NP-MRD: Showing NP-Card for 20-epi-3,20-di-O-deacetylteupyreinidin (NP0024167)

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Record Information

Version

2.0

Created at

2021-06-19 16:37:24 UTC

Updated at

2021-06-29 23:48:18 UTC

NP-MRD ID

NP0024167

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-epi-3,20-di-O-deacetylteupyreinidin

Provided By

JEOL Database JEOL Logo

Description

20-epi-3,20-di-O-deacetylteupyreinidin is found in Teucrium montbretii and Teucrium montbretii subsp. libanoticum. 20-epi-3,20-di-O-deacetylteupyreinidin was first documented in 2002 (Bruno, M., et al.). Based on a literature review very few articles have been published on (2R,3R,5S,2'R,5'R,8'abeta)-5-(3-Furyl)-2'alpha-methyl-4'aalpha-(acetoxymethyl)-4,5-dihydrodispiro[furan-3(2H),1'-decalin-5',2''-oxirane]-2,4'alpha,6'beta-triol 4'-acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192118373D          

 65 69  0  0  0  0            999 V2000
   -4.1927    0.1802   -3.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    1.2641   -2.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0210    0.7121   -2.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069    1.6609   -2.0749 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3696    0.9878   -1.7416 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2187    2.0236   -0.9304 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.3254    4.0512   -1.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192118373D          

 65 69  0  0  0  0            999 V2000
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    0.7118    2.2326    0.4990 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6526    0.9299    1.3022 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.3930    2.9325    1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5307   -2.3457    0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2348   -0.6075   -0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1031    1.1334    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874   -0.6479   -0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -2.4829   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -1.4232   -1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1434   -2.5811   -3.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957   -2.1295   -2.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -0.2303   -4.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.0599   -5.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749    1.3891   -2.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.2936   -4.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
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 28 29  1  0  0  0  0
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  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
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 22 21  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  2  0  0  0  0
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 31  6  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 27  1  0  0  0  0
 13 14  1  0  0  0  0
 26 15  1  0  0  0  0
 26 57  1  1  0  0  0
 31 33  1  6  0  0  0
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  6  7  1  0  0  0  0
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  6  5  1  6  0  0  0
  2  3  2  0  0  0  0
  7 12  1  0  0  0  0
  2  1  1  0  0  0  0
 29 30  1  0  0  0  0
 24 25  1  0  0  0  0
 12 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 15 16  1  1  0  0  0
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 13 15  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0024167

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])O[C@]([H])(C2=C([H])OC([H])=C2[H])C([H])([H])[C@]11[C@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]21OC1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O9/c1-13-8-20(32-15(3)26)23(11-30-14(2)25)18(4-5-19(27)24(23)12-31-24)22(13)9-17(33-21(22)28)16-6-7-29-10-16/h6-7,10,13,17-21,27-28H,4-5,8-9,11-12H2,1-3H3/t13-,17+,18-,19+,20+,21-,22-,23+,24-/m1/s1

> <INCHI_KEY>
QGKJGQDHZIBMKX-QAIOPYPPSA-N

> <FORMULA>
C24H32O9

> <MOLECULAR_WEIGHT>
464.511

> <EXACT_MASS>
464.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.66616160105531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,2'S,2''R,4'aS,5'R,5''S,6'R,8'S,8'aR)-8'-(acetyloxy)-5''-(furan-3-yl)-2',2''-dihydroxy-6'-methyl-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
0.7504024696666669

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.900197789731717

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.918704656399964

> <JCHEM_PKA_STRONGEST_BASIC>
-2.855538788018883

> <JCHEM_POLAR_SURFACE_AREA>
127.96000000000002

> <JCHEM_REFRACTIVITY>
111.91279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'S,2''R,4'aS,5'R,5''S,6'R,8'S,8'aR)-8'-(acetyloxy)-5''-(furan-3-yl)-2',2''-dihydroxy-6'-methyl-hexahydro-2'H-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
   -4.1927    0.1802   -3.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
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 25 56  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      -4.193   0.180  -3.118  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.216   1.264  -2.780  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.468   2.459  -2.817  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.021   0.712  -2.426  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.007   1.661  -2.075  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.370   0.988  -1.742  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.219   2.024  -0.930  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.187   3.309  -1.587  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.325   4.051  -1.544  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.124   5.338  -2.283  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.367   3.725  -0.992  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.712   2.233   0.499  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.653   0.930   1.302  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.236   1.257   2.747  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.167  -0.221   0.602  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.107  -1.535   1.393  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.237  -1.957   1.982  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.136  -2.531   3.352  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.677  -3.833   3.709  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.759  -3.916   5.079  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.239  -2.758   5.594  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.468  -1.926   4.548  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.056  -0.781   1.938  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.703  -0.107   0.737  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.171   1.213   0.808  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.327  -0.358  -0.894  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.302  -1.550  -1.675  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.368  -1.776  -3.030  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.380  -0.511  -3.872  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.066  -0.793  -5.092  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.056   0.606  -3.102  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.518   0.927  -3.412  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.440   1.718  -3.930  0.00  0.00           O+0
HETATM   34  H   UNK     0      -5.146   0.629  -3.411  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.814  -0.411  -3.956  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.359  -0.454  -2.244  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.881   2.356  -2.915  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.378   2.247  -1.232  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.247   1.654  -0.852  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.315   5.909  -1.819  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.041   5.931  -2.235  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.896   5.130  -3.332  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.393   2.933   1.003  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.250   2.755   0.504  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.693   0.575   1.366  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.765   1.695   2.803  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.930   1.985   3.183  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.259   0.376   3.392  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.852  -1.382   2.183  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.531  -2.346   0.794  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.708  -2.699   1.323  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.329  -4.615   3.048  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.528  -4.688   5.800  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.860  -0.950   4.802  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.235  -0.608  -0.075  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.103   1.133   1.074  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.387  -0.648  -0.796  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.202  -2.483  -1.112  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.375  -1.423  -1.828  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.143  -2.581  -3.571  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.396  -2.130  -2.875  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.638  -0.230  -4.155  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.123   0.060  -5.563  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.175   1.389  -2.689  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.063   0.294  -4.105  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    4    6   37   38                                             
CONECT    6   26   31    7    5                                             
CONECT    7    6   12    8   39                                             
CONECT    8    7    9                                                       
CONECT    9   10   11    8                                                  
CONECT   10    9   40   41   42                                             
CONECT   11    9                                                            
CONECT   12    7   13   43   44                                             
CONECT   13   14   12   15   45                                             
CONECT   14   13   46   47   48                                             
CONECT   15   24   26   16   13                                             
CONECT   16   17   15   49   50                                             
CONECT   17   16   23   18   51                                             
CONECT   18   17   22   19                                                  
CONECT   19   20   18   52                                                  
CONECT   20   21   19   53                                                  
CONECT   21   22   20                                                       
CONECT   22   18   21   54                                                  
CONECT   23   24   17                                                       
CONECT   24   15   23   25   55                                             
CONECT   25   24   56                                                       
CONECT   26    6   27   15   57                                             
CONECT   27   28   26   58   59                                             
CONECT   28   29   27   60   61                                             
CONECT   29   28   31   30   62                                             
CONECT   30   29   63                                                       
CONECT   31   29    6   32   33                                             
CONECT   32   31   33   64   65                                             
CONECT   33   32   31                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    7                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   22                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   32                                                            
CONECT   65   32                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  138    0
END

RDKit          3D

65 69  0  0  0  0  0  0  0  0999 V2000
   -4.1927    0.1802   -3.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    1.2641   -2.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4676    2.4588   -2.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210    0.7121   -2.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069    1.6609   -2.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3696    0.9878   -1.7416 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2187    2.0236   -0.9304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1865    3.3093   -1.5867 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254    4.0512   -1.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1236    5.3378   -2.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    3.7254   -0.9919 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7118    2.2326    0.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526    0.9299    1.3022 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2357    1.2572    2.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670   -0.2205    0.6015 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1067   -1.5349    1.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2366   -1.9566    1.9817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1363   -2.5314    3.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -3.8333    3.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7589   -3.9164    5.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387   -2.7576    5.5944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4677   -1.9259    4.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0561   -0.7814    1.9383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7033   -0.1074    0.7374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1710    1.2133    0.8083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -0.3577   -0.8942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3015   -1.5504   -1.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675   -1.7758   -3.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3798   -0.5110   -3.8716 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0657   -0.7926   -5.0917 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558    0.6056   -3.1017 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5179    0.9270   -3.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    1.7177   -3.9304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460    0.6294   -3.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142   -0.4108   -3.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3590   -0.4540   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    2.3562   -2.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783    2.2465   -1.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    1.6536   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154    5.9089   -1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0412    5.9311   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8964    5.1302   -3.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3930    2.9325    1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2499    2.7551    0.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6927    0.5746    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645    1.6947    2.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9295    1.9848    3.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    0.3763    3.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8522   -1.3822    2.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5307   -2.3457    0.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081   -2.6985    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3287   -4.6149    3.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5278   -4.6882    5.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604   -0.9504    4.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2348   -0.6075   -0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1031    1.1334    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874   -0.6479   -0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -2.4829   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -1.4232   -1.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1434   -2.5811   -3.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957   -2.1295   -2.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -0.2303   -4.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234    0.0599   -5.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749    1.3891   -2.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627    0.2936   -4.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 24  1  0
 28 29  1  0
 24 23  1  0
  9 10  1  0
 16 17  1  0
 17 23  1  0
 26  6  1  0
 17 18  1  0
 18 22  2  0
  9 11  2  0
 28 27  1  0
 29 31  1  0
 22 21  1  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 31  6  1  0
 31 32  1  0
 32 33  1  0
 26 27  1  0
 13 14  1  0
 26 15  1  0
 26 57  1  1
 31 33  1  6
  5  4  1  0
  6  7  1  0
  4  2  1  0
  6  5  1  6
  2  3  2  0
  7 12  1  0
  2  1  1  0
 29 30  1  0
 24 25  1  0
 12 13  1  0
  7  8  1  0
  8  9  1  0
 15 16  1  1
 17 51  1  6
 13 15  1  0
 24 55  1  6
 10 40  1  0
 10 41  1  0
 10 42  1  0
  7 39  1  1
 12 43  1  0
 12 44  1  0
 13 45  1  1
 28 60  1  0
 28 61  1  0
 29 62  1  6
 27 58  1  0
 27 59  1  0
  5 37  1  0
  5 38  1  0
 30 63  1  0
 16 49  1  0
 16 50  1  0
 22 54  1  0
 20 53  1  0
 19 52  1  0
 32 64  1  0
 32 65  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 25 56  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(2R,3R,5S,2'r,5'r,8'Abeta)-5-(3-furyl)-2'a-methyl-4'aalpha-(acetoxymethyl)-4,5-dihydrodispiro[furan-3(2H),1'-decalin-5',2''-oxirane]-2,4'a,6'b-triol 4'-acetate	Generator
(2R,3R,5S,2'r,5'r,8'Abeta)-5-(3-furyl)-2'a-methyl-4'aalpha-(acetoxymethyl)-4,5-dihydrodispiro[furan-3(2H),1'-decalin-5',2''-oxirane]-2,4'a,6'b-triol 4'-acetic acid	Generator
(2R,3R,5S,2'r,5'r,8'Abeta)-5-(3-furyl)-2'alpha-methyl-4'aalpha-(acetoxymethyl)-4,5-dihydrodispiro[furan-3(2H),1'-decalin-5',2''-oxirane]-2,4'alpha,6'beta-triol 4'-acetic acid	Generator
(2R,3R,5S,2'r,5'r,8'Abeta)-5-(3-furyl)-2'α-methyl-4'aalpha-(acetoxymethyl)-4,5-dihydrodispiro[furan-3(2H),1'-decalin-5',2''-oxirane]-2,4'α,6'β-triol 4'-acetate	Generator
(2R,3R,5S,2'r,5'r,8'Abeta)-5-(3-furyl)-2'α-methyl-4'aalpha-(acetoxymethyl)-4,5-dihydrodispiro[furan-3(2H),1'-decalin-5',2''-oxirane]-2,4'α,6'β-triol 4'-acetic acid	Generator
[(2R,2's,2''R,4'as,5'r,5''s,6'r,8's,8'ar)-8'-(acetyloxy)-5''-(furan-3-yl)-2',2''-dihydroxy-6'-methyl-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₉

Average Mass

464.5110 Da

Monoisotopic Mass

464.20463 Da

IUPAC Name

[(2R,2'S,2''R,4'aS,5'R,5''S,6'R,8'S,8'aR)-8'-(acetyloxy)-5''-(furan-3-yl)-2',2''-dihydroxy-6'-methyl-octahydrodispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-yl]methyl acetate

Traditional Name

(2R,2'S,2''R,4'aS,5'R,5''S,6'R,8'S,8'aR)-8'-(acetyloxy)-5''-(furan-3-yl)-2',2''-dihydroxy-6'-methyl-hexahydro-2'H-dispiro[oxirane-2,1'-naphthalene-5',3''-oxolane]-8'a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])O[C@]([H])(C2=C([H])OC([H])=C2[H])C([H])([H])[C@]11[C@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]21OC1([H])[H]

InChI Identifier

InChI=1S/C24H32O9/c1-13-8-20(32-15(3)26)23(11-30-14(2)25)18(4-5-19(27)24(23)12-31-24)22(13)9-17(33-21(22)28)16-6-7-29-10-16/h6-7,10,13,17-21,27-28H,4-5,8-9,11-12H2,1-3H3/t13-,17+,18-,19+,20+,21-,22-,23+,24-/m1/s1

InChI Key

QGKJGQDHZIBMKX-QAIOPYPPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Teucrium montbretii	LOTUS Database	35616633
Teucrium montbretii subsp. libanoticum	JEOL database	Bruno, M., et al, J. Nat. Prod. 65, 142 (2002)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.54	ALOGPS
logP	0.75	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.92	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.91 m³·mol⁻¹	ChemAxon
Polarizability	47.67 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	Yes	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

9937059

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11762362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bruno, M., et al. (2002). Bruno, M., et al, J. Nat. Prod. 65, 142 (2002). J. Nat. Prod..

Showing NP-Card for 20-epi-3,20-di-O-deacetylteupyreinidin (NP0024167)

MOL for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

3D MOL for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

3D SDF for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

3D-SDF for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

PDB for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

3D PDB for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

SMILES for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

INCHI for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

Structure for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)

3D Structure for NP0024167 (20-epi-3,20-di-O-deacetylteupyreinidin)