NP-MRD: Showing NP-Card for Butyrolactone VI (NP0009546)

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Record Information

Version

2.0

Created at

2021-01-05 19:08:02 UTC

Updated at

2021-07-15 17:03:34 UTC

NP-MRD ID

NP0009546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Butyrolactone VI

Provided By

NPAtlas

Description

Methyl (2R)-2-{[3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxyphenyl]methyl}-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Butyrolactone VI is found in Aspergillus. Butyrolactone VI was first documented in 2016 (PMID: 26299734). Based on a literature review very few articles have been published on methyl (2R)-2-{[3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxyphenyl]methyl}-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate (PMID: 27604497) (PMID: 27658145).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106363D          

 59 61  0  0  0  0            999 V2000
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  5 21  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242106363D          

 59 61  0  0  0  0            999 V2000
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   -4.4313    1.6351   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0188    2.8531    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4818    2.9789    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0620    4.1974    1.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713    1.9479    2.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7902    0.7782    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3081   -1.8612   -4.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570   -0.3560   -4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -0.3934   -3.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    0.4087    1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687   -1.1522    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800   -3.0666    1.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9253   -3.9672    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866   -3.6757    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084    0.6283   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -0.7968   -1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7097   -0.4949    1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9946    3.4050   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8864    1.9542    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3606    2.4413    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6215   -0.1184   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449    1.4725   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320    0.6708   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042    3.3103   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    0.4986   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8953   -2.4137    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    1.5038   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0848    3.6374   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0531    4.3801    1.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368    2.0681    3.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6867   -0.0630    2.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  6  0  0  0
 12 20  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26  5  1  0  0  0  0
 33 27  1  0  0  0  0
 20  7  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  0  0  0  0
 11 41  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 14 44  1  1  0  0  0
 15 45  1  0  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 19 52  1  0  0  0  0
 20 53  1  0  0  0  0
 25 54  1  0  0  0  0
 28 55  1  0  0  0  0
 29 56  1  0  0  0  0
 31 57  1  0  0  0  0
 32 58  1  0  0  0  0
 33 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C2=C([H])C([H])=C(O[H])C([H])=C2[H])[C@@](OC1=O)(C(=O)OC([H])([H])[H])C([H])([H])C1=C([H])C([H])=C(O[H])C(=C1[H])C([H])([H])[C@@]([H])(O[H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O9/c1-23(2,31)18(27)11-15-10-13(4-9-17(15)26)12-24(22(30)32-3)19(20(28)21(29)33-24)14-5-7-16(25)8-6-14/h4-10,18,25-28,31H,11-12H2,1-3H3/t18-,24-/m1/s1

> <INCHI_KEY>
JICCDSOXRQWNCM-VCUSLETLSA-N

> <FORMULA>
C24H26O9

> <MOLECULAR_WEIGHT>
458.463

> <EXACT_MASS>
458.157682417

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.792708285190635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-2-({3-[(2R)-2,3-dihydroxy-3-methylbutyl]-4-hydroxyphenyl}methyl)-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.4397799360000003

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.412043128725395

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.470423584693462

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0940529950743114

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
118.07529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-2-({3-[(2R)-2,3-dihydroxy-3-methylbutyl]-4-hydroxyphenyl}methyl)-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
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    5.0062   -0.3786    0.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0351    0.8452   -1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9962   -0.4980    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -2.4515   -0.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4995   -2.9801    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7705   -4.1975    0.4325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3298   -1.8403    0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6611   -1.9683    1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6492   -0.6889    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2905    0.5730    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4313    1.6351   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0188    2.8531    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4818    2.9789    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0620    4.1974    1.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713    1.9479    2.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7902    0.7782    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2570   -0.3560   -4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2800   -3.0666    1.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9253   -3.9672    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866   -3.6757    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084    0.6283   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -0.7968   -1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    1.1561    0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7097   -0.4949    1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9946    3.4050   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8864    1.9542    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3606    2.4413    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6215   -0.1184   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449    1.4725   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320    0.6708   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042    3.3103   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    0.4986   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8953   -2.4137    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    1.5038   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0848    3.6374   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0531    4.3801    1.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368    2.0681    3.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6867   -0.0630    2.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  6
 12 20  2  0
  5 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 26  5  1  0
 33 27  1  0
 20  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  6 37  1  0
  6 38  1  0
  8 39  1  0
  9 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  1
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 25 54  1  0
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 33 59  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      -1.410  -0.955  -3.636  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.782  -1.435  -2.352  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.931  -0.520  -1.279  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.711   0.664  -1.589  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.316  -1.025   0.054  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.251  -0.672   1.089  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.076  -1.243   0.762  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.426  -2.493   1.204  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.676  -2.980   0.896  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.575  -2.228   0.152  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.826  -2.752  -0.138  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.249  -0.963  -0.308  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.213  -0.129  -1.095  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.242   0.504  -0.185  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.006  -0.379   0.525  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.097   1.490  -0.955  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.872   2.393  -0.008  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.035   0.845  -1.926  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.259   2.361  -1.686  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.996  -0.498   0.012  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.290  -2.451  -0.011  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.499  -2.980   0.382  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.771  -4.197   0.433  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.330  -1.840   0.702  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.661  -1.968   1.147  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.649  -0.689   0.513  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.290   0.573   0.832  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.431   1.635  -0.017  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.019   2.853   0.343  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.482   2.979   1.635  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.062   4.197   1.970  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.371   1.948   2.535  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.790   0.778   2.139  0.00  0.00           C+0
HETATM   34  H   UNK     0      -1.308  -1.861  -4.291  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.257  -0.356  -4.002  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.459  -0.393  -3.625  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.192   0.409   1.285  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.569  -1.152   2.038  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.280  -3.067   1.784  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.925  -3.967   1.259  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.087  -3.676   0.191  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.708   0.628  -1.718  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.772  -0.797  -1.800  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.633   1.156   0.518  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.710  -0.495   1.461  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.995   3.405  -0.436  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.886   1.954   0.126  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.361   2.441   0.994  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.622  -0.118  -2.298  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.245   1.472  -2.815  0.00  0.00           H+0
HETATM   51  H   UNK     0       7.032   0.671  -1.431  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.404   3.310  -1.466  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.721   0.499  -0.341  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.895  -2.414   2.023  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.081   1.504  -1.051  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.085   3.637  -0.399  0.00  0.00           H+0
HETATM   57  H   UNK     0      -7.053   4.380   1.858  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.737   2.068   3.532  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.687  -0.063   2.835  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   21   26                                             
CONECT    6    5    7   37   38                                             
CONECT    7    6    8   20                                                  
CONECT    8    7    9   39                                                  
CONECT    9    8   10   40                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   41                                                       
CONECT   12   10   13   20                                                  
CONECT   13   12   14   42   43                                             
CONECT   14   13   15   16   44                                             
CONECT   15   14   45                                                       
CONECT   16   14   17   18   19                                             
CONECT   17   16   46   47   48                                             
CONECT   18   16   49   50   51                                             
CONECT   19   16   52                                                       
CONECT   20   12    7   53                                                  
CONECT   21    5   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24   54                                                       
CONECT   26   24   27    5                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29   55                                                  
CONECT   29   28   30   56                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   57                                                       
CONECT   32   30   33   58                                                  
CONECT   33   32   27   59                                                  
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   11                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   25                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   31                                                            
CONECT   58   32                                                            
CONECT   59   33                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
   -1.4100   -0.9550   -3.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816   -1.4347   -2.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308   -0.5199   -1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    0.6637   -1.5889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3161   -1.0250    0.0542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2513   -0.6723    1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -1.2426    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -2.4928    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763   -2.9800    0.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5755   -2.2281    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8261   -2.7517   -0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2490   -0.9634   -0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2134   -0.1290   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2418    0.5043   -0.1849 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0062   -0.3786    0.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0966    1.4902   -0.9548 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8722    2.3934   -0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0351    0.8452   -1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2591    2.3615   -1.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9962   -0.4980    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -2.4515   -0.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4995   -2.9801    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7705   -4.1975    0.4325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3298   -1.8403    0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6611   -1.9683    1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6492   -0.6889    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2905    0.5730    0.8317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4313    1.6351   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0188    2.8531    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4818    2.9789    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0620    4.1974    1.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713    1.9479    2.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7902    0.7782    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3081   -1.8612   -4.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570   -0.3560   -4.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4593   -0.3934   -3.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916    0.4087    1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687   -1.1522    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2800   -3.0666    1.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9253   -3.9672    1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866   -3.6757    0.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084    0.6283   -1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -0.7968   -1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331    1.1561    0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7097   -0.4949    1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9946    3.4050   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8864    1.9542    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3606    2.4413    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6215   -0.1184   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449    1.4725   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0320    0.6708   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042    3.3103   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    0.4986   -0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8953   -2.4137    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0812    1.5038   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0848    3.6374   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0531    4.3801    1.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7368    2.0681    3.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6867   -0.0630    2.8354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  6
 12 20  2  0
  5 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
 26  5  1  0
 33 27  1  0
 20  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  6 37  1  0
  6 38  1  0
  8 39  1  0
  9 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  1
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 25 54  1  0
 28 55  1  0
 29 56  1  0
 31 57  1  0
 32 58  1  0
 33 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (2R)-2-{[3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxyphenyl]methyl}-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylic acid	Generator

Chemical Formula

C₂₄H₂₆O₉

Average Mass

458.4630 Da

Monoisotopic Mass

458.15768 Da

IUPAC Name

methyl (2R)-2-({3-[(2R)-2,3-dihydroxy-3-methylbutyl]-4-hydroxyphenyl}methyl)-4-hydroxy-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl (2R)-2-({3-[(2R)-2,3-dihydroxy-3-methylbutyl]-4-hydroxyphenyl}methyl)-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(CC2=CC(CC(O)C(C)(C)O)=C(O)C=C2)OC(=O)C(O)=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H26O9/c1-23(2,31)18(27)11-15-10-13(4-9-17(15)26)12-24(22(30)32-3)19(20(28)21(29)33-24)14-5-7-16(25)8-6-14/h4-10,18,25-28,31H,11-12H2,1-3H3/t18?,24-/m1/s1

InChI Key

JICCDSOXRQWNCM-VCUSLETLSA-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
Aspergillus	NPAtlas	21048353

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Monocyclic benzene moiety
2-furanone
Dicarboxylic acid or derivatives
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Dihydrofuran
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Enol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.11	ALOGPS
logP	2.44	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	118.08 m³·mol⁻¹	ChemAxon
Polarizability	46.79 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	Yes	ChemAxon

External Links

NPAtlas ID

NPA004543

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436772

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49800901

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Elkhayat ES, Ibrahim SR, Mohamed GA, Ross SA: Terrenolide S, a new antileishmanial butenolide from the endophytic fungus Aspergillus terreus. Nat Prod Res. 2016;30(7):814-20. doi: 10.1080/14786419.2015.1072711. Epub 2015 Aug 24. [PubMed:26299734 ]
An X, Feng BM, Chen G, Chen SF, Bai J, Hua HM, Wang HF, Pei YH: Isolation and identification of phase I metabolites of butyrolactone I in rats. Xenobiotica. 2017 Mar;47(3):236-244. doi: 10.3109/00498254.2016.1172280. Epub 2016 Sep 8. [PubMed:27604497 ]
Ibrahim SRM, Mohamed GA, Ross SA: Aspernolides L and M, new butyrolactones from the endophytic fungus Aspergillus versicolor. Z Naturforsch C J Biosci. 2017 May 1;72(5-6):155-160. doi: 10.1515/znc-2016-0138. [PubMed:27658145 ]

Showing NP-Card for Butyrolactone VI (NP0009546)

MOL for NP0009546 (Butyrolactone VI)

3D MOL for NP0009546 (Butyrolactone VI)

3D SDF for NP0009546 (Butyrolactone VI)

3D-SDF for NP0009546 (Butyrolactone VI)

PDB for NP0009546 (Butyrolactone VI)

3D PDB for NP0009546 (Butyrolactone VI)

SMILES for NP0009546 (Butyrolactone VI)

INCHI for NP0009546 (Butyrolactone VI)

Structure for NP0009546 (Butyrolactone VI)

3D Structure for NP0009546 (Butyrolactone VI)