NP-MRD: Showing NP-Card for rufescenolide A (NP0041204)

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Record Information

Version

2.0

Created at

2021-06-20 23:10:19 UTC

Updated at

2026-02-13 00:01:55 UTC

NP-MRD ID

NP0041204

Natural Product DOI

https://doi.org/10.57994/6551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rufescenolide A

Provided By

JEOL Database JEOL Logo

Description

Rufescenolide A 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. rufescenolide A is found in Piptocoma rufescens. rufescenolide A was first documented in 2012 (PMID: 22685350). Based on a literature review very few articles have been published on Rufescenolide A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101103D          

 48 50  0  0  0  0            999 V2000
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   -2.6740   -0.3110   -0.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212101103D          

 48 50  0  0  0  0            999 V2000
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 22 23  2  0  0  0  0
 11  9  1  0  0  0  0
 24 25  2  3  0  0  0
  4  5  2  0  0  0  0
  9 10  1  6  0  0  0
  7  6  1  0  0  0  0
 20 21  1  0  0  0  0
 16 17  1  0  0  0  0
  4  2  1  0  0  0  0
 18 19  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
 20 45  1  1  0  0  0
 26 48  1  6  0  0  0
 13 38  1  0  0  0  0
 16 39  1  6  0  0  0
 18 43  1  6  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  7 32  1  1  0  0  0
 25 46  1  0  0  0  0
 25 47  1  0  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 17 40  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 19 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041204

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O7/c1-8(2)17(22)24-12-7-19(5)13(20)6-11(26-19)9(3)15(21)16-14(12)10(4)18(23)25-16/h6,9,12,14-16,21H,1,4,7H2,2-3,5H3/t9-,12-,14+,15-,16-,19+/m0/s1

> <INCHI_KEY>
FBWFHGQZIPHZBF-SCKGQUEHSA-N

> <FORMULA>
C19H22O7

> <MOLECULAR_WEIGHT>
362.378

> <EXACT_MASS>
362.136553048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.4305202022464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4S,8R,9S,11R)-3-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-1(13)-en-9-yl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
1.8223081656666666

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.15237618137328

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.75114771417428

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3364274234414593

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
91.1973

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,8R,9S,11R)-3-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-1(13)-en-9-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -4.2885   -2.0433   -1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085   -1.4825   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0634   -1.7607    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8648   -0.5423    0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2202   -0.0570    1.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -0.3110   -0.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754    0.6174    0.3863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9609   -0.1703    1.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0106   -1.2845    0.9527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6362   -2.6694    0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695   -0.9697   -0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -0.3222   -0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115   -0.5317    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -1.2661    1.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4876   -1.7154    2.8437 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637    0.5999   -1.3154 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5601    0.5683   -1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.0444   -1.0809 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5195    2.8221   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089    2.1674   -0.2563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1884    3.5585   -0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120    3.7431   -1.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    4.8179   -1.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8071    2.4137   -1.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8155    2.2637   -2.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879    1.3513   -0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9246   -2.7261   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   -1.8491   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6409   -0.8344    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6406   -2.4521   -0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9710   -2.2106    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    1.3741    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600   -0.6229    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008    0.5533    2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -3.4209    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4728   -2.7145    0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937   -2.9650    1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -0.1432    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514    0.2158   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8787   -0.4481   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    0.9049   -0.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7795    1.2124   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    2.5302   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    3.7149   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490    1.9716    0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250    3.1256   -2.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.2810   -2.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122    0.6362   -1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  9 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
  4  6  1  0
 12 16  1  0
  2  1  2  3
 16 18  1  0
 18 20  1  0
 21 22  1  0
  9  8  1  0
 22 24  1  0
  8  7  1  0
  7 26  1  0
 26 24  1  0
 14 15  2  0
 26 20  1  0
 22 23  2  0
 11  9  1  0
 24 25  2  3
  4  5  2  0
  9 10  1  6
  7  6  1  0
 20 21  1  0
 16 17  1  0
  4  2  1  0
 18 19  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 20 45  1  1
 26 48  1  6
 13 38  1  0
 16 39  1  6
 18 43  1  6
  8 33  1  0
  8 34  1  0
  7 32  1  1
 25 46  1  0
 25 47  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.289  -2.043  -1.602  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.708  -1.482  -0.455  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.063  -1.761   0.125  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.865  -0.542   0.338  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.220  -0.057   1.401  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.674  -0.311  -0.271  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.775   0.617   0.386  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.961  -0.170   1.450  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.011  -1.285   0.953  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.636  -2.669   0.931  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.470  -0.970  -0.365  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.689  -0.322  -0.185  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.312  -0.532   0.974  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.295  -1.266   1.725  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.488  -1.715   2.844  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.064   0.600  -1.315  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.560   0.568  -1.640  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.522   2.044  -1.081  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.519   2.822  -0.393  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.209   2.167  -0.256  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.188   3.559  -0.273  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.312   3.743  -1.009  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.807   4.818  -1.286  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.807   2.414  -1.408  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.816   2.264  -2.276  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.988   1.351  -0.745  0.00  0.00           C+0
HETATM   27  H   UNK     0      -4.925  -2.726  -2.158  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.307  -1.849  -2.023  0.00  0.00           H+0
HETATM   29  H   UNK     0      -6.641  -0.834   0.212  0.00  0.00           H+0
HETATM   30  H   UNK     0      -6.641  -2.452  -0.499  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.971  -2.211   1.119  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.364   1.374   0.925  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.660  -0.623   2.166  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.401   0.553   2.054  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.090  -3.421   0.600  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.473  -2.715   0.227  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.994  -2.965   1.923  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.232  -0.143   1.365  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.551   0.216  -2.209  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.879  -0.448  -1.898  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.176   0.905  -0.800  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.780   1.212  -2.499  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.394   2.530  -2.056  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.142   3.715  -0.267  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.449   1.972   0.791  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.325   3.126  -2.701  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.162   1.281  -2.579  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.712   0.636  -1.527  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    3    1    4                                                  
CONECT    3    2   29   30   31                                             
CONECT    4    6    5    2                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    8   26    6   32                                             
CONECT    8    9    7   33   34                                             
CONECT    9   14    8   11   10                                             
CONECT   10    9   35   36   37                                             
CONECT   11   12    9                                                       
CONECT   12   13   11   16                                                  
CONECT   13   14   12   38                                                  
CONECT   14    9   13   15                                                  
CONECT   15   14                                                            
CONECT   16   12   18   17   39                                             
CONECT   17   16   40   41   42                                             
CONECT   18   16   20   19   43                                             
CONECT   19   18   44                                                       
CONECT   20   18   26   21   45                                             
CONECT   21   22   20                                                       
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   22   26   25                                                  
CONECT   25   24   46   47                                                  
CONECT   26    7   24   20   48                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   13                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   25                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  100    0
END

RDKit          3D

48 50  0  0  0  0  0  0  0  0999 V2000
   -4.2885   -2.0433   -1.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085   -1.4825   -0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0634   -1.7607    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8648   -0.5423    0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2202   -0.0570    1.4012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6740   -0.3110   -0.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754    0.6174    0.3863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9609   -0.1703    1.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0106   -1.2845    0.9527 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6362   -2.6694    0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695   -0.9697   -0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -0.3222   -0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115   -0.5317    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -1.2661    1.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4876   -1.7154    2.8437 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637    0.5999   -1.3154 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5601    0.5683   -1.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.0444   -1.0809 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5195    2.8221   -0.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089    2.1674   -0.2563 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1884    3.5585   -0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120    3.7431   -1.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8066    4.8179   -1.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8071    2.4137   -1.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8155    2.2637   -2.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879    1.3513   -0.7452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9246   -2.7261   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   -1.8491   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6409   -0.8344    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6406   -2.4521   -0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9710   -2.2106    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    1.3741    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600   -0.6229    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4008    0.5533    2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -3.4209    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4728   -2.7145    0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937   -2.9650    1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -0.1432    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514    0.2158   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8787   -0.4481   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    0.9049   -0.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7795    1.2124   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    2.5302   -2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    3.7149   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4490    1.9716    0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250    3.1256   -2.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1615    1.2810   -2.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122    0.6362   -1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  9 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
  4  6  1  0
 12 16  1  0
  2  1  2  3
 16 18  1  0
 18 20  1  0
 21 22  1  0
  9  8  1  0
 22 24  1  0
  8  7  1  0
  7 26  1  0
 26 24  1  0
 14 15  2  0
 26 20  1  0
 22 23  2  0
 11  9  1  0
 24 25  2  3
  4  5  2  0
  9 10  1  6
  7  6  1  0
 20 21  1  0
 16 17  1  0
  4  2  1  0
 18 19  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
 20 45  1  1
 26 48  1  6
 13 38  1  0
 16 39  1  6
 18 43  1  6
  8 33  1  0
  8 34  1  0
  7 32  1  1
 25 46  1  0
 25 47  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 19 44  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₇

Average Mass

362.3780 Da

Monoisotopic Mass

362.13655 Da

IUPAC Name

(2R,3S,4S,8R,9S,11R)-3-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-1(13)-en-9-yl 2-methylprop-2-enoate

Traditional Name

(2R,3S,4S,8R,9S,11R)-3-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-1(13)-en-9-yl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H22O7/c1-8(2)17(22)24-12-7-19(5)13(20)6-11(26-19)9(3)15(21)16-14(12)10(4)18(23)25-16/h6,9,12,14-16,21H,1,4,7H2,2-3,5H3/t9-,12-,14+,15-,16-,19+/m0/s1

InChI Key

FBWFHGQZIPHZBF-SCKGQUEHSA-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
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.6, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400.0, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.6, Chloroform-d, simulated)	[email protected]	Not Available	Not Available	2026-02-12	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Piptocoma rufescens		Not Available
Piptocoma rufescens		Not Available
Piptocoma rufescens	JEOL database	Ren, Y., et al, Tetrahedron 68, 2671 (2012)

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

Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Dihydrofuran
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Ketone
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.75	ALOGPS
logP	1.82	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.2 m³·mol⁻¹	ChemAxon
Polarizability	36.43 Å³	ChemAxon
Number of Rings	3	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

28289805

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101565654

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren Y, Acuna UM, Jimenez F, Garcia R, Mejia M, Chai H, Gallucci JC, Farnsworth NR, Soejarto DD, Carcache de Blanco EJ, Kinghorn AD: Cytotoxic and NF-kappaB inhibitory sesquiterpene lactones from Piptocoma rufescens. Tetrahedron. 2012 Mar 25;68(12):2671-2678. doi: 10.1016/j.tet.2012.01.061. Epub 2012 Jan 26. [PubMed:22685350 ]
Ren, Y., et al. (2012). Ren, Y., et al, Tetrahedron 68, 2671 (2012). Tetrahedron.
DOI: 10.1016/j.tet.2012.01.061
PMID: 22685350

Showing NP-Card for rufescenolide A (NP0041204)

MOL for NP0041204 (rufescenolide A)

3D MOL for NP0041204 (rufescenolide A)

3D SDF for NP0041204 (rufescenolide A)

3D-SDF for NP0041204 (rufescenolide A)

PDB for NP0041204 (rufescenolide A)

3D PDB for NP0041204 (rufescenolide A)

SMILES for NP0041204 (rufescenolide A)

INCHI for NP0041204 (rufescenolide A)

Structure for NP0041204 (rufescenolide A)

3D Structure for NP0041204 (rufescenolide A)