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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:11:57 UTC

Update Date

2022-03-07 02:55:08 UTC

HMDB ID

HMDB0036962

Secondary Accession Numbers

HMDB36962

Metabolite Identification

Common Name

3-Epioleanolic acid

Description

3-Epioleanolic acid, also known as 3-epioleanolate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a significant number of articles have been published on 3-Epioleanolic acid.

Structure

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


  Mrv0541 02241215292D          

 36 40  0  0  0  0            999 V2000
   -1.4023   -1.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6812   -2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -1.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -0.8013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0411   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.4003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6812    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411    0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    0.8013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4023    1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    0.4003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1247   -0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.4003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6812   -1.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7647   -1.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7647   -0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -0.8013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4023   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871    0.4003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -0.8013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236    2.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247    2.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244    2.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6878    1.2138    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -1.2253    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4863   -2.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -2.4271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -2.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8449   -2.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 22  1  0  0  0  0
  1 24  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  4 17  1  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 29  1  0  0  0  0
 12 13  1  0  0  0  0
 12 29  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 10 31  1  1  0  0  0
  6 32  1  6  0  0  0
 19 33  1  6  0  0  0
  1 34  1  6  0  0  0
 24 35  1  0  0  0  0
 24 36  1  0  0  0  0
M  END

HMDB0036962
     RDKit          3D
3-Epioleanolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -5.4535    1.3126   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301    1.4620    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1717    2.8326    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3267    0.4481    1.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581   -0.9456    1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -1.1294    0.6309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4999   -2.3566   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811   -2.2781   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8797   -3.5774    0.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700   -1.4580    1.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -1.1433    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -0.4142    0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3497    1.0155    1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -0.2343   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -0.2704   -1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164   -0.4920   -2.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426   -0.1255   -0.8766 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6100   -0.0669   -1.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1044   -1.1685   -2.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8247    1.2296   -1.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    2.2478   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    1.6176   -0.8976 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7444    2.6120   -0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    0.4144   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7130   -0.7051   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.8839    1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395    0.0677    0.0972 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0985   -1.1191    0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548   -1.1139    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025   -0.9958    0.2429 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3884   -2.4133   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -0.0129   -0.1987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3159    1.3656    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5966    0.2724   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4335    1.8683   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    1.8524   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8166    2.9551    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2956    2.8607    0.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8373    3.6475    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4333    0.5166    1.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9962    0.7323    2.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5432   -1.2057    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2525   -1.6128    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316   -4.4379    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -0.9103    2.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -2.5401    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -0.6400    2.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -2.1212    1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045    1.2247    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8268    1.1987    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362    1.7850    0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -0.1234   -2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -1.5645   -2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5913    0.1026   -2.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    0.9400   -0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -0.8068   -2.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184   -1.3684   -2.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3490   -2.1046   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8566    1.7070   -2.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465    1.0541   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    2.6909   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331    3.0734   -1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4234    1.3712   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515    3.5033   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7103   -0.4887    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3710   -1.6461    0.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656   -0.8214   -1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321    1.5070    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    0.0272    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834    1.4237    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    0.9343    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -2.0779    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7070   -0.9648    1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904   -2.1165    1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6364   -2.5495   -0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5452   -0.0923   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9188    2.0938   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  2  0
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 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 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
 24 27  1  0
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 28 29  1  0
 29 30  1  0
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 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
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  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
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  9 44  1  0
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 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  6
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  1
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  6
 33 80  1  0
 33 81  1  0
M  END


  Mrv0541 02241215292D          

 36 40  0  0  0  0            999 V2000
   -1.4023   -1.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6812   -2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -1.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -0.8013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0411   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.4003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.6812    0.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023    0.8013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4023    1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4023   -0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -2.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1247    2.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1233   -2.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8449   -2.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 22  1  0  0  0  0
  1 24  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  4 17  1  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 29  1  0  0  0  0
 12 13  1  0  0  0  0
 12 29  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 26  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 10 31  1  1  0  0  0
  6 32  1  6  0  0  0
 19 33  1  6  0  0  0
  1 34  1  6  0  0  0
 24 35  1  0  0  0  0
 24 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036962

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23+,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
MIJYXULNPSFWEK-KDQGZELNSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.7003

> <EXACT_MASS>
456.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
54.611895472859494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
7.09

> <JCHEM_LOGP>
6.594833433333333

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433291560097

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744260336518661

> <JCHEM_PKA_STRONGEST_BASIC>
-0.835123022210091

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.6245

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.17e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036962
     RDKit          3D
3-Epioleanolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -5.4535    1.3126   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301    1.4620    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1717    2.8326    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3267    0.4481    1.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581   -0.9456    1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -1.1294    0.6309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4999   -2.3566   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811   -2.2781   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8797   -3.5774    0.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700   -1.4580    1.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -1.1433    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -0.4142    0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3497    1.0155    1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -0.2343   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -0.2704   -1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164   -0.4920   -2.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426   -0.1255   -0.8766 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6100   -0.0669   -1.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1044   -1.1685   -2.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8247    1.2296   -1.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    2.2478   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    1.6176   -0.8976 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7444    2.6120   -0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    0.4144   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7130   -0.7051   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.8839    1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395    0.0677    0.0972 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0985   -1.1191    0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548   -1.1139    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025   -0.9958    0.2429 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3884   -2.4133   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -0.0129   -0.1987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3159    1.3656    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5966    0.2724   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4335    1.8683   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    1.8524   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8166    2.9551    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2956    2.8607    0.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8373    3.6475    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4333    0.5166    1.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9962    0.7323    2.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5432   -1.2057    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2525   -1.6128    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316   -4.4379    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -0.9103    2.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -2.5401    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -0.6400    2.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -2.1212    1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045    1.2247    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8268    1.1987    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362    1.7850    0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -0.1234   -2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -1.5645   -2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5913    0.1026   -2.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    0.9400   -0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -0.8068   -2.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184   -1.3684   -2.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3490   -2.1046   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8566    1.7070   -2.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465    1.0541   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    2.6909   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331    3.0734   -1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4234    1.3712   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515    3.5033   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7103   -0.4887    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3710   -1.6461    0.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656   -0.8214   -1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321    1.5070    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    0.0272    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834    1.4237    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    0.9343    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -2.0779    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7070   -0.9648    1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904   -2.1165    1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850   -0.4003    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254   -3.0772    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6364   -2.5495   -0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1469   -2.7764   -0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -0.0923   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    1.6156    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9188    2.0938   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 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
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  6
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  1
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  6
 33 80  1  0
 33 81  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.618  -2.991   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.272  -3.739   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.077  -2.991   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.077  -1.496   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.077  -0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.272  -0.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.272   0.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.077   1.496   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.272   0.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.618   1.496   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.618   2.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.312   2.993   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.312   1.496   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.966   0.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.966  -0.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.618  -1.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.272  -0.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.272  -2.244   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.161  -2.991   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.161  -1.496   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.963  -0.747   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.618  -1.496   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.618  -0.001   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.963  -3.739   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.509   0.747   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.312  -0.001   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.312  -1.496   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.217   5.088   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.966   3.742   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.712   5.088   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.284   2.266   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.272  -2.287   0.000  0.00  0.00           H+0
HETATM   33  O   UNK     0      -6.508  -3.737   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -2.618  -4.531   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0      -3.963  -5.279   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.310  -4.486   0.000  0.00  0.00           C+0
CONECT    1    2   22   24   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6   17                                             
CONECT    5    4                                                            
CONECT    6    4    7   22   32                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14   31                                             
CONECT   11   10   29                                                       
CONECT   12   13   29                                                       
CONECT   13   12   14                                                       
CONECT   14   10   13   15   26                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    4    9   16   18                                             
CONECT   18   17                                                            
CONECT   19   20   24   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    1    6   21   23                                             
CONECT   23   22                                                            
CONECT   24    1   19   35   36                                             
CONECT   25   26                                                            
CONECT   26   14   25   27                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   11   12   28   30                                             
CONECT   30   29                                                            
CONECT   31   10                                                            
CONECT   32    6                                                            
CONECT   33   19                                                            
CONECT   34    1                                                            
CONECT   35   24                                                            
CONECT   36   24                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0036962
HETATM    1  C1  UNL     1      -5.454   1.313  -1.001  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.830   1.462   0.346  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.172   2.833   0.889  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.327   0.448   1.361  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.958  -0.946   1.000  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.485  -1.129   0.631  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.500  -2.357  -0.232  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.181  -2.278  -1.438  1.00  0.00           O  
HETATM    9  O2  UNL     1      -3.880  -3.577   0.352  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.670  -1.458   1.839  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.242  -1.143   1.850  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.637  -0.414   0.713  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.350   1.015   1.200  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.539  -0.234  -0.459  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.101  -0.270  -1.713  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.316  -0.492  -2.099  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.143  -0.125  -0.877  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.610  -0.067  -1.179  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.104  -1.169  -2.080  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.825   1.230  -1.980  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.614   2.248  -1.220  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.961   1.618  -0.898  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.744   2.612  -0.324  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.800   0.414  -0.015  1.00  0.00           C  
HETATM   25  C22 UNL     1       5.713  -0.705  -0.344  1.00  0.00           C  
HETATM   26  C23 UNL     1       5.200   0.884   1.399  1.00  0.00           C  
HETATM   27  C24 UNL     1       3.339   0.068   0.097  1.00  0.00           C  
HETATM   28  C25 UNL     1       3.098  -1.119   0.993  1.00  0.00           C  
HETATM   29  C26 UNL     1       1.655  -1.114   1.392  1.00  0.00           C  
HETATM   30  C27 UNL     1       0.702  -0.996   0.243  1.00  0.00           C  
HETATM   31  C28 UNL     1       0.388  -2.413  -0.216  1.00  0.00           C  
HETATM   32  C29 UNL     1      -2.983  -0.013  -0.199  1.00  0.00           C  
HETATM   33  C30 UNL     1      -3.316   1.366   0.297  1.00  0.00           C  
HETATM   34  H1  UNL     1      -5.597   0.272  -1.332  1.00  0.00           H  
HETATM   35  H2  UNL     1      -6.434   1.868  -1.026  1.00  0.00           H  
HETATM   36  H3  UNL     1      -4.795   1.852  -1.732  1.00  0.00           H  
HETATM   37  H4  UNL     1      -4.817   2.955   1.932  1.00  0.00           H  
HETATM   38  H5  UNL     1      -6.296   2.861   0.958  1.00  0.00           H  
HETATM   39  H6  UNL     1      -4.837   3.647   0.216  1.00  0.00           H  
HETATM   40  H7  UNL     1      -6.433   0.517   1.346  1.00  0.00           H  
HETATM   41  H8  UNL     1      -4.996   0.732   2.359  1.00  0.00           H  
HETATM   42  H9  UNL     1      -5.543  -1.206   0.072  1.00  0.00           H  
HETATM   43  H10 UNL     1      -5.252  -1.613   1.828  1.00  0.00           H  
HETATM   44  H11 UNL     1      -3.432  -4.438   0.013  1.00  0.00           H  
HETATM   45  H12 UNL     1      -3.178  -0.910   2.692  1.00  0.00           H  
HETATM   46  H13 UNL     1      -2.871  -2.540   2.107  1.00  0.00           H  
HETATM   47  H14 UNL     1      -0.969  -0.640   2.833  1.00  0.00           H  
HETATM   48  H15 UNL     1      -0.677  -2.121   1.953  1.00  0.00           H  
HETATM   49  H16 UNL     1       0.704   1.225   1.353  1.00  0.00           H  
HETATM   50  H17 UNL     1      -0.827   1.199   2.207  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.736   1.785   0.522  1.00  0.00           H  
HETATM   52  H19 UNL     1      -1.855  -0.123  -2.512  1.00  0.00           H  
HETATM   53  H20 UNL     1       0.378  -1.564  -2.369  1.00  0.00           H  
HETATM   54  H21 UNL     1       0.591   0.103  -2.983  1.00  0.00           H  
HETATM   55  H22 UNL     1       0.837   0.940  -0.656  1.00  0.00           H  
HETATM   56  H23 UNL     1       3.968  -0.807  -2.718  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.318  -1.368  -2.835  1.00  0.00           H  
HETATM   58  H25 UNL     1       3.349  -2.105  -1.589  1.00  0.00           H  
HETATM   59  H26 UNL     1       1.857   1.707  -2.255  1.00  0.00           H  
HETATM   60  H27 UNL     1       3.347   1.054  -2.932  1.00  0.00           H  
HETATM   61  H28 UNL     1       3.116   2.691  -0.360  1.00  0.00           H  
HETATM   62  H29 UNL     1       3.833   3.073  -1.930  1.00  0.00           H  
HETATM   63  H30 UNL     1       5.423   1.371  -1.886  1.00  0.00           H  
HETATM   64  H31 UNL     1       5.551   3.503  -0.670  1.00  0.00           H  
HETATM   65  H32 UNL     1       6.710  -0.489   0.143  1.00  0.00           H  
HETATM   66  H33 UNL     1       5.371  -1.646   0.131  1.00  0.00           H  
HETATM   67  H34 UNL     1       5.966  -0.821  -1.412  1.00  0.00           H  
HETATM   68  H35 UNL     1       6.132   1.507   1.289  1.00  0.00           H  
HETATM   69  H36 UNL     1       5.488   0.027   2.024  1.00  0.00           H  
HETATM   70  H37 UNL     1       4.383   1.424   1.886  1.00  0.00           H  
HETATM   71  H38 UNL     1       2.910   0.934   0.645  1.00  0.00           H  
HETATM   72  H39 UNL     1       3.429  -2.078   0.555  1.00  0.00           H  
HETATM   73  H40 UNL     1       3.707  -0.965   1.911  1.00  0.00           H  
HETATM   74  H41 UNL     1       1.490  -2.116   1.900  1.00  0.00           H  
HETATM   75  H42 UNL     1       1.485  -0.400   2.222  1.00  0.00           H  
HETATM   76  H43 UNL     1       0.525  -3.077   0.664  1.00  0.00           H  
HETATM   77  H44 UNL     1      -0.636  -2.550  -0.548  1.00  0.00           H  
HETATM   78  H45 UNL     1       1.147  -2.776  -0.945  1.00  0.00           H  
HETATM   79  H46 UNL     1      -3.545  -0.092  -1.184  1.00  0.00           H  
HETATM   80  H47 UNL     1      -2.964   1.616   1.295  1.00  0.00           H  
HETATM   81  H48 UNL     1      -2.919   2.094  -0.426  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    4   33
CONECT    3   37   38   39
CONECT    4    5   40   41
CONECT    5    6   42   43
CONECT    6    7   10   32
CONECT    7    8    8    9
CONECT    9   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   14   30
CONECT   13   49   50   51
CONECT   14   15   15   32
CONECT   15   16   52
CONECT   16   17   53   54
CONECT   17   18   30   55
CONECT   18   19   20   27
CONECT   19   56   57   58
CONECT   20   21   59   60
CONECT   21   22   61   62
CONECT   22   23   24   63
CONECT   23   64
CONECT   24   25   26   27
CONECT   25   65   66   67
CONECT   26   68   69   70
CONECT   27   28   71
CONECT   28   29   72   73
CONECT   29   30   74   75
CONECT   30   31
CONECT   31   76   77   78
CONECT   32   33   79
CONECT   33   80   81
END

HMDB0036962
     RDKit          3D
3-Epioleanolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -5.4535    1.3126   -1.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301    1.4620    0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1717    2.8326    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3267    0.4481    1.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581   -0.9456    1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -1.1294    0.6309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4999   -2.3566   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811   -2.2781   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8797   -3.5774    0.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6700   -1.4580    1.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -1.1433    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370   -0.4142    0.7128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3497    1.0155    1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5391   -0.2343   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011   -0.2704   -1.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164   -0.4920   -2.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426   -0.1255   -0.8766 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6100   -0.0669   -1.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1044   -1.1685   -2.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8247    1.2296   -1.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    2.2478   -1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    1.6176   -0.8976 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7444    2.6120   -0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    0.4144   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7130   -0.7051   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.8839    1.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395    0.0677    0.0972 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0985   -1.1191    0.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548   -1.1139    1.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7025   -0.9958    0.2429 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3884   -2.4133   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -0.0129   -0.1987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3159    1.3656    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5966    0.2724   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4335    1.8683   -1.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    1.8524   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8166    2.9551    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2956    2.8607    0.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8373    3.6475    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4333    0.5166    1.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9962    0.7323    2.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5432   -1.2057    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2525   -1.6128    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316   -4.4379    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -0.9103    2.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -2.5401    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9691   -0.6400    2.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -2.1212    1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045    1.2247    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8268    1.1987    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362    1.7850    0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -0.1234   -2.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -1.5645   -2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5913    0.1026   -2.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    0.9400   -0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -0.8068   -2.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184   -1.3684   -2.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3490   -2.1046   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8566    1.7070   -2.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465    1.0541   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    2.6909   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331    3.0734   -1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4234    1.3712   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515    3.5033   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7103   -0.4887    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3710   -1.6461    0.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656   -0.8214   -1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321    1.5070    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    0.0272    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3834    1.4237    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101    0.9343    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4293   -2.0779    0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7070   -0.9648    1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4904   -2.1165    1.9002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4850   -0.4003    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254   -3.0772    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6364   -2.5495   -0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1469   -2.7764   -0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452   -0.0923   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9637    1.6156    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9188    2.0938   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 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
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  1
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  6
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  1
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  6
 33 80  1  0
 33 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Epioleanolate	Generator
Epi-oleanolic acid	ChEMBL, HMDB
Epi-oleanolate	Generator, HMDB
3-alpha-Hydroxyolean-12-en-28-Oate	HMDB
3-alpha-Hydroxyolean-12-en-28-Oic acid	HMDB

Chemical Formula

C₃₀H₄₈O₃

Average Molecular Weight

456.7003

Monoisotopic Molecular Weight

456.360345402

IUPAC Name

(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

25499-90-5

SMILES

[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23+,27-,28+,29+,30-/m0/s1

InChI Key

MIJYXULNPSFWEK-KDQGZELNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triterpenoid (CHEBI:68103 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036962)
Cell membrane (HMDB: HMDB0036962)

Cellular substructure

Extracellular (HMDB: HMDB0036962)
Membrane (HMDB: HMDB0036962)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036962)

Source

Endogenous

Endogenous (HMDB: HMDB0036962)

Plant

Plant (HMDB: HMDB0036962)

Animal

Animal (HMDB: HMDB0036962)

Exogenous

Food

Food (HMDB: HMDB0036962)

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036962)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036962)

Cellular process

Cell signaling (HMDB: HMDB0036962)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036962)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036962)

Nutrient

Nutrient (HMDB: HMDB0036962)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036962)

Emulsifier (HMDB: HMDB0036962)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	297 - 299 °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	0.00082 g/L	ALOGPS
logP	7.09	ALOGPS
logP	6.59	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.61 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	205.733	31661259
DarkChem	[M-H]-	197.791	31661259
DeepCCS	[M-2H]-	234.809	30932474
DeepCCS	[M+Na]+	208.957	30932474
AllCCS	[M+H]+	216.4	32859911
AllCCS	[M+H-H2O]+	214.8	32859911
AllCCS	[M+NH4]+	217.9	32859911
AllCCS	[M+Na]+	218.4	32859911
AllCCS	[M-H]-	212.7	32859911
AllCCS	[M+Na-2H]-	214.7	32859911
AllCCS	[M+HCOO]-	217.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Epioleanolic acid	[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O	3223.1	Standard polar	33892256
3-Epioleanolic acid	[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O	3628.5	Standard non polar	33892256
3-Epioleanolic acid	[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O	3683.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Epioleanolic acid,1TMS,isomer #1	CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	3725.7	Semi standard non polar	33892256
3-Epioleanolic acid,1TMS,isomer #2	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	3618.0	Semi standard non polar	33892256
3-Epioleanolic acid,2TMS,isomer #1	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	3591.4	Semi standard non polar	33892256
3-Epioleanolic acid,1TBDMS,isomer #1	CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	3953.4	Semi standard non polar	33892256
3-Epioleanolic acid,1TBDMS,isomer #2	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	3887.1	Semi standard non polar	33892256
3-Epioleanolic acid,2TBDMS,isomer #1	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	4090.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epioleanolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0023900000-56b699a28dcac02b8121	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epioleanolic acid GC-MS (2 TMS) - 70eV, Positive	splash10-000i-1011190000-4d07cbb48cd57a724a3c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Epioleanolic acid 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-Epioleanolic acid 10V, Positive-QTOF	splash10-052r-0001900000-948551e80a675e804945	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 20V, Positive-QTOF	splash10-01vx-0116900000-a7bbd734cfb389f003ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 40V, Positive-QTOF	splash10-001l-3459300000-fe5b4ff0a697d946a205	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-24b5f92b17a675bd0042	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 20V, Negative-QTOF	splash10-08fu-0003900000-df302b7b4b1f9bf77cc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 40V, Negative-QTOF	splash10-000e-2007900000-2e9882aa899cbe3bd6da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 10V, Positive-QTOF	splash10-0a4i-0000900000-a2106bcf05d5c3dc7def	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 20V, Positive-QTOF	splash10-052r-0694700000-aa642e480c6b2dafc5d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 40V, Positive-QTOF	splash10-00ei-0940000000-67c9b141383d1a95ec29	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-0d11296813b631a2140f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 20V, Negative-QTOF	splash10-0a4i-0000900000-a04074ef438068f127bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Epioleanolic acid 40V, Negative-QTOF	splash10-0a4i-0001900000-ec650846439f5cbbb4c2	2021-09-24	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

FDB015933

KNApSAcK ID

C00029494

Chemspider ID

10043989

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11869658

PDB ID

Not Available

ChEBI ID

68103

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

Caldwell CG, Franzblau SG, Suarez E, Timmermann BN: Oleanane triterpenes from Junellia tridens. J Nat Prod. 2000 Dec;63(12):1611-4. [PubMed:11141098 ]
Deepak M, Handa SS: Antiinflammatory activity and chemical composition of extracts of Verbena officinalis. Phytother Res. 2000 Sep;14(6):463-5. [PubMed:10960904 ]
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-Epioleanolic acid (HMDB0036962)

MOL for HMDB0036962 (3-Epioleanolic acid)

3D MOL for HMDB0036962 (3-Epioleanolic acid)

3D SDF for HMDB0036962 (3-Epioleanolic acid)

3D-SDF for HMDB0036962 (3-Epioleanolic acid)

PDB for HMDB0036962 (3-Epioleanolic acid)

3D PDB for HMDB0036962 (3-Epioleanolic acid)

SMILES for HMDB0036962 (3-Epioleanolic acid)

INCHI for HMDB0036962 (3-Epioleanolic acid)

Structure for HMDB0036962 (3-Epioleanolic acid)

3D Structure for HMDB0036962 (3-Epioleanolic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra