NP-MRD: Showing NP-Card for 15-epi-eubol (NP0034278)

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Record Information

Version

2.0

Created at

2021-06-20 18:03:11 UTC

Updated at

2021-06-30 00:04:33 UTC

NP-MRD ID

NP0034278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-epi-eubol

Provided By

JEOL Database JEOL Logo

Description

15-epi-eubol is found in Sideritis arguta and Sideritis euboea. 15-epi-eubol was first documented in 2009 (Ertas, A., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120033D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202120033D          

 60 63  0  0  0  0            999 V2000
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   -0.3762   -1.3683   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543    0.9840    2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.0397    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1123    1.5691    0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -0.7608   -3.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    0.0976   -3.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2199    0.7303   -4.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046    2.5381    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    2.6804   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.5354   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3904    2.9168    0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016    3.9208   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    3.8581   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3501    1.9699   -3.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4018    1.8066   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2706    0.5820   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    0.8081    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7935   -0.4176   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -1.2876   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.2486    0.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086    0.2306    2.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1356    1.3459    1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816    1.7433    2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870   -0.6460    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.9676    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 20 16  1  0  0  0  0
 16 17  1  1  0  0  0
 23  6  1  0  0  0  0
 23 24  1  1  0  0  0
 15 14  1  0  0  0  0
  6 34  1  6  0  0  0
 14  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9  7  1  0  0  0  0
  7 25  1  0  0  0  0
  6  7  1  0  0  0  0
  3  2  1  0  0  0  0
  2 25  1  0  0  0  0
 16 15  1  0  0  0  0
  2  1  2  3  0  0  0
 23 22  1  0  0  0  0
 10 11  1  0  0  0  0
 23 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 21 20  1  0  0  0  0
 16 18  1  0  0  0  0
 21 22  1  0  0  0  0
 18 19  1  0  0  0  0
  6  5  1  0  0  0  0
 25 26  1  0  0  0  0
  3  8  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
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 15 43  1  6  0  0  0
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 14 42  1  0  0  0  0
  9 37  1  1  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  3 29  1  1  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
 17 44  1  0  0  0  0
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 17 46  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  6  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
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 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
 19 49  1  0  0  0  0
 26 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034278

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-13-15-6-7-16-21(4)9-5-8-20(3,12-23)17(21)10-18(26-14(2)24)22(16,11-15)19(13)25/h15-19,23,25H,1,5-12H2,2-4H3/t15-,16+,17-,18+,19-,20-,21+,22-/m1/s1

> <INCHI_KEY>
MMPSMJLFQSNILL-PHGHRUFFSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.843015206299214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,5S,9R,10S,13R,15R)-15-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-2-yl acetate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.470777745000002

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.592292898622826

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.062996832640962

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2275303596104625

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
99.44960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5S,9R,10S,13R,15R)-15-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    2.9597   -2.6957    2.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1778   -1.6988    2.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7432   -1.8562    1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556   -0.7911    0.7520 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9602   -0.1121    0.9467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1271    0.4034    2.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    0.9973   -0.0939 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4905    0.3727   -1.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226    1.0268   -2.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    0.2146   -3.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    2.1207   -2.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465    1.9585   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.1960   -0.6750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3499    2.0909   -1.3284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8279    3.2501   -0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7955    2.7327   -2.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    3.3787   -3.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    1.1924   -1.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247    0.2457   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889   -0.6115   -0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    0.2082    0.4670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1347    0.9223    1.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356   -1.1523    0.9164 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9668   -2.1833   -0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -3.0146    3.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -3.2087    2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -0.7208    4.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8279   -0.9243    3.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3210   -2.8097    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.3683   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543    0.9840    2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.0397    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1123    1.5691    0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -0.7608   -3.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2199    0.7303   -4.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046    2.5381    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    2.6804   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.5354   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3904    2.9168    0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016    3.9208   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    3.8581   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353    3.4897   -2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501    1.9699   -3.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4141    3.7655   -4.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4018    1.8066   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2706    0.5820   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    0.8081    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7935   -0.4176   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -1.2876   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.2486    0.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086    0.2306    2.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1356    1.3459    1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816    1.7433    2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870   -0.6460    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.9676    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  1
  3  4  1  0
  4  5  1  0
 20 16  1  0
 16 17  1  1
 23  6  1  0
 23 24  1  1
 15 14  1  0
  6 34  1  6
 14  9  1  0
  9 10  1  0
  9  7  1  0
  7 25  1  0
  6  7  1  0
  3  2  1  0
  2 25  1  0
 16 15  1  0
  2  1  2  3
 23 22  1  0
 10 11  1  0
 23 15  1  0
 11 12  1  0
 11 13  2  0
 21 20  1  0
 16 18  1  0
 21 22  1  0
 18 19  1  0
  6  5  1  0
 25 26  1  0
  3  8  1  0
 21 52  1  0
 21 53  1  0
 20 50  1  0
 20 51  1  0
 22 54  1  0
 22 55  1  0
 15 43  1  6
 14 41  1  0
 14 42  1  0
  9 37  1  1
  8 35  1  0
  8 36  1  0
  3 29  1  1
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  6
  1 27  1  0
  1 28  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 26 60  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       2.960  -2.696   2.761  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.178  -1.699   2.325  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.228  -0.899   3.182  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.147  -1.567   3.239  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.743  -1.856   1.852  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.456  -0.791   0.752  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.960  -0.112   0.947  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.127   0.403   2.390  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.228   0.997  -0.094  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.490   0.373  -1.372  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.323   1.027  -2.223  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.519   0.215  -3.466  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.830   2.121  -2.023  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.047   1.958  -0.266  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.231   1.196  -0.675  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.350   2.091  -1.328  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.828   3.250  -0.431  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.796   2.733  -2.642  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.829   3.379  -3.380  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.551   1.192  -1.725  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.025   0.246  -0.631  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.889  -0.612  -0.072  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.676   0.208   0.467  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.135   0.922   1.758  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.136  -1.152   0.916  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.967  -2.183  -0.038  0.00  0.00           O+0
HETATM   27  H   UNK     0       2.943  -3.015   3.799  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.643  -3.209   2.090  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.620  -0.721   4.188  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.085  -2.508   3.800  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.828  -0.924   3.808  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.811  -2.061   1.963  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.321  -2.810   1.508  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.376  -1.368  -0.182  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.054   0.984   2.497  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.319   1.040   2.747  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.112   1.569   0.216  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.940  -0.761  -3.208  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.566   0.098  -3.986  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.220   0.730  -4.129  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.105   2.538   0.649  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.317   2.680  -1.040  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.933   0.535  -1.505  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.390   2.917   0.439  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.502   3.921  -0.978  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.988   3.858  -0.080  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.035   3.490  -2.428  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.350   1.970  -3.290  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.414   3.765  -4.170  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.402   1.807  -2.047  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.271   0.582  -2.594  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.521   0.808   0.166  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.793  -0.418  -1.046  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.549  -1.288  -0.868  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.309  -1.249   0.713  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.209   0.231   2.599  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.136   1.346   1.677  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.482   1.743   2.053  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.087  -0.646   0.710  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.631  -2.968   0.426  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    3   25    1                                                  
CONECT    3    4    2    8   29                                             
CONECT    4    3    5   30   31                                             
CONECT    5    4    6   32   33                                             
CONECT    6   23   34    7    5                                             
CONECT    7    8    9   25    6                                             
CONECT    8    7    3   35   36                                             
CONECT    9   14   10    7   37                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   38   39   40                                             
CONECT   13   11                                                            
CONECT   14   15    9   41   42                                             
CONECT   15   14   16   23   43                                             
CONECT   16   20   17   15   18                                             
CONECT   17   16   44   45   46                                             
CONECT   18   16   19   47   48                                             
CONECT   19   18   49                                                       
CONECT   20   16   21   50   51                                             
CONECT   21   20   22   52   53                                             
CONECT   22   23   21   54   55                                             
CONECT   23    6   24   22   15                                             
CONECT   24   23   56   57   58                                             
CONECT   25    7    2   26   59                                             
CONECT   26   25   60                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
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
    2.9597   -2.6957    2.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1778   -1.6988    2.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278   -0.8991    3.1818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1470   -1.5665    3.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7432   -1.8562    1.8524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4556   -0.7911    0.7520 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9602   -0.1121    0.9467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1271    0.4034    2.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    0.9973   -0.0939 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4905    0.3727   -1.3719 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226    1.0268   -2.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    0.2146   -3.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8305    2.1207   -2.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0465    1.9585   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2314    1.1960   -0.6750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3499    2.0909   -1.3284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8279    3.2501   -0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7955    2.7327   -2.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    3.3787   -3.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    1.1924   -1.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247    0.2457   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889   -0.6115   -0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    0.2082    0.4670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1347    0.9223    1.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356   -1.1523    0.9164 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9668   -2.1833   -0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -3.0146    3.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -3.2087    2.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -0.7208    4.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851   -2.5079    3.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8279   -0.9243    3.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113   -2.0613    1.9632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210   -2.8097    1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762   -1.3683   -0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543    0.9840    2.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.0397    2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1123    1.5691    0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9402   -0.7608   -3.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5656    0.0976   -3.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2199    0.7303   -4.1290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046    2.5381    0.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    2.6804   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.5354   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3904    2.9168    0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5016    3.9208   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881    3.8581   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353    3.4897   -2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501    1.9699   -3.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4141    3.7655   -4.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4018    1.8066   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2706    0.5820   -2.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    0.8081    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7935   -0.4176   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -1.2876   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -1.2486    0.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086    0.2306    2.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1356    1.3459    1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816    1.7433    2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870   -0.6460    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.9676    0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  1
  3  4  1  0
  4  5  1  0
 20 16  1  0
 16 17  1  1
 23  6  1  0
 23 24  1  1
 15 14  1  0
  6 34  1  6
 14  9  1  0
  9 10  1  0
  9  7  1  0
  7 25  1  0
  6  7  1  0
  3  2  1  0
  2 25  1  0
 16 15  1  0
  2  1  2  3
 23 22  1  0
 10 11  1  0
 23 15  1  0
 11 12  1  0
 11 13  2  0
 21 20  1  0
 16 18  1  0
 21 22  1  0
 18 19  1  0
  6  5  1  0
 25 26  1  0
  3  8  1  0
 21 52  1  0
 21 53  1  0
 20 50  1  0
 20 51  1  0
 22 54  1  0
 22 55  1  0
 15 43  1  6
 14 41  1  0
 14 42  1  0
  9 37  1  1
  8 35  1  0
  8 36  1  0
  3 29  1  1
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  6
  1 27  1  0
  1 28  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 26 60  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

(1S,2S,4S,5S,9R,10S,13R,15R)-15-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-2-yl acetate

Traditional Name

(1S,2S,4S,5S,9R,10S,13R,15R)-15-hydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-2-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H34O4/c1-13-15-6-7-16-21(4)9-5-8-20(3,12-23)17(21)10-18(26-14(2)24)22(16,11-15)19(13)25/h15-19,23,25H,1,5-12H2,2-4H3/t15-,16+,17-,18+,19-,20-,21+,22-/m1/s1

InChI Key

MMPSMJLFQSNILL-PHGHRUFFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Sideritis arguta	JEOL database	Ertas, A., et al, J. Nat. Prod. 72, 500 (2009)
Sideritis euboea	Plant	KNApSAcK

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	2.56	ALOGPS
logP	2.47	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	-1.2	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	3	ChemAxon
Refractivity	99.45 m³·mol⁻¹	ChemAxon
Polarizability	40.84 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

Not Available

References

General References

Ertas, A., et al. (2009). Ertas, A., et al, J. Nat. Prod. 72, 500 (2009). J. Nat. Prod..

Showing NP-Card for 15-epi-eubol (NP0034278)

MOL for NP0034278 (15-epi-eubol)

3D MOL for NP0034278 (15-epi-eubol)

3D SDF for NP0034278 (15-epi-eubol)

3D-SDF for NP0034278 (15-epi-eubol)

PDB for NP0034278 (15-epi-eubol)

3D PDB for NP0034278 (15-epi-eubol)

SMILES for NP0034278 (15-epi-eubol)

INCHI for NP0034278 (15-epi-eubol)

Structure for NP0034278 (15-epi-eubol)

3D Structure for NP0034278 (15-epi-eubol)