NP-MRD: Showing NP-Card for Butyrolactone I (NP0022909)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-01-06 08:03:51 UTC

Updated at

2025-08-01 00:01:41 UTC

NP-MRD ID

NP0022909

Natural Product DOI

https://doi.org/10.57994/4417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Butyrolactone I

Provided By

NPAtlas

Description

Butyrolactone I is found in Aspergillus, Aspergillus flavipes, Aspergillus terreus DRCC 152 and Mallotus nudiflorus. Butyrolactone I was first documented in 1993 (PMID: 8395680). Based on a literature review a small amount of articles have been published on butyrolactone i (PMID: 34459930) (PMID: 34199488) (PMID: 34068647) (PMID: 40684465).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105383D          

 55 57  0  0  0  0            999 V2000
   -3.4828   -2.4651    3.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -2.0192    2.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -2.7549    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -3.8957    0.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.1727    0.0203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1422   -1.9325    0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8544   -1.3689   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -2.2548   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -1.7018   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609   -0.3428   -1.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1719   -2.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.5453   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    1.9850   -1.3097 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4235    2.4743   -0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3610    1.9167    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    2.8392    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5241    0.5052    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.0198   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   -3.0235   -1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6931   -2.4126   -2.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -2.8746   -3.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416   -1.1372   -1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -0.1759   -2.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -0.9775   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    0.1952    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619    0.7083   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5698    1.8035    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    2.4427    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6062    3.5637    1.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8130    1.9595    1.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.8519    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -3.3087    2.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.5692    3.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -2.7451    4.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722   -1.4460    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064   -2.9880    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -3.3238   -0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724   -2.3568   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001   -0.4197   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    2.3351   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416    2.4656   -0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471    3.6070   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1287    3.2513    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6002    3.6190   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    2.2842    0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -0.0234    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232    0.4289    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -0.1024   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    0.7133    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.4279   -3.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4306    0.2185   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    2.1967   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    3.8853    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    2.4493    2.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.5397    1.6545 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  1  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  2  3  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 12 18  2  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 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
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 24  5  1  0  0  0  0
 31 25  1  0  0  0  0
 18  7  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  8 37  1  0  0  0  0
  9 38  1  0  0  0  0
 11 39  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 14 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 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
 23 50  1  0  0  0  0
 26 51  1  0  0  0  0
 27 52  1  0  0  0  0
 29 53  1  0  0  0  0
 30 54  1  0  0  0  0
 31 55  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.4828   -2.4651    3.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -2.0192    2.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -2.7549    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -3.8957    0.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.1727    0.0203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1422   -1.9325    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544   -1.3689   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -2.2548   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -1.7018   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609   -0.3428   -1.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1719   -2.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.5453   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    1.9850   -1.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235    2.4743   -0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3610    1.9167    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    2.8392    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5241    0.5052    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.0198   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   -3.0235   -1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6931   -2.4126   -2.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -2.8746   -3.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416   -1.1372   -1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -0.1759   -2.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -0.9775   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    0.1952    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619    0.7083   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5698    1.8035    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    2.4427    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6062    3.5637    1.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8130    1.9595    1.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.8519    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -3.3087    2.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.5692    3.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -2.7451    4.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722   -1.4460    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064   -2.9880    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -3.3238   -0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724   -2.3568   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001   -0.4197   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    2.3351   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416    2.4656   -0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471    3.6070   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1287    3.2513    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6002    3.6190   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    2.2842    0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -0.0234    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232    0.4289    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -0.1024   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    0.7133    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.4279   -3.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4306    0.2185   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    2.1967   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    3.8853    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    2.4493    2.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.5397    1.6545 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  1
  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  2  3
 15 16  1  0
 15 17  1  0
 12 18  2  0
  5 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 24  5  1  0
 31 25  1  0
 18  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 23 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
M  END


  Mrv1652306242105383D          

 55 57  0  0  0  0            999 V2000
   -3.4828   -2.4651    3.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -2.0192    2.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -2.7549    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -3.8957    0.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.1727    0.0203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1422   -1.9325    0.6756 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8544   -1.3689   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -2.2548   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -1.7018   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609   -0.3428   -1.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1719   -2.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.5453   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    1.9850   -1.3097 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4235    2.4743   -0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3610    1.9167    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    2.8392    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5241    0.5052    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.0198   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   -3.0235   -1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6931   -2.4126   -2.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -2.8746   -3.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416   -1.1372   -1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -0.1759   -2.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -0.9775   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    0.1952    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619    0.7083   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5698    1.8035    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    2.4427    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6062    3.5637    1.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8130    1.9595    1.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.8519    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -3.3087    2.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.5692    3.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -2.7451    4.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722   -1.4460    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064   -2.9880    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -3.3238   -0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724   -2.3568   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001   -0.4197   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    2.3351   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416    2.4656   -0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471    3.6070   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1287    3.2513    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6002    3.6190   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    2.2842    0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -0.0234    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232    0.4289    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -0.1024   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    0.7133    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.4279   -3.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4306    0.2185   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    2.1967   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    3.8853    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    2.4493    2.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.5397    1.6545 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  1  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  2  3  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 12 18  2  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 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
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 24  5  1  0  0  0  0
 31 25  1  0  0  0  0
 18  7  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  8 37  1  0  0  0  0
  9 38  1  0  0  0  0
 11 39  1  0  0  0  0
 13 40  1  0  0  0  0
 13 41  1  0  0  0  0
 14 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 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
 23 50  1  0  0  0  0
 26 51  1  0  0  0  0
 27 52  1  0  0  0  0
 29 53  1  0  0  0  0
 30 54  1  0  0  0  0
 31 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022909

> <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])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m0/s1

> <INCHI_KEY>
NGOLMNWQNHWEKU-DEOSSOPVSA-N

> <FORMULA>
C24H24O7

> <MOLECULAR_WEIGHT>
424.449

> <EXACT_MASS>
424.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.12762542374117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
4.580218746666667

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.241389491595562

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.476985809043944

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2939366654575224

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
115.7277

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.4828   -2.4651    3.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -2.0192    2.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -2.7549    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -3.8957    0.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.1727    0.0203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1422   -1.9325    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544   -1.3689   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -2.2548   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -1.7018   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609   -0.3428   -1.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1719   -2.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.5453   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    1.9850   -1.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235    2.4743   -0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3610    1.9167    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    2.8392    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5241    0.5052    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.0198   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   -3.0235   -1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6931   -2.4126   -2.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -2.8746   -3.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416   -1.1372   -1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -0.1759   -2.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -0.9775   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    0.1952    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619    0.7083   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5698    1.8035    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    2.4427    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6062    3.5637    1.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8130    1.9595    1.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.8519    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -3.3087    2.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.5692    3.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -2.7451    4.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722   -1.4460    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064   -2.9880    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -3.3238   -0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724   -2.3568   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001   -0.4197   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    2.3351   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416    2.4656   -0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471    3.6070   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1287    3.2513    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6002    3.6190   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    2.2842    0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -0.0234    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232    0.4289    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -0.1024   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    0.7133    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.4279   -3.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4306    0.2185   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    2.1967   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    3.8853    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    2.4493    2.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.5397    1.6545 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  1
  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  2  3
 15 16  1  0
 15 17  1  0
 12 18  2  0
  5 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 24  5  1  0
 31 25  1  0
 18  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 23 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  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      -3.483  -2.465   3.229  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.664  -2.019   2.179  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.379  -2.755   1.050  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.856  -3.896   0.909  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.504  -2.173   0.020  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.142  -1.933   0.676  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.854  -1.369  -0.228  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.616  -2.255  -0.999  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.554  -1.702  -1.836  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.761  -0.343  -1.935  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.723   0.172  -2.797  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.021   0.545  -1.183  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.232   1.985  -1.310  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.424   2.474  -0.646  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.361   1.917   0.064  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.462   2.839   0.583  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.524   0.505   0.452  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.067  -0.020  -0.332  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.283  -3.023  -1.099  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.693  -2.413  -2.259  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.604  -2.875  -3.420  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.242  -1.137  -1.844  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.795  -0.176  -2.714  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.156  -0.978  -0.504  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.745   0.195   0.141  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.962   0.708  -0.340  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.570   1.804   0.228  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.997   2.443   1.304  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.606   3.564   1.897  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.813   1.960   1.789  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.213   0.852   1.202  0.00  0.00           C+0
HETATM   32  H   UNK     0      -4.130  -3.309   2.958  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.104  -1.569   3.527  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.865  -2.745   4.109  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.272  -1.446   1.623  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.206  -2.988   0.917  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.467  -3.324  -0.935  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.172  -2.357  -2.458  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.300  -0.420  -3.376  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.143   2.335  -2.375  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.342   2.466  -0.777  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.547   3.607  -0.793  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.129   3.251   1.535  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.600   3.619  -0.188  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.410   2.284   0.722  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.633  -0.023   0.771  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.223   0.429   1.358  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.072  -0.102  -0.319  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.511   0.713   0.241  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.193   0.428  -3.276  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.431   0.219  -1.173  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.518   2.197  -0.153  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.486   3.885   1.502  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.357   2.449   2.628  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.289   0.540   1.655  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   19   24                                             
CONECT    6    5    7   35   36                                             
CONECT    7    6    8   18                                                  
CONECT    8    7    9   37                                                  
CONECT    9    8   10   38                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10   39                                                       
CONECT   12   10   13   18                                                  
CONECT   13   12   14   40   41                                             
CONECT   14   13   15   42                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   43   44   45                                             
CONECT   17   15   46   47   48                                             
CONECT   18   12    7   49                                                  
CONECT   19    5   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22   50                                                       
CONECT   24   22   25    5                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27   51                                                  
CONECT   27   26   28   52                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   53                                                       
CONECT   30   28   31   54                                                  
CONECT   31   30   25   55                                                  
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   23                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
CONECT   53   29                                                            
CONECT   54   30                                                            
CONECT   55   31                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
   -3.4828   -2.4651    3.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -2.0192    2.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786   -2.7549    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556   -3.8957    0.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.1727    0.0203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1422   -1.9325    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544   -1.3689   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -2.2548   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -1.7018   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7609   -0.3428   -1.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.1719   -2.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0206    0.5453   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    1.9850   -1.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4235    2.4743   -0.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3610    1.9167    0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623    2.8392    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5241    0.5052    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.0198   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   -3.0235   -1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6931   -2.4126   -2.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038   -2.8746   -3.4200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416   -1.1372   -1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -0.1759   -2.7144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -0.9775   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    0.1952    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9619    0.7083   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5698    1.8035    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9968    2.4427    1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6062    3.5637    1.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8130    1.9595    1.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2131    0.8519    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302   -3.3087    2.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1042   -1.5692    3.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -2.7451    4.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722   -1.4460    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064   -2.9880    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673   -3.3238   -0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724   -2.3568   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001   -0.4197   -3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430    2.3351   -2.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416    2.4656   -0.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5471    3.6070   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1287    3.2513    1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6002    3.6190   -0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4095    2.2842    0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6328   -0.0234    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2232    0.4289    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0715   -0.1024   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    0.7133    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1931    0.4279   -3.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4306    0.2185   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178    2.1967   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    3.8853    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3570    2.4493    2.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    0.5397    1.6545 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  1
  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  2  3
 15 16  1  0
 15 17  1  0
 12 18  2  0
  5 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 24  5  1  0
 31 25  1  0
 18  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  9 38  1  0
 11 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  0
 23 50  1  0
 26 51  1  0
 27 52  1  0
 29 53  1  0
 30 54  1  0
 31 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
alpha-oxo-beta-(4-Hydroxyphenyl)-gamma-(4-hydroxy-m-3,3-dimethylallylbenzyl)-gamma-methoxycarbonyl-gamma-butyrolactone	MeSH
Methyl (2S)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylic acid	Generator

Chemical Formula

C₂₄H₂₄O₇

Average Mass

424.4490 Da

Monoisotopic Mass

424.15220 Da

IUPAC Name

methyl (2S)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-3-(4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-2-carboxylate

Traditional Name

methyl (2S)-4-hydroxy-2-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]methyl}-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(29)30-3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m0/s1

InChI Key

NGOLMNWQNHWEKU-DEOSSOPVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	gabi.almeida@usp.br	University of São Paulo	Gabriela de Oliveira Almeida	2025-07-30	View Spectrum

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	8395680
Aspergillus flavipes	LOTUS Database	35616633
Aspergillus terreus		Not Available
Aspergillus terreus DRCC 152	Fungi	KNApSAcK
Trewia nudiflora	LOTUS Database	35616633

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	3.87	ALOGPS
logP	4.58	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	115.73 m³·mol⁻¹	ChemAxon
Polarizability	43.13 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

NPA010585

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00032791

Chemspider ID

26349728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51340302

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kitagawa M, Okabe T, Ogino H, Matsumoto H, Suzuki-Takahashi I, Kokubo T, Higashi H, Saitoh S, Taya Y, Yasuda H, et al.: Butyrolactone I, a selective inhibitor of cdk2 and cdc2 kinase. Oncogene. 1993 Sep;8(9):2425-32. [PubMed:8395680 ]
Du X, Li H, Qi J, Chen C, Lu Y, Wang Y: Genome mining of secondary metabolites from a marine-derived Aspergillus terreus B12. Arch Microbiol. 2021 Nov;203(9):5621-5633. doi: 10.1007/s00203-021-02548-4. Epub 2021 Aug 30. [PubMed:34459930 ]
Uras IS, Ebada SS, Korinek M, Albohy A, Abdulrazik BS, Wang YH, Chen BH, Horng JT, Lin W, Hwang TL, Konuklugil B: Anti-Inflammatory, Antiallergic, and COVID-19 Main Protease (M(pro)) Inhibitory Activities of Butenolides from a Marine-Derived Fungus Aspergillus terreus. Molecules. 2021 Jun 2;26(11). pii: molecules26113354. doi: 10.3390/molecules26113354. [PubMed:34199488 ]
Ghfar AA, El-Metwally MM, Shaaban M, Gabr SA, Gabr NS, Diab MSM, Aqel A, Habila MA, Al-Qahtani WH, Alfaifi MY, Elbehairi SEI, AlJumah BA: Production of Terretonin N and Butyrolactone I by Thermophilic Aspergillus terreus TM8 Promoted Apoptosis and Cell Death in Human Prostate and Ovarian Cancer Cells. Molecules. 2021 May 10;26(9). pii: molecules26092816. doi: 10.3390/molecules26092816. [PubMed:34068647 ]
de Oliveira Almeida G, Mazucato VS, Tonani L, von Zeska Kress MR, Barbosa G, Krogh R, Andricopulo AD, Gomes Ferreira LL, Vieira PC: Exploring Bioactive Metabolites From Fusarium falciforme and Aspergillus terreus Isolated From Protease-Rich Fruits: Antifungal, Antitrypanosomal, and Enzymatic Inhibitory Activities. Chem Biodivers. 2025 Jul 20:e00673. doi: 10.1002/cbdv.202500673. [PubMed:40684465 ]
DOI: 10.1002/cbdv.202500673
PMID: 40684465

Showing NP-Card for Butyrolactone I (NP0022909)

MOL for NP0022909 (Butyrolactone I)

3D MOL for NP0022909 (Butyrolactone I)

3D SDF for NP0022909 (Butyrolactone I)

3D-SDF for NP0022909 (Butyrolactone I)

PDB for NP0022909 (Butyrolactone I)

3D PDB for NP0022909 (Butyrolactone I)

SMILES for NP0022909 (Butyrolactone I)

INCHI for NP0022909 (Butyrolactone I)

Structure for NP0022909 (Butyrolactone I)

3D Structure for NP0022909 (Butyrolactone I)