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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:51:23 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036690

Secondary Accession Numbers

HMDB36690

Metabolite Identification

Common Name

3-Epinobilin

Description

3-Epinobilin 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 3-Epinobilin.

Structure

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


  Mrv1652307301920062D          

 28 29  0  0  0  0            999 V2000
    2.2588   -2.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890    1.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273   -0.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -1.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610    3.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219   -1.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061    2.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642   -1.4826    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240    0.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    1.9757    0.0000 H   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
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  2  0  0  0  0
 13  4  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  2  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
 25 17  1  0  0  0  0
 25 20  1  0  0  0  0
 26  6  1  0  0  0  0
 27  7  1  0  0  0  0
 28 10  1  0  0  0  0
M  END

HMDB0036690
     RDKit          3D
3-Epinobilin
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.3806   -0.6191   -2.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706   -0.9575   -2.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.1719   -2.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318   -3.0727   -3.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -2.2663   -1.4219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346   -1.4122   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -1.2813    0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539   -0.4391    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -0.6293    2.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389    0.7604    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.4689   -0.9568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    1.9711    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    2.4228   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036    2.4391   -1.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565    2.9251   -2.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2981    2.0238   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271    0.5299   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    0.0430   -0.1240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3476   -0.6185    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312   -0.7549    1.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -1.1109    0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773   -0.8994   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553   -1.7282    1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545   -1.9794    3.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143   -0.2128   -1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    0.2964   -2.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -1.2810   -3.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871   -1.9584    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8893   -2.0928    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    0.3100    3.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7514   -0.8405    2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2483   -1.4155    3.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4628    1.0809    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4317    1.0454   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572    1.7950    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1313    2.8565    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    2.7459   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    3.6865   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    2.0684   -3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    3.3868   -2.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822    2.5019    0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2256    2.5301   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    0.2585    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -1.4960   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -1.2582   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390    0.1672   -0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -2.0902    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6636   -2.5893    2.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830   -2.5081    3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -1.0399    3.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1621    0.4099   -1.6198 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
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 17 25  1  0
 25  2  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
M  END


  Mrv1652307301920062D          

 28 29  0  0  0  0            999 V2000
    2.2588   -2.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890    1.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273   -0.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652    0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -1.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832    1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610    3.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219   -1.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061    2.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642   -1.4826    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240    0.6993    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    1.9757    0.0000 H   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
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  2  0  0  0  0
 13  4  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  2  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
 25 17  1  0  0  0  0
 25 20  1  0  0  0  0
 26  6  1  0  0  0  0
 27  7  1  0  0  0  0
 28 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036690

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(C)=C(/C)C(=O)OC1C\C(C)=C([H])\CC(O)\C(C)=C([H])\C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,15-18,21H,5,8-9H2,1-4H3/b11-7+,12-6-,13-10+

> <INCHI_KEY>
QFINJHBXXJQKPB-QLDBJWRKSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.76327902475996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.4531310143333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.554788584696674

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9935354730536687

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
96.8624

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036690
     RDKit          3D
3-Epinobilin
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.3806   -0.6191   -2.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706   -0.9575   -2.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.1719   -2.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318   -3.0727   -3.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -2.2663   -1.4219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346   -1.4122   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -1.2813    0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539   -0.4391    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -0.6293    2.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389    0.7604    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.4689   -0.9568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    1.9711    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    2.4228   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036    2.4391   -1.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565    2.9251   -2.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2981    2.0238   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271    0.5299   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    0.0430   -0.1240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3476   -0.6185    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312   -0.7549    1.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -1.1109    0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773   -0.8994   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553   -1.7282    1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545   -1.9794    3.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143   -0.2128   -1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    0.2964   -2.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -1.2810   -3.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871   -1.9584    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8893   -2.0928    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    0.3100    3.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7514   -0.8405    2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2483   -1.4155    3.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4628    1.0809    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4317    1.0454   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572    1.7950    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1313    2.8565    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    2.7459   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    3.6865   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    2.0684   -3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    3.3868   -2.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822    2.5019    0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2256    2.5301   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    0.2585    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -1.4960   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -1.2582   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390    0.1672   -0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -2.0902    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6636   -2.5893    2.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830   -2.5081    3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -1.0399    3.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1621    0.4099   -1.6198 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
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 17 25  1  0
 25  2  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       4.216  -4.458   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.406   2.637   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.328  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.488   6.071   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.644   0.618   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.760  -3.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.416   2.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.959   3.937   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.352   0.806   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.920   3.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.896   2.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.784  -1.826   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.464   4.879   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.682   1.820   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.983   5.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.833   0.557   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.400   3.189   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.857   1.748   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.265  -2.075   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.089   3.305   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.527   6.570   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.721  -3.516   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.530   3.849   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.289  -0.884   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.198   4.151   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       6.280  -2.768   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.391   1.305   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.440   3.688   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6    1   12   26                                                  
CONECT    7    8   11   27                                                  
CONECT    8    7   15                                                       
CONECT    9   11   16                                                       
CONECT   10   13   17   28                                                  
CONECT   11    2    7    9                                                  
CONECT   12    3    6   19                                                  
CONECT   13    4   10   15                                                  
CONECT   14    5   18   20                                                  
CONECT   15    8   13   21                                                  
CONECT   16    9   18   24                                                  
CONECT   17   10   18   25                                                  
CONECT   18   14   16   17                                                  
CONECT   19   12   22   24                                                  
CONECT   20   14   23   25                                                  
CONECT   21   15                                                            
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24   16   19                                                       
CONECT   25   17   20                                                       
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28   10                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0036690
HETATM    1  C1  UNL     1       1.381  -0.619  -2.700  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.271  -0.957  -2.103  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.482  -2.172  -2.355  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.332  -3.073  -3.216  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.542  -2.266  -1.422  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.135  -1.412  -0.361  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.011  -1.281   0.761  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.954  -0.439   1.124  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.704  -0.629   2.448  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.439   0.760   0.384  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.734   0.469  -0.957  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.594   1.971   0.583  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.093   2.423  -0.742  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.804   2.439  -1.066  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.456   2.925  -2.453  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.298   2.024  -0.163  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.427   0.530  -0.096  1.00  0.00           C  
HETATM   18  O4  UNL     1       1.721   0.043  -0.124  1.00  0.00           O  
HETATM   19  C15 UNL     1       2.348  -0.618   0.915  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.631  -0.755   1.934  1.00  0.00           O  
HETATM   21  C16 UNL     1       3.713  -1.111   0.833  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.477  -0.899  -0.418  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.255  -1.728   1.843  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.554  -1.979   3.132  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.514  -0.213  -1.023  1.00  0.00           C  
HETATM   26  H1  UNL     1       1.927   0.296  -2.494  1.00  0.00           H  
HETATM   27  H2  UNL     1       1.804  -1.281  -3.456  1.00  0.00           H  
HETATM   28  H3  UNL     1      -0.187  -1.958   0.003  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.889  -2.093   1.544  1.00  0.00           H  
HETATM   30  H5  UNL     1      -3.661   0.310   3.034  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.751  -0.841   2.127  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.248  -1.416   3.043  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.463   1.081   0.775  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.432   1.045  -1.323  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.757   1.795   1.313  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.131   2.857   1.011  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.879   2.746  -1.442  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.358   3.686  -2.358  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.146   2.068  -3.088  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.322   3.387  -2.947  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.082   2.502   0.830  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.226   2.530  -0.503  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.045   0.258   0.938  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.004  -1.496  -1.240  1.00  0.00           H  
HETATM   45  H20 UNL     1       5.518  -1.258  -0.345  1.00  0.00           H  
HETATM   46  H21 UNL     1       4.439   0.167  -0.748  1.00  0.00           H  
HETATM   47  H22 UNL     1       5.274  -2.090   1.769  1.00  0.00           H  
HETATM   48  H23 UNL     1       2.664  -2.589   2.947  1.00  0.00           H  
HETATM   49  H24 UNL     1       4.183  -2.508   3.851  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.224  -1.040   3.619  1.00  0.00           H  
HETATM   51  H26 UNL     1      -1.162   0.410  -1.620  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3   25
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   25   28
CONECT    7    8    8   29
CONECT    8    9   10
CONECT    9   30   31   32
CONECT   10   11   12   33
CONECT   11   34
CONECT   12   13   35   36
CONECT   13   14   14   37
CONECT   14   15   16
CONECT   15   38   39   40
CONECT   16   17   41   42
CONECT   17   18   25   43
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   23   23
CONECT   22   44   45   46
CONECT   23   24   47
CONECT   24   48   49   50
CONECT   25   51
END

HMDB0036690
     RDKit          3D
3-Epinobilin
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.3806   -0.6191   -2.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706   -0.9575   -2.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.1719   -2.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318   -3.0727   -3.2159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5418   -2.2663   -1.4219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1346   -1.4122   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111   -1.2813    0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9539   -0.4391    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -0.6293    2.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389    0.7604    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7337    0.4689   -0.9568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938    1.9711    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930    2.4228   -0.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036    2.4391   -1.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565    2.9251   -2.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2981    2.0238   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271    0.5299   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7211    0.0430   -0.1240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3476   -0.6185    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312   -0.7549    1.9339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -1.1109    0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4773   -0.8994   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553   -1.7282    1.8433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545   -1.9794    3.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143   -0.2128   -1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9267    0.2964   -2.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -1.2810   -3.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1871   -1.9584    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8893   -2.0928    1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607    0.3100    3.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7514   -0.8405    2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2483   -1.4155    3.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4628    1.0809    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4317    1.0454   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7572    1.7950    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1313    2.8565    1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8794    2.7459   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3576    3.6865   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1455    2.0684   -3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    3.3868   -2.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822    2.5019    0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2256    2.5301   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445    0.2585    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -1.4960   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -1.2582   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4390    0.1672   -0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739   -2.0902    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6636   -2.5893    2.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830   -2.5081    3.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2237   -1.0399    3.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1621    0.4099   -1.6198 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
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 17 25  1  0
 25  2  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoic acid	HMDB

Chemical Formula

C₂₀H₂₆O₅

Average Molecular Weight

346.423

Monoisotopic Molecular Weight

346.178023937

IUPAC Name

9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

9-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)OC1C\C(C)=C\CC(O)\C(C)=C\C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C20H26O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,15-18,21H,5,8-9H2,1-4H3/b11-7+,12-6-,13-10+

InChI Key

QFINJHBXXJQKPB-QLDBJWRKSA-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
Tetrahydrofuran
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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: HMDB0036690)

Source

Exogenous

Food

Food (HMDB: HMDB0036690)

Herb and spice

Herb

Roman camomile (FooDB: FOOD00046)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036690)

Endogenous

Plant

Plant (HMDB: HMDB0036690)

Animal

Animal (HMDB: HMDB0036690)

Endogenous (HMDB: HMDB0036690)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036690)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036690)

Lipid metabolism pathway (HMDB: HMDB0036690)

Cellular process

Cell signaling (HMDB: HMDB0036690)

Biochemical process

Lipid transport (HMDB: HMDB0036690)

Role

Biological role

Energy source (HMDB: HMDB0036690)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036690)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	137 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.45	ChemAxon
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.86 m³·mol⁻¹	ChemAxon
Polarizability	36.76 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
DarkChem	[M+H]+	184.075	31661259
DarkChem	[M-H]-	180.055	31661259
DeepCCS	[M-2H]-	221.26	30932474
DeepCCS	[M+Na]+	196.656	30932474
AllCCS	[M+H]+	186.2	32859911
AllCCS	[M+H-H2O]+	183.3	32859911
AllCCS	[M+NH4]+	188.8	32859911
AllCCS	[M+Na]+	189.6	32859911
AllCCS	[M-H]-	188.1	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	188.9	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. Predicted by Afia on May 17, 2022.	7.71 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3655 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.71 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2784.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	433.5 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	526.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1100.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	529.6 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	1276.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	177.2 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	16.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Epinobilin	C\C=C(\C)C(=O)OC1C\C(C)=C\CC(O)\C(C)=C\C2OC(=O)C(=C)C12	3856.1	Standard polar	33892256
3-Epinobilin	C\C=C(\C)C(=O)OC1C\C(C)=C\CC(O)\C(C)=C\C2OC(=O)C(=C)C12	2588.6	Standard non polar	33892256
3-Epinobilin	C\C=C(\C)C(=O)OC1C\C(C)=C\CC(O)\C(C)=C\C2OC(=O)C(=C)C12	2631.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Epinobilin,1TMS,isomer #1	C=C1C(=O)OC2/C=C(\C)C(O[Si](C)(C)C)C/C=C(\C)CC(OC(=O)/C(C)=C\C)C12	2679.1	Semi standard non polar	33892256
3-Epinobilin,1TBDMS,isomer #1	C=C1C(=O)OC2/C=C(\C)C(O[Si](C)(C)C(C)(C)C)C/C=C(\C)CC(OC(=O)/C(C)=C\C)C12	2896.7	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 - 3-Epinobilin GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9022000000-40b15452d12f24aa44ab	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epinobilin GC-MS (1 TMS) - 70eV, Positive	splash10-053r-9001000000-bd362f2d4d8527669e25	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epinobilin 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 - 3-Epinobilin 10V, Positive-QTOF	splash10-002b-2049000000-4ada8c8f5b1aa75552bf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Positive-QTOF	splash10-057j-9182000000-93f1c8852bfe5265a632	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Positive-QTOF	splash10-100r-9220000000-09cce363075ad08956ed	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 10V, Negative-QTOF	splash10-0002-0029000000-dc8b56399c4a82daee30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Negative-QTOF	splash10-0002-5059000000-0ae00cdbb81c3908b3f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Negative-QTOF	splash10-05mt-9640000000-7f88f9d74127f2a45e6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 10V, Positive-QTOF	splash10-0002-0090000000-532ee58b0a32582e7047	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Positive-QTOF	splash10-004i-0090000000-196551c9eb839176ef5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Positive-QTOF	splash10-0032-2090000000-07e2a081ad01a389a6bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 10V, Negative-QTOF	splash10-0002-9076000000-1d4096873c48c96b380e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 20V, Negative-QTOF	splash10-0002-9050000000-4e8ea669f117f307e35a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epinobilin 40V, Negative-QTOF	splash10-0pdj-9070000000-7966e503f790225b8675	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

FDB015621

KNApSAcK ID

C00003339

Chemspider ID

35014202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752037

PDB ID

Not Available

ChEBI ID

175404

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 3-Epinobilin (HMDB0036690)

MOL for HMDB0036690 (3-Epinobilin)

3D MOL for HMDB0036690 (3-Epinobilin)

3D SDF for HMDB0036690 (3-Epinobilin)

3D-SDF for HMDB0036690 (3-Epinobilin)

PDB for HMDB0036690 (3-Epinobilin)

3D PDB for HMDB0036690 (3-Epinobilin)

SMILES for HMDB0036690 (3-Epinobilin)

INCHI for HMDB0036690 (3-Epinobilin)

Structure for HMDB0036690 (3-Epinobilin)

3D Structure for HMDB0036690 (3-Epinobilin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra