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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:01:50 UTC

Update Date

2022-03-07 02:55:30 UTC

HMDB ID

HMDB0037772

Secondary Accession Numbers

HMDB37772

Metabolite Identification

Common Name

8-Acetylegelolide

Description

8-Acetylegelolide, also known as 3-oxa-achillicin, belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 8-Acetylegelolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 8-acetylegelolide has been detected, but not quantified in, herbs and spices. This could make 8-acetylegelolide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0037772
     RDKit          3D
8-Acetylegelolide
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.6201   -0.1120   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323   -0.1065   -0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9177   -0.0499    0.5812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7902   -0.1645   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -0.1667    1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.5043    1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -2.1489    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -2.3949   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735   -3.4076    0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832   -1.3799   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -1.8250   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976   -0.9019   -1.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541    0.1147   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393    1.3179   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896   -0.1290    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    0.8144    1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    2.1170    1.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162    3.0171    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5661    4.2615    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530    2.1619    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894    1.8875   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184    0.9958    1.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -0.5259   -1.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    0.9477   -2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -0.7620   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0707   -0.1097    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059   -2.2205    1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.3407    2.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787   -1.5674   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3327   -3.2905   -1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967   -2.6649   -0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040   -3.1847    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -2.7772   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048    1.6312    0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2978    2.0925   -0.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7489    1.0915   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5439    0.5411    2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041    2.6725    0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067    1.0209   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616    1.8344   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.7780   -1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237    1.4370    2.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
M  END


  Mrv0541 05061310002D          

 22 24  0  0  0  0            999 V2000
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 16  4  1  0  0  0  0
 16  5  1  0  0  0  0
 16 10  1  0  0  0  0
 17  9  2  0  0  0  0
 18 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20  6  1  0  0  0  0
 20  8  1  0  0  0  0
 21  9  1  0  0  0  0
 21 11  1  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037772

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1=C(C)OC=C1C(C)(O)CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O6/c1-7-12-11(21-9(3)17)5-16(4,19)10-6-20-8(2)13(10)14(12)22-15(7)18/h6-7,11-12,14,19H,5H2,1-4H3

> <INCHI_KEY>
KOUVNGDGNNAPQW-UHFFFAOYSA-N

> <FORMULA>
C16H20O6

> <MOLECULAR_WEIGHT>
308.3264

> <EXACT_MASS>
308.125988372

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.429311731705297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-5,9,13-trimethyl-4-oxo-3,12-dioxatricyclo[8.3.0.0²,⁶]trideca-1(13),10-dien-7-yl acetate

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
0.7487567983333341

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.80574782262265

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8584566169665853

> <JCHEM_POLAR_SURFACE_AREA>
85.97000000000001

> <JCHEM_REFRACTIVITY>
75.9724

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-5,9,13-trimethyl-4-oxo-3,12-dioxatricyclo[8.3.0.0²,⁶]trideca-1(13),10-dien-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037772
     RDKit          3D
8-Acetylegelolide
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.6201   -0.1120   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323   -0.1065   -0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9177   -0.0499    0.5812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7902   -0.1645   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -0.1667    1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.5043    1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -2.1489    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -2.3949   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735   -3.4076    0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832   -1.3799   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -1.8250   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976   -0.9019   -1.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541    0.1147   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393    1.3179   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896   -0.1290    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    0.8144    1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    2.1170    1.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162    3.0171    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5661    4.2615    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530    2.1619    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894    1.8875   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184    0.9958    1.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -0.5259   -1.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    0.9477   -2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -0.7620   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0707   -0.1097    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059   -2.2205    1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.3407    2.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787   -1.5674   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3327   -3.2905   -1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967   -2.6649   -0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040   -3.1847    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -2.7772   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048    1.6312    0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2978    2.0925   -0.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7489    1.0915   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5439    0.5411    2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041    2.6725    0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067    1.0209   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616    1.8344   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.7780   -1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237    1.4370    2.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.001   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.803   3.882   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.176  -1.200   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   16                                                            
CONECT    5   11   16                                                       
CONECT    6   10   20                                                       
CONECT    7    1   12   15                                                  
CONECT    8    2   13   20                                                  
CONECT    9    3   17   21                                                  
CONECT   10    6   13   16                                                  
CONECT   11    5   12   21                                                  
CONECT   12    7   11   14                                                  
CONECT   13    8   10   14                                                  
CONECT   14   12   13   22                                                  
CONECT   15    7   18   22                                                  
CONECT   16    4    5   10   19                                             
CONECT   17    9                                                            
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20    6    8                                                       
CONECT   21    9   11                                                       
CONECT   22   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0037772
HETATM    1  C1  UNL     1       3.620  -0.112  -1.797  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.132  -0.106  -0.397  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.918  -0.050   0.581  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.790  -0.165  -0.158  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.187  -0.167   1.132  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.567  -1.504   1.435  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.108  -2.149   0.286  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.761  -2.395  -0.904  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.574  -3.408   0.734  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.283  -1.380  -0.113  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.200  -1.825  -1.042  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.098  -0.902  -1.150  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.854   0.115  -0.373  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.739   1.318  -0.306  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.690  -0.129   0.329  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.145   0.814   1.282  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.638   2.117   1.028  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.616   3.017   0.821  1.00  0.00           C  
HETATM   19  O6  UNL     1      -0.566   4.261   0.934  1.00  0.00           O  
HETATM   20  C14 UNL     1       0.553   2.162   0.391  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.389   1.887  -1.044  1.00  0.00           C  
HETATM   22  C16 UNL     1       0.318   0.996   1.320  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.644  -0.526  -1.895  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.554   0.948  -2.153  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.946  -0.762  -2.408  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.071  -0.110   1.842  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.306  -2.220   1.851  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.182  -1.341   2.235  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.679  -1.567  -1.660  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.333  -3.290  -1.446  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.797  -2.665  -0.671  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.304  -3.185   1.395  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.127  -2.777  -1.551  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.905   1.631   0.747  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.298   2.092  -0.941  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.749   1.092  -0.709  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.544   0.541   2.303  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.504   2.673   0.578  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.207   1.021  -1.324  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.362   1.834  -1.615  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.127   2.778  -1.515  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.524   1.437   2.347  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   26
CONECT    6    7   27   28
CONECT    7    8    9   10
CONECT    8   29   30   31
CONECT    9   32
CONECT   10   11   11   15
CONECT   11   12   33
CONECT   12   13
CONECT   13   14   15   15
CONECT   14   34   35   36
CONECT   15   16
CONECT   16   17   22   37
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   22   38
CONECT   21   39   40   41
CONECT   22   42
END

HMDB0037772
     RDKit          3D
8-Acetylegelolide
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.6201   -0.1120   -1.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323   -0.1065   -0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9177   -0.0499    0.5812 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7902   -0.1645   -0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -0.1667    1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.5043    1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -2.1489    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -2.3949   -0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735   -3.4076    0.7340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832   -1.3799   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -1.8250   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976   -0.9019   -1.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541    0.1147   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393    1.3179   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896   -0.1290    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    0.8144    1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384    2.1170    1.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162    3.0171    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5661    4.2615    0.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530    2.1619    0.3912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894    1.8875   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184    0.9958    1.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -0.5259   -1.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541    0.9477   -2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -0.7620   -2.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0707   -0.1097    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059   -2.2205    1.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.3407    2.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787   -1.5674   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3327   -3.2905   -1.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7967   -2.6649   -0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3040   -3.1847    1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -2.7772   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048    1.6312    0.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2978    2.0925   -0.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7489    1.0915   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5439    0.5411    2.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5041    2.6725    0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067    1.0209   -1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616    1.8344   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.7780   -1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237    1.4370    2.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22  5  1  0
 15 10  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Oxa-achillicin	HMDB
3-Oxaachillicin	HMDB
8-Acetylegeloide	HMDB
9-Hydroxy-5,9,13-trimethyl-4-oxo-3,12-dioxatricyclo[8.3.0.0²,⁶]trideca-1(13),10-dien-7-yl acetic acid	Generator

Chemical Formula

C₁₆H₂₀O₆

Average Molecular Weight

308.3264

Monoisotopic Molecular Weight

308.125988372

IUPAC Name

9-hydroxy-5,9,13-trimethyl-4-oxo-3,12-dioxatricyclo[8.3.0.0²,⁶]trideca-1(13),10-dien-7-yl acetate

Traditional Name

9-hydroxy-5,9,13-trimethyl-4-oxo-3,12-dioxatricyclo[8.3.0.0²,⁶]trideca-1(13),10-dien-7-yl acetate

CAS Registry Number

142449-62-5

SMILES

CC1C2C(OC1=O)C1=C(C)OC=C1C(C)(O)CC2OC(C)=O

InChI Identifier

InChI=1S/C16H20O6/c1-7-12-11(21-9(3)17)5-16(4,19)10-6-20-8(2)13(10)14(12)22-15(7)18/h6-7,11-12,14,19H,5H2,1-4H3

InChI Key

KOUVNGDGNNAPQW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Cycloheptafurans

Sub Class

Not Available

Direct Parent

Cycloheptafurans

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037772)
Cytoplasm (HMDB: HMDB0037772)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037772)

Source

Exogenous

Food

Food (HMDB: HMDB0037772)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037772)

Not Available

Nutrient (HMDB: HMDB0037772)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 - 221 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	1.72	ALOGPS
logP	0.75	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.97 m³·mol⁻¹	ChemAxon
Polarizability	31.43 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.699	31661259
DarkChem	[M-H]-	165.078	31661259
DeepCCS	[M+H]+	173.501	30932474
DeepCCS	[M-H]-	171.143	30932474
DeepCCS	[M-2H]-	204.332	30932474
DeepCCS	[M+Na]+	179.594	30932474
AllCCS	[M+H]+	170.3	32859911
AllCCS	[M+H-H2O]+	167.1	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	175.2	32859911
AllCCS	[M+Na-2H]-	175.1	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Acetylegelolide	CC1C2C(OC1=O)C1=C(C)OC=C1C(C)(O)CC2OC(C)=O	3396.5	Standard polar	33892256
8-Acetylegelolide	CC1C2C(OC1=O)C1=C(C)OC=C1C(C)(O)CC2OC(C)=O	2100.0	Standard non polar	33892256
8-Acetylegelolide	CC1C2C(OC1=O)C1=C(C)OC=C1C(C)(O)CC2OC(C)=O	2298.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Acetylegelolide,1TMS,isomer #1	CC(=O)OC1CC(C)(O[Si](C)(C)C)C2=COC(C)=C2C2OC(=O)C(C)C12	2405.2	Semi standard non polar	33892256
8-Acetylegelolide,1TBDMS,isomer #1	CC(=O)OC1CC(C)(O[Si](C)(C)C(C)(C)C)C2=COC(C)=C2C2OC(=O)C(C)C12	2631.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Acetylegelolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9780000000-462e11e7275ef9ac7dbd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Acetylegelolide GC-MS (1 TMS) - 70eV, Positive	splash10-00fv-7269000000-907caa523497ce90145a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Acetylegelolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 10V, Positive-QTOF	splash10-052f-0093000000-64e13b0653ba56dc47a5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 20V, Positive-QTOF	splash10-00kb-1290000000-0b55eea74621d2aa700e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 40V, Positive-QTOF	splash10-002b-1290000000-40238e3aa7d76ac5839e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 10V, Negative-QTOF	splash10-0a4i-1096000000-9ff14db34dce3ce5f694	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 20V, Negative-QTOF	splash10-0a4j-1091000000-9a3b8c8eff8eed7fbe98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 40V, Negative-QTOF	splash10-0a4i-4290000000-f891b4ba21fa63cd375f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 10V, Negative-QTOF	splash10-014i-0090000000-53ad44f20b18b71f5b17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 20V, Negative-QTOF	splash10-00kb-1090000000-9b97c925a5297adcf11a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 40V, Negative-QTOF	splash10-0a4l-9370000000-d4010e94731bce194c5f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 10V, Positive-QTOF	splash10-0002-0091000000-7518c8a12fbabd6f48ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 20V, Positive-QTOF	splash10-001i-0090000000-0c49867002df9c68eaae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Acetylegelolide 40V, Positive-QTOF	splash10-0007-9270000000-68d0f64f3fe9c68c23bc	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016914

KNApSAcK ID

C00034766

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

131752229

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 8-Acetylegelolide (HMDB0037772)

MOL for HMDB0037772 (8-Acetylegelolide)

3D MOL for HMDB0037772 (8-Acetylegelolide)

3D SDF for HMDB0037772 (8-Acetylegelolide)

3D-SDF for HMDB0037772 (8-Acetylegelolide)

PDB for HMDB0037772 (8-Acetylegelolide)

3D PDB for HMDB0037772 (8-Acetylegelolide)

SMILES for HMDB0037772 (8-Acetylegelolide)

INCHI for HMDB0037772 (8-Acetylegelolide)

Structure for HMDB0037772 (8-Acetylegelolide)

3D Structure for HMDB0037772 (8-Acetylegelolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra