NP-MRD: Showing NP-Card for methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate (NP0201628)

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Record Information

Version

2.0

Created at

2022-09-04 20:42:39 UTC

Updated at

2022-09-04 20:42:40 UTC

NP-MRD ID

NP0201628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate

Description

Methyl (1R,2S,5R,7S,10R,11R,16S,18R)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,17-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadecane-5-carboxylate belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. Based on a literature review very few articles have been published on methyl (1R,2S,5R,7S,10R,11R,16S,18R)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,17-tetraoxo-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadecane-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222422D          

 34 37  0  0  1  0            999 V2000
    1.5246    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4149    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -1.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0647   -1.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7946   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8165    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6160    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    1.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3218    1.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8422    2.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9845    1.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    1.7473    2.8791    0.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1772    1.9612    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2933    1.9450   -0.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539    0.5654   -0.1870 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.3311    1.1477    1.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0262    1.5570   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    1.7186   -0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0435    0.3885    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1084    0.3049    0.6851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2322   -0.7903   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1529   -0.8783   -1.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0089   -2.0251    0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020   -0.7668    0.3834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0416   -1.8092   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -2.7042   -0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5712   -1.8565    0.0110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3390   -2.7798    1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296   -0.5049    0.3386 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2648   -0.4624    1.8268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -0.4841   -0.3186 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3551   -1.3576    0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038   -2.6087    0.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3934   -0.7516    1.1594 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2061    0.2542    0.5864 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9152    1.0622    1.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2720   -0.4027   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1488    0.2414   -0.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3112   -1.7805   -0.2538 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2891   -2.5021   -0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551    1.0806   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173    2.0577   -0.8080 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    0.8715   -0.6035 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7728    1.1800   -2.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167    3.6267    1.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079    2.9374    1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4471    2.5023   -1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471    2.6034    0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9932    0.3283   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417    0.3879    2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540    2.0072    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4016    1.4993    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664    1.3581   -1.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    2.5612   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9884    2.1153   -1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6416    2.4566    0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7383   -0.0029   -2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460   -0.9299   -2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023   -1.7728   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323   -2.8944   -0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7933   -2.2450    1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0884   -1.7759    0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -1.0942    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1295   -2.2153   -0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -3.6822    0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7563    0.4679    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -0.7505    2.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0277   -1.2739    2.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185   -1.0239   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211    1.0398    2.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9028    0.6228    1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1142    2.1035    1.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2567   -1.9423   -0.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4257   -3.4923   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797   -2.5360   -2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1527    2.0526   -2.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3530    0.2666   -2.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7519    1.3523   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 25 27  1  6
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 21 19  1  0
 19 20  1  1
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 17 18  1  0
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 11 12  1  0
 11 13  1  0
 11  9  1  0
  9 10  2  0
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  8  7  1  0
  7  5  1  0
  5  6  1  1
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 33  1  0
 33 34  1  6
 33 31  1  0
 31 32  2  0
 31 25  1  0
 33 21  1  0
  4 19  1  0
  5 14  1  0
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 30 64  1  0
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  8 45  1  0
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  4 39  1  6
  3 37  1  0
  3 38  1  0
  1 35  1  0
  1 36  1  0
 34 66  1  0
 34 67  1  0
 34 68  1  0
M  END


  Mrv1652309042222422D          

 34 37  0  0  1  0            999 V2000
    1.5246    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4149    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1154    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4731   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850   -1.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0647   -1.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546   -1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8165    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
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 29 30  1  0  0  0  0
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0201628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)OC(=O)[C@H]2[C@]3(C)[C@@H](O)C(=O)[C@@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3CC(=C)[C@@]2(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O8/c1-12-11-13-23(4)10-9-14(27)22(2,3)16(23)15(28)18(29)25(13,6)17-19(30)34-26(7,21(32)33-8)20(31)24(12,17)5/h13,16-18,29H,1,9-11H2,2-8H3/t13-,16-,17-,18+,23-,24-,25-,26-/m1/s1

> <INCHI_KEY>
VOCWMGRIYMFSCC-FOHVMROESA-N

> <FORMULA>
C26H34O8

> <MOLECULAR_WEIGHT>
474.55

> <EXACT_MASS>
474.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.37422060067274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,5R,7S,10R,11R,16S,18R)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,17-tetraoxo-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-5-carboxylate

> <JCHEM_LOGP>
3.238482509666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.350494324682106

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.92492964515759

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7064284398599954

> <JCHEM_POLAR_SURFACE_AREA>
124.04000000000002

> <JCHEM_REFRACTIVITY>
119.80309999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,5R,7S,10R,11R,16S,18R)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,17-tetraoxo-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.846   4.553   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.375   2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.415   0.188   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.346  -2.124   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.216  -1.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.879  -3.013   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.854  -2.431   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.350  -0.976   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.342  -2.140   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.326  -0.394   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.524   0.312   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.150   2.256   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.671   2.012   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.601   3.695   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.572   4.890   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.838   3.389   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11    5   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    4   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   25   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    2   21   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,5R,7S,10R,11R,16S,18R)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,17-tetraoxo-4-oxatetracyclo[8.8.0.0,.0,]octadecane-5-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₄O₈

Average Mass

474.5500 Da

Monoisotopic Mass

474.22537 Da

IUPAC Name

methyl (1R,2S,5R,7S,10R,11R,16S,18R)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,17-tetraoxo-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-5-carboxylate

Traditional Name

methyl (1R,2S,5R,7S,10R,11R,16S,18R)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,17-tetraoxo-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)OC(=O)[C@H]2[C@]3(C)[C@@H](O)C(=O)[C@@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3CC(=C)[C@@]2(C)C1=O

InChI Identifier

InChI=1S/C26H34O8/c1-12-11-13-23(4)10-9-14(27)22(2,3)16(23)15(28)18(29)25(13,6)17-19(30)34-26(7,21(32)33-8)20(31)24(12,17)5/h13,16-18,29H,1,9-11H2,2-8H3/t13-,16-,17-,18+,23-,24-,25-,26-/m1/s1

InChI Key

VOCWMGRIYMFSCC-FOHVMROESA-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 oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

18-oxosteroid
17-oxosteroid
Oxosteroid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Oxane
Pyran
Methyl ester
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.24	ChemAxon
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	124.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	119.8 m³·mol⁻¹	ChemAxon
Polarizability	49.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

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

162972316

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate (NP0201628)

MOL for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

3D MOL for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

3D SDF for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

3D-SDF for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

PDB for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

3D PDB for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

SMILES for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

INCHI for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

Structure for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)

3D Structure for NP0201628 (methyl (2r,4as,4br,5r,6as,10ar,10br,12as)-5-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,6,8-tetraoxo-hexahydro-4ah-phenanthro[1,2-c]pyran-2-carboxylate)