MiMeDB: Showing metabocard for Linoleoyl-CoA (MMDBc0048666)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:06:28 UTC

Update Date

2024-04-30 20:37:03 UTC

Metabolite ID

MMDBc0048666

Metabolite Identification

Common Name

Linoleoyl-CoA

Description

Linoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long-chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid beta-oxidation. ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates (PMID: 17184976 , 16020546 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304302200062D          

129131  0  0  1  0            999 V2000
   11.2743    2.0262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5598    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5598    0.7887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2743    1.2012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2743    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2743   -0.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9888    0.7887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4013    1.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7033    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3330   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0735   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4177    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7880    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0475    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1322    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1322   -0.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8467    0.7887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8467    1.6137    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5611    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1909   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9314   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6459    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   16.9901    0.3762    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7046    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7046    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.5038    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   19.8480    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.6472   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   22.3616    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.6211    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.7059    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3356   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   24.1348    0.3762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4203    1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1348    2.0262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.7059    2.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.1335    3.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0986    4.0879    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4105    3.6609    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   17.6205    3.0583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.0103    2.1345    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7234    0.9944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3908    1.4793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8096    0.1739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2364    1.3682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.6565    1.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4411    1.4937    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.1861    0.7091    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.6960    2.2783    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.2257    1.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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100101  1  6  0  0  0
100102  1  0  0  0  0
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103104  1  6  0  0  0
103105  1  1  0  0  0
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106108  2  0  0  0  0
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110111  1  0  0  0  0
111112  2  0  0  0  0
112113  1  0  0  0  0
112114  1  0  0  0  0
114115  2  0  0  0  0
105115  1  0  0  0  0
109115  1  0  0  0  0
110116  1  0  0  0  0
116117  1  0  0  0  0
116118  1  0  0  0  0
103119  1  0  0  0  0
119120  1  1  0  0  0
119121  1  6  0  0  0
121122  1  0  0  0  0
119123  1  0  0  0  0
100123  1  0  0  0  0
123124  1  1  0  0  0
123125  1  1  0  0  0
125126  1  0  0  0  0
126127  1  0  0  0  0
126128  1  0  0  0  0
126129  2  0  0  0  0
M  CHG  4  90  -1  94  -1 127  -1 128  -1
M  END


  Mrv1652304302200062D          

129131  0  0  1  0            999 V2000
   11.2743    2.0262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5598    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5598    0.7887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2743    1.2012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2743    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2743   -0.4488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9888    0.7887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4013    1.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7033    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3330   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0735   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4177    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7880    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0475    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1322    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9314   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2756    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6459    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7046    1.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.5038    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   20.9327    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.1922    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2769    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9066   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.6472   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.9914    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3616    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.6211    1.5259    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.7059    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3356   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.0761   -0.3611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4203    0.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1348    0.3762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4203    1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1348    2.0262    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.7059    2.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9180    2.2710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4203    2.4387    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   23.1184    3.5656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.9914    3.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9914    4.0887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2769    2.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7912    2.1843    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2769    3.6762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5624    3.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4192    4.0761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.9305    3.7940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.8480    2.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4777    2.1139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.2182    2.1139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1335    3.2637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0986    4.0879    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4105    3.6609    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4190    2.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6205    3.0583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.0103    2.1345    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0039    2.2693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8454    0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4329    1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1473    1.5031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0204    1.8051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7184    0.6781    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2579   -0.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5434   -0.7508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6704   -1.0528    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9723    0.0742    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1309   -0.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -0.3185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7020   -0.0363    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.2895    0.6781    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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    3.4303    0.6446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2257    1.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
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103104  1  6  0  0  0
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111112  2  0  0  0  0
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105115  1  0  0  0  0
109115  1  0  0  0  0
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116118  1  0  0  0  0
103119  1  0  0  0  0
119120  1  1  0  0  0
119121  1  6  0  0  0
121122  1  0  0  0  0
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100123  1  0  0  0  0
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123125  1  1  0  0  0
125126  1  0  0  0  0
126127  1  0  0  0  0
126128  1  0  0  0  0
126129  2  0  0  0  0
M  CHG  4  90  -1  94  -1 127  -1 128  -1
M  END
> <DATABASE_ID>
MMDBc0048666

> <DATABASE_NAME>
MIME

> <SMILES>
[H]O[C@@]([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C(N=C([H])N=C23)N([H])[H])[C@]([H])(O[H])[C@]1([H])OP([O-])([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/p-4/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1

> <INCHI_KEY>
YECLLIMZHNYFCK-RRNJGNTNSA-J

> <FORMULA>
C39H62N7O17P3S

> <MOLECULAR_WEIGHT>
1025.94

> <EXACT_MASS>
1025.315770052

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
129

> <JCHEM_AVERAGE_POLARIZABILITY>
101.39031085937464

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxy)phosphonate

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
0.7636033955187073

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776186

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398224

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
374.95

> <JCHEM_REFRACTIVITY>
243.5963000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-22         0                                  
HETATM    1  H   UNK     0      21.045   3.782   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      19.712   3.012   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      19.712   1.472   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      21.045   2.242   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      21.045   0.702   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      21.045  -0.838   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      22.379   1.472   0.000  0.00  0.00           N+0
HETATM    8  H   UNK     0      23.149   2.806   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      23.713   0.702   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      23.022  -0.674   0.000  0.00  0.00           H+0
HETATM   11  H   UNK     0      24.404  -0.674   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      25.046   1.472   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      25.738   2.848   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      24.355   2.848   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      26.380   0.702   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      26.380  -0.838   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      27.714   1.472   0.000  0.00  0.00           N+0
HETATM   18  H   UNK     0      27.714   3.012   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      29.047   0.702   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      28.356  -0.674   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      29.739  -0.674   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      30.381   1.472   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      31.072   2.848   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      29.690   2.848   0.000  0.00  0.00           H+0
HETATM   25  S   UNK     0      31.715   0.702   0.000  0.00  0.00           S+0
HETATM   26  C   UNK     0      33.049   1.472   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      33.049   3.012   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      34.382   0.702   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.691  -0.674   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      35.073  -0.674   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      35.716   1.472   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      36.407   2.848   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      35.025   2.848   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0      37.050   0.702   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      36.358  -0.674   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      37.741  -0.674   0.000  0.00  0.00           H+0
HETATM   37  C   UNK     0      38.383   1.472   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0      39.074   2.848   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      37.692   2.848   0.000  0.00  0.00           H+0
HETATM   40  C   UNK     0      39.717   0.702   0.000  0.00  0.00           C+0
HETATM   41  H   UNK     0      39.026  -0.674   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      40.408  -0.674   0.000  0.00  0.00           H+0
HETATM   43  C   UNK     0      41.051   1.472   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0      41.742   2.848   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0      40.359   2.848   0.000  0.00  0.00           H+0
HETATM   46  C   UNK     0      42.384   0.702   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0      41.693  -0.674   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      43.075  -0.674   0.000  0.00  0.00           H+0
HETATM   49  C   UNK     0      43.718   1.472   0.000  0.00  0.00           C+0
HETATM   50  H   UNK     0      45.052   0.702   0.000  0.00  0.00           H+0
HETATM   51  C   UNK     0      43.718   3.012   0.000  0.00  0.00           C+0
HETATM   52  H   UNK     0      45.052   3.782   0.000  0.00  0.00           H+0
HETATM   53  C   UNK     0      42.384   3.782   0.000  0.00  0.00           C+0
HETATM   54  H   UNK     0      40.914   4.239   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      43.718   4.552   0.000  0.00  0.00           H+0
HETATM   56  C   UNK     0      42.384   5.322   0.000  0.00  0.00           C+0
HETATM   57  H   UNK     0      43.154   6.656   0.000  0.00  0.00           H+0
HETATM   58  C   UNK     0      41.051   6.092   0.000  0.00  0.00           C+0
HETATM   59  H   UNK     0      41.051   7.632   0.000  0.00  0.00           H+0
HETATM   60  C   UNK     0      39.717   5.322   0.000  0.00  0.00           C+0
HETATM   61  H   UNK     0      38.810   4.077   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      39.717   6.862   0.000  0.00  0.00           H+0
HETATM   63  C   UNK     0      38.383   6.092   0.000  0.00  0.00           C+0
HETATM   64  H   UNK     0      38.116   7.609   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      37.204   7.082   0.000  0.00  0.00           H+0
HETATM   66  C   UNK     0      37.050   5.322   0.000  0.00  0.00           C+0
HETATM   67  H   UNK     0      36.358   3.946   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      37.741   3.946   0.000  0.00  0.00           H+0
HETATM   69  C   UNK     0      35.716   6.092   0.000  0.00  0.00           C+0
HETATM   70  H   UNK     0      35.651   7.631   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      34.366   6.834   0.000  0.00  0.00           H+0
HETATM   72  C   UNK     0      34.382   5.322   0.000  0.00  0.00           C+0
HETATM   73  H   UNK     0      32.892   5.709   0.000  0.00  0.00           H+0
HETATM   74  H   UNK     0      33.619   3.984   0.000  0.00  0.00           H+0
HETATM   75  H   UNK     0      35.474   4.236   0.000  0.00  0.00           H+0
HETATM   76  C   UNK     0      18.378   0.702   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      17.608   2.036   0.000  0.00  0.00           C+0
HETATM   78  H   UNK     0      18.942   2.806   0.000  0.00  0.00           H+0
HETATM   79  H   UNK     0      16.838   3.370   0.000  0.00  0.00           H+0
HETATM   80  H   UNK     0      16.274   1.266   0.000  0.00  0.00           H+0
HETATM   81  C   UNK     0      19.148  -0.632   0.000  0.00  0.00           C+0
HETATM   82  H   UNK     0      17.814  -1.402   0.000  0.00  0.00           H+0
HETATM   83  H   UNK     0      19.918  -1.965   0.000  0.00  0.00           H+0
HETATM   84  H   UNK     0      20.482   0.138   0.000  0.00  0.00           H+0
HETATM   85  C   UNK     0      17.044  -0.068   0.000  0.00  0.00           C+0
HETATM   86  H   UNK     0      15.597  -0.595   0.000  0.00  0.00           H+0
HETATM   87  H   UNK     0      16.518  -1.515   0.000  0.00  0.00           H+0
HETATM   88  O   UNK     0      15.711   0.702   0.000  0.00  0.00           O+0
HETATM   89  P   UNK     0      14.377  -0.068   0.000  0.00  0.00           P+0
HETATM   90  O   UNK     0      13.607   1.266   0.000  0.00  0.00           O-1
HETATM   91  O   UNK     0      15.147  -1.402   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      13.043  -0.838   0.000  0.00  0.00           O+0
HETATM   93  P   UNK     0      11.710  -0.068   0.000  0.00  0.00           P+0
HETATM   94  O   UNK     0      12.480   1.266   0.000  0.00  0.00           O-1
HETATM   95  O   UNK     0      10.940  -1.402   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0      10.376   0.702   0.000  0.00  0.00           O+0
HETATM   97  C   UNK     0       9.042  -0.068   0.000  0.00  0.00           C+0
HETATM   98  H   UNK     0       8.351  -1.444   0.000  0.00  0.00           H+0
HETATM   99  H   UNK     0       9.733  -1.444   0.000  0.00  0.00           H+0
HETATM  100  C   UNK     0       7.709   0.702   0.000  0.00  0.00           C+0
HETATM  101  H   UNK     0       9.000   1.541   0.000  0.00  0.00           H+0
HETATM  102  O   UNK     0       6.302   0.076   0.000  0.00  0.00           O+0
HETATM  103  C   UNK     0       5.271   1.220   0.000  0.00  0.00           C+0
HETATM  104  H   UNK     0       4.433   2.512   0.000  0.00  0.00           H+0
HETATM  105  N   UNK     0       3.740   1.059   0.000  0.00  0.00           N+0
HETATM  106  C   UNK     0       2.970  -0.274   0.000  0.00  0.00           C+0
HETATM  107  H   UNK     0       3.596  -1.681   0.000  0.00  0.00           H+0
HETATM  108  N   UNK     0       1.463   0.046   0.000  0.00  0.00           N+0
HETATM  109  C   UNK     0       1.302   1.577   0.000  0.00  0.00           C+0
HETATM  110  C   UNK     0       0.057   2.483   0.000  0.00  0.00           C+0
HETATM  111  N   UNK     0       0.217   4.014   0.000  0.00  0.00           N+0
HETATM  112  C   UNK     0       1.624   4.640   0.000  0.00  0.00           C+0
HETATM  113  H   UNK     0       1.785   6.172   0.000  0.00  0.00           H+0
HETATM  114  N   UNK     0       2.870   3.735   0.000  0.00  0.00           N+0
HETATM  115  C   UNK     0       2.709   2.204   0.000  0.00  0.00           C+0
HETATM  116  N   UNK     0      -1.350   1.856   0.000  0.00  0.00           N+0
HETATM  117  H   UNK     0      -2.596   2.761   0.000  0.00  0.00           H+0
HETATM  118  H   UNK     0      -1.511   0.325   0.000  0.00  0.00           H+0
HETATM  119  C   UNK     0       6.041   2.554   0.000  0.00  0.00           C+0
HETATM  120  H   UNK     0       7.010   3.751   0.000  0.00  0.00           H+0
HETATM  121  O   UNK     0       5.415   3.961   0.000  0.00  0.00           O+0
HETATM  122  H   UNK     0       4.784   5.366   0.000  0.00  0.00           H+0
HETATM  123  C   UNK     0       7.548   2.234   0.000  0.00  0.00           C+0
HETATM  124  H   UNK     0       6.403   1.203   0.000  0.00  0.00           H+0
HETATM  125  O   UNK     0       8.692   3.264   0.000  0.00  0.00           O+0
HETATM  126  P   UNK     0      10.157   2.788   0.000  0.00  0.00           P+0
HETATM  127  O   UNK     0       9.681   1.324   0.000  0.00  0.00           O-1
HETATM  128  O   UNK     0      10.633   4.253   0.000  0.00  0.00           O-1
HETATM  129  O   UNK     0      11.621   2.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   76                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   41   42   43                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   40   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55   56                                             
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   53   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   62   63                                             
CONECT   61   60                                                            
CONECT   62   60                                                            
CONECT   63   60   64   65   66                                             
CONECT   64   63                                                            
CONECT   65   63                                                            
CONECT   66   63   67   68   69                                             
CONECT   67   66                                                            
CONECT   68   66                                                            
CONECT   69   66   70   71   72                                             
CONECT   70   69                                                            
CONECT   71   69                                                            
CONECT   72   69   73   74   75                                             
CONECT   73   72                                                            
CONECT   74   72                                                            
CONECT   75   72                                                            
CONECT   76    3   77   81   85                                             
CONECT   77   76   78   79   80                                             
CONECT   78   77                                                            
CONECT   79   77                                                            
CONECT   80   77                                                            
CONECT   81   76   82   83   84                                             
CONECT   82   81                                                            
CONECT   83   81                                                            
CONECT   84   81                                                            
CONECT   85   76   86   87   88                                             
CONECT   86   85                                                            
CONECT   87   85                                                            
CONECT   88   85   89                                                       
CONECT   89   88   90   91   92                                             
CONECT   90   89                                                            
CONECT   91   89                                                            
CONECT   92   89   93                                                       
CONECT   93   92   94   95   96                                             
CONECT   94   93                                                            
CONECT   95   93                                                            
CONECT   96   93   97                                                       
CONECT   97   96   98   99  100                                             
CONECT   98   97                                                            
CONECT   99   97                                                            
CONECT  100   97  101  102  123                                             
CONECT  101  100                                                            
CONECT  102  100  103                                                       
CONECT  103  102  104  105  119                                             
CONECT  104  103                                                            
CONECT  105  103  106  115                                                  
CONECT  106  105  107  108                                                  
CONECT  107  106                                                            
CONECT  108  106  109                                                       
CONECT  109  108  110  115                                                  
CONECT  110  109  111  116                                                  
CONECT  111  110  112                                                       
CONECT  112  111  113  114                                                  
CONECT  113  112                                                            
CONECT  114  112  115                                                       
CONECT  115  114  105  109                                                  
CONECT  116  110  117  118                                                  
CONECT  117  116                                                            
CONECT  118  116                                                            
CONECT  119  103  120  121  123                                             
CONECT  120  119                                                            
CONECT  121  119  122                                                       
CONECT  122  121                                                            
CONECT  123  119  100  124  125                                             
CONECT  124  123                                                            
CONECT  125  123  126                                                       
CONECT  126  125  127  128  129                                             
CONECT  127  126                                                            
CONECT  128  126                                                            
CONECT  129  126                                                            
MASTER        0    0    0    0    0    0    0    0  129    0  262    0
END

Synonyms

Value	Source
(9Z,12Z)-Octadecadienoyl-CoA	ChEBI

Molecular Formula

C₃₉H₆₂N₇O₁₇P₃S

Average Mass

1025.94

Monoisotopic Mass

1025.315770052

IUPAC Name

(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxy)phosphonate

Traditional Name

(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propyl {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl phosphono}oxyphosphonate

CAS Registry Number

6709-57-5

SMILES

[H]O[C@@]([H])(C(=O)N([H])C([H])([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])SC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=NC3=C(N=C([H])N=C23)N([H])[H])[C@]([H])(O[H])[C@]1([H])OP([O-])([O-])=O

InChI Identifier

InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/p-4/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1

InChI Key

YECLLIMZHNYFCK-RRNJGNTNSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
Ribonucleoside 3'-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Alkyl phosphate
Organic phosphoric acid derivative
N-acyl-amine
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Imidolactam
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Thiocarboxylic acid ester
Carbothioic s-ester
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Thiocarboxylic acid or derivatives
Sulfenyl compound
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Primary amine
Organic oxide
Amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyunsaturated fatty acyl-CoA(4-) (CHEBI:57383 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	3.72	ALOGPS
logP	0.76	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	374.95 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	243.6 m³·mol⁻¹	ChemAxon
Polarizability	101.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000651	Linoleoyl-CoA	Gamma-linolenoyl-CoA	fatty acid desaturase 1	VMH	30371894
MMDBr0001108	Linoleic acid	Linoleoyl-CoA	Not Available	VMH	15292367
MMDBr0001161	Linoleoyl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001576	L-Carnitine	Linoleyl carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	30371894
MMDBr0001577	Linoleyl carnitine	L-Carnitine	carnitine palmitoyltransferase 2	VMH	30371894
MMDBr0002557	L-Carnitine	Linoleyl carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	1735445 1988962 2355017 6361812 7892212
MMDBr0002558	L-Carnitine	Linoleyl carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	1735445 1988962 2355017 6361812 7892212
MMDBr0002875	Cholesterol	CE(18:2(9Z,12Z))	sterol O-acyltransferase 1	VMH	2760547 7822296 9242919
MMDBr0002894	Glycerol 3-phosphate	LysoPA(18:2(9Z,12Z)/0:0)	1-acylglycerol-3-phosphate O-acyltransferase 6	VMH	12573444 17170135 17389595
MMDBr0002901	Linoleic acid	Linoleoyl-CoA	Not Available	VMH	8584017
MMDBr0003986	Linoleic acid	Linoleoyl-CoA	Not Available	VMH	10479480 10675551 11707336 9784915
MMDBr0003987	Linoleic acid	Linoleoyl-CoA	Not Available	VMH	10479480 10675551 11707336 9784915
MMDBr0003988	Linoleoyl-CoA	Trans,Cis,Cis-2,9,12-Octadecatrienoyl Coenzyme A	acyl-CoA dehydrogenase, long chain	VMH	10407780 11356167 8973539
MMDBr0003989	Linoleoyl-CoA	Trans,Cis,Cis-2,9,12-Octadecatrienoyl Coenzyme A	acyl-CoA oxidase 1, palmitoyl	VMH	10407780 11356167 8973539
MMDBr0004565	Linoleoyl-CoA	3-Oxoeicosa-Cis,Cis-11,14-Dienoyl Coenzyme A	ELOVL fatty acid elongase 2	VMH	10970790
MMDBr0004566	Linoleoyl-CoA	3-Oxoeicosa-Cis,Cis-11,14-Dienoyl Coenzyme A	ELOVL fatty acid elongase 1	VMH	10970790
MMDBr0005260	Linoleoyl-CoA	7,10-Hexadecadienoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH
MMDBr0006776	Linoleyl carnitine	L-Carnitine	Not Available	VMH	30371894
MMDBr0009290	Linoleoyl-CoA	Linoleic acid	acyl-CoA thioesterase 1	VMH	30371894
MMDBr0009714	Linoleoyl-CoA	Gamma-linolenoyl-CoA	fatty acid desaturase 1	VMH; KEGG	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
Bacteria	nah	2	Human
Eukaryota/Fungi	Mucoromycota	2
Eukaryota/Fungi	Ascomycota	3
Eukaryota/Fungi	Basidiomycota	8	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26330756

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245440

PDB ID

Not Available

ChEBI ID

57383

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramsay RR, Mancinelli G, Arduini A: Carnitine palmitoyltransferase in human erythrocyte membrane. Properties and malonyl-CoA sensitivity. Biochem J. 1991 May 1;275 ( Pt 3):685-8. doi: 10.1042/bj2750685. [PubMed:2039446 ]
Kawasaki T, Snyder F: Synthesis of a novel acetylated neutral lipid related to platelet-activating factor by acyl-CoA:1-O-alkyl-2-acetyl-sn-glycerol acyltransferase in HL-60 cells. J Biol Chem. 1988 Feb 25;263(6):2593-6. [PubMed:3422635 ]
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 ]
Domergue F, Abbadi A, Ott C, Zank TK, Zahringer U, Heinz E: Acyl carriers used as substrates by the desaturases and elongases involved in very long-chain polyunsaturated fatty acids biosynthesis reconstituted in yeast. J Biol Chem. 2003 Sep 12;278(37):35115-26. doi: 10.1074/jbc.M305990200. Epub 2003 Jun 30. [PubMed:12835316 ]
Ensenauer R, He M, Willard JM, Goetzman ES, Corydon TJ, Vandahl BB, Mohsen AW, Isaya G, Vockley J: Human acyl-CoA dehydrogenase-9 plays a novel role in the mitochondrial beta-oxidation of unsaturated fatty acids. J Biol Chem. 2005 Sep 16;280(37):32309-16. doi: 10.1074/jbc.M504460200. Epub 2005 Jul 14. [PubMed:16020546 ]
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 ]
Ciapaite J, Bakker SJ, Van Eikenhorst G, Wagner MJ, Teerlink T, Schalkwijk CG, Fodor M, Ouwens DM, Diamant M, Heine RJ, Westerhoff HV, Krab K: Functioning of oxidative phosphorylation in liver mitochondria of high-fat diet fed rats. Biochim Biophys Acta. 2007 Mar;1772(3):307-16. doi: 10.1016/j.bbadis.2006.10.018. Epub 2006 Nov 10. [PubMed:17184976 ]
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 ]
Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Silva C, Loyola G, Valenzuela R, García-Huidobro T, Monasterio O, Bronfman M. (1999). Silva C, Loyola G, Valenzuela R, García-Huidobro T, Monasterio O, Bronfman M. High-affinity binding of fatty acyl-CoAs and peroxisome proliferator-CoA esters to glutathione S-transferases effect on enzymatic activity. Eur J Biochem. 1999 Nov;266(1):143-50.. Eur J Biochem..

Showing metabocard for Linoleoyl-CoA (MMDBc0048666)

MOL for #<Metabolite:0x00007fece41c79f0>

3D MOL for #<Metabolite:0x00007fece41c79f0>

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3D PDB for #<Metabolite:0x00007fece41c79f0>

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Structure for #<Metabolite:0x00007fece41c79f0>

3D Structure for #<Metabolite:0x00007fece41c79f0>