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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:27 UTC

Update Date

2022-03-07 02:53:27 UTC

HMDB ID

HMDB0032731

Secondary Accession Numbers

HMDB32731

Metabolite Identification

Common Name

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

Description

(1E,4Z,6a,8b,10a)-8-Angeloyloxy-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-Angeloyloxy-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 05061306392D          

 27 28  0  0  0  0            999 V2000
    0.7395   -0.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482    0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746   -0.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -0.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -1.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574   -1.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    0.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    1.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    1.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714   -0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    0.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3659    0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572    1.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344    2.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6797    1.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    2.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112    3.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2729   -0.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813    1.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993    0.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    0.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061   -1.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148   -2.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -2.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 25  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 17  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 22  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0032731
     RDKit          3D
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrie...
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.6050    0.9499   -2.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279    1.3784   -1.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759    2.7368   -1.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    3.7914   -1.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803    2.6666   -1.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699    1.4804   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8868    0.9851   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004    0.5562   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0398    0.0621   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9859    0.8837   -0.1406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    0.5109    1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610    0.6947    1.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    0.3100    1.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4215   -0.6824    1.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5749   -1.7585    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2344   -3.0549    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432   -1.9679    0.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218   -1.6304   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1098   -0.2604   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -0.3457   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    0.2089    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756    0.7940    1.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791    0.1377    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4240   -0.5544   -0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7186    0.6783    1.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1855    0.6424    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059    0.5601   -1.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2499    1.6770   -2.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914   -0.0912   -2.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118    1.8575    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    0.9876   -2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1468    0.2353   -1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2347   -0.9711   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7112    1.8261   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404    1.0484    2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382   -0.7374    2.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -2.8588    2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162   -3.8398    0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -3.3492    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -2.5866   -0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320   -2.3531    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751   -1.7774   -1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0318    0.2873    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7852    0.2138   -1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -1.2073   -0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -1.1459   -1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423    1.1739    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5632   -0.3375    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268    1.4143    0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6242    0.8718    2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -0.1108   -2.0025 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  2  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
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
M  END

  Mrv0541 05061306392D          

 27 28  0  0  0  0            999 V2000
    0.7395   -0.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4482    0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0746   -0.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -0.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308   -1.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574   -1.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0764    0.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    1.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    1.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9714   -0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100    0.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3659    0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572    1.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344    2.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6797    1.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2025    2.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112    3.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2729   -0.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4813    1.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993    0.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    0.3010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061   -1.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148   -2.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -2.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 25  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 17  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 22  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032731

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O7/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/h5-8,15-17,21,25H,3,9-10H2,1-2,4H3/b7-6-,11-5+,13-8-

> <INCHI_KEY>
NEJKUCWBWUMARI-IOZUUXKMSA-N

> <FORMULA>
C20H24O7

> <MOLECULAR_WEIGHT>
376.4004

> <EXACT_MASS>
376.152203122

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.21356549268255

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

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
1.8292430333333336

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.478838404880754

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.1964517824796355

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8183420633325786

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
99.61959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e-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 (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032731
     RDKit          3D
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrie...
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.6050    0.9499   -2.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279    1.3784   -1.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759    2.7368   -1.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    3.7914   -1.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803    2.6666   -1.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699    1.4804   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8868    0.9851   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004    0.5562   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0398    0.0621   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9859    0.8837   -0.1406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    0.5109    1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610    0.6947    1.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    0.3100    1.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4215   -0.6824    1.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5749   -1.7585    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2344   -3.0549    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432   -1.9679    0.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218   -1.6304   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1098   -0.2604   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -0.3457   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    0.2089    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756    0.7940    1.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791    0.1377    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4240   -0.5544   -0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7186    0.6783    1.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1855    0.6424    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059    0.5601   -1.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2499    1.6770   -2.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914   -0.0912   -2.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118    1.8575    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    0.9876   -2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1468    0.2353   -1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2347   -0.9711   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7112    1.8261   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404    1.0484    2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382   -0.7374    2.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -2.8588    2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162   -3.8398    0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -3.3492    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -2.5866   -0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320   -2.3531    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751   -1.7774   -1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0318    0.2873    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7852    0.2138   -1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -1.2073   -0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -1.1459   -1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423    1.1739    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5632   -0.3375    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268    1.4143    0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6242    0.8718    2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -0.1108   -2.0025 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  2  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
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  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       1.380  -0.468   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.837   0.973   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.139  -0.219   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.405  -1.660   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.924  -1.909   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.720  -2.281   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.900  -0.718   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.876   0.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.332   1.914   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.813   2.164   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.788   3.355   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.813  -1.279   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.885   0.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.683   1.222   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.227   2.663   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.251   3.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.269   3.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.245   4.796   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.701   6.237   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.243  -1.472   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.765   2.591   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.172   1.106   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.613   0.562   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.091  -2.602   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.571  -2.851   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.028  -4.292   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.004  -5.483   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    1    6    8   20                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13   12   14   22                                                  
CONECT   14    2   13   15                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    7                                                            
CONECT   21   15   22                                                       
CONECT   22   13   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25    4   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0032731
HETATM    1  C1  UNL     1       1.605   0.950  -2.526  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.528   1.378  -1.912  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.076   2.737  -1.780  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.751   3.791  -1.871  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.280   2.667  -1.526  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.570   1.480  -0.759  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.887   0.985  -1.183  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.700   0.556  -0.241  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.040   0.062  -0.762  1.00  0.00           C  
HETATM   10  O3  UNL     1      -5.986   0.884  -0.141  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.466   0.511   1.181  1.00  0.00           C  
HETATM   12  O4  UNL     1      -4.561   0.695   1.868  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.298   0.310   1.960  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.421  -0.682   1.884  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.575  -1.758   0.918  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.234  -3.055   1.688  1.00  0.00           C  
HETATM   17  O5  UNL     1      -2.843  -1.968   0.429  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.522  -1.630  -0.139  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.110  -0.260  -0.090  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.530  -0.346  -0.310  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.438   0.209   0.577  1.00  0.00           C  
HETATM   22  O7  UNL     1       1.976   0.794   1.587  1.00  0.00           O  
HETATM   23  C16 UNL     1       3.879   0.138   0.380  1.00  0.00           C  
HETATM   24  C17 UNL     1       4.424  -0.554  -0.815  1.00  0.00           C  
HETATM   25  C18 UNL     1       4.719   0.678   1.246  1.00  0.00           C  
HETATM   26  C19 UNL     1       6.185   0.642   1.108  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.506   0.560  -1.194  1.00  0.00           C  
HETATM   28  H1  UNL     1       2.250   1.677  -2.997  1.00  0.00           H  
HETATM   29  H2  UNL     1       1.891  -0.091  -2.593  1.00  0.00           H  
HETATM   30  H3  UNL     1      -1.512   1.857   0.270  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.143   0.988  -2.236  1.00  0.00           H  
HETATM   32  H5  UNL     1      -5.147   0.235  -1.847  1.00  0.00           H  
HETATM   33  H6  UNL     1      -5.235  -0.971  -0.476  1.00  0.00           H  
HETATM   34  H7  UNL     1      -5.711   1.826  -0.130  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.040   1.048   2.746  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.538  -0.737   2.545  1.00  0.00           H  
HETATM   37  H10 UNL     1      -0.404  -2.859   2.408  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.916  -3.840   0.991  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.110  -3.349   2.302  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.769  -2.587  -0.338  1.00  0.00           H  
HETATM   41  H14 UNL     1       0.332  -2.353   0.018  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.975  -1.777  -1.141  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.032   0.287   0.840  1.00  0.00           H  
HETATM   44  H17 UNL     1       4.785   0.214  -1.523  1.00  0.00           H  
HETATM   45  H18 UNL     1       5.276  -1.207  -0.512  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.635  -1.146  -1.324  1.00  0.00           H  
HETATM   47  H20 UNL     1       4.242   1.174   2.107  1.00  0.00           H  
HETATM   48  H21 UNL     1       6.563  -0.338   0.810  1.00  0.00           H  
HETATM   49  H22 UNL     1       6.527   1.414   0.383  1.00  0.00           H  
HETATM   50  H23 UNL     1       6.624   0.872   2.122  1.00  0.00           H  
HETATM   51  H24 UNL     1      -0.923  -0.111  -2.002  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   25
CONECT   24   44   45   46
CONECT   25   26   47
CONECT   26   48   49   50
CONECT   27   51
END

HMDB0032731
     RDKit          3D
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrie...
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.6050    0.9499   -2.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279    1.3784   -1.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759    2.7368   -1.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    3.7914   -1.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803    2.6666   -1.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5699    1.4804   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8868    0.9851   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004    0.5562   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0398    0.0621   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9859    0.8837   -0.1406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665    0.5109    1.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5610    0.6947    1.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2979    0.3100    1.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4215   -0.6824    1.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5749   -1.7585    0.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2344   -3.0549    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432   -1.9679    0.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218   -1.6304   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1098   -0.2604   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -0.3457   -0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    0.2089    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9756    0.7940    1.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8791    0.1377    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4240   -0.5544   -0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7186    0.6783    1.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1855    0.6424    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059    0.5601   -1.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2499    1.6770   -2.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8914   -0.0912   -2.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5118    1.8575    0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    0.9876   -2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1468    0.2353   -1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2347   -0.9711   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7112    1.8261   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404    1.0484    2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382   -0.7374    2.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -2.8588    2.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9162   -3.8398    0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -3.3492    2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7690   -2.5866   -0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320   -2.3531    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751   -1.7774   -1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0318    0.2873    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7852    0.2138   -1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -1.2073   -0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -1.1459   -1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2423    1.1739    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5632   -0.3375    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268    1.4143    0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6242    0.8718    2.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -0.1108   -2.0025 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  2  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
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  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 (2E)-2-methylbut-2-enoic acid	HMDB

Chemical Formula

C₂₀H₂₄O₇

Average Molecular Weight

376.4004

Monoisotopic Molecular Weight

376.152203122

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

Traditional Name

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

CAS Registry Number

84588-88-5

SMILES

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

InChI Identifier

InChI=1S/C20H24O7/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/h5-8,15-17,21,25H,3,9-10H2,1-2,4H3/b7-6-,11-5+,13-8-

InChI Key

NEJKUCWBWUMARI-IOZUUXKMSA-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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032731)

Source

Endogenous

Endogenous (HMDB: HMDB0032731)

Animal

Animal (HMDB: HMDB0032731)

Exogenous

Food

Food (HMDB: HMDB0032731)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0032731)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032731)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032731)

Lipid metabolism pathway (HMDB: HMDB0032731)

Cellular process

Cell signaling (HMDB: HMDB0032731)

Biochemical process

Lipid transport (HMDB: HMDB0032731)

Role

Biological role

Energy source (HMDB: HMDB0032731)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032731)

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	0.38 g/L	ALOGPS
logP	0.83	ALOGPS
logP	1.83	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.2	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	4	ChemAxon
Refractivity	99.62 m³·mol⁻¹	ChemAxon
Polarizability	37.21 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]-	225.12	30932474
DeepCCS	[M+Na]+	200.348	30932474
AllCCS	[M+H]+	189.9	32859911
AllCCS	[M+H-H2O]+	187.1	32859911
AllCCS	[M+NH4]+	192.4	32859911
AllCCS	[M+Na]+	193.1	32859911
AllCCS	[M-H]-	189.8	32859911
AllCCS	[M+Na-2H]-	190.2	32859911
AllCCS	[M+HCOO]-	190.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide	C\C=C(/C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12	4402.1	Standard polar	33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide	C\C=C(/C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12	2873.3	Standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide	C\C=C(/C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12	2928.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-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)=C/C)C12	3075.0	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-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)=C/C)C12	2941.5	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-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)=C/C)C12	3011.0	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-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)=C/C)C12	3297.7	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-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)=C/C)C12	3177.4	Semi standard non polar	33892256
(1E,4Z,6a,8b,10a)-8-Angeloyloxy-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)=C/C)C12	3450.5	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-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9016000000-bef2adbc2c92f96a5561	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide GC-MS (2 TMS) - 70eV, Positive	splash10-053r-9000200000-f51b0b0c97c620e21b5f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-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-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOF	splash10-0a6r-1029000000-c8039e5eac9db449ee78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOF	splash10-0a6r-7098000000-3a3561582a65f03839ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOF	splash10-0kcr-9030000000-703e73dd13c0ae75111b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOF	splash10-004i-0019000000-bff603d61758396f465f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOF	splash10-056s-3029000000-9b5dfb1c37a88b9b4718	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOF	splash10-052b-9531000000-88a0ee7cf89497b3968c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Negative-QTOF	splash10-004i-1091000000-4bc3070da694ddf765ee	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Negative-QTOF	splash10-004j-5090000000-b8a31a8898119e2691c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Negative-QTOF	splash10-0bvj-2090000000-43dbba88bb426f1099b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 10V, Positive-QTOF	splash10-0a6r-0090000000-d4a1b38335caef243fae	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 20V, Positive-QTOF	splash10-0a4i-0090000000-a75aa32864f24d08a45d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide 40V, Positive-QTOF	splash10-0aor-9040000000-1f5b5a179dee9f5c3ad6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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

FDB010692

KNApSAcK ID

Not Available

Chemspider ID

35013476

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751292

PDB ID

Not Available

ChEBI ID

175829

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-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide (HMDB0032731)

MOL for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D MOL for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D SDF for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D-SDF for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

PDB for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D PDB for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

SMILES for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

INCHI for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

Structure for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide)

3D Structure for HMDB0032731 ((1E,4Z,6a,8b,10a)-8-Angeloyloxy-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