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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:31:15 UTC

Update Date

2022-03-07 02:54:10 UTC

HMDB ID

HMDB0034631

Secondary Accession Numbers

HMDB34631

Metabolite Identification

Common Name

(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one

Description

(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one.

Structure

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

HMDB0034631
     RDKit          3D
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.5330   -1.4830   -2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -0.8449   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575    0.4950   -0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    0.2527    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930    0.5826    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9415    1.1340   -0.9795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6282    0.3401    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0386    0.7300    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766   -0.2320    2.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117   -0.6474    2.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2413    1.3681   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    0.6347    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8781    1.6721    0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724    1.2008    1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637    2.8948    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -0.2297   -0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830   -0.9343   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9095   -0.4811   -0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0574   -1.4236   -0.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080   -2.3726   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975   -3.3033   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010   -2.5948   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -1.3799   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.0525   -2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694   -2.4723   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803    0.9803   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865   -0.1324    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209    0.9808   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634    1.5858    1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868   -0.3871    2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289    0.2330    2.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -1.3919    1.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -1.1036    3.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274    1.9850    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299    2.0816   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376    0.0212    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889    2.0827    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390    1.6268    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2216    0.1250    1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583    1.6708    2.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.6378   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1943    3.5833    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    3.4647    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    0.2512   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.5715   -1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8269   -2.2807   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1861   -1.7732    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9820   -0.9487   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -3.4871   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147   -2.6319   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -1.5985    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
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 17 18  2  0
 18 19  1  0
 17 20  1  0
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 20 22  1  0
 22 23  1  0
 23  2  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
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 11 34  1  0
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 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
M  END


  Mrv0541 05061307582D          

 23 24  0  0  0  0            999 V2000
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    2.0361    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
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    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
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    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
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    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
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    3.2789    1.2375    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
    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
    4.7079   -1.2375    0.0000 C   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
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  2  0  0  0  0
 13  6  2  0  0  0  0
 14  8  2  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 20  2  0  0  0  0
 23 18  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034631

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-7-12(5)20(22)23-18-10-15(11(3)4)19-14(8-2)17(21)9-16(19)13(18)6/h7-8,11,15-16,18-19H,6,9-10H2,1-5H3/b12-7-,14-8+

> <INCHI_KEY>
PGPPNCWYWQGYAU-FHGRNIPQSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.93841161097346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1Z)-1-ethylidene-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
4.821124174333335

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.819283571034714

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
93.56439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1Z)-1-ethylidene-7-isopropyl-4-methylidene-2-oxo-hexahydroinden-5-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034631
     RDKit          3D
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.5330   -1.4830   -2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -0.8449   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575    0.4950   -0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    0.2527    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930    0.5826    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9415    1.1340   -0.9795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6282    0.3401    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0386    0.7300    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766   -0.2320    2.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117   -0.6474    2.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2413    1.3681   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    0.6347    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8781    1.6721    0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724    1.2008    1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637    2.8948    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -0.2297   -0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830   -0.9343   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9095   -0.4811   -0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0574   -1.4236   -0.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080   -2.3726   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975   -3.3033   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010   -2.5948   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -1.3799   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.0525   -2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694   -2.4723   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803    0.9803   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865   -0.1324    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1371    0.5715   -1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8269   -2.2807   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1861   -1.7732    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9820   -0.9487   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -3.4871   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147   -2.6319   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -1.5985    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
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 23  2  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
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 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 22 49  1  0
 22 50  1  0
 23 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       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.340   3.801   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.322   2.016   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       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.454  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   11                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   13                                                            
CONECT    7    1   12                                                       
CONECT    8    2   14                                                       
CONECT    9   16   17                                                       
CONECT   10   15   18                                                       
CONECT   11    3    4   15                                                  
CONECT   12    5    7   20                                                  
CONECT   13    6   16   18                                                  
CONECT   14    8   17   19                                                  
CONECT   15   10   11   19                                                  
CONECT   16    9   13   19                                                  
CONECT   17    9   14   21                                                  
CONECT   18   10   13   23                                                  
CONECT   19   14   15   16                                                  
CONECT   20   12   22   23                                                  
CONECT   21   17                                                            
CONECT   22   20                                                            
CONECT   23   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0034631
HETATM    1  C1  UNL     1       1.533  -1.483  -2.066  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.820  -0.845  -1.178  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.258   0.495  -0.714  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.273   0.253   0.268  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.593   0.583   0.102  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.942   1.134  -0.980  1.00  0.00           O  
HETATM    7  C5  UNL     1       4.628   0.340   1.092  1.00  0.00           C  
HETATM    8  C6  UNL     1       6.039   0.730   0.830  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.377  -0.232   2.263  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.012  -0.647   2.603  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.241   1.368  -0.115  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.013   0.635   0.391  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.878   1.672   0.979  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.172   1.201   1.581  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.064   2.895   0.107  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.437  -0.230  -0.698  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.683  -0.934  -0.752  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.910  -0.481  -0.924  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.057  -1.424  -0.941  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.408  -2.373  -0.621  1.00  0.00           C  
HETATM   21  O3  UNL     1      -3.097  -3.303  -0.172  1.00  0.00           O  
HETATM   22  C19 UNL     1      -1.001  -2.595  -1.172  1.00  0.00           C  
HETATM   23  C20 UNL     1      -0.396  -1.380  -0.612  1.00  0.00           C  
HETATM   24  H1  UNL     1       2.455  -1.052  -2.482  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.269  -2.472  -2.449  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.780   0.980  -1.570  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.687  -0.132   1.103  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.121   0.981  -0.246  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.363   1.586   1.485  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.187  -0.387   2.960  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.329   0.233   2.599  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.595  -1.392   1.885  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.010  -1.104   3.637  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.627   1.985   0.724  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.130   2.082  -0.882  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.638   0.021   1.260  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.289   2.083   1.860  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.039   1.627   1.039  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.222   0.125   1.785  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.258   1.671   2.611  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.206   2.638  -0.959  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.194   3.583   0.156  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.932   3.465   0.521  1.00  0.00           H  
HETATM   44  H21 UNL     1      -1.212   0.251  -1.702  1.00  0.00           H  
HETATM   45  H22 UNL     1      -4.137   0.572  -1.068  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.827  -2.281  -1.620  1.00  0.00           H  
HETATM   47  H24 UNL     1      -5.186  -1.773   0.119  1.00  0.00           H  
HETATM   48  H25 UNL     1      -5.982  -0.949  -1.277  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.560  -3.487  -0.693  1.00  0.00           H  
HETATM   50  H27 UNL     1      -1.015  -2.632  -2.262  1.00  0.00           H  
HETATM   51  H28 UNL     1      -0.197  -1.599   0.487  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   23
CONECT    3    4   11   26
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    9    9
CONECT    8   27   28   29
CONECT    9   10   30
CONECT   10   31   32   33
CONECT   11   12   34   35
CONECT   12   13   16   36
CONECT   13   14   15   37
CONECT   14   38   39   40
CONECT   15   41   42   43
CONECT   16   17   23   44
CONECT   17   18   18   20
CONECT   18   19   45
CONECT   19   46   47   48
CONECT   20   21   21   22
CONECT   22   23   49   50
CONECT   23   51
END

HMDB0034631
     RDKit          3D
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.5330   -1.4830   -2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8205   -0.8449   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575    0.4950   -0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735    0.2527    0.2685 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5930    0.5826    0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9415    1.1340   -0.9795 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6282    0.3401    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0386    0.7300    0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3766   -0.2320    2.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0117   -0.6474    2.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2413    1.3681   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    0.6347    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8781    1.6721    0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724    1.2008    1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637    2.8948    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -0.2297   -0.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830   -0.9343   -0.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9095   -0.4811   -0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0574   -1.4236   -0.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080   -2.3726   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975   -3.3033   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010   -2.5948   -1.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -1.3799   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.0525   -2.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694   -2.4723   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803    0.9803   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865   -0.1324    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209    0.9808   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634    1.5858    1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868   -0.3871    2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289    0.2330    2.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -1.3919    1.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -1.1036    3.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6274    1.9850    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1299    2.0816   -0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376    0.0212    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889    2.0827    1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0390    1.6268    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2216    0.1250    1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2583    1.6708    2.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.6378   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1943    3.5833    0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    3.4647    0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116    0.2512   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1371    0.5715   -1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8269   -2.2807   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1861   -1.7732    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9820   -0.9487   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -3.4871   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147   -2.6319   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1968   -1.5985    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23  2  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1Z)-1-Ethylidene-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

(1Z)-1-ethylidene-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1Z)-1-ethylidene-7-isopropyl-4-methylidene-2-oxo-hexahydroinden-5-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

237407-00-0

SMILES

C\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C

InChI Identifier

InChI=1S/C20H28O3/c1-7-12(5)20(22)23-18-10-15(11(3)4)19-14(8-2)17(21)9-16(19)13(18)6/h7-8,11,15-16,18-19H,6,9-10H2,1-5H3/b12-7-,14-8+

InChI Key

PGPPNCWYWQGYAU-FHGRNIPQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oplopane sesquiterpenoid
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0034631)
Cell membrane (HMDB: HMDB0034631)

Cellular substructure

Extracellular (HMDB: HMDB0034631)
Membrane (HMDB: HMDB0034631)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034631)

Source

Endogenous

Endogenous (HMDB: HMDB0034631)

Plant

Plant (HMDB: HMDB0034631)

Animal

Animal (HMDB: HMDB0034631)

Exogenous

Food

Food (HMDB: HMDB0034631)

Tea

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034631)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034631)

Cellular process

Cell signaling (HMDB: HMDB0034631)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034631)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034631)

Nutrient

Nutrient (HMDB: HMDB0034631)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034631)

Emulsifier (HMDB: HMDB0034631)

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	0.0071 g/L	ALOGPS
logP	4.31	ALOGPS
logP	4.82	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.56 m³·mol⁻¹	ChemAxon
Polarizability	36.94 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+H]+	182.653	30932474
DeepCCS	[M-H]-	179.916	30932474
DeepCCS	[M-2H]-	214.712	30932474
DeepCCS	[M+Na]+	190.588	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.7	32859911
AllCCS	[M+NH4]+	181.3	32859911
AllCCS	[M+Na]+	182.0	32859911
AllCCS	[M-H]-	183.5	32859911
AllCCS	[M+Na-2H]-	183.9	32859911
AllCCS	[M+HCOO]-	184.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one	C\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C	3064.6	Standard polar	33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one	C\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C	2278.3	Standard non polar	33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one	C\C=C(\C)C(=O)OC1CC(C(C)C)C2C(CC(=O)\C2=C/C)C1=C	2232.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TMS,isomer #1	C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C)=CC12	2386.7	Semi standard non polar	33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TMS,isomer #1	C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C)=CC12	2294.5	Standard non polar	33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TBDMS,isomer #1	C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C(C)(C)C)=CC12	2585.8	Semi standard non polar	33892256
(4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one,1TBDMS,isomer #1	C=C1C(OC(=O)/C(C)=C\C)CC(C(C)C)C2/C(=C/C)C(O[Si](C)(C)C(C)(C)C)=CC12	2477.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9450000000-54f00f86b994862fe3ae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 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 - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Positive-QTOF	splash10-014i-5198000000-84101fb2b248fa151904	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Positive-QTOF	splash10-067i-9251000000-0f632006241f27e8078f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Positive-QTOF	splash10-0kai-9100000000-73fc2c490c9e370affea	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Negative-QTOF	splash10-014i-1029000000-8b65b825ead3f1586150	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Negative-QTOF	splash10-0159-8096000000-4429db6f947b1a88031d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Negative-QTOF	splash10-0kuu-9170000000-a541544a77ba6375a490	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Positive-QTOF	splash10-00or-0981000000-d48931654e4edefaa994	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Positive-QTOF	splash10-014r-0950000000-ff10e14aa37ecd22001e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Positive-QTOF	splash10-066r-9711000000-139616b086d8969b88db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 10V, Negative-QTOF	splash10-014j-6029000000-98fbf5687e6b0abd8778	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 20V, Negative-QTOF	splash10-0002-9010000000-1f90606de09292b5f3a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one 40V, Negative-QTOF	splash10-0pi0-9430000000-ffda12de702a2957574c	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB013153

KNApSAcK ID

Not Available

Chemspider ID

35013752

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751596

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 (4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one (HMDB0034631)

MOL for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

3D MOL for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

3D SDF for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

3D-SDF for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

PDB for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

3D PDB for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

SMILES for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

INCHI for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

Structure for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

3D Structure for HMDB0034631 ((4Z,9a)-9-Angeloyloxy-4,10(14)-oplopadien-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra