MiMeDB: Showing metabocard for 9Z-eicosenoic acid (MMDBc0049545)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:36:34 UTC

Update Date

2024-10-09 16:10:14 UTC

Metabolite ID

MMDBc0049545

Metabolite Identification

Common Name

9Z-eicosenoic acid

Description

9Z-Eicosenoic acid, also known as gadoleic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 9Z-Eicosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 9Z-Eicosenoic acid can be found in a number of food items such as lemon, sugar, garlic, and mung bean, which makes 9Z-eicosenoic acid a potential biomarker for the consumption of these food products. 9Z-Eicosenoic acid can be found in feces, blood, and urine.

Structure

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

HMDB0062436
     RDKit          3D
9Z-Eicosenoic acid
 60 59  0  0  0  0  0  0  0  0999 V2000
   -8.4386   -0.7467   -1.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7215    0.4781   -1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0656    0.2515   -0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0596   -0.8749   -0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634   -1.1587    1.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6079    0.0145    1.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5209    0.5102    0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -0.5936    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4074   -0.2189   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043    0.9502    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068    1.3210   -0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7793    1.2785   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665    0.8652    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -0.3395    1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.3161    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742   -0.0316   -0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758   -0.2326   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0473    0.6488   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5199    0.4746   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9552   -0.8734   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2031   -1.7366    0.1889 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -1.2251   -0.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9411   -1.2123   -2.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4841   -0.5164   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5375   -1.5188   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9229    0.7978   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4457    1.3106   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4927    1.1775    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8415    0.0430    0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6230   -1.8016   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -0.6975   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7621   -2.0599    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1852   -1.3620    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0896   -0.3259    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104    0.8239    1.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9372    0.9224   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838    1.3179    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544   -0.9027    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393   -1.4978    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123    0.0270   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7665   -1.1145   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    0.8768    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3443    1.8248    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.6577   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485    1.6002   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.8660    1.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688    1.7152    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696   -0.6515    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951   -1.2405    0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0035    0.3512    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8736   -1.3293    0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5514    1.0485   -1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734   -0.6265   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3318    0.0215   -2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820   -1.3118   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628    0.4420    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199    1.7218   -0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6725    0.7626   -1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0805    1.1939    0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7679   -0.7779   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 22 60  1  0
M  END


  Mrv1652306301800182D          

 24 23  0  0  0  0            999 V2000
    4.2355   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5237    0.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2381    1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    2.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526    2.9171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6671    1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -4.0954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -3.2704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049545

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-

> <INCHI_KEY>
LQJBNNIYVWPHFW-QXMHVHEDSA-N

> <FORMULA>
C20H38O2

> <MOLECULAR_WEIGHT>
310.522

> <EXACT_MASS>
310.287180464

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.32220070505214

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z)-icos-9-enoic acid

> <ALOGPS_LOGP>
8.41

> <JCHEM_LOGP>
7.672935781000001

> <ALOGPS_LOGS>
-6.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
96.60419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.92e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gadoleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062436
     RDKit          3D
9Z-Eicosenoic acid
 60 59  0  0  0  0  0  0  0  0999 V2000
   -8.4386   -0.7467   -1.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7215    0.4781   -1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0656    0.2515   -0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0596   -0.8749   -0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634   -1.1587    1.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6079    0.0145    1.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5209    0.5102    0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -0.5936    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4074   -0.2189   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043    0.9502    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068    1.3210   -0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7793    1.2785   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665    0.8652    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -0.3395    1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.3161    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742   -0.0316   -0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758   -0.2326   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0473    0.6488   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5199    0.4746   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9552   -0.8734   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2031   -1.7366    0.1889 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -1.2251   -0.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9411   -1.2123   -2.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4841   -0.5164   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5375   -1.5188   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9229    0.7978   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4457    1.3106   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4927    1.1775    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8415    0.0430    0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6230   -1.8016   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -0.6975   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7621   -2.0599    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1852   -1.3620    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0896   -0.3259    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104    0.8239    1.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9372    0.9224   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838    1.3179    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544   -0.9027    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393   -1.4978    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123    0.0270   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7665   -1.1145   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    0.8768    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3443    1.8248    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.6577   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485    1.6002   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.8660    1.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688    1.7152    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696   -0.6515    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951   -1.2405    0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0035    0.3512    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8736   -1.3293    0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5514    1.0485   -1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734   -0.6265   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3318    0.0215   -2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820   -1.3118   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628    0.4420    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199    1.7218   -0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6725    0.7626   -1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0805    1.1939    0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7679   -0.7779   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 22 60  1  0
M  END

HEADER    PROTEIN                                 30-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-18         0                                  
HETATM    1  C   UNK     0       7.906  -6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.574  -6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.907  -5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.241  -6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.575  -5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.908  -6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.242  -5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.576  -6.105   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.909  -5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.243  -6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.577  -5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.577  -3.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.910  -3.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.910  -1.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.244  -0.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.244   0.825   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.578   1.595   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.578   3.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.912   3.905   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      27.912   5.445   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      29.245   3.135   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      21.243  -7.645   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      23.910  -6.105   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

COMPND    HMDB0062436
HETATM    1  C1  UNL     1      -8.439  -0.747  -1.894  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.721   0.478  -1.402  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.066   0.251  -0.058  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.060  -0.875  -0.189  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.363  -1.159   1.117  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.608   0.015   1.650  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.521   0.510   0.721  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.543  -0.594   0.495  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.407  -0.219  -0.416  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.604   0.950   0.137  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.507   1.321  -0.743  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.779   1.279  -0.343  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.166   0.865   0.985  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.015  -0.340   1.057  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.372  -0.316   0.525  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.674  -0.032  -0.882  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.176  -0.233  -1.144  1.00  0.00           C  
HETATM   18  C18 UNL     1       7.047   0.649  -0.344  1.00  0.00           C  
HETATM   19  C19 UNL     1       8.520   0.475  -0.626  1.00  0.00           C  
HETATM   20  C20 UNL     1       8.955  -0.873  -0.307  1.00  0.00           C  
HETATM   21  O1  UNL     1       8.203  -1.737   0.189  1.00  0.00           O  
HETATM   22  O2  UNL     1      10.283  -1.225  -0.567  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.941  -1.212  -2.771  1.00  0.00           H  
HETATM   24  H2  UNL     1      -9.484  -0.516  -2.226  1.00  0.00           H  
HETATM   25  H3  UNL     1      -8.538  -1.519  -1.104  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.923   0.798  -2.122  1.00  0.00           H  
HETATM   27  H5  UNL     1      -8.446   1.311  -1.366  1.00  0.00           H  
HETATM   28  H6  UNL     1      -6.493   1.177   0.190  1.00  0.00           H  
HETATM   29  H7  UNL     1      -7.841   0.043   0.677  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.623  -1.802  -0.455  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.354  -0.698  -1.024  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.762  -2.060   1.016  1.00  0.00           H  
HETATM   33  H11 UNL     1      -6.185  -1.362   1.863  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.090  -0.326   2.581  1.00  0.00           H  
HETATM   35  H13 UNL     1      -5.310   0.824   1.927  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.937   0.922  -0.218  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.984   1.318   1.298  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.154  -0.903   1.501  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.039  -1.498   0.087  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.812   0.027  -1.419  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.767  -1.115  -0.544  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.415   0.877   1.190  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.344   1.825   0.048  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.319   1.658  -1.794  1.00  0.00           H  
HETATM   45  H23 UNL     1       2.548   1.600  -1.071  1.00  0.00           H  
HETATM   46  H24 UNL     1       1.356   0.866   1.759  1.00  0.00           H  
HETATM   47  H25 UNL     1       2.869   1.715   1.389  1.00  0.00           H  
HETATM   48  H26 UNL     1       3.070  -0.651   2.169  1.00  0.00           H  
HETATM   49  H27 UNL     1       2.495  -1.241   0.584  1.00  0.00           H  
HETATM   50  H28 UNL     1       5.003   0.351   1.230  1.00  0.00           H  
HETATM   51  H29 UNL     1       4.874  -1.329   0.745  1.00  0.00           H  
HETATM   52  H30 UNL     1       4.551   1.048  -1.172  1.00  0.00           H  
HETATM   53  H31 UNL     1       4.073  -0.627  -1.556  1.00  0.00           H  
HETATM   54  H32 UNL     1       6.332   0.022  -2.238  1.00  0.00           H  
HETATM   55  H33 UNL     1       6.382  -1.312  -1.090  1.00  0.00           H  
HETATM   56  H34 UNL     1       6.863   0.442   0.753  1.00  0.00           H  
HETATM   57  H35 UNL     1       6.820   1.722  -0.571  1.00  0.00           H  
HETATM   58  H36 UNL     1       8.672   0.763  -1.690  1.00  0.00           H  
HETATM   59  H37 UNL     1       9.081   1.194   0.038  1.00  0.00           H  
HETATM   60  H38 UNL     1      10.768  -0.778  -1.325  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   40   41
CONECT   10   11   42   43
CONECT   11   12   12   44
CONECT   12   13   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   50   51
CONECT   16   17   52   53
CONECT   17   18   54   55
CONECT   18   19   56   57
CONECT   19   20   58   59
CONECT   20   21   21   22
CONECT   22   60
END

HMDB0062436
     RDKit          3D
9Z-Eicosenoic acid
 60 59  0  0  0  0  0  0  0  0999 V2000
   -8.4386   -0.7467   -1.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7215    0.4781   -1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0656    0.2515   -0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0596   -0.8749   -0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3634   -1.1587    1.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6079    0.0145    1.6499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5209    0.5102    0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -0.5936    0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4074   -0.2189   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043    0.9502    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068    1.3210   -0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7793    1.2785   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665    0.8652    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0152   -0.3395    1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -0.3161    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6742   -0.0316   -0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758   -0.2326   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0473    0.6488   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5199    0.4746   -0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9552   -0.8734   -0.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2031   -1.7366    0.1889 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2829   -1.2251   -0.5669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9411   -1.2123   -2.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4841   -0.5164   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5375   -1.5188   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9229    0.7978   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4457    1.3106   -1.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4927    1.1775    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8415    0.0430    0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6230   -1.8016   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -0.6975   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7621   -2.0599    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1852   -1.3620    1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0896   -0.3259    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104    0.8239    1.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9372    0.9224   -0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838    1.3179    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544   -0.9027    1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393   -1.4978    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123    0.0270   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7665   -1.1145   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    0.8768    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3443    1.8248    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.6577   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485    1.6002   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558    0.8660    1.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688    1.7152    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696   -0.6515    2.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4951   -1.2405    0.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0035    0.3512    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8736   -1.3293    0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5514    1.0485   -1.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734   -0.6265   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3318    0.0215   -2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820   -1.3118   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628    0.4420    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199    1.7218   -0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6725    0.7626   -1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0805    1.1939    0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7679   -0.7779   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 22 60  1  0
M  END

Synonyms

Value	Source
(Z)-Eicos-9-enoic acid	ChEBI
9C-Eicosensaeure	ChEBI
C20:1C	ChEBI
cis-9-Eicosenoic acid	ChEBI
cis-Delta(9)-Eicosenoic acid	ChEBI
Eicos-9C-enoic acid	ChEBI
Eicos-9C-ensaeure	ChEBI
(Z)-Eicos-9-enoate	Generator
cis-9-Eicosenoate	Generator
cis-delta(9)-Eicosenoate	Generator
cis-Δ(9)-eicosenoate	Generator
cis-Δ(9)-eicosenoic acid	Generator
Eicos-9C-enoate	Generator
9Z-Eicosenoate	Generator
Gadoleate	HMDB
Gadoleic acid	HMDB
FA(20:1(9Z))	HMDB
cis-Gadoleate	HMDB

Molecular Formula

C₂₀H₃₈O₂

Average Mass

310.522

Monoisotopic Mass

310.287180464

IUPAC Name

(9Z)-icos-9-enoic acid

Traditional Name

gadoleic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCCCCC)=C(/[H])CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-

InChI Key

LQJBNNIYVWPHFW-QXMHVHEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

icosenoic acid (CHEBI:32419 )
Unsaturated fatty acids (LMFA01030084 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.9e-05 g/L	ALOGPS
logP	8.41	ALOGPS
logP	7.67	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	96.6 m³·mol⁻¹	ChemAxon
Polarizability	41.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9770000000-8bafce752dcc0e83c211	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00vi-9561000000-84617bccb2d2f0e64718	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0197000000-f6093bc2d61dbe668e18	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxu-3591000000-835bb134b9d517428e95	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-8960000000-fa7ac5e35243596e982c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0029000000-053d5a3b1d592fd190c2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1079000000-323c653227521538a43c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9230000000-33c06ae5cc68dad15291	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-4297000000-a679e8ed0942db48f672	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06r6-9572000000-31bd41e72217aeb75998	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9100000000-e4e0ee937a9dc02d22a0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0019000000-0d96115f81e42756fc2f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1069000000-e54a7d130deccefa86bb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9020000000-c097ab1d18e1ea28f2f1	2021-09-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank
Acylcarnitine (9Z)-icos-9-enoylcarnitine

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0009229	9Z-eicosenoic acid	9Z-Eicosenoyl Coenzyme A	Not Available	VMH	30371894
MMDBr0009230	9Z-Eicosenoyl Coenzyme A	9Z-eicosenoic acid	acyl-CoA thioesterase 1	VMH	30371894
MMDBr0009980	9Z-eicosenoic acid	9Z-Eicosenoyl Coenzyme A	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	3	Human feces

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	11.722	5.378	uM	Adult (>18 years old)	Female	Normal	HMDB	9368807
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0062436

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003771

KNApSAcK ID

C00053190

Chemspider ID

4445894

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gadoleic acid

METLIN ID

Not Available

PubChem Compound

5282767

PDB ID

Not Available

ChEBI ID

32419

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. 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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 9Z-eicosenoic acid (MMDBc0049545)

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3D Structure for #<Metabolite:0x0000556b6af87390>