Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:38:04 UTC

Update Date

2022-03-07 02:56:50 UTC

HMDB ID

HMDB0041002

Secondary Accession Numbers

HMDB41002

Metabolite Identification

Common Name

(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide

Description

(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a small amount of articles have been published on (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide.

Structure

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


  Mrv0541 05061312192D          

 27 28  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8668    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902    5.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737    1.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093    1.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808    3.7987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.0366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968    0.4548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    4.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    1.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  2  0  0  0  0
 11  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  3  2  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20  4  1  0  0  0  0
 20  7  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 22 14  2  0  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
 25 20  1  0  0  0  0
 26 15  1  0  0  0  0
 26 19  1  0  0  0  0
 27 16  1  0  0  0  0
 27 18  1  0  0  0  0
M  END

HMDB0041002
     RDKit          3D
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-ge...
 53 54  0  0  0  0  0  0  0  0999 V2000
   -0.8914    3.0572   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    2.6083    0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062    3.4502    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832    4.5921    0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    2.7746    1.9352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    1.4085    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0286    1.2005    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333    0.2792    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5383    0.2952   -1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0106    1.2802   -2.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3610   -0.6515    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6911   -0.8871    0.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9675   -1.4406    2.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8201   -1.9726    2.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939   -1.8057    1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -3.2448    1.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386   -1.7047    0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005   -0.9309    2.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734    0.2457    1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -0.0685   -0.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -0.1174   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.1637    0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -0.4837   -1.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925   -0.1263   -1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956    0.0391   -2.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -0.4716   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    1.5282    1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    3.9652   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    2.4070   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    0.7507    2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    1.8897   -0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6364    0.3593   -1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171   -0.6694   -1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    2.1935   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271   -1.6788    3.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -2.5806    3.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0121   -3.6663    0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0020   -3.1816    1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -3.8895    2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372   -2.5352   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0947   -0.6687    3.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337   -1.5108    2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604    0.4475    1.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773   -1.6189   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9368    0.6330   -1.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282   -1.0220   -1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282    0.3927   -2.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712   -0.3537   -3.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495    1.1363   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -0.4822   -3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.1744   -2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444   -1.5161   -2.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848    2.0073    2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  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 26  1  0
 19 27  1  0
 27  2  1  0
 27  6  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
M  END


  Mrv0541 05061312192D          

 27 28  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8668    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2902    5.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6737    1.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093    1.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808    3.7987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.0366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968    0.4548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    4.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    1.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  2  0  0  0  0
 11  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  3  2  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20  4  1  0  0  0  0
 20  7  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 22 14  2  0  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
 25 20  1  0  0  0  0
 26 15  1  0  0  0  0
 26 19  1  0  0  0  0
 27 16  1  0  0  0  0
 27 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041002

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O7/c1-5-11(2)18(23)27-16-9-20(4,25)7-6-14(22)13(10-21)8-15-17(16)12(3)19(24)26-15/h6-8,11,15-17,21,25H,3,5,9-10H2,1-2,4H3/b7-6-,13-8-

> <INCHI_KEY>
CUICTWWBLRZLES-DGOUITMESA-N

> <FORMULA>
C20H26O7

> <MOLECULAR_WEIGHT>
378.4162

> <EXACT_MASS>
378.167853186

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
38.331463434968654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3aH,4H,5H,6H,9H,11aH-cyclodeca[b]furan-4-yl 2-methylbutanoate

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
1.7455219993333333

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.478886523333092

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.2065431928502095

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8183420631235476

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
98.74369999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-3aH,4H,5H,11aH-cyclodeca[b]furan-4-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041002
     RDKit          3D
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-ge...
 53 54  0  0  0  0  0  0  0  0999 V2000
   -0.8914    3.0572   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    2.6083    0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062    3.4502    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832    4.5921    0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    2.7746    1.9352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    1.4085    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0286    1.2005    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333    0.2792    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5383    0.2952   -1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0106    1.2802   -2.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3610   -0.6515    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6911   -0.8871    0.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9675   -1.4406    2.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8201   -1.9726    2.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939   -1.8057    1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -3.2448    1.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386   -1.7047    0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005   -0.9309    2.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734    0.2457    1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -0.0685   -0.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -0.1174   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.1637    0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -0.4837   -1.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925   -0.1263   -1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956    0.0391   -2.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -0.4716   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    1.5282    1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    3.9652   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    2.4070   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    0.7507    2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    1.8897   -0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6364    0.3593   -1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171   -0.6694   -1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    2.1935   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271   -1.6788    3.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -2.5806    3.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0121   -3.6663    0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0020   -3.1816    1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -3.8895    2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372   -2.5352   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0947   -0.6687    3.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337   -1.5108    2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604    0.4475    1.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773   -1.6189   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9368    0.6330   -1.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282   -1.0220   -1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282    0.3927   -2.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712   -0.3537   -3.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495    1.1363   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -0.4822   -3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.1744   -2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444   -1.5161   -2.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848    2.0073    2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  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 26  1  0
 19 27  1  0
 27  2  1  0
 27  6  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  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       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.671   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.351   3.910   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.142   9.917   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.858   3.590   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.484   2.183   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.804   7.091   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   7.535   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.714   0.849   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.152   8.203   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.016   2.344   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   20                                                            
CONECT    5    1   11                                                       
CONECT    6    7   14                                                       
CONECT    7    6   20                                                       
CONECT    8   13   15                                                       
CONECT    9   16   20                                                       
CONECT   10   13   21                                                       
CONECT   11    2    5   18                                                  
CONECT   12    3   17   19                                                  
CONECT   13    8   10   14                                                  
CONECT   14    6   13   22                                                  
CONECT   15    8   17   26                                                  
CONECT   16    9   17   27                                                  
CONECT   17   12   15   16                                                  
CONECT   18   11   23   27                                                  
CONECT   19   12   24   26                                                  
CONECT   20    4    7    9   25                                             
CONECT   21   10                                                            
CONECT   22   14                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   15   19                                                       
CONECT   27   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0041002
HETATM    1  C1  UNL     1      -0.891   3.057  -0.625  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.232   2.608   0.421  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.906   3.450   0.902  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.283   4.592   0.478  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.529   2.775   1.935  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.289   1.409   1.631  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.029   1.200   0.366  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.933   0.279   0.146  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.538   0.295  -1.270  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.011   1.280  -2.040  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.361  -0.652   1.122  1.00  0.00           C  
HETATM   12  O4  UNL     1       4.691  -0.887   0.940  1.00  0.00           O  
HETATM   13  C9  UNL     1       2.968  -1.441   2.217  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.820  -1.973   2.448  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.694  -1.806   1.528  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.075  -3.245   1.541  1.00  0.00           C  
HETATM   17  O5  UNL     1       1.039  -1.705   0.191  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.400  -0.931   2.009  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.873   0.246   1.249  1.00  0.00           C  
HETATM   20  O6  UNL     1      -1.439  -0.068  -0.005  1.00  0.00           O  
HETATM   21  C15 UNL     1      -2.742  -0.117  -0.368  1.00  0.00           C  
HETATM   22  O7  UNL     1      -3.525   0.164   0.543  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.153  -0.484  -1.745  1.00  0.00           C  
HETATM   24  C17 UNL     1      -4.592  -0.126  -1.966  1.00  0.00           C  
HETATM   25  C18 UNL     1      -2.296   0.039  -2.832  1.00  0.00           C  
HETATM   26  C19 UNL     1      -0.854  -0.472  -2.708  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.227   1.528   1.339  1.00  0.00           C  
HETATM   28  H1  UNL     1      -0.700   3.965  -1.169  1.00  0.00           H  
HETATM   29  H2  UNL     1      -1.715   2.407  -0.973  1.00  0.00           H  
HETATM   30  H3  UNL     1       1.507   0.751   2.443  1.00  0.00           H  
HETATM   31  H4  UNL     1       1.785   1.890  -0.466  1.00  0.00           H  
HETATM   32  H5  UNL     1       4.636   0.359  -1.202  1.00  0.00           H  
HETATM   33  H6  UNL     1       3.317  -0.669  -1.773  1.00  0.00           H  
HETATM   34  H7  UNL     1       3.359   2.194  -1.814  1.00  0.00           H  
HETATM   35  H8  UNL     1       3.727  -1.679   3.068  1.00  0.00           H  
HETATM   36  H9  UNL     1       1.653  -2.581   3.384  1.00  0.00           H  
HETATM   37  H10 UNL     1      -0.012  -3.666   0.541  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.002  -3.182   1.882  1.00  0.00           H  
HETATM   39  H12 UNL     1       0.549  -3.889   2.279  1.00  0.00           H  
HETATM   40  H13 UNL     1       1.337  -2.535  -0.226  1.00  0.00           H  
HETATM   41  H14 UNL     1      -0.095  -0.669   3.074  1.00  0.00           H  
HETATM   42  H15 UNL     1      -1.334  -1.511   2.218  1.00  0.00           H  
HETATM   43  H16 UNL     1      -1.860   0.447   1.792  1.00  0.00           H  
HETATM   44  H17 UNL     1      -3.077  -1.619  -1.811  1.00  0.00           H  
HETATM   45  H18 UNL     1      -4.937   0.633  -1.199  1.00  0.00           H  
HETATM   46  H19 UNL     1      -5.228  -1.022  -1.954  1.00  0.00           H  
HETATM   47  H20 UNL     1      -4.728   0.393  -2.953  1.00  0.00           H  
HETATM   48  H21 UNL     1      -2.671  -0.354  -3.815  1.00  0.00           H  
HETATM   49  H22 UNL     1      -2.250   1.136  -2.918  1.00  0.00           H  
HETATM   50  H23 UNL     1      -0.399  -0.482  -3.743  1.00  0.00           H  
HETATM   51  H24 UNL     1      -0.272   0.174  -2.033  1.00  0.00           H  
HETATM   52  H25 UNL     1      -0.944  -1.516  -2.395  1.00  0.00           H  
HETATM   53  H26 UNL     1      -0.585   2.007   2.314  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3   27
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   27   30
CONECT    7    8    8   31
CONECT    8    9   11
CONECT    9   10   32   33
CONECT   10   34
CONECT   11   12   12   13
CONECT   13   14   14   35
CONECT   14   15   36
CONECT   15   16   17   18
CONECT   16   37   38   39
CONECT   17   40
CONECT   18   19   41   42
CONECT   19   20   27   43
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   25   44
CONECT   24   45   46   47
CONECT   25   26   48   49
CONECT   26   50   51   52
CONECT   27   53
END

HMDB0041002
     RDKit          3D
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-ge...
 53 54  0  0  0  0  0  0  0  0999 V2000
   -0.8914    3.0572   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    2.6083    0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062    3.4502    0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832    4.5921    0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    2.7746    1.9352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    1.4085    1.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0286    1.2005    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333    0.2792    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5383    0.2952   -1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0106    1.2802   -2.0399 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3610   -0.6515    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6911   -0.8871    0.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9675   -1.4406    2.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8201   -1.9726    2.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939   -1.8057    1.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0750   -3.2448    1.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0386   -1.7047    0.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005   -0.9309    2.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734    0.2457    1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -0.0685   -0.0052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7422   -0.1174   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246    0.1637    0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1531   -0.4837   -1.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5925   -0.1263   -1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956    0.0391   -2.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535   -0.4716   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    1.5282    1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    3.9652   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    2.4070   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    0.7507    2.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    1.8897   -0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6364    0.3593   -1.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171   -0.6694   -1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592    2.1935   -1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271   -1.6788    3.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -2.5806    3.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0121   -3.6663    0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0020   -3.1816    1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -3.8895    2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372   -2.5352   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0947   -0.6687    3.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337   -1.5108    2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604    0.4475    1.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773   -1.6189   -1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9368    0.6330   -1.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282   -1.0220   -1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282    0.3927   -2.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6712   -0.3537   -3.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495    1.1363   -2.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   -0.4822   -3.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2719    0.1744   -2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444   -1.5161   -2.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848    2.0073    2.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  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 26  1  0
 19 27  1  0
 27  2  1  0
 27  6  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3ah,4H,5H,6H,9H,11ah-cyclodeca[b]furan-4-yl 2-methylbutanoic acid	HMDB

Chemical Formula

C₂₀H₂₆O₇

Average Molecular Weight

378.4162

Monoisotopic Molecular Weight

378.167853186

IUPAC Name

6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3aH,4H,5H,6H,9H,11aH-cyclodeca[b]furan-4-yl 2-methylbutanoate

Traditional Name

6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-3aH,4H,5H,11aH-cyclodeca[b]furan-4-yl 2-methylbutanoate

CAS Registry Number

166528-79-6

SMILES

CCC(C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C20H26O7/c1-5-11(2)18(23)27-16-9-20(4,25)7-6-14(22)13(10-21)8-15-17(16)12(3)19(24)26-15/h6-8,11,15-17,21,25H,3,5,9-10H2,1-2,4H3/b7-6-,13-8-

InChI Key

CUICTWWBLRZLES-DGOUITMESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041002)

Cellular substructure

Extracellular (HMDB: HMDB0041002)
Cytoplasm (HMDB: HMDB0041002)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041002)

Source

Endogenous

Endogenous (HMDB: HMDB0041002)

Animal

Animal (HMDB: HMDB0041002)

Exogenous

Food

Food (HMDB: HMDB0041002)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0041002)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0041002)

Cellular process

Cell signaling (HMDB: HMDB0041002)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0041002)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0041002)

Nutrient

Nutrient (HMDB: HMDB0041002)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041002)

Emulsifier (HMDB: HMDB0041002)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.58 g/L	ALOGPS
logP	0.88	ALOGPS
logP	1.75	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.74 m³·mol⁻¹	ChemAxon
Polarizability	38.33 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M-2H]-	229.248	30932474
DeepCCS	[M+Na]+	204.619	30932474
AllCCS	[M+H]+	190.5	32859911
AllCCS	[M+H-H2O]+	187.8	32859911
AllCCS	[M+NH4]+	192.9	32859911
AllCCS	[M+Na]+	193.6	32859911
AllCCS	[M-H]-	189.9	32859911
AllCCS	[M+Na-2H]-	190.4	32859911
AllCCS	[M+HCOO]-	191.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide	CCC(C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12	4006.9	Standard polar	33892256
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide	CCC(C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12	2664.2	Standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide	CCC(C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12	2796.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TMS,isomer #1	C=C1C(=O)OC2/C=C(/CO)C(=O)/C=C\C(C)(O[Si](C)(C)C)CC(OC(=O)C(C)CC)C12	3012.1	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TMS,isomer #2	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C)C(=O)/C=C\C(C)(O)CC(OC(=O)C(C)CC)C12	2883.7	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,2TMS,isomer #1	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C)C(=O)/C=C\C(C)(O[Si](C)(C)C)CC(OC(=O)C(C)CC)C12	2942.3	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/CO)C(=O)/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(OC(=O)C(C)CC)C12	3234.1	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,1TBDMS,isomer #2	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C(C)(C)C)C(=O)/C=C\C(C)(O)CC(OC(=O)C(C)CC)C12	3115.3	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide,2TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C(C)(C)C)C(=O)/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(OC(=O)C(C)CC)C12	3379.1	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 - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvi-9037000000-d0cb39a4adfcecf2855b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-9000210000-95688c8f7f052f2414d5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 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 - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOF	splash10-03fr-1029000000-68c53521c603a2bd4e57	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOF	splash10-06tu-7098000000-20cb1ccbee6b4bc13737	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOF	splash10-0a4r-9030000000-b1e4965a98af056bafb9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOF	splash10-004i-0009000000-59286d1dc8d0f25b6559	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOF	splash10-057i-1119000000-9a335c3ec97b36b1656e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOF	splash10-0k9m-2191000000-237801f29f2b71480d2d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOF	splash10-004i-0198000000-0cde953b424455423288	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOF	splash10-004i-0190000000-ceb0cbe25d74aabb64b4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOF	splash10-03fr-1090000000-6b253f92c9358b106a6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOF	splash10-056r-0090000000-8b908888385c901bc8a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOF	splash10-0bvi-0090000000-e1d61d3a34323452011f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOF	splash10-0avi-9030000000-8db442f75ec3d1922b24	2021-09-22	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

FDB020862

KNApSAcK ID

Not Available

Chemspider ID

35015074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753010

PDB ID

Not Available

ChEBI ID

175855

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide (HMDB0041002)

MOL for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D MOL for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D SDF for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D-SDF for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

PDB for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D PDB for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

SMILES for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

INCHI for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

Structure for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D Structure for HMDB0041002 ((1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra