NP-MRD: Showing NP-Card for Lobarin (NP0011152)

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Record Information

Version

2.0

Created at

2021-01-05 20:56:35 UTC

Updated at

2021-07-15 17:08:06 UTC

NP-MRD ID

NP0011152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lobarin

Provided By

NPAtlas

Description

Lobarin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Lobarin is found in Stereocaulon. Lobarin was first documented in 2012 (PMID: 23041521). Based on a literature review very few articles have been published on lobarin (PMID: 29878768).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107443D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242107443D          

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    3.7426    1.5894   -2.6333 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2956    1.3023   -2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0156    1.0555   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401    1.3097   -1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633    2.7315   -0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168   -2.7355   -0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -5.5567   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058   -4.5226   -0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8531    1.6893    0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    2.5141   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9823   -0.5490    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0360    1.6446    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1691   -0.1436    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5869    1.8465    2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -1.5727    3.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056   -0.0029    4.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2212    1.6611    5.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
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 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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  7 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
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 31  6  1  0  0  0  0
 16  9  1  0  0  0  0
 20 15  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
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  3 40  1  0  0  0  0
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 27 61  1  0  0  0  0
 28 62  1  0  0  0  0
 30 63  1  0  0  0  0
 34 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[H])C([H])=C(O[H])C(OC2=C([H])C(OC([H])([H])[H])=C([H])C3=C2C(=O)O[C@@]3(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=C1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O9/c1-4-6-8-9-15-20(23(28)29)17(26)13-18(27)22(15)33-19-12-14(32-3)11-16-21(19)24(30)34-25(16,31)10-7-5-2/h11-13,26-27,31H,4-10H2,1-3H3,(H,28,29)/t25-/m0/s1

> <INCHI_KEY>
BWRBGHBJBQFFAW-UHFFFAOYSA-N

> <FORMULA>
C25H30O9

> <MOLECULAR_WEIGHT>
474.506

> <EXACT_MASS>
474.188982546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.35265969321026

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(1S)-1-butyl-1-hydroxy-6-methoxy-3-oxo-1,3-dihydro-2-benzofuran-4-yl]oxy}-4,6-dihydroxy-2-pentylbenzoic acid

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
6.272563554666667

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.816595423538661

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7125030612300143

> <JCHEM_PKA_STRONGEST_BASIC>
-3.742904589696949

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
123.72759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1S)-1-butyl-1-hydroxy-6-methoxy-3-oxo-2-benzofuran-4-yl]oxy}-4,6-dihydroxy-2-pentylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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    1.8380   -5.5567   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7579    0.5828    2.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2212    1.6611    5.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    4.2419    3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
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  9 10  2  0
 10 11  1  0
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 11 14  2  0
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 17 19  1  0
 19 20  1  0
 20 21  1  6
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 23 24  1  0
 24 25  1  0
  7 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 31  6  1  0
 16  9  1  0
 20 15  1  0
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  1 36  1  0
  1 37  1  0
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  3 40  1  0
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 25 60  1  0
 27 61  1  0
 28 62  1  0
 30 63  1  0
 34 64  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.643  -2.772  -2.095  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.035  -1.302  -2.006  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.833  -0.590  -1.389  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.075   0.873  -1.242  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.936   1.662  -0.660  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.529   1.232   0.705  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.625   0.192   0.860  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.019  -0.394  -0.180  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.261  -0.582  -0.596  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.601  -1.944  -0.814  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.869  -2.206  -1.234  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.244  -3.533  -1.461  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.326  -4.590  -1.260  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.797  -1.212  -1.442  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.482   0.136  -1.231  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.194   0.412  -0.806  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.128   1.884  -0.701  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.114   2.531  -0.335  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.353   2.386  -1.069  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.282   1.356  -1.338  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.743   1.589  -2.633  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.363   1.518  -0.310  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.403   0.466  -0.266  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.470   0.726   0.777  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.917   0.807   2.172  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.352  -0.230   2.166  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.452  -1.273   2.380  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.935   0.344   3.263  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.821   1.370   3.063  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.435   1.980   4.165  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.142   1.841   1.785  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.109   2.926   1.681  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.463   3.414   0.602  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.653   3.427   2.883  0.00  0.00           O+0
HETATM   35  H   UNK     0      -3.542  -2.839  -2.232  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.205  -3.285  -2.884  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.837  -3.194  -1.067  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.221  -0.879  -3.022  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.912  -1.196  -1.337  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.972  -0.782  -2.051  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.608  -1.084  -0.407  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.296   1.302  -2.259  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.016   1.056  -0.669  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.040   1.310  -1.312  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.963   2.732  -0.781  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.117  -2.736  -0.653  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.838  -5.557  -1.280  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.806  -4.523  -0.276  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.541  -4.596  -2.025  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.805  -1.422  -1.794  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.408   0.946  -3.285  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.853   1.689   0.666  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.846   2.514  -0.539  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.982  -0.549   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.912   0.339  -1.235  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.036   1.645   0.578  0.00  0.00           H+0
HETATM   57  H   UNK     0       7.169  -0.144   0.746  0.00  0.00           H+0
HETATM   58  H   UNK     0       5.135   0.051   2.373  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.758   0.583   2.866  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.587   1.847   2.447  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.259  -1.573   3.317  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.706  -0.003   4.271  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.221   1.661   5.079  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.250   4.242   3.335  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3   38   39                                             
CONECT    3    2    4   40   41                                             
CONECT    4    3    5   42   43                                             
CONECT    5    4    6   44   45                                             
CONECT    6    5    7   31                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   46                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12   47   48   49                                             
CONECT   14   11   15   50                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17    9                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   15                                             
CONECT   21   20   51                                                       
CONECT   22   20   23   52   53                                             
CONECT   23   22   24   54   55                                             
CONECT   24   23   25   56   57                                             
CONECT   25   24   58   59   60                                             
CONECT   26    7   27   28                                                  
CONECT   27   26   61                                                       
CONECT   28   26   29   62                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   63                                                       
CONECT   31   29   32    6                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   64                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    2                                                            
CONECT   39    2                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    5                                                            
CONECT   46   10                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
CONECT   62   28                                                            
CONECT   63   30                                                            
CONECT   64   34                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
   -4.6429   -2.7724   -2.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0353   -1.3016   -2.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8326   -0.5899   -1.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0749    0.8729   -1.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360    1.6619   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5293    1.2315    0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6250    0.1917    0.8603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -0.3935   -0.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2610   -0.5819   -0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011   -1.9436   -0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8691   -2.2064   -1.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -3.5331   -1.4613 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264   -4.5903   -1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965   -1.2121   -1.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4816    0.1359   -1.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935    0.4119   -0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282    1.8839   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1136    2.5308   -0.3348 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532    2.3858   -1.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818    1.3556   -1.3376 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7426    1.5894   -2.6333 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    1.5184   -0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4032    0.4662   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4697    0.7262    0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9168    0.8072    2.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3519   -0.2295    2.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4524   -1.2733    2.3796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9353    0.3439    3.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8207    1.3697    3.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4350    1.9801    4.1648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1423    1.8407    1.7846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1088    2.9260    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4634    3.4145    0.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6527    3.4273    2.8828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5415   -2.8386   -2.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2051   -3.2847   -2.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8367   -3.1937   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2213   -0.8789   -3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9119   -1.1960   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9718   -0.7823   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6081   -1.0837   -0.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2956    1.3023   -2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0156    1.0555   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0401    1.3097   -1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633    2.7315   -0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168   -2.7355   -0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -5.5567   -1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058   -4.5226   -0.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5410   -4.5957   -2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055   -1.4221   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4079    0.9458   -3.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8531    1.6893    0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8455    2.5141   -0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9823   -0.5490    0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9124    0.3393   -1.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0360    1.6446    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1691   -0.1436    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    0.0505    2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7579    0.5828    2.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5869    1.8465    2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -1.5727    3.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056   -0.0029    4.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2212    1.6611    5.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    4.2419    3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  7 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 31  6  1  0
 16  9  1  0
 20 15  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
 10 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 27 61  1  0
 28 62  1  0
 30 63  1  0
 34 64  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Lobariol carboxylic acid	ChEBI
Lobariol carboxylate	Generator

Chemical Formula

C₂₅H₃₀O₉

Average Mass

474.5060 Da

Monoisotopic Mass

474.18898 Da

IUPAC Name

3-{[(1S)-1-butyl-1-hydroxy-6-methoxy-3-oxo-1,3-dihydro-2-benzofuran-4-yl]oxy}-4,6-dihydroxy-2-pentylbenzoic acid

Traditional Name

3-{[(1S)-1-butyl-1-hydroxy-6-methoxy-3-oxo-2-benzofuran-4-yl]oxy}-4,6-dihydroxy-2-pentylbenzoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=C(C(O)=O)C(O)=CC(O)=C1OC1=C2C(=O)OC(O)(CCCC)C2=CC(OC)=C1

InChI Identifier

InChI=1S/C25H30O9/c1-4-6-8-9-15-20(23(28)29)17(26)13-18(27)22(15)33-19-12-14(32-3)11-16-21(19)24(30)34-25(16,31)10-7-5-2/h11-13,26-27,31H,4-10H2,1-3H3,(H,28,29)

InChI Key

BWRBGHBJBQFFAW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Stereocaulon	NPAtlas	23041521

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	3.92	ALOGPS
logP	6.27	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	123.73 m³·mol⁻¹	ChemAxon
Polarizability	49.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA011414

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

76962531

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56960992

PDB ID

Not Available

ChEBI ID

144069

Good Scents ID

Not Available

References

General References

Ismed F, Lohezic-Le Devehat F, Delalande O, Sinbandhit S, Bakhtiar A, Boustie J: Lobarin from the Sumatran lichen, Stereocaulon halei. Fitoterapia. 2012 Dec;83(8):1693-8. doi: 10.1016/j.fitote.2012.09.025. Epub 2012 Oct 4. [PubMed:23041521 ]
Kim TK, Kim JE, Youn UJ, Han SJ, Kim IC, Cho CG, Yim JH: Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum. J Nat Prod. 2018 Jun 22;81(6):1460-1467. doi: 10.1021/acs.jnatprod.8b00227. Epub 2018 Jun 7. [PubMed:29878768 ]

Showing NP-Card for Lobarin (NP0011152)

MOL for NP0011152 (Lobarin)

3D MOL for NP0011152 (Lobarin)

3D SDF for NP0011152 (Lobarin)

3D-SDF for NP0011152 (Lobarin)

PDB for NP0011152 (Lobarin)

3D PDB for NP0011152 (Lobarin)

SMILES for NP0011152 (Lobarin)

INCHI for NP0011152 (Lobarin)

Structure for NP0011152 (Lobarin)

3D Structure for NP0011152 (Lobarin)