NP-MRD: Showing NP-Card for Stypolactone (NP0024352)

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Record Information

Version

2.0

Created at

2021-06-19 16:45:33 UTC

Updated at

2021-06-29 23:48:38 UTC

NP-MRD ID

NP0024352

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stypolactone

Provided By

JEOL Database JEOL Logo

Description

Stypolactone is found in Stypopodium zonale. Stypolactone was first documented in 2002 (Dorta, E. et al.). Based on a literature review very few articles have been published on Stypolactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192118453D          

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     RDKit          3D

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  Mrv1652306192118453D          

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    1.6670    2.0510   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214    2.0747    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -1.2886    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -0.0523   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544   -1.3640   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320    0.8903    2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    1.2620    3.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854   -1.4385    3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.3783    4.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300   -0.7134    4.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -2.2200    5.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083   -2.9401    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -3.2875    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961   -3.9497    2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1048   -2.7126    2.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1417   -1.4303    3.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5270   -3.0365    3.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054    0.1546    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750   -1.2805    0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   -1.4559   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9402    0.3288   -1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    1.0792    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5402    1.2794   -2.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727   -0.2737   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    0.8047   -2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336    2.6231   -3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080    4.0074   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0  0  0  0
  6  5  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 10  1  0  0  0  0
 24 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 22  2  0  0  0  0
  9  8  1  0  0  0  0
 10 12  1  0  0  0  0
 12 15  1  0  0  0  0
  6  8  1  0  0  0  0
  5  4  1  0  0  0  0
  6  7  1  6  0  0  0
 18 20  1  0  0  0  0
 18 19  1  6  0  0  0
 20  2  1  0  0  0  0
 10 11  1  0  0  0  0
  2  3  1  0  0  0  0
 12 13  1  6  0  0  0
  3  4  1  0  0  0  0
 12 14  1  0  0  0  0
  6 15  1  0  0  0  0
  2  1  1  0  0  0  0
 24 26  1  0  0  0  0
  5 35  1  1  0  0  0
 15 51  1  1  0  0  0
  5 18  1  0  0  0  0
 24 25  2  0  0  0  0
 20 26  1  1  0  0  0
 23 60  1  0  0  0  0
 21 59  1  0  0  0  0
  2 30  1  6  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
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  9 41  1  0  0  0  0
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  8 39  1  0  0  0  0
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  7 38  1  0  0  0  0
 19 56  1  0  0  0  0
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 11 44  1  0  0  0  0
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 14 50  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024352

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])[C@]2(OC1=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]21C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-13-6-7-16-20(4)10-9-17(24)19(2,3)15(20)8-11-21(16,5)22(13)12-14(23)18(25)26-22/h12-13,15-17,23-24H,6-11H2,1-5H3/t13-,15-,16+,17-,20-,21+,22-/m0/s1

> <INCHI_KEY>
WXKINGCYMWMSHZ-AVIIFFOXSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.92981884573385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-4,7'-dihydroxy-2',4'b,8',8',10'a-pentamethyl-3',4',4'a,4'b,5',6',7',8',8'a,9',10',10'a-dodecahydro-2'H,5H-spiro[furan-2,1'-phenanthrene]-5-one

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.217126068333334

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.48943338559104

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.684150371056583

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351217126308278

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
100.91959999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-4,7'-dihydroxy-2',4'b,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydrospiro[furan-2,1'-phenanthrene]-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -0.7623    5.2959   -1.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1459   -0.6746    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257    0.4837    2.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498   -0.7170    3.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.4047    3.7916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1707   -2.5384    4.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -1.8245    2.4871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4664   -3.0574    1.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2111   -0.5711    1.5395 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.3582    0.5393   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3995    0.7801   -1.9815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    2.8995   -1.1754 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.7274    3.4306   -1.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8349    3.6212   -2.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6313    3.7686   -0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5363    4.2486    0.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802    3.4561   -0.0876 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1354    5.9054   -1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0587    4.3613    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    4.4541   -0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    2.5910    1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    2.0510   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214    2.0747    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -1.2886    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -0.0523   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544   -1.3640   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320    0.8903    2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    1.2620    3.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854   -1.4385    3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.3783    4.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300   -0.7134    4.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -2.2200    5.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083   -2.9401    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -3.2875    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961   -3.9497    2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1048   -2.7126    2.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1417   -1.4303    3.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5270   -3.0365    3.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054    0.1546    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750   -1.2805    0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   -1.4559   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0333    1.0792    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1727   -0.2737   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    0.8047   -2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336    2.6231   -3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080    4.0074   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  6  5  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  9 10  1  0
 24 22  1  0
 22 23  1  0
 21 22  2  0
  9  8  1  0
 10 12  1  0
 12 15  1  0
  6  8  1  0
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  6  7  1  6
 18 20  1  0
 18 19  1  6
 20  2  1  0
 10 11  1  0
  2  3  1  0
 12 13  1  6
  3  4  1  0
 12 14  1  0
  6 15  1  0
  2  1  1  0
 24 26  1  0
  5 35  1  1
 15 51  1  1
  5 18  1  0
 24 25  2  0
 20 26  1  1
 23 60  1  0
 21 59  1  0
  2 30  1  6
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  1
  8 39  1  0
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  7 36  1  0
  7 37  1  0
  7 38  1  0
 19 56  1  0
 19 57  1  0
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 14 48  1  0
 14 49  1  0
 14 50  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.762   5.296  -1.740  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.376   3.843  -1.414  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.555   3.860  -0.191  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.993   2.467   0.253  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.213   1.537   0.512  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.148   0.168   1.240  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.146  -0.675   0.410  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.826   0.484   2.609  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.950  -0.717   3.545  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.388  -1.405   3.792  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.171  -2.538   4.631  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.126  -1.825   2.487  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.466  -3.057   1.836  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.556  -2.273   2.898  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.211  -0.571   1.540  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.021  -0.792   0.248  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.358   0.539  -0.428  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.127   1.427  -0.772  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.400   0.780  -1.982  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.595   2.900  -1.175  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.556   2.936  -2.324  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.727   3.431  -1.942  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.835   3.621  -2.713  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.631   3.769  -0.518  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.536   4.249   0.141  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.380   3.456  -0.088  0.00  0.00           O+0
HETATM   27  H   UNK     0      -1.339   5.755  -0.931  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.135   5.905  -1.893  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.351   5.357  -2.660  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.197   3.474  -2.274  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.059   4.361   0.650  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.450   4.454  -0.417  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.590   2.591   1.161  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.667   2.051  -0.502  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.821   2.075   1.256  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.800  -1.289   1.034  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.826  -0.052  -0.176  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.654  -1.364  -0.278  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.832   0.890   2.455  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.253   1.262   3.131  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.685  -1.438   3.173  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.361  -0.378   4.505  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.030  -0.713   4.354  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.233  -2.220   5.457  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.608  -2.940   1.696  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.913  -3.288   0.864  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.596  -3.950   2.461  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.105  -2.713   2.059  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.142  -1.430   3.282  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.527  -3.037   3.684  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.805   0.155   2.121  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.975  -1.281   0.471  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.502  -1.456  -0.448  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.940   0.329  -1.334  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.033   1.079   0.247  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.540   1.279  -2.228  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.173  -0.274  -1.827  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.022   0.805  -2.882  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.334   2.623  -3.333  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.508   4.007  -2.116  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2   20    3    1   30                                             
CONECT    3    2    4   31   32                                             
CONECT    4    5    3   33   34                                             
CONECT    5    6    4   35   18                                             
CONECT    6    5    8    7   15                                             
CONECT    7    6   36   37   38                                             
CONECT    8    9    6   39   40                                             
CONECT    9   10    8   41   42                                             
CONECT   10    9   12   11   43                                             
CONECT   11   10   44                                                       
CONECT   12   10   15   13   14                                             
CONECT   13   12   45   46   47                                             
CONECT   14   12   48   49   50                                             
CONECT   15   16   12    6   51                                             
CONECT   16   15   17   52   53                                             
CONECT   17   16   18   54   55                                             
CONECT   18   17   20   19    5                                             
CONECT   19   18   56   57   58                                             
CONECT   20   21   18    2   26                                             
CONECT   21   20   22   59                                                  
CONECT   22   24   23   21                                                  
CONECT   23   22   60                                                       
CONECT   24   22   26   25                                                  
CONECT   25   24                                                            
CONECT   26   24   20                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   19                                                            
CONECT   57   19                                                            
CONECT   58   19                                                            
CONECT   59   21                                                            
CONECT   60   23                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
   -0.7623    5.2959   -1.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3755    3.8429   -1.4135 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5554    3.8604   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934    2.4669    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    1.5370    0.5118 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1481    0.1676    1.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1459   -0.6746    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257    0.4837    2.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498   -0.7170    3.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.4047    3.7916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1707   -2.5384    4.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1257   -1.8245    2.4871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4664   -3.0574    1.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5563   -2.2732    2.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111   -0.5711    1.5395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0213   -0.7921    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582    0.5393   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    1.4265   -0.7715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3995    0.7801   -1.9815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    2.8995   -1.1754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5559    2.9364   -2.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274    3.4306   -1.9425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8349    3.6212   -2.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6313    3.7686   -0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5363    4.2486    0.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802    3.4561   -0.0876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    5.7548   -0.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354    5.9054   -1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3509    5.3575   -2.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1973    3.4739   -2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587    4.3613    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    4.4541   -0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899    2.5910    1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6670    2.0510   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214    2.0747    1.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7997   -1.2886    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8261   -0.0523   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544   -1.3640   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320    0.8903    2.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    1.2620    3.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854   -1.4385    3.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.3783    4.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300   -0.7134    4.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -2.2200    5.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083   -2.9401    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -3.2875    0.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961   -3.9497    2.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1048   -2.7126    2.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1417   -1.4303    3.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5270   -3.0365    3.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054    0.1546    2.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750   -1.2805    0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   -1.4559   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9402    0.3288   -1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    1.0792    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5402    1.2794   -2.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1727   -0.2737   -1.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    0.8047   -2.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3336    2.6231   -3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080    4.0074   -2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  6  5  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  9 10  1  0
 24 22  1  0
 22 23  1  0
 21 22  2  0
  9  8  1  0
 10 12  1  0
 12 15  1  0
  6  8  1  0
  5  4  1  0
  6  7  1  6
 18 20  1  0
 18 19  1  6
 20  2  1  0
 10 11  1  0
  2  3  1  0
 12 13  1  6
  3  4  1  0
 12 14  1  0
  6 15  1  0
  2  1  1  0
 24 26  1  0
  5 35  1  1
 15 51  1  1
  5 18  1  0
 24 25  2  0
 20 26  1  1
 23 60  1  0
 21 59  1  0
  2 30  1  6
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  1
  8 39  1  0
  8 40  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

(2R,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-4,7'-dihydroxy-2',4'b,8',8',10'a-pentamethyl-3',4',4'a,4'b,5',6',7',8',8'a,9',10',10'a-dodecahydro-2'H,5H-spiro[furan-2,1'-phenanthrene]-5-one

Traditional Name

(2R,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-4,7'-dihydroxy-2',4'b,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydrospiro[furan-2,1'-phenanthrene]-5-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])[C@]2(OC1=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]1([H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]21C([H])([H])[H]

InChI Identifier

InChI=1S/C22H34O4/c1-13-6-7-16-20(4)10-9-17(24)19(2,3)15(20)8-11-21(16,5)22(13)12-14(23)18(25)26-22/h12-13,15-17,23-24H,6-11H2,1-5H3/t13-,15-,16+,17-,20-,21+,22-/m0/s1

InChI Key

WXKINGCYMWMSHZ-AVIIFFOXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stypopodium zonale	JEOL database	Dorta, E. et al, Tetrahedron Lett. 43, 9043 (2002)

Chemical Taxonomy

Classification

Not classified

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	4.08	ALOGPS
logP	4.22	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	100.92 m³·mol⁻¹	ChemAxon
Polarizability	40.93 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

9047439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10872160

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dorta, E. et al. (2002). Dorta, E. et al, Tetrahedron Lett. 43, 9043 (2002). Tetrahedron Lett.

Showing NP-Card for Stypolactone (NP0024352)

MOL for NP0024352 (Stypolactone)

3D MOL for NP0024352 (Stypolactone)

3D SDF for NP0024352 (Stypolactone)

3D-SDF for NP0024352 (Stypolactone)

PDB for NP0024352 (Stypolactone)

3D PDB for NP0024352 (Stypolactone)

SMILES for NP0024352 (Stypolactone)

INCHI for NP0024352 (Stypolactone)

Structure for NP0024352 (Stypolactone)

3D Structure for NP0024352 (Stypolactone)