NP-MRD: Showing NP-Card for Butylrolactone IV (NP0003238)

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Record Information

Version

1.0

Created at

2020-12-09 00:32:13 UTC

Updated at

2021-07-15 16:45:52 UTC

NP-MRD ID

NP0003238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Butylrolactone IV

Provided By

NPAtlas

Description

Butylrolactone IV is found in Aspergillus terreus. It was first documented in 2000 (PMID: 10783079). Based on a literature review very few articles have been published on methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-{[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-2,5-dihydrofuran-2-carboxylate (PMID: 34380192) (PMID: 34380191) (PMID: 34380190) (PMID: 34380189).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 56 59  0  0  0  0            999 V2000
    0.3676    3.2018   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8915    2.4592   -0.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4886    0.7201   -1.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5414   -0.6190    2.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  7  8  2  0  0  0  0
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M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117463D          

 56 59  0  0  0  0            999 V2000
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    1.4602    1.1855   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8074    2.9413   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    3.0864   -1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7820   -1.4889    1.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086   -1.4900   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1797   -0.6743    3.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -0.3166    3.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -0.7869   -0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6959    0.6477   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5607   -1.0890   -1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018   -1.7542    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9844    1.9224    0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2360    1.7236   -1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7123    1.9869    0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7163   -0.5983   -1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3428   -0.1061   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3283   -1.7335   -1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6666   -1.1272    1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8766    1.4503    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1246   -1.6043    1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8276   -2.8769    0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2204   -2.1956   -2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523   -0.7639   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.4937   -1.8234 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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  1  0  0  0
 14 19  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 25  5  1  0  0  0  0
 32 26  1  0  0  0  0
 12  7  1  0  0  0  0
 19 10  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
  8 38  1  0  0  0  0
  9 39  1  0  0  0  0
 12 40  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 14 43  1  1  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 18 50  1  0  0  0  0
 24 51  1  0  0  0  0
 27 52  1  0  0  0  0
 28 53  1  0  0  0  0
 30 54  1  0  0  0  0
 31 55  1  0  0  0  0
 32 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003238

> <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])=C2O[C@]([H])(C([H])([H])C2=C1[H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O8/c1-23(2,29)18-11-15-10-13(4-9-17(15)31-18)12-24(22(28)30-3)19(20(26)21(27)32-24)14-5-7-16(25)8-6-14/h4-10,18,25-26,29H,11-12H2,1-3H3/t18-,24-/m1/s1

> <INCHI_KEY>
NVAIFFOQCAKMAH-HOYKHHGWSA-N

> <FORMULA>
C24H24O8

> <MOLECULAR_WEIGHT>
440.448

> <EXACT_MASS>
440.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.69870799911577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-{[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-2,5-dihydrofuran-2-carboxylate

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.104251060666667

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.739370709306751

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.50716144072115

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106376113520443

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
114.29629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-{[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxofuran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    0.3676    3.2018   -1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8915    2.4592   -0.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4602    1.1855   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886    0.7201   -1.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    0.4023    0.8403 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3289   -0.9801    0.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077   -0.7529    1.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414   -0.6190    2.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -0.4184    2.6315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8228   -0.3420    1.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050   -0.4728    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0464   -0.6772    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5971   -0.3569   -0.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7300   -0.6600    0.4083 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0224   -0.0126    0.0367 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9437    1.4584   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6134   -0.6652   -1.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9239   -0.2791    1.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2195   -0.1462    1.6286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6686    1.1337    1.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    1.4374    2.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8322    2.0931    3.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.8732    1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433    0.9460    2.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4600    0.2580    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4184   -0.4655    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2471   -1.4252    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1821   -2.1223   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3491   -1.9021   -1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2895   -2.5948   -2.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484   -0.9643   -2.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5842   -0.2453   -1.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5487    4.2866   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8074    2.9413   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    3.0864   -1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7820   -1.4889    1.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086   -1.4900   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1797   -0.6743    3.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -0.3166    3.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -0.7869   -0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6959    0.6477   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5607   -1.0890   -1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018   -1.7542    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9844    1.9224    0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2360    1.7236   -1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7123    1.9869    0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7163   -0.5983   -1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3428   -0.1061   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3283   -1.7335   -1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6666   -1.1272    1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8766    1.4503    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1246   -1.6043    1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8276   -2.8769    0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2204   -2.1956   -2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523   -0.7639   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.4937   -1.8234 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
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  1
 14 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 25  5  1  0
 32 26  1  0
 12  7  1  0
 19 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  1
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  0
 24 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
 32 56  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       0.368   3.202  -1.230  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.892   2.459  -0.144  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.460   1.186  -0.292  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.489   0.720  -1.440  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.010   0.402   0.840  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.329  -0.980   0.894  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.108  -0.753   1.083  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.541  -0.619   2.409  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.883  -0.418   2.632  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.823  -0.342   1.628  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.405  -0.473   0.323  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.046  -0.677   0.072  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.597  -0.357  -0.550  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.730  -0.660   0.408  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.022  -0.013   0.037  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.944   1.458  -0.205  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.613  -0.665  -1.194  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.924  -0.279   1.093  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.220  -0.146   1.629  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.669   1.134   1.990  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.768   1.437   2.710  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.832   2.093   3.812  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.890   0.873   1.992  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.243   0.946   2.379  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.460   0.258   0.886  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.418  -0.466   0.013  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.247  -1.425   0.595  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.182  -2.122  -0.110  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.349  -1.902  -1.453  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.290  -2.595  -2.197  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.548  -0.964  -2.050  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.584  -0.245  -1.320  0.00  0.00           C+0
HETATM   33  H   UNK     0       0.549   4.287  -0.972  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.807   2.941  -2.198  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.744   3.086  -1.214  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.782  -1.489   1.760  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.609  -1.490  -0.026  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.180  -0.674   3.238  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.197  -0.317   3.674  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.711  -0.787  -0.956  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.696   0.648  -1.016  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.561  -1.089  -1.385  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.902  -1.754   0.459  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.984   1.922   0.019  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.236   1.724  -1.257  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.712   1.987   0.431  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.716  -0.598  -1.107  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.343  -0.106  -2.120  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.328  -1.734  -1.276  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.667  -1.127   1.561  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.877   1.450   1.773  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.125  -1.604   1.643  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.828  -2.877   0.369  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.220  -2.196  -2.271  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.652  -0.764  -3.110  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.998   0.494  -1.823  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   20   25                                             
CONECT    6    5    7   36   37                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9   38                                                  
CONECT    9    8   10   39                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7   40                                                  
CONECT   13   11   14   41   42                                             
CONECT   14   13   15   19   43                                             
CONECT   15   14   16   17   18                                             
CONECT   16   15   44   45   46                                             
CONECT   17   15   47   48   49                                             
CONECT   18   15   50                                                       
CONECT   19   14   10                                                       
CONECT   20    5   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23   51                                                       
CONECT   25   23   26    5                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28   52                                                  
CONECT   28   27   29   53                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   54                                                       
CONECT   31   29   32   55                                                  
CONECT   32   31   26   56                                                  
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    6                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   24                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   30                                                            
CONECT   55   31                                                            
CONECT   56   32                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  118    0
END

RDKit          3D

56 59  0  0  0  0  0  0  0  0999 V2000
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    6.1821   -2.1223   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3491   -1.9021   -1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2895   -2.5948   -2.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484   -0.9643   -2.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5842   -0.2453   -1.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7820   -1.4889    1.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6086   -1.4900   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1797   -0.6743    3.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -0.3166    3.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110   -0.7869   -0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6959    0.6477   -1.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9844    1.9224    0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2360    1.7236   -1.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7123    1.9869    0.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7163   -0.5983   -1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3428   -0.1061   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3283   -1.7335   -1.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6666   -1.1272    1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8766    1.4503    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1246   -1.6043    1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8276   -2.8769    0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2204   -2.1956   -2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523   -0.7639   -3.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9977    0.4937   -1.8234 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
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  6  7  1  0
  7  8  2  0
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  9 10  2  0
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 13 14  1  0
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 15 17  1  0
 15 18  1  1
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  5 20  1  0
 20 21  1  0
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 23 24  1  0
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 25 26  1  0
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 29 31  1  0
 31 32  2  0
 25  5  1  0
 32 26  1  0
 12  7  1  0
 19 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  1
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 16 45  1  0
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 17 47  1  0
 17 48  1  0
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 24 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 31 55  1  0
 32 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-{[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-2,5-dihydrofuran-2-carboxylic acid	Generator

Chemical Formula

C₂₄H₂₄O₈

Average Mass

440.4480 Da

Monoisotopic Mass

440.14712 Da

IUPAC Name

methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-{[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-{[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxofuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(CC2=CC3=C(O[C@H](C3)C(C)(C)O)C=C2)OC(=O)C(O)=C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H24O8/c1-23(2,29)18-11-15-10-13(4-9-17(15)31-18)12-24(22(28)30-3)19(20(26)21(27)32-24)14-5-7-16(25)8-6-14/h4-10,18,25-26,29H,11-12H2,1-3H3/t18-,24-/m1/s1

InChI Key

NVAIFFOQCAKMAH-HOYKHHGWSA-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 terreus	NPAtlas	10783079

Species Where Detected

Species Name	Source	Reference
Aspergillus terreus DRCC 152	KNApSAcK Database	22123792

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	3.1	ALOGPS
logP	3.1	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.3 m³·mol⁻¹	ChemAxon
Polarizability	45.7 Å³	ChemAxon
Number of Rings	4	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

NPA004486

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9918657

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11743953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rao KV, Sadhukhan AK, Veerender M, Ravikumar V, Mohan EV, Dhanvantri SD, Sitaramkumar M, Babu JM, Vyas K, Reddy GO: Butyrolactones from Aspergillus terreus. Chem Pharm Bull (Tokyo). 2000 Apr;48(4):559-62. doi: 10.1248/cpb.48.559. [PubMed:10783079 ]
Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]
Lee Y, Kim SH, Hwang HY, Sohn SH, Choi JW, Kim KH: Perfusion parameters during cardiopulmonary bypass as a predictor of acute kidney injury after aortic valve replacement. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00094. doi: 10.4266/acc.2021.00094. [PubMed:34380189 ]

Showing NP-Card for Butylrolactone IV (NP0003238)

MOL for NP0003238 (Butylrolactone IV)

3D MOL for NP0003238 (Butylrolactone IV)

3D SDF for NP0003238 (Butylrolactone IV)

3D-SDF for NP0003238 (Butylrolactone IV)

PDB for NP0003238 (Butylrolactone IV)

3D PDB for NP0003238 (Butylrolactone IV)

SMILES for NP0003238 (Butylrolactone IV)

INCHI for NP0003238 (Butylrolactone IV)

Structure for NP0003238 (Butylrolactone IV)

3D Structure for NP0003238 (Butylrolactone IV)