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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:53:36 UTC

Update Date

2022-03-07 02:56:56 UTC

HMDB ID

HMDB0041228

Secondary Accession Numbers

HMDB41228

Metabolite Identification

Common Name

6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide

Description

6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide.

Structure

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


  Mrv0541 05061312292D          

 27 29  0  0  0  0            999 V2000
    1.8500   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  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  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  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 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 27 20  1  0  0  0  0
M  END

HMDB0041228
     RDKit          3D
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide
 55 57  0  0  0  0  0  0  0  0999 V2000
    5.2165   -0.8290    1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8311   -0.4142    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    0.1300   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7179    0.3146   -1.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2304    0.5274   -0.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.0430   -1.9876 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1563    0.3770   -0.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    0.7302   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907    1.7959    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    2.5486    1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191    2.5520    1.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644    3.3718    2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189    4.2378    3.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    3.0529    1.6464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061    2.1396    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845    2.8639   -0.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138    0.9442    0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869    0.4751    1.9112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5215   -0.1626   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195   -1.3811    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9193   -2.6228   -0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206   -2.7337   -1.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -3.6236   -0.3072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -1.4478   -1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -0.9054   -2.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0746   -0.4676   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7965   -1.1504    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1585   -1.8842    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582   -0.2336    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187   -0.6862    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455   -0.5701    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0751   -0.6558   -1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852    0.9022   -2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    0.9139   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    1.1709   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6082    3.2639    2.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9829    2.8132    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6753    1.5422    2.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6521    3.5539   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978    1.2647    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899    1.1955    2.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922    0.1383   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376   -1.4773    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3945   -1.1233   -0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -3.4832    0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.8201   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5362   -3.2526   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489   -3.8918   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -1.7041   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.1726   -2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1254   -1.3776   -3.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.1824   -3.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736   -1.4546    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872   -2.0524    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -0.4479    1.9616 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  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26  8  1  0
 15  9  1  0
 26 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
M  END


  Mrv0541 05061312292D          

 27 29  0  0  0  0            999 V2000
    1.8500   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  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  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16 14  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 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 27 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041228

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(/C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O)C(C)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O7/c1-6-9(2)17(23)26-16-14-10(3)18(24)27-20(14,25)15(22)12-7-8-13(21)11(4)19(12,16)5/h6,11-13,15-16,21-22,25H,7-8H2,1-5H3/b9-6+

> <INCHI_KEY>
MSDFIROCDXOIAM-RMKNXTFCSA-N

> <FORMULA>
C20H28O7

> <MOLECULAR_WEIGHT>
380.4321

> <EXACT_MASS>
380.18350325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.59387128619885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
2.32461828

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.723098657487757

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.290212623195357

> <JCHEM_PKA_STRONGEST_BASIC>
-2.826600616314903

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
96.68439999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxo-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041228
     RDKit          3D
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide
 55 57  0  0  0  0  0  0  0  0999 V2000
    5.2165   -0.8290    1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8311   -0.4142    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    0.1300   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7179    0.3146   -1.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2304    0.5274   -0.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.0430   -1.9876 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1563    0.3770   -0.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    0.7302   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907    1.7959    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    2.5486    1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191    2.5520    1.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644    3.3718    2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189    4.2378    3.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    3.0529    1.6464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061    2.1396    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845    2.8639   -0.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138    0.9442    0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869    0.4751    1.9112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5215   -0.1626   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195   -1.3811    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9193   -2.6228   -0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206   -2.7337   -1.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -3.6236   -0.3072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -1.4478   -1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -0.9054   -2.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0746   -0.4676   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7965   -1.1504    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1585   -1.8842    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582   -0.2336    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187   -0.6862    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455   -0.5701    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0751   -0.6558   -1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852    0.9022   -2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    0.9139   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    1.1709   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6082    3.2639    2.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9829    2.8132    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6753    1.5422    2.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6521    3.5539   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978    1.2647    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899    1.1955    2.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922    0.1383   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376   -1.4773    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3945   -1.1233   -0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -3.4832    0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.8201   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5362   -3.2526   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489   -3.8918   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -1.7041   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.1726   -2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1254   -1.3776   -3.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.1824   -3.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736   -1.4546    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872   -2.0524    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -0.4479    1.9616 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  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26  8  1  0
 15  9  1  0
 26 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  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       3.453  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.453  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.455  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.453  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.626   3.072   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.322   2.016   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    8   12                                                       
CONECT    8    7   13                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3   14   18                                                  
CONECT   11    4   13   19                                                  
CONECT   12    7   15   19                                                  
CONECT   13    8   11   21                                                  
CONECT   14   10   16   20                                                  
CONECT   15   12   20   22                                                  
CONECT   16   14   19   26                                                  
CONECT   17    9   23   26                                                  
CONECT   18   10   24   27                                                  
CONECT   19    5   11   12   16                                             
CONECT   20   14   15   25   27                                             
CONECT   21   13                                                            
CONECT   22   15                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   20                                                            
CONECT   26   16   17                                                       
CONECT   27   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0041228
HETATM    1  C1  UNL     1       5.217  -0.829   1.010  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.831  -0.414   0.649  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.588   0.130  -0.528  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.718   0.315  -1.467  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.230   0.527  -0.861  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.027   1.043  -1.988  1.00  0.00           O  
HETATM    7  O2  UNL     1       1.156   0.377  -0.027  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.155   0.730  -0.276  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.691   1.796   0.642  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.066   2.549   1.505  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.419   2.552   1.818  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.064   3.372   2.168  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.819   4.238   3.078  1.00  0.00           O  
HETATM   14  O4  UNL     1      -2.295   3.053   1.646  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.106   2.140   0.626  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.384   2.864  -0.575  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.014   0.944   0.629  1.00  0.00           C  
HETATM   18  O6  UNL     1      -3.187   0.475   1.911  1.00  0.00           O  
HETATM   19  C13 UNL     1      -2.521  -0.163  -0.268  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.319  -1.381   0.047  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.919  -2.623  -0.644  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.521  -2.734  -1.103  1.00  0.00           C  
HETATM   23  O7  UNL     1      -0.757  -3.624  -0.307  1.00  0.00           O  
HETATM   24  C17 UNL     1      -0.789  -1.448  -1.314  1.00  0.00           C  
HETATM   25  C18 UNL     1      -1.174  -0.905  -2.655  1.00  0.00           C  
HETATM   26  C19 UNL     1      -1.075  -0.468  -0.190  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.797  -1.150   1.133  1.00  0.00           C  
HETATM   28  H1  UNL     1       5.159  -1.884   1.343  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.558  -0.234   1.873  1.00  0.00           H  
HETATM   30  H3  UNL     1       5.919  -0.686   0.182  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.045  -0.570   1.366  1.00  0.00           H  
HETATM   32  H5  UNL     1       5.075  -0.656  -1.869  1.00  0.00           H  
HETATM   33  H6  UNL     1       4.385   0.902  -2.369  1.00  0.00           H  
HETATM   34  H7  UNL     1       5.542   0.914  -1.027  1.00  0.00           H  
HETATM   35  H8  UNL     1      -0.216   1.171  -1.291  1.00  0.00           H  
HETATM   36  H9  UNL     1       1.608   3.264   2.639  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.983   2.813   0.906  1.00  0.00           H  
HETATM   38  H11 UNL     1       1.675   1.542   2.177  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.652   3.554  -0.664  1.00  0.00           H  
HETATM   40  H13 UNL     1      -3.998   1.265   0.235  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.190   1.196   2.577  1.00  0.00           H  
HETATM   42  H15 UNL     1      -2.792   0.138  -1.323  1.00  0.00           H  
HETATM   43  H16 UNL     1      -3.338  -1.477   1.174  1.00  0.00           H  
HETATM   44  H17 UNL     1      -4.395  -1.123  -0.198  1.00  0.00           H  
HETATM   45  H18 UNL     1      -3.109  -3.483   0.067  1.00  0.00           H  
HETATM   46  H19 UNL     1      -3.654  -2.820  -1.480  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.536  -3.253  -2.111  1.00  0.00           H  
HETATM   48  H21 UNL     1       0.049  -3.892  -0.805  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.311  -1.704  -1.337  1.00  0.00           H  
HETATM   50  H23 UNL     1      -1.293   0.173  -2.707  1.00  0.00           H  
HETATM   51  H24 UNL     1      -2.125  -1.378  -3.016  1.00  0.00           H  
HETATM   52  H25 UNL     1      -0.391  -1.182  -3.419  1.00  0.00           H  
HETATM   53  H26 UNL     1       0.274  -1.455   1.153  1.00  0.00           H  
HETATM   54  H27 UNL     1      -1.387  -2.052   1.301  1.00  0.00           H  
HETATM   55  H28 UNL     1      -1.040  -0.448   1.962  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3   31
CONECT    3    4    5
CONECT    4   32   33   34
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   26   35
CONECT    9   10   10   15
CONECT   10   11   12
CONECT   11   36   37   38
CONECT   12   13   13   14
CONECT   14   15
CONECT   15   16   17
CONECT   16   39
CONECT   17   18   19   40
CONECT   18   41
CONECT   19   20   26   42
CONECT   20   21   43   44
CONECT   21   22   45   46
CONECT   22   23   24   47
CONECT   23   48
CONECT   24   25   26   49
CONECT   25   50   51   52
CONECT   26   27
CONECT   27   53   54   55
END

HMDB0041228
     RDKit          3D
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide
 55 57  0  0  0  0  0  0  0  0999 V2000
    5.2165   -0.8290    1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8311   -0.4142    0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    0.1300   -0.5276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7179    0.3146   -1.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2304    0.5274   -0.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.0430   -1.9876 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1563    0.3770   -0.0269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    0.7302   -0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907    1.7959    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0662    2.5486    1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191    2.5520    1.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0644    3.3718    2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8189    4.2378    3.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953    3.0529    1.6464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061    2.1396    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845    2.8639   -0.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138    0.9442    0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1869    0.4751    1.9112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5215   -0.1626   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195   -1.3811    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9193   -2.6228   -0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206   -2.7337   -1.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575   -3.6236   -0.3072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -1.4478   -1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1735   -0.9054   -2.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0746   -0.4676   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7965   -1.1504    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1585   -1.8842    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582   -0.2336    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9187   -0.6862    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455   -0.5701    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0751   -0.6558   -1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852    0.9022   -2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5421    0.9139   -1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    1.1709   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6082    3.2639    2.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9829    2.8132    0.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6753    1.5422    2.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6521    3.5539   -0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978    1.2647    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899    1.1955    2.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922    0.1383   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376   -1.4773    1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3945   -1.1233   -0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -3.4832    0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -2.8201   -1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5362   -3.2526   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0489   -3.8918   -0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -1.7041   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2927    0.1726   -2.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1254   -1.3776   -3.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.1824   -3.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736   -1.4546    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3872   -2.0524    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -0.4479    1.9616 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  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26  8  1  0
 15  9  1  0
 26 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,9,9a-Trihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₇

Average Molecular Weight

380.4321

Monoisotopic Molecular Weight

380.18350325

IUPAC Name

6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate

Traditional Name

6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxo-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

171422-89-2

SMILES

C\C=C(/C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O)C(C)C12C

InChI Identifier

InChI=1S/C20H28O7/c1-6-9(2)17(23)26-16-14-10(3)18(24)27-20(14,25)15(22)12-7-8-13(21)11(4)19(12,16)5/h6,11-13,15-16,21-22,25H,7-8H2,1-5H3/b9-6+

InChI Key

MSDFIROCDXOIAM-RMKNXTFCSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
Fatty acid ester
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
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: HMDB0041228)

Source

Endogenous

Endogenous (HMDB: HMDB0041228)

Plant

Plant (HMDB: HMDB0041228)

Animal

Animal (HMDB: HMDB0041228)

Exogenous

Food

Food (HMDB: HMDB0041228)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0041228)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0041228)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0041228)

Lipid metabolism pathway (HMDB: HMDB0041228)

Cellular process

Cell signaling (HMDB: HMDB0041228)

Biochemical process

Lipid transport (HMDB: HMDB0041228)

Role

Biological role

Energy source (HMDB: HMDB0041228)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041228)

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	1.76 g/L	ALOGPS
logP	1.38	ALOGPS
logP	2.32	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.68 m³·mol⁻¹	ChemAxon
Polarizability	39.59 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]+	189.16	31661259
DarkChem	[M-H]-	184.279	31661259
DeepCCS	[M-2H]-	218.391	30932474
DeepCCS	[M+Na]+	193.451	30932474
AllCCS	[M+H]+	188.9	32859911
AllCCS	[M+H-H2O]+	186.4	32859911
AllCCS	[M+NH4]+	191.2	32859911
AllCCS	[M+Na]+	191.9	32859911
AllCCS	[M-H]-	192.5	32859911
AllCCS	[M+Na-2H]-	193.0	32859911
AllCCS	[M+HCOO]-	193.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.45 minutes	32390414
Predicted by Siyang on May 30, 2022	13.0659 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2771.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	128.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	473.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	566.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	910.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	502.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1497.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	282.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	303.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	180.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	103.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide	C\C=C(/C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O)C(C)C12C	4281.9	Standard polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide	C\C=C(/C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O)C(C)C12C	2764.4	Standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide	C\C=C(/C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O)C(C)C12C	2861.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #1	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C)C(O)C2CCC(O)C(C)C12C	2953.2	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #2	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O[Si](C)(C)C)C2CCC(O)C(C)C12C	2920.5	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,1TMS,isomer #3	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O[Si](C)(C)C)C(C)C12C	2894.0	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,2TMS,isomer #1	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C)C(O[Si](C)(C)C)C2CCC(O)C(C)C12C	2966.2	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,2TMS,isomer #2	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C)C(O)C2CCC(O[Si](C)(C)C)C(C)C12C	2960.5	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,2TMS,isomer #3	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O[Si](C)(C)C)C2CCC(O[Si](C)(C)C)C(C)C12C	2911.5	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,3TMS,isomer #1	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C)C(O[Si](C)(C)C)C2CCC(O[Si](C)(C)C)C(C)C12C	2955.1	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #1	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C(C)(C)C)C(O)C2CCC(O)C(C)C12C	3188.9	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #2	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O[Si](C)(C)C(C)(C)C)C2CCC(O)C(C)C12C	3167.7	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,1TBDMS,isomer #3	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O[Si](C)(C)C(C)(C)C)C(C)C12C	3139.0	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #1	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2CCC(O)C(C)C12C	3414.3	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #2	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C(C)(C)C)C(O)C2CCC(O[Si](C)(C)C(C)(C)C)C(C)C12C	3411.0	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,2TBDMS,isomer #3	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O[Si](C)(C)C(C)(C)C)C2CCC(O[Si](C)(C)C(C)(C)C)C(C)C12C	3386.8	Semi standard non polar	33892256
6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide,3TBDMS,isomer #1	C/C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2CCC(O[Si](C)(C)C(C)(C)C)C(C)C12C	3624.4	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 - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bwi-9828000000-f5fdbc0a44844a0bcd04	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide GC-MS (3 TMS) - 70eV, Positive	splash10-001i-9211070000-da192b32324dc665684e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-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 - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-01q9-2039000000-55917ac26ca1f4c0fd4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-06si-9143000000-8539669f7d3a6bfe596d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-0kur-9300000000-6c181456077dc3e8d218	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-004i-1019000000-cff25006d4898451d956	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-06vs-4029000000-f6ec16d26c1168ecdab9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-054n-7191000000-425b4247b7724ad0f8c6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 10V, Positive-QTOF	splash10-001i-0009000000-43a6402d4255458b3e59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 20V, Positive-QTOF	splash10-03e9-0092000000-332fe50fe0bc4d6ee280	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 40V, Positive-QTOF	splash10-0a4i-3921000000-ee057317259ab33e94e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 10V, Negative-QTOF	splash10-0002-9004000000-aeb999bf40dca4c8a4fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 20V, Negative-QTOF	splash10-0002-9002000000-439267d29970209d3e84	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide 40V, Negative-QTOF	splash10-0pb9-9000000000-ea9f932913091753ea73	2021-09-23	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

FDB021130

KNApSAcK ID

Not Available

Chemspider ID

35015133

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753077

PDB ID

Not Available

ChEBI ID

175880

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 ]
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Showing metabocard for 6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide (HMDB0041228)

MOL for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

3D MOL for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

3D SDF for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

3D-SDF for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

PDB for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

3D PDB for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

SMILES for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

INCHI for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

Structure for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

3D Structure for HMDB0041228 (6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra