ecdysteroid
25-hydroxysteroid
Trihydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
6-oxosteroid
Delta-7-steroid
Monoalkyl phosphate
Cyclohexenone
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.95	ALOGPS
logP	2.64	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.94 m³·mol⁻¹	ChemAxon
Polarizability	56.59 Å³	ChemAxon
Number of Rings	4	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

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

73830897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid (NP0244845)

MOL for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

3D MOL for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

3D SDF for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

3D-SDF for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

PDB for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

3D PDB for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

SMILES for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

INCHI for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

Structure for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)

3D Structure for NP0244845 ([1-(3,6-dihydroxy-6-methylheptan-2-yl)-3a-hydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxyphosphonic acid)