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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:01:53 UTC

Update Date

2022-03-07 02:55:30 UTC

HMDB ID

HMDB0037773

Secondary Accession Numbers

HMDB37773

Metabolite Identification

Common Name

8-Angeloylegelolide

Description

8-Angeloylegelolide 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-Angeloylegelolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 8-angeloylegelolide has been detected, but not quantified in, herbs and spices. This could make 8-angeloylegelolide a potential biomarker for the consumption of these foods.

Structure

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

HMDB0037773
     RDKit          3D
8-Angeloylegelolide
 49 51  0  0  0  0  0  0  0  0999 V2000
    6.1895    0.3553    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    0.9211    0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572    0.2171    0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9065   -1.2648    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658    0.8693    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    2.1108    0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.1787   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    0.7044   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641    0.4674   -1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -0.9260   -1.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.9873   -1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607   -0.9748   -3.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -1.2072   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -2.2403   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -2.1653   -1.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -1.1505   -0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478   -0.7464    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -0.5102   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558    0.6911    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    0.9523    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    1.1432    2.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    1.1759    3.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451    1.3184    1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    2.7329    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639    0.3824    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315    0.9940    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -0.6576    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288    0.2172   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7414    2.0083    0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489   -1.6525    1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010   -1.5243   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120   -1.7927   -0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    1.8271   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300    0.6919   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561    1.1578   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -2.8424   -2.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292   -2.4551   -0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -1.5920   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496   -1.8261   -3.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581   -2.9805   -2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9203   -1.5454    0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348    0.1917    0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7644   -0.7071    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    1.5652   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1748    1.0922    2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496    3.1114    1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    2.9869    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277    3.3656    2.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -0.6812    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25  8  1  0
 18 13  1  0
 25 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
M  END


  Mrv0541 05061310002D          

 25 27  0  0  0  0            999 V2000
    0.8210    4.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5751    2.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.8217    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4660    3.9357    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
    1.3431    3.1199    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
    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
    1.9881    2.6055    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
  6  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  5  1  0  0  0  0
 19  7  1  0  0  0  0
 19 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21 18  2  0  0  0  0
 22 19  1  0  0  0  0
 23  8  1  0  0  0  0
 23 11  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037773

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(/C)C(=O)OC1CC(C)(O)C2=COC(C)=C2C2OC(=O)C(C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O6/c1-6-9(2)17(20)24-13-7-19(5,22)12-8-23-11(4)15(12)16-14(13)10(3)18(21)25-16/h6,8,10,13-14,16,22H,7H2,1-5H3/b9-6+

> <INCHI_KEY>
UUYOHEAYCPQMKY-RMKNXTFCSA-N

> <FORMULA>
C19H24O6

> <MOLECULAR_WEIGHT>
348.3903

> <EXACT_MASS>
348.1572885

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.73519583597048

> <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 (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.5205686226666666

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.805730522526435

> <JCHEM_PKA_STRONGEST_BASIC>
-2.858443533347751

> <JCHEM_POLAR_SURFACE_AREA>
85.97000000000001

> <JCHEM_REFRACTIVITY>
90.65069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-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 (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037773
     RDKit          3D
8-Angeloylegelolide
 49 51  0  0  0  0  0  0  0  0999 V2000
    6.1895    0.3553    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    0.9211    0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572    0.2171    0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9065   -1.2648    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658    0.8693    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    2.1108    0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.1787   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    0.7044   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641    0.4674   -1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -0.9260   -1.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.9873   -1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607   -0.9748   -3.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -1.2072   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -2.2403   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -2.1653   -1.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -1.1505   -0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478   -0.7464    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -0.5102   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558    0.6911    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    0.9523    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    1.1432    2.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    1.1759    3.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451    1.3184    1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    2.7329    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639    0.3824    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315    0.9940    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -0.6576    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288    0.2172   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7414    2.0083    0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489   -1.6525    1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010   -1.5243   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120   -1.7927   -0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    1.8271   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300    0.6919   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561    1.1578   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -2.8424   -2.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292   -2.4551   -0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -1.5920   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496   -1.8261   -3.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581   -2.9805   -2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9203   -1.5454    0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348    0.1917    0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7644   -0.7071    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    1.5652   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1748    1.0922    2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496    3.1114    1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    2.9869    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277    3.3656    2.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -0.6812    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25  8  1  0
 18 13  1  0
 25 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  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       1.533   8.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.074   5.261   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.001   2.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.737   7.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.803   3.882   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.176  -1.200   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   19                                                            
CONECT    6    1    9                                                       
CONECT    7   13   19                                                       
CONECT    8   12   23                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3   14   18                                                  
CONECT   11    4   15   23                                                  
CONECT   12    8   15   19                                                  
CONECT   13    7   14   24                                                  
CONECT   14   10   13   16                                                  
CONECT   15   11   12   16                                                  
CONECT   16   14   15   25                                                  
CONECT   17    9   20   24                                                  
CONECT   18   10   21   25                                                  
CONECT   19    5    7   12   22                                             
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23    8   11                                                       
CONECT   24   13   17                                                       
CONECT   25   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0037773
HETATM    1  C1  UNL     1       6.189   0.355   0.742  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.856   0.921   0.543  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.757   0.217   0.342  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.906  -1.265   0.321  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.466   0.869   0.152  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.406   2.111   0.181  1.00  0.00           O  
HETATM    7  O2  UNL     1       1.317   0.179  -0.056  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.032   0.704  -0.248  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.364   0.467  -1.668  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.797  -0.926  -1.997  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.183  -1.987  -1.630  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.961  -0.975  -3.385  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.173  -1.207  -1.441  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.977  -2.240  -1.836  1.00  0.00           C  
HETATM   15  O4  UNL     1      -4.080  -2.165  -1.143  1.00  0.00           O  
HETATM   16  C12 UNL     1      -4.063  -1.151  -0.313  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.148  -0.746   0.643  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.856  -0.510  -0.473  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.356   0.691   0.236  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.138   0.952   1.400  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.326   1.143   2.501  1.00  0.00           C  
HETATM   22  O6  UNL     1      -2.613   1.176   3.723  1.00  0.00           O  
HETATM   23  C17 UNL     1      -0.945   1.318   1.973  1.00  0.00           C  
HETATM   24  C18 UNL     1      -0.811   2.733   1.524  1.00  0.00           C  
HETATM   25  C19 UNL     1      -0.964   0.382   0.791  1.00  0.00           C  
HETATM   26  H1  UNL     1       6.732   0.994   1.469  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.107  -0.658   1.213  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.729   0.217  -0.208  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.741   2.008   0.557  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.149  -1.652   1.354  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.801  -1.524  -0.289  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.012  -1.793  -0.002  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.190   1.827  -0.184  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.530   0.692  -2.298  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.156   1.158  -2.021  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.170  -2.842  -2.362  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.129  -2.455  -0.654  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.217  -1.592  -1.582  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.650  -1.826  -3.776  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.758  -2.980  -2.574  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.920  -1.545   0.628  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.635   0.192   0.344  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.764  -0.707   1.683  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.353   1.565  -0.423  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.175   1.092   2.708  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.250   3.111   1.553  1.00  0.00           H  
HETATM   47  H22 UNL     1      -1.298   2.987   0.582  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.328   3.366   2.306  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.003  -0.681   1.092  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3   29
CONECT    3    4    5
CONECT    4   30   31   32
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   25   33
CONECT    9   10   34   35
CONECT   10   11   12   13
CONECT   11   36   37   38
CONECT   12   39
CONECT   13   14   14   18
CONECT   14   15   40
CONECT   15   16
CONECT   16   17   18   18
CONECT   17   41   42   43
CONECT   18   19
CONECT   19   20   25   44
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   25   45
CONECT   24   46   47   48
CONECT   25   49
END

HMDB0037773
     RDKit          3D
8-Angeloylegelolide
 49 51  0  0  0  0  0  0  0  0999 V2000
    6.1895    0.3553    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    0.9211    0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572    0.2171    0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9065   -1.2648    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658    0.8693    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4062    2.1108    0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.1787   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    0.7044   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641    0.4674   -1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7968   -0.9260   -1.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.9873   -1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607   -0.9748   -3.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1726   -1.2072   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -2.2403   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -2.1653   -1.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -1.1505   -0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478   -0.7464    0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -0.5102   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558    0.6911    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    0.9523    1.3998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    1.1432    2.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132    1.1759    3.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451    1.3184    1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    2.7329    1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639    0.3824    0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7315    0.9940    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -0.6576    1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288    0.2172   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7414    2.0083    0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1489   -1.6525    1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010   -1.5243   -0.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120   -1.7927   -0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    1.8271   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300    0.6919   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561    1.1578   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -2.8424   -2.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292   -2.4551   -0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -1.5920   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496   -1.8261   -3.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581   -2.9805   -2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9203   -1.5454    0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6348    0.1917    0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7644   -0.7071    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    1.5652   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1748    1.0922    2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2496    3.1114    1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981    2.9869    0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277    3.3656    2.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -0.6812    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25  8  1  0
 18 13  1  0
 25 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8a-Angeloyloxy-3-oxaartabsin	HMDB
9-Hydroxy-5,9,13-trimethyl-4-oxo-3,12-dioxatricyclo[8.3.0.0²,⁶]trideca-1(13),10-dien-7-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₄O₆

Average Molecular Weight

348.3903

Monoisotopic Molecular Weight

348.1572885

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 (2E)-2-methylbut-2-enoate

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 (2E)-2-methylbut-2-enoate

CAS Registry Number

142449-63-6

SMILES

C\C=C(/C)C(=O)OC1CC(C)(O)C2=COC(C)=C2C2OC(=O)C(C)C12

InChI Identifier

InChI=1S/C19H24O6/c1-6-9(2)17(20)24-13-7-19(5,22)12-8-23-11(4)15(12)16-14(13)10(3)18(21)25-16/h6,8,10,13-14,16,22H,7H2,1-5H3/b9-6+

InChI Key

UUYOHEAYCPQMKY-RMKNXTFCSA-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

Cell membrane (HMDB: HMDB0037773)

Cellular substructure

Membrane (HMDB: HMDB0037773)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037773)

Source

Exogenous

Food

Food (HMDB: HMDB0037773)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037773)

Not Available

Nutrient (HMDB: HMDB0037773)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037773)

Emulsifier (HMDB: HMDB0037773)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 154 °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	0.12 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.52	ChemAxon
logS	-3.5	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	3	ChemAxon
Refractivity	90.65 m³·mol⁻¹	ChemAxon
Polarizability	36.74 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]+	184.109	31661259
DarkChem	[M-H]-	178.077	31661259
DeepCCS	[M-2H]-	216.308	30932474
DeepCCS	[M+Na]+	191.536	30932474
AllCCS	[M+H]+	181.9	32859911
AllCCS	[M+H-H2O]+	179.1	32859911
AllCCS	[M+NH4]+	184.5	32859911
AllCCS	[M+Na]+	185.3	32859911
AllCCS	[M-H]-	187.0	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	187.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Angeloylegelolide	C\C=C(/C)C(=O)OC1CC(C)(O)C2=COC(C)=C2C2OC(=O)C(C)C12	3770.4	Standard polar	33892256
8-Angeloylegelolide	C\C=C(/C)C(=O)OC1CC(C)(O)C2=COC(C)=C2C2OC(=O)C(C)C12	2451.5	Standard non polar	33892256
8-Angeloylegelolide	C\C=C(/C)C(=O)OC1CC(C)(O)C2=COC(C)=C2C2OC(=O)C(C)C12	2508.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Angeloylegelolide,1TMS,isomer #1	C/C=C(\C)C(=O)OC1CC(C)(O[Si](C)(C)C)C2=COC(C)=C2C2OC(=O)C(C)C12	2688.4	Semi standard non polar	33892256
8-Angeloylegelolide,1TBDMS,isomer #1	C/C=C(\C)C(=O)OC1CC(C)(O[Si](C)(C)C(C)(C)C)C2=COC(C)=C2C2OC(=O)C(C)C12	2912.2	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-Angeloylegelolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ai-6942000000-2cc112ed25a289c4d49e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Angeloylegelolide GC-MS (1 TMS) - 70eV, Positive	splash10-06si-9147000000-1654ea5b0b0fd9ae6d40	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Angeloylegelolide 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-Angeloylegelolide 10V, Positive-QTOF	splash10-001j-2049000000-a2fd5d77177e7e7c805d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 20V, Positive-QTOF	splash10-001i-9273000000-ed83deb7d90e5130a970	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 40V, Positive-QTOF	splash10-0f89-9120000000-65e5085e96e60a68b9b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 10V, Negative-QTOF	splash10-0002-0029000000-d234db74b2beda81b8aa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 20V, Negative-QTOF	splash10-0002-5089000000-be6594ad538da50c01c7	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 40V, Negative-QTOF	splash10-0a5a-7590000000-6d5f3b9addb84cf985a1	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 10V, Negative-QTOF	splash10-0002-1090000000-bdd65c7ad84f1e7fbbd3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 20V, Negative-QTOF	splash10-0002-5090000000-d08b05cb1db14a42595a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 40V, Negative-QTOF	splash10-0002-5290000000-890962b9f8f5e45b5399	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 10V, Positive-QTOF	splash10-0002-0090000000-5e13c0e43882b450a896	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 20V, Positive-QTOF	splash10-001j-0090000000-48cecb8c871ce701193c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Angeloylegelolide 40V, Positive-QTOF	splash10-0a4i-9320000000-e728d5958846ba559bdb	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB016915

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

131752230

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-Angeloylegelolide (HMDB0037773)

MOL for HMDB0037773 (8-Angeloylegelolide)

3D MOL for HMDB0037773 (8-Angeloylegelolide)

3D SDF for HMDB0037773 (8-Angeloylegelolide)

3D-SDF for HMDB0037773 (8-Angeloylegelolide)

PDB for HMDB0037773 (8-Angeloylegelolide)

3D PDB for HMDB0037773 (8-Angeloylegelolide)

SMILES for HMDB0037773 (8-Angeloylegelolide)

INCHI for HMDB0037773 (8-Angeloylegelolide)

Structure for HMDB0037773 (8-Angeloylegelolide)

3D Structure for HMDB0037773 (8-Angeloylegelolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra