NP-MRD: Showing NP-Card for (1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate (NP0255460)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 19:58:23 UTC

Updated at

2022-09-07 19:58:24 UTC

NP-MRD ID

NP0255460

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate

Description

(1R,2R,5S,10S,11R,14S,15R,16R)-5,10,11,14-tetrahydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl pyridine-3-carboxylate belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. (1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate is found in Cynanchum caudatum. Based on a literature review very few articles have been published on (1R,2R,5S,10S,11R,14S,15R,16R)-5,10,11,14-tetrahydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl pyridine-3-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221582D          

 35 39  0  0  1  0            999 V2000
    1.7243   -2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561   -2.6347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1278   -3.3123    0.0000 O   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  2  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  2  0  0  0  0  0  0  0  0  0
    4.6744   -0.8310    0.0000 O   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
    6.6095   -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  1  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  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  1  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883   -4.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277   -5.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6474   -6.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8353   -6.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035   -6.2507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -5.4748    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  1  0  0  0
  4  2  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 24 34  1  0  0  0  0
  4 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
    4.2430   -2.9635   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -1.7721    0.0238 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5477   -1.8650    1.4170 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0129   -2.0704   -0.3199 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7684   -3.3962    0.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6552   -2.0671   -1.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1217   -1.9892   -1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907   -1.8988   -0.3125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3603   -3.2005    0.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5767   -1.2237   -0.0347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0892   -1.7583    1.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5524   -1.6471   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616   -0.7912   -1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082    0.2943   -0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    1.0406   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3759    2.0621    0.7118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8596    1.4246    1.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1594    2.8853    0.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8772    2.3298    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8050    0.8301    0.5819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9752    0.5129    2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5279    0.2727   -0.0118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2940    0.8483    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9025    0.1929   -0.0756 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0652    0.9392    0.0682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6884    1.6222   -0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1119    1.5135   -2.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026    2.3882   -0.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4749    2.4589    0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279    3.1994    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2282    3.8675   -0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387    3.7739   -1.6551 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4983    3.0511   -1.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453   -1.2341    0.3063 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8705   -1.4776    1.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3157   -2.7839   -0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8606   -3.8843   -0.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0202   -2.9994   -1.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881   -0.9036   -0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881   -2.8278    1.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8383   -4.0424   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9790   -3.0379   -2.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -1.2221   -2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845   -1.1610   -2.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2715   -2.9217   -2.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7818   -3.2143    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9498   -2.1957    1.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8409   -2.7028   -0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382   -1.6044   -2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6473   -1.0806   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0259    0.3039   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3100    1.5632   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2006    2.7470    0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3453    0.5975    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184    3.1298    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2815    3.9035    0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7888    2.6162   -0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481    2.7839    1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -0.2603    2.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0496    0.1261    2.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2449    1.4011    2.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5380    0.6039   -1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    1.9318    0.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3164    0.7302    1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318    0.2444   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0631    1.9650    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856    3.2628    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1425    4.4402   -0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    3.0316   -2.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6387   -0.8943    2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988   -2.5812    1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0961   -1.2176    2.2220 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  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 34  1  0
 34 35  1  1
 34 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  1
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 10  1  0
 10 11  1  1
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 34  4  1  0
 10 22  1  0
 33 28  1  0
 10  8  1  0
 14 20  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  6
  3 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  0
  7 45  1  0
  9 46  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 24 65  1  6
 23 63  1  0
 23 64  1  0
 22 62  1  6
 21 59  1  0
 21 60  1  0
 21 61  1  0
 19 57  1  0
 19 58  1  0
 18 55  1  0
 18 56  1  0
 16 53  1  6
 17 54  1  0
 15 51  1  0
 15 52  1  0
 13 50  1  0
 12 48  1  0
 12 49  1  0
 11 47  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  0
 33 69  1  0
M  END


  Mrv1652309072221582D          

 35 39  0  0  1  0            999 V2000
    1.7243   -2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561   -2.6347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1278   -3.3123    0.0000 O   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  2  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  2  0  0  0  0  0  0  0  0  0
    4.6744   -0.8310    0.0000 O   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
    6.6095   -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  1  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  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  1  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883   -4.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277   -5.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6474   -6.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8353   -6.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3035   -6.2507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -5.4748    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  1  0  0  0
  4  2  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 24 34  1  0  0  0  0
  4 34  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0255460

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@]1(O)CC[C@@]2(O)[C@]1(C)[C@@H](C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O)OC(=O)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO7/c1-16(29)25(32)10-11-27(34)24(25,3)21(35-22(31)17-5-4-12-28-15-17)14-20-23(2)8-7-19(30)13-18(23)6-9-26(20,27)33/h4-6,12,15-16,19-21,29-30,32-34H,7-11,13-14H2,1-3H3/t16-,19-,20+,21+,23-,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
DRPIMPNUZUSUTN-IGFLRYHPSA-N

> <FORMULA>
C27H37NO7

> <MOLECULAR_WEIGHT>
487.593

> <EXACT_MASS>
487.257002535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.20839761464521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,10S,11R,14S,15R,16R)-5,10,11,14-tetrahydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl pyridine-3-carboxylate

> <JCHEM_LOGP>
0.4104970906666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.455295372009854

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.789740578294158

> <JCHEM_PKA_STRONGEST_BASIC>
3.2408962177412657

> <JCHEM_POLAR_SURFACE_AREA>
140.34000000000003

> <JCHEM_REFRACTIVITY>
128.08769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,10S,11R,14S,15R,16R)-5,10,11,14-tetrahydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.219  -3.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.211  -4.918   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.688  -6.367   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.839  -6.183   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.725  -1.551   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.245  -8.229   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.206  -9.949   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.198 -11.126   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.675 -12.574   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.159 -12.845   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       6.166 -11.668   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       6.690 -10.220   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   35  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    6   34                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   34                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   10   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   24    4    8   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5S,10S,11R,14S,15R,16R)-5,10,11,14-Tetrahydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-16-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₇NO₇

Average Mass

487.5930 Da

Monoisotopic Mass

487.25700 Da

IUPAC Name

(1R,2R,5S,10S,11R,14S,15R,16R)-5,10,11,14-tetrahydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl pyridine-3-carboxylate

Traditional Name

(1R,2R,5S,10S,11R,14S,15R,16R)-5,10,11,14-tetrahydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@]1(O)CC[C@@]2(O)[C@]1(C)[C@@H](C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O)OC(=O)C1=CC=CN=C1

InChI Identifier

InChI=1S/C27H37NO7/c1-16(29)25(32)10-11-27(34)24(25,3)21(35-22(31)17-5-4-12-28-15-17)14-20-23(2)8-7-19(30)13-18(23)6-9-26(20,27)33/h4-6,12,15-16,19-21,29-30,32-34H,7-11,13-14H2,1-3H3/t16-,19-,20+,21+,23-,24+,25+,26-,27+/m0/s1

InChI Key

DRPIMPNUZUSUTN-IGFLRYHPSA-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
Cynanchum caudatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
17-hydroxysteroid
3-beta-hydroxysteroid
Delta-5-steroid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Tertiary alcohol
Cyclic alcohol
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.41	ChemAxon
pKa (Strongest Acidic)	12.79	ChemAxon
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	140.34 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.09 m³·mol⁻¹	ChemAxon
Polarizability	51.21 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162887732

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate (NP0255460)

MOL for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

3D MOL for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

3D SDF for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

3D-SDF for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

PDB for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

3D PDB for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

SMILES for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

INCHI for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

Structure for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)

3D Structure for NP0255460 ((1s,3ar,3bs,7s,9ar,9br,11r,11ar)-1,3a,3b,7-tetrahydroxy-1-[(1s)-1-hydroxyethyl]-9a,11a-dimethyl-2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl pyridine-3-carboxylate)