NP-MRD: Showing NP-Card for Leonotinin (NP0030262)

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Record Information

Version

2.0

Created at

2021-06-19 21:39:39 UTC

Updated at

2021-06-29 23:58:07 UTC

NP-MRD ID

NP0030262

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leonotinin

Provided By

JEOL Database JEOL Logo

Description

Leonotinin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Leonotinin is found in Leonotis nepetaefolia , Leonotis nepetifolia, Leonotis ocymifolia and Leonurus sibiricus L. . Leonotinin was first documented in 2015 (PMID: 26319953). Based on a literature review very few articles have been published on Leonotinin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123393D          

 51 55  0  0  0  0            999 V2000
    2.5966   -4.5138    1.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -3.3926    0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0474   -2.4741   -0.2221 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6610   -1.0406   -0.5699 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6894   -0.4339    0.4432 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3809   -1.2657    0.5465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2744   -1.2463   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8217   -2.6775    1.0759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3144   -3.6799    1.0133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7029   -3.0871    1.2259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6803   -1.7915    2.0042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2716   -1.8048    3.4102 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0109   -1.3161    2.2916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476   -0.6886    1.6254 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1080   -0.4287    2.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    0.6228    1.1335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9365    1.5547    2.2012 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.3975    3.3960    4.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4957   -4.5100   -1.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7911    1.8201    5.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
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 15 44  1  0  0  0  0
M  END

     RDKit          3D

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    0.5820    4.0613    3.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3975    3.3960    4.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1877   -4.2592   -0.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192123393D          

 51 55  0  0  0  0            999 V2000
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    1.9298   -3.3926    0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.6203    1.2150    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4860    0.9983    2.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6785    2.1976    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    3.8714    1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2942    4.8741    3.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911    1.8201    5.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 16 17  1  0  0  0  0
  6  8  1  0  0  0  0
 17 18  1  0  0  0  0
 21 20  1  0  0  0  0
 18 22  2  0  0  0  0
 19 18  1  0  0  0  0
 21 22  1  0  0  0  0
  6  7  1  6  0  0  0
 20 19  2  0  0  0  0
 11 12  1  0  0  0  0
  4  3  1  0  0  0  0
  2 24  1  0  0  0  0
  4  5  1  0  0  0  0
  9 23  1  0  0  0  0
 24 23  1  0  0  0  0
  3  2  1  0  0  0  0
 24 25  2  0  0  0  0
  6 14  1  0  0  0  0
  2  1  1  1  0  0  0
  8  9  1  0  0  0  0
  8 38  1  1  0  0  0
  9 10  1  0  0  0  0
  9 39  1  1  0  0  0
 10 11  1  0  0  0  0
 11 13  1  6  0  0  0
 11 14  1  0  0  0  0
 12 42  1  0  0  0  0
  2  8  1  0  0  0  0
 12 43  1  0  0  0  0
 14 16  1  0  0  0  0
 14 15  1  1  0  0  0
 13 12  1  0  0  0  0
 20 50  1  0  0  0  0
 19 49  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 22 51  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 15 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030262

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(C([H])([H])C([H])([H])C2=C([H])OC([H])=C2[H])[C@@]2(OC2([H])[H])C([H])([H])[C@@]2([H])OC(=O)[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]1(C([H])([H])[H])[C@@]23[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-17-6-3-7-18(2)15(17)14(25-16(17)21)10-19(12-24-19)20(18,22)8-4-13-5-9-23-11-13/h5,9,11,14-15,22H,3-4,6-8,10,12H2,1-2H3/t14-,15+,17+,18+,19-,20+/m1/s1

> <INCHI_KEY>
TYPXWADRUZBXSO-FHZWTMRJSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.1508577701591

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,4'R,7'S,8'S,12'R)-7'-[2-(furan-3-yl)ethyl]-7'-hydroxy-1',8'-dimethyl-3'-oxaspiro[oxirane-2,6'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.6399526883333335

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.261409024192744

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7705512281632227

> <JCHEM_POLAR_SURFACE_AREA>
72.19999999999999

> <JCHEM_REFRACTIVITY>
89.2961

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,4'R,7'S,8'S,12'R)-7'-[2-(furan-3-yl)ethyl]-7'-hydroxy-1',8'-dimethyl-3'-oxaspiro[oxirane-2,6'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
    2.5966   -4.5138    1.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -3.3926    0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0474   -2.4741   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610   -1.0406   -0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -0.4339    0.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3809   -1.2657    0.5465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2744   -1.2463   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8217   -2.6775    1.0759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3144   -3.6799    1.0133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7029   -3.0871    1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -1.7915    2.0042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2716   -1.8048    3.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109   -1.3161    2.2916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476   -0.6886    1.6254 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1080   -0.4287    2.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    0.6228    1.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365    1.5547    2.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9367    2.4562    2.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142    3.5283    2.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5820    4.0613    3.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3975    3.3960    4.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312    2.4359    4.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877   -4.2592   -0.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016   -4.1037   -0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4957   -4.5100   -1.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -4.1096    2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3887   -5.0051    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8955   -5.3017    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -2.3985    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.9272   -1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696   -0.4265   -0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -1.0024   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958   -0.3814    1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4746    0.5994    0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537   -1.8641   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -0.2292   -1.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150   -1.5692   -0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443   -2.5613    2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675   -4.4842    1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -3.8339    1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2338   -2.9529    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -1.0849    4.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792   -2.7474    3.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    0.4073    2.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386    0.3530    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203    1.2150    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4860    0.9983    2.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6785    2.1976    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    3.8714    1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2942    4.8741    3.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911    1.8201    5.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
 16 17  1  0
  6  8  1  0
 17 18  1  0
 21 20  1  0
 18 22  2  0
 19 18  1  0
 21 22  1  0
  6  7  1  6
 20 19  2  0
 11 12  1  0
  4  3  1  0
  2 24  1  0
  4  5  1  0
  9 23  1  0
 24 23  1  0
  3  2  1  0
 24 25  2  0
  6 14  1  0
  2  1  1  1
  8  9  1  0
  8 38  1  1
  9 10  1  0
  9 39  1  1
 10 11  1  0
 11 13  1  6
 11 14  1  0
 12 42  1  0
  2  8  1  0
 12 43  1  0
 14 16  1  0
 14 15  1  1
 13 12  1  0
 20 50  1  0
 19 49  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  5 33  1  0
  5 34  1  0
 10 40  1  0
 10 41  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 22 51  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 15 44  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       2.597  -4.514   1.131  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.930  -3.393   0.299  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.047  -2.474  -0.222  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.661  -1.041  -0.570  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.689  -0.434   0.443  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.381  -1.266   0.547  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.274  -1.246  -0.869  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.822  -2.678   1.076  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.314  -3.680   1.013  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.703  -3.087   1.226  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.680  -1.792   2.004  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.272  -1.805   3.410  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.011  -1.316   2.292  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.648  -0.689   1.625  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.108  -0.429   2.817  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.336   0.623   1.133  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.937   1.555   2.201  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.937   2.456   2.852  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.214   3.528   2.254  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.582   4.061   3.240  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.398   3.396   4.407  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.531   2.436   4.172  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.188  -4.259  -0.296  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.102  -4.104  -0.753  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.496  -4.510  -1.833  0.00  0.00           O+0
HETATM   26  H   UNK     0       3.048  -4.110   2.044  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.389  -5.005   0.552  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.896  -5.302   1.426  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.822  -2.398   0.554  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.542  -2.927  -1.090  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.570  -0.427  -0.605  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.247  -1.002  -1.583  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.196  -0.381   1.415  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.475   0.599   0.149  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.254  -1.864  -1.597  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.277  -0.229  -1.280  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.315  -1.569  -0.876  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.144  -2.561   2.120  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.168  -4.484   1.745  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.310  -3.834   1.756  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.234  -2.953   0.278  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.922  -1.085   4.140  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.579  -2.747   3.846  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.593   0.407   2.695  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.139   0.353   0.435  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.620   1.215   0.552  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.486   0.998   2.965  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.679   2.198   1.708  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.270   3.871   1.230  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.294   4.874   3.272  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.791   1.820   5.023  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2   24    3    1    8                                             
CONECT    3    4    2   29   30                                             
CONECT    4    3    5   31   32                                             
CONECT    5    6    4   33   34                                             
CONECT    6    5    8    7   14                                             
CONECT    7    6   35   36   37                                             
CONECT    8    6    9   38    2                                             
CONECT    9   23    8   10   39                                             
CONECT   10    9   11   40   41                                             
CONECT   11   12   10   13   14                                             
CONECT   12   11   42   43   13                                             
CONECT   13   11   12                                                       
CONECT   14    6   11   16   15                                             
CONECT   15   14   44                                                       
CONECT   16   17   14   45   46                                             
CONECT   17   16   18   47   48                                             
CONECT   18   17   22   19                                                  
CONECT   19   18   20   49                                                  
CONECT   20   21   19   50                                                  
CONECT   21   20   22                                                       
CONECT   22   18   21   51                                                  
CONECT   23    9   24                                                       
CONECT   24    2   23   25                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   22                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

RDKit          3D

51 55  0  0  0  0  0  0  0  0999 V2000
    2.5966   -4.5138    1.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -3.3926    0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0474   -2.4741   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610   -1.0406   -0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -0.4339    0.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3809   -1.2657    0.5465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2744   -1.2463   -0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8217   -2.6775    1.0759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3144   -3.6799    1.0133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7029   -3.0871    1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6803   -1.7915    2.0042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2716   -1.8048    3.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109   -1.3161    2.2916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476   -0.6886    1.6254 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1080   -0.4287    2.8173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    0.6228    1.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365    1.5547    2.2012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9367    2.4562    2.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142    3.5283    2.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5820    4.0613    3.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3975    3.3960    4.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312    2.4359    4.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1877   -4.2592   -0.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016   -4.1037   -0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4957   -4.5100   -1.8328 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0478   -4.1096    2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3887   -5.0051    0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8955   -5.3017    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8221   -2.3985    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.9272   -1.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696   -0.4265   -0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -1.0024   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958   -0.3814    1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4746    0.5994    0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537   -1.8641   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -0.2292   -1.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150   -1.5692   -0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443   -2.5613    2.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675   -4.4842    1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099   -3.8339    1.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2338   -2.9529    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -1.0849    4.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5792   -2.7474    3.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    0.4073    2.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386    0.3530    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203    1.2150    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4860    0.9983    2.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6785    2.1976    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2700    3.8714    1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2942    4.8741    3.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911    1.8201    5.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
 16 17  1  0
  6  8  1  0
 17 18  1  0
 21 20  1  0
 18 22  2  0
 19 18  1  0
 21 22  1  0
  6  7  1  6
 20 19  2  0
 11 12  1  0
  4  3  1  0
  2 24  1  0
  4  5  1  0
  9 23  1  0
 24 23  1  0
  3  2  1  0
 24 25  2  0
  6 14  1  0
  2  1  1  1
  8  9  1  0
  8 38  1  1
  9 10  1  0
  9 39  1  1
 10 11  1  0
 11 13  1  6
 11 14  1  0
 12 42  1  0
  2  8  1  0
 12 43  1  0
 14 16  1  0
 14 15  1  1
 13 12  1  0
 20 50  1  0
 19 49  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  5 33  1  0
  5 34  1  0
 10 40  1  0
 10 41  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 22 51  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 15 44  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

(1'S,2R,4'R,7'S,8'S,12'R)-7'-[2-(furan-3-yl)ethyl]-7'-hydroxy-1',8'-dimethyl-3'-oxaspiro[oxirane-2,6'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

Traditional Name

(1'S,2R,4'R,7'S,8'S,12'R)-7'-[2-(furan-3-yl)ethyl]-7'-hydroxy-1',8'-dimethyl-3'-oxaspiro[oxirane-2,6'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(C([H])([H])C([H])([H])C2=C([H])OC([H])=C2[H])[C@@]2(OC2([H])[H])C([H])([H])[C@@]2([H])OC(=O)[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]1(C([H])([H])[H])[C@@]23[H]

InChI Identifier

InChI=1S/C20H26O5/c1-17-6-3-7-18(2)15(17)14(25-16(17)21)10-19(12-24-19)20(18,22)8-4-13-5-9-23-11-13/h5,9,11,14-15,22H,3-4,6-8,10,12H2,1-2H3/t14-,15+,17+,18+,19-,20+/m1/s1

InChI Key

TYPXWADRUZBXSO-FHZWTMRJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Leonotis nepetaefolia	Plant	KNApSAcK
Leonotis nepetifolia	LOTUS Database	35616633
Leonotis ocymifolia	JEOL database	Hussein, A. A., et al, Magn. Reson. Chem. 41, 147 (2003)
Leonurus sibiricus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Cyclic alcohol
Furan
Tertiary alcohol
Tetrahydrofuran
Heteroaromatic compound
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.63	ALOGPS
logP	2.64	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.3 m³·mol⁻¹	ChemAxon
Polarizability	36.15 Å³	ChemAxon
Number of Rings	5	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

552618

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636934

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ueda F, Iizuka K, Tago K, Narukawa Y, Kiuchi F, Kasahara T, Tamura H, Funakoshi-Tago M: Nepetaefuran and leonotinin isolated from Leonotis nepetaefolia R. Br. potently inhibit the LPS signaling pathway by suppressing the transactivation of NF-kappaB. Int Immunopharmacol. 2015 Oct;28(2):967-76. doi: 10.1016/j.intimp.2015.08.015. Epub 2015 Aug 28. [PubMed:26319953 ]
Hussein, A. A., et al. (2003). Hussein, A. A., et al, Magn. Reson. Chem. 41, 147 (2003). Mag. Reson. Chem..

Showing NP-Card for Leonotinin (NP0030262)

MOL for NP0030262 (Leonotinin)

3D MOL for NP0030262 (Leonotinin)

3D SDF for NP0030262 (Leonotinin)

3D-SDF for NP0030262 (Leonotinin)

PDB for NP0030262 (Leonotinin)

3D PDB for NP0030262 (Leonotinin)

SMILES for NP0030262 (Leonotinin)

INCHI for NP0030262 (Leonotinin)

Structure for NP0030262 (Leonotinin)

3D Structure for NP0030262 (Leonotinin)