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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-21 16:59:43 UTC

Update Date

2021-10-01 16:51:00 UTC

HMDB ID

HMDB0300586

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dec-4-enedioyl-CoA

Description

Dec-4-enedioyl-coa, also known as 2-methylbutanoyl-CoA is an acyl-CoA or acyl-coenzyme A. More specifically, it is a dec-4-enedioic acid thioester of coenzyme A. Dec-4-enedioyl-coa is an acyl-CoA with 10 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. Dec-4-enedioyl-coa is therefore classified as a medium chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. Dec-4-enedioyl-coa, being a medium chain acyl-CoA is a substrate for medium chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, Dec-4-enedioyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of Dec-4-enedioyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts Dec-4-enedioyl-CoA into Dec-4-enedioylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, Dec-4-enedioylcarnitine is converted back to Dec-4-enedioyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of Dec-4-enedioyl-CoA occurs in four steps. First, since Dec-4-enedioyl-CoA is a medium chain acyl-CoA it is the substrate for a medium chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of Dec-4-enedioyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until Dec-4-enedioyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.

Structure

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


  Mrv1652306222023452D          

 60 62  0  0  1  0            999 V2000
   -2.9315   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   15.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817   17.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5317   17.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2170   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2132   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5001   21.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3567   18.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6714   24.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0308   24.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2145   22.3717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7843   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3365   25.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5203   22.6493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9682   22.0362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3567   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0902   25.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2503   24.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1078   23.3638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7880   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3567   17.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1764   26.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698   16.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277   16.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7576   24.9601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9177   23.8040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5828   25.4450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4433   24.1174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7843   15.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3407   22.5630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   16.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   15.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880   17.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9746   21.2903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0787   20.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9136   20.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1981   20.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3731   21.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8961   19.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461   19.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5001   21.1342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   18.6592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3008   23.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1397   21.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   20.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5267   20.6772    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.7856   20.7217    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   19.4842    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   16.1842    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2170   15.7717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2577   21.5479    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8159   21.8791    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7967   22.8432    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   17.0092    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9316   23.4069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  1  0  0  0  0
 15 10  1  1  0  0  0
 16  6  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 11  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  8  1  4  0  0  0
 28 16  2  0  0  0  0
 29  7  1  4  0  0  0
 29 23  2  0  0  0  0
 30 12  2  0  0  0  0
 30 21  1  0  0  0  0
 31 12  1  0  0  0  0
 31 22  2  0  0  0  0
 32 13  2  0  0  0  0
 32 17  1  0  0  0  0
 33 13  1  0  0  0  0
 33 22  1  0  0  0  0
 24 33  1  1  0  0  0
 34 16  1  0  0  0  0
 18 35  1  6  0  0  0
 36 20  1  0  0  0  0
 37 23  1  0  0  0  0
 38 25  2  0  0  0  0
 46 10  1  0  0  0  0
 47 11  1  0  0  0  0
 48 15  1  0  0  0  0
 48 24  1  0  0  0  0
 19 49  1  1  0  0  0
 51 39  1  0  0  0  0
 51 40  1  0  0  0  0
 51 41  2  0  0  0  0
 51 49  1  0  0  0  0
 52 42  1  0  0  0  0
 52 43  2  0  0  0  0
 52 46  1  0  0  0  0
 52 50  1  0  0  0  0
 53 44  1  0  0  0  0
 53 45  2  0  0  0  0
 53 47  1  0  0  0  0
 53 50  1  0  0  0  0
 54  9  1  0  0  0  0
 54 25  1  0  0  0  0
 55 14  1  0  0  0  0
 15 56  1  6  0  0  0
 18 57  1  1  0  0  0
 19 58  1  1  0  0  0
 59 20  1  0  0  0  0
 24 60  1  6  0  0  0
M  END

HMDB0300586
     RDKit          3D
Dec-4-enedioyl-CoA
 98100  0  0  0  0  0  0  0  0999 V2000
   13.1588    0.5344   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7181    0.8144   -1.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8177    0.4678   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9782   -0.9972    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1587    1.3535    0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9141    2.3527    0.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6439    1.1993    2.5094 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5057   -0.0721    2.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0893    0.1380    2.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8838    0.2747    1.0593 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9456    0.8768    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0245    0.8322   -0.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8290    1.5875    1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838    1.0079    0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.3766    1.0227 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556   -1.0947    1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -2.4238    1.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.5167    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088   -0.6536    1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -1.2671   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571   -2.7236   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4094   -1.1638   -1.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -0.6967   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443   -1.3694   -1.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -0.7467   -2.4121 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9424   -0.3700   -3.8864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -1.9170   -2.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859    0.5773   -1.4343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401    1.7693   -2.2616 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.3811    3.0744   -2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126    1.4137   -3.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6396    1.9603   -1.5531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    0.9279   -1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8416    1.2009   -1.1385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7576    0.1812   -1.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6613    0.2420   -0.2968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.5030   -0.9073   -0.2472 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3265   -2.1583   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4088   -2.8948   -0.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2998   -2.1381    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5704   -2.4133    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1678   -3.6993    0.6082 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2617   -1.4289    1.3063 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7204   -0.1964    1.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4756    0.0718    0.9298 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7427   -0.8832    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554    0.2685    0.8615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2417    0.6114    2.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7033    1.3489    0.3491 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2061    2.6096    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1037    3.5721    1.4895 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.2158    2.8166    2.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1088    4.4349    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9837    4.7312    2.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6635    1.4878   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7222    0.1788   -2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2825   -0.2142   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5366    1.8512   -1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3751    0.1334   -2.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8090    0.7157   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6158   -1.1465    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9612   -1.4375    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4858   -1.4795   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8229   -1.0985    2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5222   -0.2287    4.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6561    0.9801    3.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019   -0.7609    2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4370    0.1155   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    1.5415    2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792    2.6585    0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596    1.1560   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6701    1.5498    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2830   -2.9589    1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027    0.5522    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -0.0995    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244   -3.0983   -0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159   -3.3111   -0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -2.8500    0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.5825   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -0.0721   -1.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0142   -1.6134   -2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921    0.3932   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -0.7791   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7670   -2.8253   -2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0115    0.7225   -4.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.0707   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7207    0.9809   -2.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2861    2.1196   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2483    1.1633   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4211   -2.4810   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6879   -4.5236    0.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0905   -3.7942    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3153    0.5623    1.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1429   -0.6906    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5232   -0.2489    2.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    1.1898    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    4.9083    0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9215    4.4410    2.4879 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  2 59  1  0
  3 60  1  0
  4 61  1  0
  4 62  1  0
  4 63  1  0
  8 64  1  0
  8 65  1  0
  9 66  1  0
  9 67  1  0
 12 68  1  0
 13 69  1  0
 13 70  1  0
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 14 72  1  0
 17 73  1  0
 18 74  1  0
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 21 76  1  0
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 23 83  1  0
 27 84  1  0
 31 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  6
 36 89  1  6
 38 90  1  0
 42 91  1  0
 42 92  1  0
 44 93  1  0
 47 94  1  1
 48 95  1  0
 49 96  1  6
 53 97  1  0
 54 98  1  0
M  END


  Mrv1652306222023452D          

 60 62  0  0  1  0            999 V2000
   -2.9315   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   15.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817   17.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5317   17.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2170   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2132   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6409   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5001   21.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3567   18.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6714   24.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0308   24.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2145   22.3717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7843   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3365   25.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5203   22.6493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9682   22.0362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3567   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0902   25.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2503   24.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   16.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1078   23.3638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7880   16.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3567   17.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1764   26.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698   16.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277   16.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7576   24.9601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9177   23.8040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5828   25.4450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4433   24.1174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7843   15.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3407   22.5630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   16.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   15.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880   17.4217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9746   21.2903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0787   20.0641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9136   20.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1981   20.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3731   21.4362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8961   19.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461   19.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5001   21.1342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   18.6592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3008   23.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1397   21.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   20.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5267   20.6772    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.7856   20.7217    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.0711   19.4842    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   16.1842    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2170   15.7717    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2577   21.5479    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8159   21.8791    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7967   22.8432    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6422   17.0092    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9316   23.4069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  1  0  0  0  0
 15 10  1  1  0  0  0
 16  6  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 11  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  8  1  4  0  0  0
 28 16  2  0  0  0  0
 29  7  1  4  0  0  0
 29 23  2  0  0  0  0
 30 12  2  0  0  0  0
 30 21  1  0  0  0  0
 31 12  1  0  0  0  0
 31 22  2  0  0  0  0
 32 13  2  0  0  0  0
 32 17  1  0  0  0  0
 33 13  1  0  0  0  0
 33 22  1  0  0  0  0
 24 33  1  1  0  0  0
 34 16  1  0  0  0  0
 18 35  1  6  0  0  0
 36 20  1  0  0  0  0
 37 23  1  0  0  0  0
 38 25  2  0  0  0  0
 46 10  1  0  0  0  0
 47 11  1  0  0  0  0
 48 15  1  0  0  0  0
 48 24  1  0  0  0  0
 19 49  1  1  0  0  0
 51 39  1  0  0  0  0
 51 40  1  0  0  0  0
 51 41  2  0  0  0  0
 51 49  1  0  0  0  0
 52 42  1  0  0  0  0
 52 43  2  0  0  0  0
 52 46  1  0  0  0  0
 52 50  1  0  0  0  0
 53 44  1  0  0  0  0
 53 45  2  0  0  0  0
 53 47  1  0  0  0  0
 53 50  1  0  0  0  0
 54  9  1  0  0  0  0
 54 25  1  0  0  0  0
 55 14  1  0  0  0  0
 15 56  1  6  0  0  0
 18 57  1  1  0  0  0
 19 58  1  1  0  0  0
 59 20  1  0  0  0  0
 24 60  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0300586

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(C)(CC)C(=O)SCCN=C(O)CCN=C(O)C([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H44N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h12-15,18-20,24,35-36H,5-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t14?,15-,18-,19-,20?,24-/m1/s1

> <INCHI_KEY>
LYNVNYDEQMMNMZ-PCLZRLGGSA-N

> <FORMULA>
C26H44N7O17P3S

> <MOLECULAR_WEIGHT>
851.651

> <EXACT_MASS>
851.172723243

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
78.36324718799239

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(2-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-3.931045274926354

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8869799249048484

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8192071150093927

> <JCHEM_PKA_STRONGEST_BASIC>
6.4830778811867065

> <JCHEM_POLAR_SURFACE_AREA>
370.61000000000007

> <JCHEM_REFRACTIVITY>
187.05380000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-methylbutyryl-coenzyme A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0300586
     RDKit          3D
Dec-4-enedioyl-CoA
 98100  0  0  0  0  0  0  0  0999 V2000
   13.1588    0.5344   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7181    0.8144   -1.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8177    0.4678   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9782   -0.9972    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1587    1.3535    0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9141    2.3527    0.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6439    1.1993    2.5094 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5057   -0.0721    2.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0893    0.1380    2.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8838    0.2747    1.0593 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9456    0.8768    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0245    0.8322   -0.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8290    1.5875    1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838    1.0079    0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.3766    1.0227 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556   -1.0947    1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -2.4238    1.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.5167    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088   -0.6536    1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -1.2671   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571   -2.7236   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4094   -1.1638   -1.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -0.6967   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443   -1.3694   -1.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -0.7467   -2.4121 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9424   -0.3700   -3.8864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -1.9170   -2.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859    0.5773   -1.4343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401    1.7693   -2.2616 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.3811    3.0744   -2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126    1.4137   -3.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6396    1.9603   -1.5531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    0.9279   -1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8416    1.2009   -1.1385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7576    0.1812   -1.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6613    0.2420   -0.2968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.5030   -0.9073   -0.2472 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3265   -2.1583   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4088   -2.8948   -0.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2998   -2.1381    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5704   -2.4133    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1678   -3.6993    0.6082 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2617   -1.4289    1.3063 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7204   -0.1964    1.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4756    0.0718    0.9298 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7427   -0.8832    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554    0.2685    0.8615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2417    0.6114    2.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7033    1.3489    0.3491 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2061    2.6096    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1037    3.5721    1.4895 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.2158    2.8166    2.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1088    4.4349    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9837    4.7312    2.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6635    1.4878   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7222    0.1788   -2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2825   -0.2142   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5366    1.8512   -1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3751    0.1334   -2.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8090    0.7157   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6158   -1.1465    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9612   -1.4375    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4858   -1.4795   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8229   -1.0985    2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5222   -0.2287    4.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6561    0.9801    3.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019   -0.7609    2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4370    0.1155   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    1.5415    2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792    2.6585    0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596    1.1560   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6701    1.5498    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2830   -2.9589    1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027    0.5522    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -0.0995    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244   -3.0983   -0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159   -3.3111   -0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -2.8500    0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.5825   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -0.0721   -1.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0142   -1.6134   -2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921    0.3932   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -0.7791   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7670   -2.8253   -2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0115    0.7225   -4.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.0707   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7207    0.9809   -2.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2861    2.1196   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2483    1.1633   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4211   -2.4810   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6879   -4.5236    0.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0905   -3.7942    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3153    0.5623    1.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1429   -0.6906    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5232   -0.2489    2.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    1.1898    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    4.9083    0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9215    4.4410    2.4879 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
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 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
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  3 60  1  0
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  8 64  1  0
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 31 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  6
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 42 91  1  0
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 44 93  1  0
 47 94  1  1
 48 95  1  0
 49 96  1  6
 53 97  1  0
 54 98  1  0
M  END

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      -5.472  30.211   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.805  28.671   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.406  32.521   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.326  32.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.138  30.981   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.531  30.981   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.865  30.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530  30.211   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.196  30.981   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.867  40.991   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.866  34.061   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.653  45.061   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.724  46.353   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.805  30.211   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.200  41.761   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.197  30.211   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.161  46.871   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.638  42.279   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.607  41.134   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.866  30.981   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.568  47.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.001  45.339   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.532  30.211   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.868  43.612   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.471  30.981   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.866  32.521   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      22.729  49.029   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       3.864  30.981   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       9.198  30.981   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      23.814  46.592   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      22.246  44.434   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      19.755  47.497   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0      19.494  45.019   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0       5.197  28.671   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      21.169  42.118   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      13.199  30.211   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.532  28.671   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.471  32.521   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      16.753  39.742   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      18.814  37.453   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      16.639  37.567   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      15.303  37.347   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      13.763  40.014   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      14.739  36.371   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      11.659  36.371   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      15.867  39.451   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      13.199  34.831   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      17.361  43.292   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      18.927  39.628   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      13.199  37.911   0.000  0.00  0.00           O+0
HETATM   51  P   UNK     0      17.783  38.597   0.000  0.00  0.00           P+0
HETATM   52  P   UNK     0      14.533  38.681   0.000  0.00  0.00           P+0
HETATM   53  P   UNK     0      13.199  36.371   0.000  0.00  0.00           P+0
HETATM   54  S   UNK     0      -0.137  30.211   0.000  0.00  0.00           S+0
HETATM   55  H   UNK     0      -4.138  29.441   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0      17.281  40.223   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      20.190  40.841   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      18.287  42.641   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      10.532  31.751   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      20.406  43.693   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   14                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5    1   14                                                       
CONECT    6    7   16                                                       
CONECT    7    6   29                                                       
CONECT    8    9   28                                                       
CONECT    9    8   54                                                       
CONECT   10   15   46                                                       
CONECT   11   26   47                                                       
CONECT   12   30   31                                                       
CONECT   13   32   33                                                       
CONECT   14    2    5   25   55                                             
CONECT   15   10   19   48   56                                             
CONECT   16    6   28   34                                                  
CONECT   17   21   22   32                                                  
CONECT   18   19   24   35   57                                             
CONECT   19   15   18   49   58                                             
CONECT   20   23   26   36   59                                             
CONECT   21   17   27   30                                                  
CONECT   22   17   31   33                                                  
CONECT   23   20   29   37                                                  
CONECT   24   18   33   48   60                                             
CONECT   25   14   38   54                                                  
CONECT   26    3    4   11   20                                             
CONECT   27   21                                                            
CONECT   28    8   16                                                       
CONECT   29    7   23                                                       
CONECT   30   12   21                                                       
CONECT   31   12   22                                                       
CONECT   32   13   17                                                       
CONECT   33   13   22   24                                                  
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
CONECT   37   23                                                            
CONECT   38   25                                                            
CONECT   39   51                                                            
CONECT   40   51                                                            
CONECT   41   51                                                            
CONECT   42   52                                                            
CONECT   43   52                                                            
CONECT   44   53                                                            
CONECT   45   53                                                            
CONECT   46   10   52                                                       
CONECT   47   11   53                                                       
CONECT   48   15   24                                                       
CONECT   49   19   51                                                       
CONECT   50   52   53                                                       
CONECT   51   39   40   41   49                                             
CONECT   52   42   43   46   50                                             
CONECT   53   44   45   47   50                                             
CONECT   54    9   25                                                       
CONECT   55   14                                                            
CONECT   56   15                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   20                                                            
CONECT   60   24                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

COMPND    HMDB0300586
HETATM    1  C1  UNL     1      13.159   0.534  -1.186  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.718   0.814  -1.483  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.818   0.468  -0.269  1.00  0.00           C  
HETATM    4  C4  UNL     1      10.978  -0.997   0.046  1.00  0.00           C  
HETATM    5  C5  UNL     1      11.159   1.354   0.856  1.00  0.00           C  
HETATM    6  O1  UNL     1      11.914   2.353   0.619  1.00  0.00           O  
HETATM    7  S1  UNL     1      10.644   1.199   2.509  1.00  0.00           S  
HETATM    8  C6  UNL     1       9.506  -0.072   2.894  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.089   0.138   2.444  1.00  0.00           C  
HETATM   10  N1  UNL     1       7.884   0.275   1.059  1.00  0.00           N  
HETATM   11  C8  UNL     1       6.946   0.877   0.439  1.00  0.00           C  
HETATM   12  O2  UNL     1       7.025   0.832  -0.968  1.00  0.00           O  
HETATM   13  C9  UNL     1       5.829   1.587   1.098  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.484   1.008   0.671  1.00  0.00           C  
HETATM   15  N2  UNL     1       4.408  -0.377   1.023  1.00  0.00           N  
HETATM   16  C11 UNL     1       3.356  -1.095   1.024  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.423  -2.424   1.387  1.00  0.00           O  
HETATM   18  C12 UNL     1       2.046  -0.517   0.638  1.00  0.00           C  
HETATM   19  O4  UNL     1       1.209  -0.654   1.756  1.00  0.00           O  
HETATM   20  C13 UNL     1       1.456  -1.267  -0.543  1.00  0.00           C  
HETATM   21  C14 UNL     1       1.257  -2.724  -0.180  1.00  0.00           C  
HETATM   22  C15 UNL     1       2.409  -1.164  -1.702  1.00  0.00           C  
HETATM   23  C16 UNL     1       0.117  -0.697  -0.909  1.00  0.00           C  
HETATM   24  O5  UNL     1      -0.444  -1.369  -1.990  1.00  0.00           O  
HETATM   25  P1  UNL     1      -1.956  -0.747  -2.412  1.00  0.00           P  
HETATM   26  O6  UNL     1      -1.942  -0.370  -3.886  1.00  0.00           O  
HETATM   27  O7  UNL     1      -3.166  -1.917  -2.125  1.00  0.00           O  
HETATM   28  O8  UNL     1      -2.286   0.577  -1.434  1.00  0.00           O  
HETATM   29  P2  UNL     1      -3.140   1.769  -2.262  1.00  0.00           P  
HETATM   30  O9  UNL     1      -2.381   3.074  -2.122  1.00  0.00           O  
HETATM   31  O10 UNL     1      -3.313   1.414  -3.904  1.00  0.00           O  
HETATM   32  O11 UNL     1      -4.640   1.960  -1.553  1.00  0.00           O  
HETATM   33  C17 UNL     1      -5.518   0.928  -1.824  1.00  0.00           C  
HETATM   34  C18 UNL     1      -6.842   1.201  -1.138  1.00  0.00           C  
HETATM   35  O12 UNL     1      -7.758   0.181  -1.383  1.00  0.00           O  
HETATM   36  C19 UNL     1      -8.661   0.242  -0.297  1.00  0.00           C  
HETATM   37  N3  UNL     1      -9.503  -0.907  -0.247  1.00  0.00           N  
HETATM   38  C20 UNL     1      -9.327  -2.158  -0.689  1.00  0.00           C  
HETATM   39  N4  UNL     1     -10.409  -2.895  -0.410  1.00  0.00           N  
HETATM   40  C21 UNL     1     -11.300  -2.138   0.212  1.00  0.00           C  
HETATM   41  C22 UNL     1     -12.570  -2.413   0.709  1.00  0.00           C  
HETATM   42  N5  UNL     1     -13.168  -3.699   0.608  1.00  0.00           N  
HETATM   43  N6  UNL     1     -13.262  -1.429   1.306  1.00  0.00           N  
HETATM   44  C23 UNL     1     -12.720  -0.196   1.417  1.00  0.00           C  
HETATM   45  N7  UNL     1     -11.476   0.072   0.930  1.00  0.00           N  
HETATM   46  C24 UNL     1     -10.743  -0.883   0.322  1.00  0.00           C  
HETATM   47  C25 UNL     1      -7.655   0.269   0.862  1.00  0.00           C  
HETATM   48  O13 UNL     1      -8.242   0.611   2.052  1.00  0.00           O  
HETATM   49  C26 UNL     1      -6.703   1.349   0.349  1.00  0.00           C  
HETATM   50  O14 UNL     1      -7.206   2.610   0.685  1.00  0.00           O  
HETATM   51  P3  UNL     1      -6.104   3.572   1.490  1.00  0.00           P  
HETATM   52  O15 UNL     1      -5.216   2.817   2.423  1.00  0.00           O  
HETATM   53  O16 UNL     1      -5.109   4.435   0.408  1.00  0.00           O  
HETATM   54  O17 UNL     1      -6.984   4.731   2.379  1.00  0.00           O  
HETATM   55  H1  UNL     1      13.664   1.488  -0.855  1.00  0.00           H  
HETATM   56  H2  UNL     1      13.722   0.179  -2.080  1.00  0.00           H  
HETATM   57  H3  UNL     1      13.283  -0.214  -0.387  1.00  0.00           H  
HETATM   58  H4  UNL     1      11.537   1.851  -1.785  1.00  0.00           H  
HETATM   59  H5  UNL     1      11.375   0.133  -2.291  1.00  0.00           H  
HETATM   60  H6  UNL     1       9.809   0.716  -0.643  1.00  0.00           H  
HETATM   61  H7  UNL     1      11.616  -1.146   0.952  1.00  0.00           H  
HETATM   62  H8  UNL     1       9.961  -1.437   0.160  1.00  0.00           H  
HETATM   63  H9  UNL     1      11.486  -1.480  -0.830  1.00  0.00           H  
HETATM   64  H10 UNL     1       9.823  -1.099   2.505  1.00  0.00           H  
HETATM   65  H11 UNL     1       9.522  -0.229   4.021  1.00  0.00           H  
HETATM   66  H12 UNL     1       7.656   0.980   3.043  1.00  0.00           H  
HETATM   67  H13 UNL     1       7.502  -0.761   2.809  1.00  0.00           H  
HETATM   68  H14 UNL     1       6.437   0.116  -1.398  1.00  0.00           H  
HETATM   69  H15 UNL     1       5.915   1.541   2.183  1.00  0.00           H  
HETATM   70  H16 UNL     1       5.879   2.659   0.803  1.00  0.00           H  
HETATM   71  H17 UNL     1       4.360   1.156  -0.404  1.00  0.00           H  
HETATM   72  H18 UNL     1       3.670   1.550   1.190  1.00  0.00           H  
HETATM   73  H19 UNL     1       4.283  -2.959   1.352  1.00  0.00           H  
HETATM   74  H20 UNL     1       2.103   0.552   0.371  1.00  0.00           H  
HETATM   75  H21 UNL     1       1.599  -0.100   2.485  1.00  0.00           H  
HETATM   76  H22 UNL     1       0.324  -3.098  -0.666  1.00  0.00           H  
HETATM   77  H23 UNL     1       2.116  -3.311  -0.527  1.00  0.00           H  
HETATM   78  H24 UNL     1       1.103  -2.850   0.917  1.00  0.00           H  
HETATM   79  H25 UNL     1       3.401  -1.583  -1.453  1.00  0.00           H  
HETATM   80  H26 UNL     1       2.533  -0.072  -1.923  1.00  0.00           H  
HETATM   81  H27 UNL     1       2.014  -1.613  -2.628  1.00  0.00           H  
HETATM   82  H28 UNL     1       0.192   0.393  -1.172  1.00  0.00           H  
HETATM   83  H29 UNL     1      -0.601  -0.779  -0.075  1.00  0.00           H  
HETATM   84  H30 UNL     1      -2.767  -2.825  -2.140  1.00  0.00           H  
HETATM   85  H31 UNL     1      -4.012   0.723  -4.026  1.00  0.00           H  
HETATM   86  H32 UNL     1      -5.133  -0.071  -1.626  1.00  0.00           H  
HETATM   87  H33 UNL     1      -5.721   0.981  -2.933  1.00  0.00           H  
HETATM   88  H34 UNL     1      -7.286   2.120  -1.623  1.00  0.00           H  
HETATM   89  H35 UNL     1      -9.248   1.163  -0.345  1.00  0.00           H  
HETATM   90  H36 UNL     1      -8.421  -2.481  -1.193  1.00  0.00           H  
HETATM   91  H37 UNL     1     -12.688  -4.524   0.995  1.00  0.00           H  
HETATM   92  H38 UNL     1     -14.090  -3.794   0.141  1.00  0.00           H  
HETATM   93  H39 UNL     1     -13.315   0.562   1.906  1.00  0.00           H  
HETATM   94  H40 UNL     1      -7.143  -0.691   0.838  1.00  0.00           H  
HETATM   95  H41 UNL     1      -8.523  -0.249   2.500  1.00  0.00           H  
HETATM   96  H42 UNL     1      -5.670   1.190   0.666  1.00  0.00           H  
HETATM   97  H43 UNL     1      -4.436   4.908   0.978  1.00  0.00           H  
HETATM   98  H44 UNL     1      -7.921   4.441   2.488  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3   58   59
CONECT    3    4    5   60
CONECT    4   61   62   63
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   64   65
CONECT    9   10   66   67
CONECT   10   11   11
CONECT   11   12   13
CONECT   12   68
CONECT   13   14   69   70
CONECT   14   15   71   72
CONECT   15   16   16
CONECT   16   17   18
CONECT   17   73
CONECT   18   19   20   74
CONECT   19   75
CONECT   20   21   22   23
CONECT   21   76   77   78
CONECT   22   79   80   81
CONECT   23   24   82   83
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   84
CONECT   28   29
CONECT   29   30   30   31   32
CONECT   31   85
CONECT   32   33
CONECT   33   34   86   87
CONECT   34   35   49   88
CONECT   35   36
CONECT   36   37   47   89
CONECT   37   38   46
CONECT   38   39   39   90
CONECT   39   40
CONECT   40   41   41   46
CONECT   41   42   43
CONECT   42   91   92
CONECT   43   44   44
CONECT   44   45   93
CONECT   45   46   46
CONECT   47   48   49   94
CONECT   48   95
CONECT   49   50   96
CONECT   50   51
CONECT   51   52   52   53   54
CONECT   53   97
CONECT   54   98
END

HMDB0300586
     RDKit          3D
Dec-4-enedioyl-CoA
 98100  0  0  0  0  0  0  0  0999 V2000
   13.1588    0.5344   -1.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7181    0.8144   -1.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8177    0.4678   -0.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9782   -0.9972    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1587    1.3535    0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9141    2.3527    0.6194 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6439    1.1993    2.5094 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5057   -0.0721    2.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0893    0.1380    2.4436 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8838    0.2747    1.0593 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9456    0.8768    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0245    0.8322   -0.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8290    1.5875    1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838    1.0079    0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.3766    1.0227 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556   -1.0947    1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -2.4238    1.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.5167    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088   -0.6536    1.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -1.2671   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571   -2.7236   -0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4094   -1.1638   -1.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -0.6967   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443   -1.3694   -1.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -0.7467   -2.4121 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.9424   -0.3700   -3.8864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1661   -1.9170   -2.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859    0.5773   -1.4343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1401    1.7693   -2.2616 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.3811    3.0744   -2.1224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126    1.4137   -3.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6396    1.9603   -1.5531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5181    0.9279   -1.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8416    1.2009   -1.1385 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7576    0.1812   -1.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6613    0.2420   -0.2968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.5030   -0.9073   -0.2472 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3265   -2.1583   -0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4088   -2.8948   -0.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2998   -2.1381    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5704   -2.4133    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1678   -3.6993    0.6082 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2617   -1.4289    1.3063 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7204   -0.1964    1.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4756    0.0718    0.9298 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7427   -0.8832    0.3219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6554    0.2685    0.8615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2417    0.6114    2.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7033    1.3489    0.3491 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2061    2.6096    0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1037    3.5721    1.4895 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.2158    2.8166    2.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1088    4.4349    0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9837    4.7312    2.3791 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6635    1.4878   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7222    0.1788   -2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2825   -0.2142   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5366    1.8512   -1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3751    0.1334   -2.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8090    0.7157   -0.6425 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6158   -1.1465    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9612   -1.4375    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4858   -1.4795   -0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8229   -1.0985    2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5222   -0.2287    4.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6561    0.9801    3.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019   -0.7609    2.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4370    0.1155   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    1.5415    2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8792    2.6585    0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3596    1.1560   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6701    1.5498    1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2830   -2.9589    1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027    0.5522    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5992   -0.0995    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244   -3.0983   -0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1159   -3.3111   -0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1033   -2.8500    0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -1.5825   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -0.0721   -1.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0142   -1.6134   -2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921    0.3932   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -0.7791   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7670   -2.8253   -2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0115    0.7225   -4.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1330   -0.0707   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7207    0.9809   -2.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2861    2.1196   -1.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2483    1.1633   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4211   -2.4810   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6879   -4.5236    0.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0905   -3.7942    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3153    0.5623    1.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1429   -0.6906    0.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5232   -0.2489    2.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6698    1.1898    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4365    4.9083    0.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9215    4.4410    2.4879 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  2 59  1  0
  3 60  1  0
  4 61  1  0
  4 62  1  0
  4 63  1  0
  8 64  1  0
  8 65  1  0
  9 66  1  0
  9 67  1  0
 12 68  1  0
 13 69  1  0
 13 70  1  0
 14 71  1  0
 14 72  1  0
 17 73  1  0
 18 74  1  0
 19 75  1  0
 21 76  1  0
 21 77  1  0
 21 78  1  0
 22 79  1  0
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 27 84  1  0
 31 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  6
 36 89  1  6
 38 90  1  0
 42 91  1  0
 42 92  1  0
 44 93  1  0
 47 94  1  1
 48 95  1  0
 49 96  1  6
 53 97  1  0
 54 98  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-2-Methylbutyryl-CoA	HMDB
(S)-2-Methylbutyryl-coenzyme A	HMDB
2-Methylbutanoyl-CoA	HMDB
2-Methylbutanoyl-coenzyme A	HMDB
2-Methylbutyryl-coenzyme A	HMDB
3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-{[3-({2-[(2-methylbutanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl] dihydrogen diphosphate}	HMDB
a-Methylbutyryl-CoA	HMDB
alpha-Methylbutyryl-CoA	HMDB
alpha-Methylbutyryl-coenzyme A	HMDB
Methylbutanoyl-CoA	HMDB
Methylbutanoyl-coenzyme A	HMDB

Chemical Formula

C₂₆H₄₄N₇O₁₇P₃S

Average Molecular Weight

851.651

Monoisotopic Molecular Weight

851.172723243

IUPAC Name

4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(2-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid

Traditional Name

α-methylbutyryl-coenzyme A

CAS Registry Number

Not Available

SMILES

[H]C(C)(CC)C(=O)SCCN=C(O)CCN=C(O)C([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O

InChI Identifier

InChI=1S/C26H44N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h12-15,18-20,24,35-36H,5-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t14?,15-,18-,19-,20?,24-/m1/s1

InChI Key

LYNVNYDEQMMNMZ-PCLZRLGGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.09	ALOGPS
logP	-3.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.48	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	187.05 m³·mol⁻¹	ChemAxon
Polarizability	78.36 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	259.854	32859911
AllCCS	[M+H-H2O]+	260.258	32859911
AllCCS	[M+Na]+	259.298	32859911
AllCCS	[M+NH4]+	259.429	32859911
AllCCS	[M-H]-	253.902	32859911
AllCCS	[M+Na-2H]-	258.242	32859911
AllCCS	[M+HCOO]-	263.051	32859911
DeepCCS	[M-2H]-	263.989	30932474
DeepCCS	[M+Na]+	237.631	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 10V, Positive-QTOF	splash10-000i-2912000120-af66a2d60f6d59648007	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 20V, Positive-QTOF	splash10-000i-1913000000-c428618786e430847e02	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 40V, Positive-QTOF	splash10-000i-2911000000-e94fe02be635ec0efbe4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 10V, Negative-QTOF	splash10-001i-9830141640-f0955b8cb6c0f08f3bcb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 20V, Negative-QTOF	splash10-001i-5910010010-1ba87f7cf29ee29ad19c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 40V, Negative-QTOF	splash10-0a7i-5900100000-514b5ace93ecafe7208b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 10V, Positive-QTOF	splash10-0udi-0000000090-8eb4cafbf643916905ae	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 20V, Positive-QTOF	splash10-014i-2801107960-e37719d3abb779243e5b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 40V, Positive-QTOF	splash10-0002-0029000000-44b78f66ed4bd9a4b67a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 10V, Negative-QTOF	splash10-0udi-0000000090-a664e1628db94106f147	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 20V, Negative-QTOF	splash10-00lr-9500001110-a261a7475d8206f30428	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dec-4-enedioyl-CoA 40V, Negative-QTOF	splash10-00fr-9201506510-e73f1cbbfd8e4ccbe3f4	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB022387

KNApSAcK ID

Not Available

Chemspider ID

388491

KEGG Compound ID

C01033

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439371

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Abe T, Fujino T, Fukuyama R, Minoshima S, Shimizu N, Toh H, Suzuki H, Yamamoto T: Human long-chain acyl-CoA synthetase: structure and chromosomal location. J Biochem. 1992 Jan;111(1):123-8. [PubMed:1607358 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for Dec-4-enedioyl-CoA (HMDB0300586)

MOL for HMDB0300586 (Dec-4-enedioyl-CoA)

3D MOL for HMDB0300586 (Dec-4-enedioyl-CoA)

3D SDF for HMDB0300586 (Dec-4-enedioyl-CoA)

3D-SDF for HMDB0300586 (Dec-4-enedioyl-CoA)

PDB for HMDB0300586 (Dec-4-enedioyl-CoA)

3D PDB for HMDB0300586 (Dec-4-enedioyl-CoA)

SMILES for HMDB0300586 (Dec-4-enedioyl-CoA)

INCHI for HMDB0300586 (Dec-4-enedioyl-CoA)

Structure for HMDB0300586 (Dec-4-enedioyl-CoA)

3D Structure for HMDB0300586 (Dec-4-enedioyl-CoA)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra