MiMeDB: Showing metabocard for Ergophilone A (MMDBc0004800)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:38:22 UTC

Update Date

2025-10-07 16:04:56 UTC

Metabolite ID

MMDBc0004800

Metabolite Identification

Common Name

Ergophilone A

Description

Ergophilone A is a polyketide compound. There is limited literature available on this metabolite, indicating that further research may be needed to fully understand its properties and potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100382D          

 71 78  0  0  1  0            999 V2000
    8.8519    6.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9338    5.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5876    7.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300    7.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    4.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1028    6.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    1.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6695    6.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0373    6.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7740    4.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5890    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285    3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843    4.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    3.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    5.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5165   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030    5.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4398    2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733    2.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452   -1.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4405    3.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255    3.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0332    2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0768    6.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4446    6.7212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2621    6.6865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5014   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292    4.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9584    2.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248    2.2459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2384   -1.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2554    3.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2182    2.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806    4.1707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1192    5.8740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9219    3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2919    3.2725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9301   -0.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1076    4.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -0.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9956    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142    4.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6996    1.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1930    0.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5883    2.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    3.5291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2179    5.4540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8846    1.7326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1069    3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1062    1.6043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -2.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6368   -0.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8113    5.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9226    4.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959    0.8343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711    0.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535    2.1273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5518    2.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8998    0.9077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265    5.6263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1803    7.7814    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4777    4.9407    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8853    3.2725    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125    7.2513    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051    7.4990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106    3.9141    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9212    1.4759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4770    3.4008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4646    6.3762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0619    3.5688    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  2  0  0  0  0
 12 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 26  3  1  6  0  0  0
 26  9  1  0  0  0  0
 26 25  1  0  0  0  0
 27  4  1  6  0  0  0
 27 10  1  0  0  0  0
 28  5  1  0  0  0  0
 28 17  2  0  0  0  0
 29 18  1  0  0  0  0
 29 23  1  0  0  0  0
 30 19  1  0  0  0  0
 30 20  2  0  0  0  0
 31 13  1  0  0  0  0
 31 19  1  0  0  0  0
 32 17  1  0  0  0  0
 32 21  2  0  0  0  0
 33 11  1  0  0  0  0
 33 22  2  0  0  0  0
 34 24  1  0  0  0  0
 35 14  1  0  0  0  0
 36 18  1  0  0  0  0
 36 27  1  1  0  0  0
 37 22  1  0  0  0  0
 37 34  2  0  0  0  0
 38 20  1  0  0  0  0
 39 21  1  0  0  0  0
 40 12  1  0  0  0  0
 41 28  1  0  0  0  0
 41 39  2  0  0  0  0
 42 35  1  0  0  0  0
 42 38  1  0  0  0  0
 43 29  1  0  0  0  0
 43 42  2  0  0  0  0
 44 34  1  0  0  0  0
 45 41  1  0  0  0  0
 47  6  1  1  0  0  0
 47 15  1  0  0  0  0
 47 30  1  0  0  0  0
 47 35  1  0  0  0  0
 48  7  1  1  0  0  0
 48 16  1  0  0  0  0
 48 36  1  0  0  0  0
 48 43  1  0  0  0  0
 49  8  1  1  0  0  0
 49 44  1  0  0  0  0
 49 46  1  0  0  0  0
 50 23  1  1  0  0  0
 50 37  1  0  0  0  0
 50 38  1  0  0  0  0
 50 46  1  0  0  0  0
 31 51  1  1  0  0  0
 52 32  1  0  0  0  0
 53 39  1  0  0  0  0
 54 40  2  0  0  0  0
 55 40  1  0  0  0  0
 56 44  2  0  0  0  0
 57 45  2  0  0  0  0
 58 46  2  0  0  0  0
 59 24  1  0  0  0  0
 59 33  1  0  0  0  0
 60 45  1  0  0  0  0
 49 60  1  6  0  0  0
 61  9  1  0  0  0  0
 62 10  1  0  0  0  0
 63 11  1  0  0  0  0
 64 12  1  0  0  0  0
 26 65  1  1  0  0  0
 27 66  1  1  0  0  0
 67 29  1  0  0  0  0
 31 68  1  6  0  0  0
 35 69  1  6  0  0  0
 36 70  1  6  0  0  0
 38 71  1  1  0  0  0
M  END


  Mrv1652305152100382D          

 71 78  0  0  1  0            999 V2000
    8.8519    6.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9338    5.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5876    7.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6300    7.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657    4.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1028    6.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    1.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6695    6.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0373    6.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7740    4.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5890    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285    3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843    4.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    3.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    5.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5165   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7030    5.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4398    2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733    2.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452   -1.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4405    3.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255    3.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0332    2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0768    6.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4446    6.7212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2621    6.6865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5014   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292    4.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9584    2.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248    2.2459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2384   -1.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2554    3.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2182    2.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806    4.1707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1192    5.8740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9219    3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2919    3.2725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9301   -0.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1076    4.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -0.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9956    4.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5142    4.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6996    1.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1930    0.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5883    2.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    3.5291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2179    5.4540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8846    1.7326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1069    3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1062    1.6043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2536   -2.8173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6368   -0.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8113    5.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9226    4.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959    0.8343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711    0.8815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535    2.1273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5518    2.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8998    0.9077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5265    5.6263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1803    7.7814    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4777    4.9407    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8853    3.2725    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125    7.2513    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051    7.4990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8106    3.9141    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9212    1.4759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4770    3.4008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4646    6.3762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0619    3.5688    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  2  0  0  0  0
 12 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 26  3  1  6  0  0  0
 26  9  1  0  0  0  0
 26 25  1  0  0  0  0
 27  4  1  6  0  0  0
 27 10  1  0  0  0  0
 28  5  1  0  0  0  0
 28 17  2  0  0  0  0
 29 18  1  0  0  0  0
 29 23  1  0  0  0  0
 30 19  1  0  0  0  0
 30 20  2  0  0  0  0
 31 13  1  0  0  0  0
 31 19  1  0  0  0  0
 32 17  1  0  0  0  0
 32 21  2  0  0  0  0
 33 11  1  0  0  0  0
 33 22  2  0  0  0  0
 34 24  1  0  0  0  0
 35 14  1  0  0  0  0
 36 18  1  0  0  0  0
 36 27  1  1  0  0  0
 37 22  1  0  0  0  0
 37 34  2  0  0  0  0
 38 20  1  0  0  0  0
 39 21  1  0  0  0  0
 40 12  1  0  0  0  0
 41 28  1  0  0  0  0
 41 39  2  0  0  0  0
 42 35  1  0  0  0  0
 42 38  1  0  0  0  0
 43 29  1  0  0  0  0
 43 42  2  0  0  0  0
 44 34  1  0  0  0  0
 45 41  1  0  0  0  0
 47  6  1  1  0  0  0
 47 15  1  0  0  0  0
 47 30  1  0  0  0  0
 47 35  1  0  0  0  0
 48  7  1  1  0  0  0
 48 16  1  0  0  0  0
 48 36  1  0  0  0  0
 48 43  1  0  0  0  0
 49  8  1  1  0  0  0
 49 44  1  0  0  0  0
 49 46  1  0  0  0  0
 50 23  1  1  0  0  0
 50 37  1  0  0  0  0
 50 38  1  0  0  0  0
 50 46  1  0  0  0  0
 31 51  1  1  0  0  0
 52 32  1  0  0  0  0
 53 39  1  0  0  0  0
 54 40  2  0  0  0  0
 55 40  1  0  0  0  0
 56 44  2  0  0  0  0
 57 45  2  0  0  0  0
 58 46  2  0  0  0  0
 59 24  1  0  0  0  0
 59 33  1  0  0  0  0
 60 45  1  0  0  0  0
 49 60  1  6  0  0  0
 61  9  1  0  0  0  0
 62 10  1  0  0  0  0
 63 11  1  0  0  0  0
 64 12  1  0  0  0  0
 26 65  1  1  0  0  0
 27 66  1  1  0  0  0
 67 29  1  0  0  0  0
 31 68  1  6  0  0  0
 35 69  1  6  0  0  0
 36 70  1  6  0  0  0
 38 71  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004800

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC2=C(CO1)C(=O)[C@](C)(OC(=O)C1=C(O)C=C(O)C=C1C)C(=O)[C@@]21CC2([H])C[C@]([H])([C@]([H])(C)C(\[H])=C(/[H])[C@]([H])(C)C(C)C)[C@@]3(C)CC[C@@]4([H])C(=C23)[C@@]1([H])C=C1C[C@@]([H])(O)CC[C@]41C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C50H60O10/c1-25(2)26(3)9-10-27(4)36-18-29-23-50(38-20-30-19-31(51)13-15-47(30,6)35-14-16-48(36,7)43(29)42(35)38)37-22-33(11-12-40(54)55)59-24-34(37)44(56)49(8,46(50)58)60-45(57)41-28(5)17-32(52)21-39(41)53/h9-12,17,20-22,25-27,29,31,35-36,38,51-53H,13-16,18-19,23-24H2,1-8H3,(H,54,55)/b10-9+,12-11+/t26-,27+,29?,31-,35-,36+,38+,47-,48+,49-,50-/m0/s1

> <INCHI_KEY>
SJCLLYRWNLKFEU-ABUJYTIISA-N

> <FORMULA>
C50H60O10

> <MOLECULAR_WEIGHT>
821.02

> <EXACT_MASS>
820.418648132

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
91.42071288617512

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-[(1'R,2'R,5R,5'S,7R,9'R,14'R,15'R)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-14'-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-5'-hydroxy-2',7,15'-trimethyl-6,8-dioxo-1,6,7,8-tetrahydrospiro[isochromene-5,10'-pentacyclo[10.5.2.0^{2,7}.0^{9,18}.0^{15,19}]nonadecane]-7',18'-dien-3-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
6.59

> <JCHEM_LOGP>
9.001195441333335

> <ALOGPS_LOGS>
-6.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.682840686472728

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.963186084130542

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3970953021544124

> <JCHEM_POLAR_SURFACE_AREA>
167.65999999999997

> <JCHEM_REFRACTIVITY>
233.61610000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.13e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(1'R,2'R,5R,5'S,7R,9'R,14'R,15'R)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-14'-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-5'-hydroxy-2',7,15'-trimethyl-6,8-dioxo-1H-spiro[isochromene-5,10'-pentacyclo[10.5.2.0^{2,7}.0^{9,18}.0^{15,19}]nonadecane]-7',18'-dien-3-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      16.524  12.084   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.810  10.040   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.164  14.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.643  13.471   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.188  -0.689   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.416   8.025   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.659  11.706   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.607   2.939   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.450  12.019   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.270  13.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.512   7.785   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.033   7.546   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.480   5.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.384   9.223   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.448   6.827   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.352  10.420   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.564  -2.974   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.646   9.877   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.554   3.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.044   4.911   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.231  -2.925   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.022   6.827   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.501   7.067   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.129   3.953   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.077  11.557   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.897  12.546   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.823  12.481   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.536  -1.434   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.948   8.504   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.522   5.150   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.033   4.192   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.912  -3.719   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.543   6.588   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.607   4.192   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.937   7.785   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.556  10.965   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.054   5.630   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.012   6.109   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.203  -1.385   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      17.001   8.744   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.855  -0.640   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.458   7.546   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.427   8.744   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.639   2.995   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.827   0.900   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.565   4.671   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.969   6.588   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.873  10.181   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.118   3.234   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.533   5.869   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       2.065   2.995   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       7.940  -5.259   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      10.522  -0.591   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      16.448  10.181   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      18.522   8.504   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      11.192   1.557   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       6.479   1.645   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       7.193   3.971   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      14.097   5.150   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       9.146   1.694   0.000  0.00  0.00           O+0
HETATM   61  H   UNK     0      12.183  10.502   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      11.537  14.525   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      13.958   9.223   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0      16.586   6.109   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      12.717  13.536   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      10.090  13.998   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0       8.980   7.306   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.586   2.755   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0       6.490   6.348   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0       8.334  11.902   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0       9.449   6.662   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   47                                                            
CONECT    7   48                                                            
CONECT    8   49                                                            
CONECT    9   10   26   61                                                  
CONECT   10    9   27   62                                                  
CONECT   11   12   33   63                                                  
CONECT   12   11   40   64                                                  
CONECT   13   15   31                                                       
CONECT   14   16   35                                                       
CONECT   15   13   47                                                       
CONECT   16   14   48                                                       
CONECT   17   28   32                                                       
CONECT   18   29   36                                                       
CONECT   19   30   31                                                       
CONECT   20   30   38                                                       
CONECT   21   32   39                                                       
CONECT   22   33   37                                                       
CONECT   23   29   50                                                       
CONECT   24   34   59                                                       
CONECT   25    1    2   26                                                  
CONECT   26    3    9   25   65                                             
CONECT   27    4   10   36   66                                             
CONECT   28    5   17   41                                                  
CONECT   29   18   23   43   67                                             
CONECT   30   19   20   47                                                  
CONECT   31   13   19   51   68                                             
CONECT   32   17   21   52                                                  
CONECT   33   11   22   59                                                  
CONECT   34   24   37   44                                                  
CONECT   35   14   42   47   69                                             
CONECT   36   18   27   48   70                                             
CONECT   37   22   34   50                                                  
CONECT   38   20   42   50   71                                             
CONECT   39   21   41   53                                                  
CONECT   40   12   54   55                                                  
CONECT   41   28   39   45                                                  
CONECT   42   35   38   43                                                  
CONECT   43   29   42   48                                                  
CONECT   44   34   49   56                                                  
CONECT   45   41   57   60                                                  
CONECT   46   49   50   58                                                  
CONECT   47    6   15   30   35                                             
CONECT   48    7   16   36   43                                             
CONECT   49    8   44   46   60                                             
CONECT   50   23   37   38   46                                             
CONECT   51   31                                                            
CONECT   52   32                                                            
CONECT   53   39                                                            
CONECT   54   40                                                            
CONECT   55   40                                                            
CONECT   56   44                                                            
CONECT   57   45                                                            
CONECT   58   46                                                            
CONECT   59   24   33                                                       
CONECT   60   45   49                                                       
CONECT   61    9                                                            
CONECT   62   10                                                            
CONECT   63   11                                                            
CONECT   64   12                                                            
CONECT   65   26                                                            
CONECT   66   27                                                            
CONECT   67   29                                                            
CONECT   68   31                                                            
CONECT   69   35                                                            
CONECT   70   36                                                            
CONECT   71   38                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  156    0
END

Synonyms

Not Available

Molecular Formula

C₅₀H₆₀O₁₀

Average Mass

821.02

Monoisotopic Mass

820.418648132

IUPAC Name

(2E)-3-[(1'R,2'R,5R,5'S,7R,9'R,14'R,15'R)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-14'-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-5'-hydroxy-2',7,15'-trimethyl-6,8-dioxo-1,6,7,8-tetrahydrospiro[isochromene-5,10'-pentacyclo[10.5.2.0^{2,7}.0^{9,18}.0^{15,19}]nonadecane]-7',18'-dien-3-yl]prop-2-enoic acid

Traditional Name

(2E)-3-[(1'R,2'R,5R,5'S,7R,9'R,14'R,15'R)-7-(2,4-dihydroxy-6-methylbenzoyloxy)-14'-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-5'-hydroxy-2',7,15'-trimethyl-6,8-dioxo-1H-spiro[isochromene-5,10'-pentacyclo[10.5.2.0^{2,7}.0^{9,18}.0^{15,19}]nonadecane]-7',18'-dien-3-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC2=C(CO1)C(=O)[C@](C)(OC(=O)C1=C(O)C=C(O)C=C1C)C(=O)[C@@]21CC2([H])C[C@]([H])([C@]([H])(C)C(\[H])=C(/[H])[C@]([H])(C)C(C)C)[C@@]3(C)CC[C@@]4([H])C(=C23)[C@@]1([H])C=C1C[C@@]([H])(O)CC[C@]41C)C(O)=O

InChI Identifier

InChI=1S/C50H60O10/c1-25(2)26(3)9-10-27(4)36-18-29-23-50(38-20-30-19-31(51)13-15-47(30,6)35-14-16-48(36,7)43(29)42(35)38)37-22-33(11-12-40(54)55)59-24-34(37)44(56)49(8,46(50)58)60-45(57)41-28(5)17-32(52)21-39(41)53/h9-12,17,20-22,25-27,29,31,35-36,38,51-53H,13-16,18-19,23-24H2,1-8H3,(H,54,55)/b10-9+,12-11+/t26-,27+,29?,31-,35-,36+,38+,47-,48+,49-,50-/m0/s1

InChI Key

SJCLLYRWNLKFEU-ABUJYTIISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Ergostane-skeleton
Steroid
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
M-cresol
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexenone
Toluene
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Pyran
Benzenoid
Cyclic alcohol
Vinylogous acid
Ketone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00061 g/L	ALOGPS
logP	6.59	ALOGPS
logP	9	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	167.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	233.62 m³·mol⁻¹	ChemAxon
Polarizability	91.42 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	27.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	63.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	908.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	1260.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1356.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	275.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	4912.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	116.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	406.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	995.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	245.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	157.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	321.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	10.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	101.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	294.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	762.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2682.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	2242.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Ergophilone A_TMS_1	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O)CC[C@@]25C)C1=O	standard non polar	2025-10-23	2232.9
Gas Chromatography	Ergophilone A_TMS_2	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O)CC[C@@]25C)C1=O	standard non polar	2025-10-23	2204.61
Gas Chromatography	Ergophilone A_TMS_3	CC1=CC(O)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O[Si](C)(C)C)CC[C@@]25C)C1=O	standard non polar	2025-10-23	1678.15
Gas Chromatography	Ergophilone A_TMS_4	CC1=CC(O)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O[Si](C)(C)C)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O)CC[C@@]25C)C1=O	standard non polar	2025-10-23	1715.63
Gas Chromatography	Ergophilone A_TMS_1	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O)CC[C@@]25C)C1=O	standard polar	2025-10-23	2195.72
Gas Chromatography	Ergophilone A_TMS_2	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O)CC[C@@]25C)C1=O	standard polar	2025-10-23	3418.8
Gas Chromatography	Ergophilone A_TMS_3	CC1=CC(O)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O[Si](C)(C)C)CC[C@@]25C)C1=O	standard polar	2025-10-23	1510.75
Gas Chromatography	Ergophilone A_TMS_4	CC1=CC(O)=CC(O)=C1C(=O)O[C@@]1(C)C(=O)C2=C(C=C(/C=C/C(=O)O[Si](C)(C)C)OC2)[C@]2(CC3C[C@H]([C@H](C)/C=C/[C@H](C)C(C)C)[C@@]4(C)CC[C@H]5C(=C34)[C@H]2C=C2C[C@@H](O)CC[C@@]25C)C1=O	standard polar	2025-10-23	2944.68

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00053007

Chemspider ID

78436718

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584222

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Ergophilone A (MMDBc0004800)

MOL for #<Metabolite:0x00005643238811e0>

3D MOL for #<Metabolite:0x00005643238811e0>

3D SDF for #<Metabolite:0x00005643238811e0>

3D-SDF for #<Metabolite:0x00005643238811e0>

PDB for #<Metabolite:0x00005643238811e0>

3D PDB for #<Metabolite:0x00005643238811e0>

SMILES for #<Metabolite:0x00005643238811e0>

INCHI for #<Metabolite:0x00005643238811e0>

Structure for #<Metabolite:0x00005643238811e0>

3D Structure for #<Metabolite:0x00005643238811e0>