MiMeDB: Showing metabocard for (4â€²E,1S,6S,7R,10S,6â€²S,7â€²R)-aspergilloid A (MMDBc0025028)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 14:47:28 UTC

Update Date

2022-08-31 06:50:17 UTC

Metabolite ID

MMDBc0025028

Metabolite Identification

Common Name

(4â€²E,1S,6S,7R,10S,6â€²S,7â€²R)-aspergilloid A

Description

CHEMBL4439706 belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on CHEMBL4439706.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152116472D          

 46 49  0  0  1  0            999 V2000
   -4.1853    1.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -0.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7762    3.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2459    3.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374    1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374    2.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3388    4.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0907    2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8813    5.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988    1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    3.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9031    2.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4940    4.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085    3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    0.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4334    3.1567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1230    0.8158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1513    3.9320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5915    1.2283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6816    4.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915    2.0533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5552    0.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    3.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5667    5.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    2.4658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604    2.0360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3710    0.3754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -0.5155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    4.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8383    5.7682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    3.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    3.0978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082    5.7426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4657    2.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    4.8505    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7156    2.3815    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915    0.4033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348    1.5862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299    2.8760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  1  0  0  0  0
 18  9  2  0  0  0  0
 18 11  1  0  0  0  0
 19 10  2  0  0  0  0
 19 13  1  0  0  0  0
 20  6  1  0  0  0  0
 20 15  1  1  0  0  0
 21  7  1  0  0  0  0
 21 16  1  1  0  0  0
 22  9  1  6  0  0  0
 22 20  1  0  0  0  0
 23 10  1  0  0  0  0
 23 21  1  0  0  0  0
 24 17  2  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 19  1  0  0  0  0
 27 18  1  0  0  0  0
 28 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30  8  1  0  0  0  0
 30 14  1  1  0  0  0
 30 25  1  0  0  0  0
 31 11  1  0  0  0  0
 32 26  2  0  0  0  0
 33 26  1  0  0  0  0
 34 27  2  0  0  0  0
 35 28  2  0  0  0  0
 36 29  2  0  0  0  0
 30 37  1  6  0  0  0
 38 12  1  0  0  0  0
 38 28  1  0  0  0  0
 39 13  1  0  0  0  0
 39 29  1  0  0  0  0
 40 14  1  0  0  0  0
 40 27  1  0  0  0  0
 41  9  1  0  0  0  0
 20 42  1  6  0  0  0
 21 43  1  6  0  0  0
 22 44  1  1  0  0  0
 23 45  1  1  0  0  0
 25 46  1  6  0  0  0
M  END


  Mrv1652305152116472D          

 46 49  0  0  1  0            999 V2000
   -4.1853    1.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -0.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7762    3.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2459    3.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374    1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374    2.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3388    4.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0907    2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8813    5.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988    1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    3.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9031    2.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4940    4.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8085    3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    0.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4334    3.1567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1230    0.8158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1513    3.9320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5915    1.2283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6816    4.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915    2.0533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5552    0.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    3.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5667    5.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    2.4658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604    2.0360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3710    0.3754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538   -0.5155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    4.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8383    5.7682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529    3.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073    3.0978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082    5.7426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    2.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4657    2.9545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566    4.8505    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7156    2.3815    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915    0.4033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348    1.5862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299    2.8760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  1  0  0  0  0
 18  9  2  0  0  0  0
 18 11  1  0  0  0  0
 19 10  2  0  0  0  0
 19 13  1  0  0  0  0
 20  6  1  0  0  0  0
 20 15  1  1  0  0  0
 21  7  1  0  0  0  0
 21 16  1  1  0  0  0
 22  9  1  6  0  0  0
 22 20  1  0  0  0  0
 23 10  1  0  0  0  0
 23 21  1  0  0  0  0
 24 17  2  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 19  1  0  0  0  0
 27 18  1  0  0  0  0
 28 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30  8  1  0  0  0  0
 30 14  1  1  0  0  0
 30 25  1  0  0  0  0
 31 11  1  0  0  0  0
 32 26  2  0  0  0  0
 33 26  1  0  0  0  0
 34 27  2  0  0  0  0
 35 28  2  0  0  0  0
 36 29  2  0  0  0  0
 30 37  1  6  0  0  0
 38 12  1  0  0  0  0
 38 28  1  0  0  0  0
 39 13  1  0  0  0  0
 39 29  1  0  0  0  0
 40 14  1  0  0  0  0
 40 27  1  0  0  0  0
 41  9  1  0  0  0  0
 20 42  1  6  0  0  0
 21 43  1  6  0  0  0
 22 44  1  1  0  0  0
 23 45  1  1  0  0  0
 25 46  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0025028

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\CO)C(=O)OC[C@]1(O)CC[C@]([H])(C(C)C)[C@@]2([H])C=C(COC(=O)[C@]12[H])C(O)=O)[C@@]1([H])C2=C(COC2=O)CC[C@]1([H])C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O10/c1-15(2)20-6-5-17-12-38-28(35)24(17)22(20)9-18(11-31)27(34)40-14-30(37)8-7-21(16(3)4)23-10-19(26(32)33)13-39-29(36)25(23)30/h9-10,15-16,20-23,25,31,37H,5-8,11-14H2,1-4H3,(H,32,33)/b18-9+/t20-,21-,22-,23-,25-,30-/m1/s1

> <INCHI_KEY>
GINWPXGJOUQXPN-AUWHNZDYSA-N

> <FORMULA>
C30H40O10

> <MOLECULAR_WEIGHT>
560.64

> <EXACT_MASS>
560.262147488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.807833046170806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aS,6R,9S,9aS)-9-hydroxy-9-({[(2E)-2-(hydroxymethyl)-3-[(4S,5R)-3-oxo-5-(propan-2-yl)-1,3,4,5,6,7-hexahydro-2-benzofuran-4-yl]prop-2-enoyl]oxy}methyl)-1-oxo-6-(propan-2-yl)-1,3,5a,6,7,8,9,9a-octahydro-2-benzoxepine-4-carboxylic acid

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.030475180333334

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.084202912183574

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.136948629381444

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8503836461182415

> <JCHEM_POLAR_SURFACE_AREA>
156.65999999999994

> <JCHEM_REFRACTIVITY>
144.52380000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aS,6R,9S,9aS)-9-hydroxy-9-({[(2E)-2-(hydroxymethyl)-3-[(4S,5R)-5-isopropyl-3-oxo-4,5,6,7-tetrahydro-1H-2-benzofuran-4-yl]prop-2-enoyl]oxy}methyl)-6-isopropyl-1-oxo-3,5a,6,7,8,9a-hexahydro-2-benzoxepine-4-carboxylic 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      -7.813   3.266   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.902   4.038   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.104  -0.787   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.563  -0.787   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.782   6.805   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.792   5.625   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.563   2.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.563   3.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.232   7.607   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.308   1.333   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.769   4.980   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.978   9.612   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.478   3.063   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.219   5.783   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.286   4.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.230  -0.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.256   8.252   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.243   6.427   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.810   1.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.276   5.893   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.230   1.523   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.749   7.340   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.104   2.293   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.739   8.519   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.104   3.833   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.770   0.471   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.726   6.695   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.525  10.044   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.308   4.793   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.230   4.603   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.779   3.801   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.293   0.701   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.207  -0.962   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.199   8.142   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -7.165  10.767   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.965   6.294   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.760   5.783   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -9.909  10.719   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       3.810   4.450   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.736   5.515   0.000  0.00  0.00           O+0
HETATM   41  H   UNK     0      -5.706   9.054   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      -8.802   4.445   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.104   0.753   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.759   6.160   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.492   2.961   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.989   5.368   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5    6   17                                                       
CONECT    6    5   20                                                       
CONECT    7    8   21                                                       
CONECT    8    7   30                                                       
CONECT    9   18   22   41                                                  
CONECT   10   19   23                                                       
CONECT   11   18   31                                                       
CONECT   12   17   38                                                       
CONECT   13   19   39                                                       
CONECT   14   30   40                                                       
CONECT   15    1    2   20                                                  
CONECT   16    3    4   21                                                  
CONECT   17    5   12   24                                                  
CONECT   18    9   11   27                                                  
CONECT   19   10   13   26                                                  
CONECT   20    6   15   22   42                                             
CONECT   21    7   16   23   43                                             
CONECT   22    9   20   24   44                                             
CONECT   23   10   21   25   45                                             
CONECT   24   17   22   28                                                  
CONECT   25   23   29   30   46                                             
CONECT   26   19   32   33                                                  
CONECT   27   18   34   40                                                  
CONECT   28   24   35   38                                                  
CONECT   29   25   36   39                                                  
CONECT   30    8   14   25   37                                             
CONECT   31   11                                                            
CONECT   32   26                                                            
CONECT   33   26                                                            
CONECT   34   27                                                            
CONECT   35   28                                                            
CONECT   36   29                                                            
CONECT   37   30                                                            
CONECT   38   12   28                                                       
CONECT   39   13   29                                                       
CONECT   40   14   27                                                       
CONECT   41    9                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
CONECT   45   23                                                            
CONECT   46   25                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   98    0
END

Synonyms

Not Available

Molecular Formula

C₃₀H₄₀O₁₀

Average Mass

560.64

Monoisotopic Mass

560.262147488

IUPAC Name

(5aS,6R,9S,9aS)-9-hydroxy-9-({[(2E)-2-(hydroxymethyl)-3-[(4S,5R)-3-oxo-5-(propan-2-yl)-1,3,4,5,6,7-hexahydro-2-benzofuran-4-yl]prop-2-enoyl]oxy}methyl)-1-oxo-6-(propan-2-yl)-1,3,5a,6,7,8,9,9a-octahydro-2-benzoxepine-4-carboxylic acid

Traditional Name

(5aS,6R,9S,9aS)-9-hydroxy-9-({[(2E)-2-(hydroxymethyl)-3-[(4S,5R)-5-isopropyl-3-oxo-4,5,6,7-tetrahydro-1H-2-benzofuran-4-yl]prop-2-enoyl]oxy}methyl)-6-isopropyl-1-oxo-3,5a,6,7,8,9a-hexahydro-2-benzoxepine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\CO)C(=O)OC[C@]1(O)CC[C@]([H])(C(C)C)[C@@]2([H])C=C(COC(=O)[C@]12[H])C(O)=O)[C@@]1([H])C2=C(COC2=O)CC[C@]1([H])C(C)C

InChI Identifier

InChI=1S/C30H40O10/c1-15(2)20-6-5-17-12-38-28(35)24(17)22(20)9-18(11-31)27(34)40-14-30(37)8-7-21(16(3)4)23-10-19(26(32)33)13-39-29(36)25(23)30/h9-10,15-16,20-23,25,31,37H,5-8,11-14H2,1-4H3,(H,32,33)/b18-9+/t20-,21-,22-,23-,25-,30-/m1/s1

InChI Key

GINWPXGJOUQXPN-AUWHNZDYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Tetracarboxylic acid or derivatives
Isobenzofuran
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	2.45	ALOGPS
logP	3.03	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	156.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	144.52 m³·mol⁻¹	ChemAxon
Polarizability	57.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

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

Metabolic Reactions

Not Available

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

Source Type	Source Sub-type	Species	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95224254

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 (4â€²E,1S,6S,7R,10S,6â€²S,7â€²R)-aspergilloid A (MMDBc0025028)

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