NP-MRD: Showing NP-Card for methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate (NP0230729)

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Record Information

Version

2.0

Created at

2022-09-06 11:16:21 UTC

Updated at

2022-09-06 11:16:21 UTC

NP-MRD ID

NP0230729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate

Description

Methyl (2S,3E,5R)-5-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-dien-14-yl]-2-methylhex-3-enoate 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. Based on a literature review very few articles have been published on methyl (2S,3E,5R)-5-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,6-dien-14-yl]-2-methylhex-3-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213162D          

 30 33  0  0  1  0            999 V2000
   -0.8225   -0.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116   -1.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8120   -0.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    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  2  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  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
    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  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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 14 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    6.8425    3.2539   -0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892    2.2655   -0.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5902    1.1663   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4334    1.0297    0.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0195    0.1429   -1.4293 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1004   -0.5169   -2.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384   -0.8576   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -0.9856   -0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0889   -1.9441   -0.1304 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0226   -2.7383    0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951   -1.4387    0.7058 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3885   -0.5196    1.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    0.2220    2.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515   -0.4641    1.3418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1991    0.2902    1.1226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0420    0.2089    2.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3690    0.9528    2.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    0.5530    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2997    0.2402    0.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9788   -0.1551   -0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1923   -0.4534   -0.3411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1444   -0.1771   -1.5300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8851    0.1389   -1.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1721    0.5414   -0.2857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6444    1.9621   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0089   -0.3848    0.0365 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2210   -0.6876   -1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9480   -1.4471   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -0.6526    0.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3222    0.6688   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4232    3.9513   -0.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5792    2.7319    0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748    3.8045    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3341    0.6601   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6330   -0.8695   -3.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8284    0.2691   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5687   -1.3686   -1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502   -1.4740    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968   -0.3266   -1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -2.7529   -0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8133   -3.2649    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -3.4677    1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -2.0714    1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3138    1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467    0.1938    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7455   -1.1040    2.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668    1.2943    2.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1583    0.0637    3.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567   -1.4498    1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617    1.3744    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3321   -0.8668    2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176    0.5403    3.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0775    0.6528    3.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2555    2.0293    2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8587    0.2811    1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6485   -0.4763   -2.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3381    0.0927   -2.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6433    2.5580    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3240    2.4642   -1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6435    1.9617   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4380   -1.3308    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    0.2021   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8453   -1.3925   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439   -1.6867   -1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746   -2.3724   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    1.0531   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    1.4868   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3733    0.7096   -1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  6
 29 11  1  0
 29 14  1  0
 26 15  1  0
 24 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  6
  6 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  6
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  1
 15 50  1  6
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 19 55  1  0
 22 56  1  0
 23 57  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 26 61  1  1
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 30 66  1  0
 30 67  1  0
 30 68  1  0
M  END


  Mrv1652309062213162D          

 30 33  0  0  1  0            999 V2000
   -0.8225   -0.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116   -1.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8120   -0.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    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  2  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  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
    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  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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 14 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0230729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O3/c1-17(6-7-18(2)25(29)30-5)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h6-7,12,14,16-18,21-24H,8-11,13,15H2,1-5H3/b7-6+/t17-,18+,21+,22-,23+,24+,26+,27-/m1/s1

> <INCHI_KEY>
SPYDBHQUKUZVQJ-KCTBVFCJSA-N

> <FORMULA>
C27H38O3

> <MOLECULAR_WEIGHT>
410.598

> <EXACT_MASS>
410.282095084

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.35389772064875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3E,5R)-5-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-methylhex-3-enoate

> <JCHEM_LOGP>
5.953087619666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.864676358172844

> <JCHEM_PKA_STRONGEST_BASIC>
-4.998752245269529

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
123.63439999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3E,5R)-5-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-methylhex-3-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.535  -0.952   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.955  -2.378   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.516  -1.373   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+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  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   15   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   14   11   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,3E,5R)-5-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,6-dien-14-yl]-2-methylhex-3-enoic acid	Generator

Chemical Formula

C₂₇H₃₈O₃

Average Mass

410.5980 Da

Monoisotopic Mass

410.28210 Da

IUPAC Name

methyl (2S,3E,5R)-5-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-methylhex-3-enoate

Traditional Name

methyl (2S,3E,5R)-5-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-methylhex-3-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](C)\C=C\[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C27H38O3/c1-17(6-7-18(2)25(29)30-5)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h6-7,12,14,16-18,21-24H,8-11,13,15H2,1-5H3/b7-6+/t17-,18+,21+,22-,23+,24+,26+,27-/m1/s1

InChI Key

SPYDBHQUKUZVQJ-KCTBVFCJSA-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

Not Available

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
3-oxo-delta-1,4-steroid
3-oxosteroid
Oxosteroid
Delta-1,4-steroid
Methyl ester
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen 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	5.95	ChemAxon
pKa (Strongest Acidic)	18.86	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.63 m³·mol⁻¹	ChemAxon
Polarizability	48.35 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	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

162972396

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate (NP0230729)

MOL for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

3D MOL for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

3D SDF for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

3D-SDF for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

PDB for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

3D PDB for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

SMILES for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

INCHI for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

Structure for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)

3D Structure for NP0230729 (methyl (2s,3e,5r)-5-[(1r,3as,3bs,9ar,9bs,11ar)-9a,11a-dimethyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhex-3-enoate)