NP-MRD: Showing NP-Card for (6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate (NP0174483)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 11:44:46 UTC

Updated at

2022-09-03 11:44:46 UTC

NP-MRD ID

NP0174483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate

Description

Diaulusterol A belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. (6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate is found in Diaulula sandiegensis. (6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate was first documented in 1999 (PMID: 10346969). Based on a literature review very few articles have been published on Diaulusterol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032213442D          

 37 40  0  0  1  0            999 V2000
   -3.2388   -5.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325   -5.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0434   -4.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152   -5.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -4.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7198   -3.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -4.8691    0.0000 O   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
    0.5660   -4.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -3.7114    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
    1.2383   -3.6793    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
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  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  1  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  2  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
    7.6731   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   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  1  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  1  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  2  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 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  6  0  0  0
 16 14  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 20  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 19 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END

     RDKit          3D

 85 88  0  0  0  0  0  0  0  0999 V2000
    7.9384    3.1143   -0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3513    2.2430   -1.1734 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9126    3.0250   -2.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0993    1.5224   -1.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698    0.7062   -0.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1073    0.6556    0.5961 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4206   -0.0636   -0.7055 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8895   -0.8534    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113   -0.0510    1.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9074   -1.9285    0.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6952   -1.6085   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6573   -0.6733   -0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4810   -1.2829   -1.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5946   -2.2202   -0.6938 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3207   -3.5049   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3010   -1.7861    0.3801 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2293   -1.1968    1.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8961   -0.3236    2.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -0.7415    1.3991 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1884    0.1576    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2795    1.3467    1.8525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4705    2.1492    1.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5540    3.2826    2.2025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5708    1.6102    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7751    2.0293    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9414    1.5698    0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6218    0.6289    1.1136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5020    0.9458   -0.9643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5872    0.2496   -1.4902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3876   -0.0565   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1440    0.6397   -0.1978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4419    1.3573   -1.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3067   -0.4017    0.4498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7965   -1.4703   -0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4022   -1.2899   -0.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3955   -0.8085    0.0033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8927    0.5412   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2619    2.6492    0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4362    4.0921   -0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8214    3.2496    0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1021    1.5321   -0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7838    2.6777   -2.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3351    2.2176   -2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4435    0.8164   -2.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5616   -0.4914    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    1.0112    1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2563   -0.1372    2.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4222   -2.2124   -0.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3743   -2.8299    1.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6275   -1.5572    1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443   -2.2733    0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1021   -2.2632   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858    0.1662   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2022   -0.1089   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590   -0.5440   -1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9175   -1.8940   -2.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1121   -2.6191   -1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1961   -3.7226   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443   -3.5647    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5932   -4.3445   -0.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8869   -2.7185    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -0.5734    1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790   -1.9992    2.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -0.5293    3.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304    0.7471    2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3355   -1.7672    1.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4472    1.6843    2.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9772    2.7686    1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6392    2.4043    0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6096    0.8741    2.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1909    1.7095   -1.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   -0.7146   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2015   -0.5599   -1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7192   -0.7929    0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4381    0.7326   -2.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1036    2.2387   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845    1.7800   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9740   -0.9097    1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4605   -1.5958   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8191   -2.4764    0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893   -2.2665   -1.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4836   -0.6079   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561    0.7519   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    0.7033   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887    1.2889    0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 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 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  6
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  6
 36 16  1  0
 36 19  1  0
 33 20  1  0
 31 24  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  1
  3 42  1  0
  4 43  1  0
  4 44  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  6
 15 58  1  0
 15 59  1  0
 15 60  1  0
 16 61  1  1
 17 62  1  0
 17 63  1  0
 18 64  1  0
 18 65  1  0
 19 66  1  1
 21 67  1  0
 25 68  1  0
 26 69  1  6
 27 70  1  0
 28 71  1  6
 29 72  1  0
 30 73  1  0
 30 74  1  0
 32 75  1  0
 32 76  1  0
 32 77  1  0
 33 78  1  1
 34 79  1  0
 34 80  1  0
 35 81  1  0
 35 82  1  0
 37 83  1  0
 37 84  1  0
 37 85  1  0
M  END

  Mrv1652309032213442D          

 37 40  0  0  1  0            999 V2000
   -3.2388   -5.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7325   -5.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0434   -4.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152   -5.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -4.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7198   -3.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -4.8691    0.0000 O   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
    0.5660   -4.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -3.7114    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
    1.2383   -3.6793    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
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  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  1  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  2  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
    7.6731   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   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  1  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  1  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  2  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 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  6  0  0  0
 16 14  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 20  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 19 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0174483

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)CC(=O)OC(C)(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)C4=C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O6/c1-18(8-7-12-29(3,4)37-28(36)14-19(2)32)21-9-10-22-20-15-25(33)24-16-26(34)27(35)17-31(24,6)23(20)11-13-30(21,22)5/h15-16,18-19,21-23,26-27,32,34-35H,7-14,17H2,1-6H3/t18-,19?,21-,22+,23+,26+,27-,30-,31-/m1/s1

> <INCHI_KEY>
HVGPOQMKFKPULV-ZAMQEXIGSA-N

> <FORMULA>
C31H48O6

> <MOLECULAR_WEIGHT>
516.719

> <EXACT_MASS>
516.345089266

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
60.09547451189793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-14-yl]-2-methylheptan-2-yl 3-hydroxybutanoate

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
4.287125627666667

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.94640415713032

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.606300530192971

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6206900808031035

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
145.15189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-14-yl]-2-methylheptan-2-yl 3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.046 -11.099   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.101  -9.884   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.681  -8.457   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.575 -10.094   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.630  -8.878   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.210  -7.452   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.104  -9.089   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.159  -7.873   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  C   UNK     0      -1.375  -6.928   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   36                                                  
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   24   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   20   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   19   16   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₈O₆

Average Mass

516.7190 Da

Monoisotopic Mass

516.34509 Da

IUPAC Name

(6R)-6-[(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-14-yl]-2-methylheptan-2-yl 3-hydroxybutanoate

Traditional Name

(6R)-6-[(1S,2R,4R,5S,11R,14R,15R)-4,5-dihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,9-dien-14-yl]-2-methylheptan-2-yl 3-hydroxybutanoate

CAS Registry Number

Not Available

SMILES

CC(O)CC(=O)OC(C)(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)C4=C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C31H48O6/c1-18(8-7-12-29(3,4)37-28(36)14-19(2)32)21-9-10-22-20-15-25(33)24-16-26(34)27(35)17-31(24,6)23(20)11-13-30(21,22)5/h15-16,18-19,21-23,26-27,32,34-35H,7-14,17H2,1-6H3/t18-,19?,21-,22+,23+,26+,27-,30-,31-/m1/s1

InChI Key

HVGPOQMKFKPULV-ZAMQEXIGSA-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
Diaulula sandiegensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Steroid ester
3-hydroxy-delta-7-steroid
3-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-alpha-hydroxysteroid
6-oxosteroid
Delta-7-steroid
Beta-hydroxy acid
Cyclohexenone
Hydroxy acid
Ketone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	4.22	ALOGPS
logP	4.29	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	145.15 m³·mol⁻¹	ChemAxon
Polarizability	60.1 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

29216076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100965129

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kubanek J, Andersen RJ: Evidence for de novo biosynthesis of the polyketide fragment of diaulusterol A by the northeastern pacific dorid nudibranch diaulula sandiegensis. J Nat Prod. 1999 May;62(5):777-9. doi: 10.1021/np9804839. [PubMed:10346969 ]
LOTUS database [Link]

Showing NP-Card for (6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate (NP0174483)

MOL for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

3D MOL for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

3D SDF for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

3D-SDF for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

PDB for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

3D PDB for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

SMILES for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

INCHI for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

Structure for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)

3D Structure for NP0174483 ((6r)-6-[(1r,3ar,7s,8r,9ar,9bs,11ar)-7,8-dihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,3ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-yl 3-hydroxybutanoate)