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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-09-21 19:06:18 UTC

Update Date

2021-10-01 16:50:19 UTC

HMDB ID

HMDB0300833

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-hydroxy-3-methylbutanedioyl-CoA

Description

2-hydroxy-3-methylbutanedioyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a 2-hydroxy-3-methylbutanedioic acid thioester of coenzyme A. 2-hydroxy-3-methylbutanedioyl-coa is an acyl-CoA with 5 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. 2-hydroxy-3-methylbutanedioyl-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. 2-hydroxy-3-methylbutanedioyl-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, 2-hydroxy-3-methylbutanedioyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of 2-hydroxy-3-methylbutanedioyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts 2-hydroxy-3-methylbutanedioyl-CoA into 2-hydroxy-3-methylbutanedioylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, 2-hydroxy-3-methylbutanedioylcarnitine is converted back to 2-hydroxy-3-methylbutanedioyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of 2-hydroxy-3-methylbutanedioyl-CoA occurs in four steps. First, since 2-hydroxy-3-methylbutanedioyl-CoA is a medium chain acyl-CoA it is the substrate for a medium chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of 2-hydroxy-3-methylbutanedioyl-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 2-hydroxy-3-methylbutanedioyl-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

  Mrv1652304102100022D          

 57 59  0  0  0  0            999 V2000
   17.6262    1.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3407    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3407    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0552    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0552    0.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7696    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4841    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4841    0.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1986    1.8710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9130    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6275    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3420    1.4585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0564    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0564    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7709    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4854    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1999    1.4585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9143    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9143    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6288    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6288    0.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3433    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7558    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9308    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0577    2.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7722    1.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4867    2.2835    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.8992    1.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0742    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2012    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9156    2.2835    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   31.5031    1.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3281    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6301    1.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3446    2.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0590    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8127    2.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3648    1.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1852    1.6797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5977    2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4047    2.2227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4909    1.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1584    0.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0721    0.0968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3185   -0.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6510    0.2462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7373    1.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9121    1.2528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9523    0.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2878    0.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1453    1.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5322    0.4985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7476    0.7535    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   33.0025    1.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4926   -0.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9629    1.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7696    2.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 42 47  2  0  0  0  0
 39 47  1  0  0  0  0
 43 48  1  0  0  0  0
 38 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 36 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
  6 57  1  0  0  0  0
M  END

HMDB0300833
     RDKit          3D
2-hydroxy-3-methylbutanedioyl-CoA
 99101  0  0  0  0  0  0  0  0999 V2000
   11.6126    0.7550    2.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6700   -0.4994    1.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4637   -1.3048    1.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6060   -2.4991    2.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7835   -0.7636    1.6030 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5721    0.9036    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0126    0.8973   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1755    0.0035   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7419    0.2119   -1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3241    1.2548   -0.8976 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566   -0.7478   -2.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6533   -0.4644   -2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.0747   -1.8385 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.0576   -1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    2.1572   -1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373    1.0879   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3446   -0.1614   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9940    2.1142   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111    1.6579   -2.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437    3.4667   -0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    2.1407   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867    3.0574   -0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    3.0418    0.4203 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.4741    4.1903    0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889    3.1484    2.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    1.6016    0.2409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721    1.9293   -0.5440 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.5447    3.0297    0.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    2.4876   -2.0965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9101    0.6282   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590   -0.5772   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -1.6831   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812   -1.7671    0.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0946   -1.1269    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8752   -1.2461    1.5969 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4735   -0.7028    2.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3726   -0.9426    3.7114 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3882   -1.6441    3.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5634   -2.1455    3.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8200   -1.9102    5.0564 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3697   -2.8124    2.8594 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0442   -2.9887    1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8818   -2.4886    1.0663 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0507   -1.8214    1.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7406   -1.6389   -0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0174   -2.9841   -0.8412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5533   -1.4527   -1.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6425   -2.4056   -2.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8337   -1.5894   -4.2891 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.5170   -1.5378   -5.0461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0034   -2.4485   -5.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3723    0.0006   -4.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9102   -1.3213    1.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0416   -0.5056    1.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9388   -1.6064    3.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8297   -1.0629    4.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0607   -2.4357    4.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6949    0.6990    3.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5564    1.6827    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4938    0.7447    3.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8676   -0.2355    0.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125    1.6699    1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5135    1.1483    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0621    0.6397   -0.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9057    1.9342   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5615   -0.8511   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213   -1.7026   -1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6304   -1.1886   -2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.2790   -3.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245    0.3906   -3.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.8992   -1.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386    1.3910    0.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -0.4443    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    2.1275   -3.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    1.9151   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915    0.5486   -2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    4.2618   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    3.6652   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665    3.5770   -1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374    2.5379    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    1.1479    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262    4.1237    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4027    2.8039   -2.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0403   -0.4912   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4739   -0.8108   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8677   -2.6419   -1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9628   -0.0138    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5436   -0.1404    2.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7905   -1.7760    5.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0444   -1.8685    5.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6995   -3.5338    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5495   -1.0071   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2428   -3.5653   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5750   -0.4246   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7379   -1.8446   -5.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0855    0.2544   -4.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0165   -2.2232    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7492    0.4237    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3662   -3.1733    4.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
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 16 18  1  0
 18 19  1  0
 18 20  1  0
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 21 22  1  0
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 23 24  2  0
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 46 93  1  0
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 51 95  1  0
 52 96  1  0
 53 97  1  0
 54 98  1  0
 57 99  1  0
M  END

  Mrv1652304102100022D          

 57 59  0  0  0  0            999 V2000
   17.6262    1.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3407    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3407    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0552    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0552    0.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7696    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4841    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4841    0.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1986    1.8710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9130    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6275    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3420    1.4585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0564    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0564    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7709    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4854    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1999    1.4585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9143    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9143    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6288    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6288    0.6335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3433    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7558    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9308    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0577    2.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7722    1.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4867    2.2835    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.8992    1.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0742    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2012    2.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9156    2.2835    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   31.5031    1.5691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3281    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6301    1.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3446    2.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0590    1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8127    2.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3648    1.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1852    1.6797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5977    2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4047    2.2227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4909    1.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1584    0.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0721    0.0968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3185   -0.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6510    0.2462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.7373    1.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9121    1.2528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9523    0.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2878    0.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1453    1.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5322    0.4985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7476    0.7535    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   33.0025    1.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4926   -0.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9629    1.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7696    2.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 42 47  2  0  0  0  0
 39 47  1  0  0  0  0
 43 48  1  0  0  0  0
 38 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 36 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 53 56  1  0  0  0  0
  6 57  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0300833

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C26H42N7O20P3S/c1-12(16(35)24(39)40)25(41)57-7-6-28-14(34)4-5-29-22(38)19(37)26(2,3)9-50-56(47,48)53-55(45,46)49-8-13-18(52-54(42,43)44)17(36)23(51-13)33-11-32-15-20(27)30-10-31-21(15)33/h10-13,16-19,23,35-37H,4-9H2,1-3H3,(H,28,34)(H,29,38)(H,39,40)(H,45,46)(H,47,48)(H2,27,30,31)(H2,42,43,44)

> <INCHI_KEY>
OTENCPQKSBPYCM-UHFFFAOYSA-N

> <FORMULA>
C26H42N7O20P3S

> <MOLECULAR_WEIGHT>
897.63

> <EXACT_MASS>
897.141818948

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
79.06725688923544

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-hydroxy-3-methyl-4-oxobutanoic acid

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-6.2297783373065165

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.8881891896039282

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8198790861849523

> <JCHEM_PKA_STRONGEST_BASIC>
4.104033671750903

> <JCHEM_POLAR_SURFACE_AREA>
421.1599999999999

> <JCHEM_REFRACTIVITY>
189.014

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-({2-[3-(3-{[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-hydroxy-3-methyl-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0300833
     RDKit          3D
2-hydroxy-3-methylbutanedioyl-CoA
 99101  0  0  0  0  0  0  0  0999 V2000
   11.6126    0.7550    2.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6700   -0.4994    1.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4637   -1.3048    1.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6060   -2.4991    2.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7835   -0.7636    1.6030 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5721    0.9036    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0126    0.8973   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1755    0.0035   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7419    0.2119   -1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3241    1.2548   -0.8976 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566   -0.7478   -2.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6533   -0.4644   -2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.0747   -1.8385 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.0576   -1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    2.1572   -1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373    1.0879   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3446   -0.1614   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9940    2.1142   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111    1.6579   -2.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437    3.4667   -0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    2.1407   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867    3.0574   -0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    3.0418    0.4203 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.4741    4.1903    0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889    3.1484    2.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    1.6016    0.2409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721    1.9293   -0.5440 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.5447    3.0297    0.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    2.4876   -2.0965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9101    0.6282   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590   -0.5772   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -1.6831   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812   -1.7671    0.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0946   -1.1269    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8752   -1.2461    1.5969 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4735   -0.7028    2.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3726   -0.9426    3.7114 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3882   -1.6441    3.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5634   -2.1455    3.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8200   -1.9102    5.0564 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3697   -2.8124    2.8594 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0442   -2.9887    1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8818   -2.4886    1.0663 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0507   -1.8214    1.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7406   -1.6389   -0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0174   -2.9841   -0.8412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5533   -1.4527   -1.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6425   -2.4056   -2.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8337   -1.5894   -4.2891 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.5170   -1.5378   -5.0461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0034   -2.4485   -5.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3723    0.0006   -4.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9102   -1.3213    1.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0416   -0.5056    1.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9388   -1.6064    3.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8297   -1.0629    4.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0607   -2.4357    4.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6949    0.6990    3.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5564    1.6827    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4938    0.7447    3.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8676   -0.2355    0.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125    1.6699    1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5135    1.1483    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0621    0.6397   -0.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9057    1.9342   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5615   -0.8511   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213   -1.7026   -1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6304   -1.1886   -2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.2790   -3.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245    0.3906   -3.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.8992   -1.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386    1.3910    0.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -0.4443    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    2.1275   -3.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    1.9151   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915    0.5486   -2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    4.2618   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    3.6652   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665    3.5770   -1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374    2.5379    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    1.1479    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262    4.1237    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4027    2.8039   -2.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0403   -0.4912   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4739   -0.8108   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8677   -2.6419   -1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9628   -0.0138    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5436   -0.1404    2.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7905   -1.7760    5.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0444   -1.8685    5.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6995   -3.5338    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5495   -1.0071   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2428   -3.5653   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5750   -0.4246   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7379   -1.8446   -5.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0855    0.2544   -4.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0165   -2.2232    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7492    0.4237    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3662   -3.1733    4.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
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 34 45  1  0
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 57 99  1  0
M  END

HEADER    PROTEIN                                 10-APR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-APR-21         0                                  
HETATM    1  O   UNK     0      32.902   2.723   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      34.236   3.493   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      34.236   5.033   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      35.570   2.723   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      35.570   1.183   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      36.903   3.493   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      38.237   2.723   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      38.237   1.183   0.000  0.00  0.00           O+0
HETATM    9  S   UNK     0      39.571   3.493   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0      40.904   2.723   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.238   3.493   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      43.572   2.723   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      44.905   3.493   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      44.905   5.033   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      46.239   2.723   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      47.573   3.493   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      48.906   2.723   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      50.240   3.493   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      50.240   5.033   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      51.574   2.723   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      51.574   1.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      52.907   3.493   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      53.677   2.159   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      52.137   4.826   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      54.241   4.263   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      55.575   3.493   0.000  0.00  0.00           O+0
HETATM   27  P   UNK     0      56.908   4.263   0.000  0.00  0.00           P+0
HETATM   28  O   UNK     0      57.678   2.929   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      56.138   5.596   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      58.242   5.033   0.000  0.00  0.00           O+0
HETATM   31  P   UNK     0      59.576   4.263   0.000  0.00  0.00           P+0
HETATM   32  O   UNK     0      58.806   2.929   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      60.346   5.596   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      60.910   3.493   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      62.243   4.263   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      63.577   3.493   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      64.984   4.119   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      66.014   2.975   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      67.546   3.136   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0      68.316   4.469   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      69.822   4.149   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      69.983   2.617   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      71.229   1.712   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0      71.068   0.181   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0      69.661  -0.446   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      68.415   0.459   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0      68.576   1.991   0.000  0.00  0.00           C+0
HETATM   48  N   UNK     0      72.636   2.339   0.000  0.00  0.00           N+0
HETATM   49  C   UNK     0      65.244   1.641   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      65.871   0.234   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      63.738   1.961   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      62.593   0.931   0.000  0.00  0.00           O+0
HETATM   53  P   UNK     0      61.129   1.406   0.000  0.00  0.00           P+0
HETATM   54  O   UNK     0      61.605   2.871   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      60.653  -0.058   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      59.664   1.882   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      36.903   5.033   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   57                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   51                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   49                                                  
CONECT   39   38   40   47                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   47                                                  
CONECT   43   42   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42   39                                                  
CONECT   48   43                                                            
CONECT   49   38   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   36   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   55   56                                             
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   53                                                            
CONECT   57    6                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

COMPND    HMDB0300833
HETATM    1  C1  UNL     1      11.613   0.755   2.440  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.670  -0.499   1.593  1.00  0.00           C  
HETATM    3  C3  UNL     1      10.464  -1.305   1.763  1.00  0.00           C  
HETATM    4  O1  UNL     1      10.606  -2.499   2.047  1.00  0.00           O  
HETATM    5  S1  UNL     1       8.783  -0.764   1.603  1.00  0.00           S  
HETATM    6  C4  UNL     1       8.572   0.904   0.986  1.00  0.00           C  
HETATM    7  C5  UNL     1       9.013   0.897  -0.475  1.00  0.00           C  
HETATM    8  N1  UNL     1       8.176   0.003  -1.198  1.00  0.00           N  
HETATM    9  C6  UNL     1       6.742   0.212  -1.399  1.00  0.00           C  
HETATM   10  O2  UNL     1       6.324   1.255  -0.898  1.00  0.00           O  
HETATM   11  C7  UNL     1       5.957  -0.748  -2.122  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.653  -0.464  -2.659  1.00  0.00           C  
HETATM   13  N2  UNL     1       3.582  -0.075  -1.839  1.00  0.00           N  
HETATM   14  C9  UNL     1       3.223   1.058  -1.117  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.833   2.157  -1.031  1.00  0.00           O  
HETATM   16  C10 UNL     1       1.937   1.088  -0.288  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.345  -0.161  -0.274  1.00  0.00           O  
HETATM   18  C11 UNL     1       0.994   2.114  -0.925  1.00  0.00           C  
HETATM   19  C12 UNL     1       0.711   1.658  -2.331  1.00  0.00           C  
HETATM   20  C13 UNL     1       1.644   3.467  -0.997  1.00  0.00           C  
HETATM   21  C14 UNL     1      -0.246   2.141  -0.079  1.00  0.00           C  
HETATM   22  O5  UNL     1      -1.187   3.057  -0.578  1.00  0.00           O  
HETATM   23  P1  UNL     1      -2.559   3.042   0.420  1.00  0.00           P  
HETATM   24  O6  UNL     1      -3.474   4.190   0.079  1.00  0.00           O  
HETATM   25  O7  UNL     1      -2.089   3.148   2.061  1.00  0.00           O  
HETATM   26  O8  UNL     1      -3.417   1.602   0.241  1.00  0.00           O  
HETATM   27  P2  UNL     1      -4.872   1.929  -0.544  1.00  0.00           P  
HETATM   28  O9  UNL     1      -5.545   3.030   0.287  1.00  0.00           O  
HETATM   29  O10 UNL     1      -4.526   2.488  -2.096  1.00  0.00           O  
HETATM   30  O11 UNL     1      -5.910   0.628  -0.556  1.00  0.00           O  
HETATM   31  C15 UNL     1      -5.359  -0.577  -0.907  1.00  0.00           C  
HETATM   32  C16 UNL     1      -6.393  -1.683  -0.867  1.00  0.00           C  
HETATM   33  O12 UNL     1      -6.881  -1.767   0.415  1.00  0.00           O  
HETATM   34  C17 UNL     1      -8.095  -1.127   0.420  1.00  0.00           C  
HETATM   35  N3  UNL     1      -8.875  -1.246   1.597  1.00  0.00           N  
HETATM   36  C18 UNL     1      -8.474  -0.703   2.782  1.00  0.00           C  
HETATM   37  N4  UNL     1      -9.373  -0.943   3.711  1.00  0.00           N  
HETATM   38  C19 UNL     1     -10.388  -1.644   3.178  1.00  0.00           C  
HETATM   39  C20 UNL     1     -11.563  -2.145   3.693  1.00  0.00           C  
HETATM   40  N5  UNL     1     -11.820  -1.910   5.056  1.00  0.00           N  
HETATM   41  N6  UNL     1     -12.370  -2.812   2.859  1.00  0.00           N  
HETATM   42  C21 UNL     1     -12.044  -2.989   1.559  1.00  0.00           C  
HETATM   43  N7  UNL     1     -10.882  -2.489   1.066  1.00  0.00           N  
HETATM   44  C22 UNL     1     -10.051  -1.821   1.850  1.00  0.00           C  
HETATM   45  C23 UNL     1      -8.741  -1.639  -0.828  1.00  0.00           C  
HETATM   46  O13 UNL     1      -9.017  -2.984  -0.841  1.00  0.00           O  
HETATM   47  C24 UNL     1      -7.553  -1.453  -1.800  1.00  0.00           C  
HETATM   48  O14 UNL     1      -7.642  -2.406  -2.814  1.00  0.00           O  
HETATM   49  P3  UNL     1      -7.834  -1.589  -4.289  1.00  0.00           P  
HETATM   50  O15 UNL     1      -6.517  -1.538  -5.046  1.00  0.00           O  
HETATM   51  O16 UNL     1      -9.003  -2.448  -5.180  1.00  0.00           O  
HETATM   52  O17 UNL     1      -8.372   0.001  -4.070  1.00  0.00           O  
HETATM   53  C25 UNL     1      12.910  -1.321   1.988  1.00  0.00           C  
HETATM   54  O18 UNL     1      14.042  -0.506   1.717  1.00  0.00           O  
HETATM   55  C26 UNL     1      12.939  -1.606   3.437  1.00  0.00           C  
HETATM   56  O19 UNL     1      13.830  -1.063   4.157  1.00  0.00           O  
HETATM   57  O20 UNL     1      12.061  -2.436   4.102  1.00  0.00           O  
HETATM   58  H1  UNL     1      10.695   0.699   3.063  1.00  0.00           H  
HETATM   59  H2  UNL     1      11.556   1.683   1.848  1.00  0.00           H  
HETATM   60  H3  UNL     1      12.494   0.745   3.124  1.00  0.00           H  
HETATM   61  H4  UNL     1      11.868  -0.236   0.526  1.00  0.00           H  
HETATM   62  H5  UNL     1       9.212   1.670   1.476  1.00  0.00           H  
HETATM   63  H6  UNL     1       7.513   1.148   1.024  1.00  0.00           H  
HETATM   64  H7  UNL     1      10.062   0.640  -0.624  1.00  0.00           H  
HETATM   65  H8  UNL     1       8.906   1.934  -0.905  1.00  0.00           H  
HETATM   66  H9  UNL     1       8.562  -0.851  -1.623  1.00  0.00           H  
HETATM   67  H10 UNL     1       5.821  -1.703  -1.445  1.00  0.00           H  
HETATM   68  H11 UNL     1       6.630  -1.189  -2.961  1.00  0.00           H  
HETATM   69  H12 UNL     1       4.312  -1.279  -3.407  1.00  0.00           H  
HETATM   70  H13 UNL     1       4.824   0.391  -3.452  1.00  0.00           H  
HETATM   71  H14 UNL     1       2.824  -0.899  -1.736  1.00  0.00           H  
HETATM   72  H15 UNL     1       2.239   1.391   0.719  1.00  0.00           H  
HETATM   73  H16 UNL     1       1.088  -0.444   0.635  1.00  0.00           H  
HETATM   74  H17 UNL     1       1.385   2.127  -3.055  1.00  0.00           H  
HETATM   75  H18 UNL     1      -0.325   1.915  -2.635  1.00  0.00           H  
HETATM   76  H19 UNL     1       0.791   0.549  -2.402  1.00  0.00           H  
HETATM   77  H20 UNL     1       0.866   4.262  -1.087  1.00  0.00           H  
HETATM   78  H21 UNL     1       2.314   3.665  -0.141  1.00  0.00           H  
HETATM   79  H22 UNL     1       2.266   3.577  -1.927  1.00  0.00           H  
HETATM   80  H23 UNL     1       0.037   2.538   0.936  1.00  0.00           H  
HETATM   81  H24 UNL     1      -0.681   1.148   0.088  1.00  0.00           H  
HETATM   82  H25 UNL     1      -1.926   4.124   2.226  1.00  0.00           H  
HETATM   83  H26 UNL     1      -5.403   2.804  -2.467  1.00  0.00           H  
HETATM   84  H27 UNL     1      -5.040  -0.491  -1.984  1.00  0.00           H  
HETATM   85  H28 UNL     1      -4.474  -0.811  -0.320  1.00  0.00           H  
HETATM   86  H29 UNL     1      -5.868  -2.642  -1.082  1.00  0.00           H  
HETATM   87  H30 UNL     1      -7.963  -0.014   0.242  1.00  0.00           H  
HETATM   88  H31 UNL     1      -7.544  -0.140   2.969  1.00  0.00           H  
HETATM   89  H32 UNL     1     -12.790  -1.776   5.395  1.00  0.00           H  
HETATM   90  H33 UNL     1     -11.044  -1.868   5.743  1.00  0.00           H  
HETATM   91  H34 UNL     1     -12.700  -3.534   0.868  1.00  0.00           H  
HETATM   92  H35 UNL     1      -9.549  -1.007  -1.223  1.00  0.00           H  
HETATM   93  H36 UNL     1      -8.243  -3.565  -0.810  1.00  0.00           H  
HETATM   94  H37 UNL     1      -7.575  -0.425  -2.194  1.00  0.00           H  
HETATM   95  H38 UNL     1      -9.738  -1.845  -5.426  1.00  0.00           H  
HETATM   96  H39 UNL     1      -9.086   0.254  -4.703  1.00  0.00           H  
HETATM   97  H40 UNL     1      13.017  -2.223   1.370  1.00  0.00           H  
HETATM   98  H41 UNL     1      13.749   0.424   1.539  1.00  0.00           H  
HETATM   99  H42 UNL     1      12.366  -3.173   4.756  1.00  0.00           H  
CONECT    1    2   58   59   60
CONECT    2    3   53   61
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   62   63
CONECT    7    8   64   65
CONECT    8    9   66
CONECT    9   10   10   11
CONECT   11   12   67   68
CONECT   12   13   69   70
CONECT   13   14   71
CONECT   14   15   15   16
CONECT   16   17   18   72
CONECT   17   73
CONECT   18   19   20   21
CONECT   19   74   75   76
CONECT   20   77   78   79
CONECT   21   22   80   81
CONECT   22   23
CONECT   23   24   24   25   26
CONECT   25   82
CONECT   26   27
CONECT   27   28   28   29   30
CONECT   29   83
CONECT   30   31
CONECT   31   32   84   85
CONECT   32   33   47   86
CONECT   33   34
CONECT   34   35   45   87
CONECT   35   36   44
CONECT   36   37   37   88
CONECT   37   38
CONECT   38   39   39   44
CONECT   39   40   41
CONECT   40   89   90
CONECT   41   42   42
CONECT   42   43   91
CONECT   43   44   44
CONECT   45   46   47   92
CONECT   46   93
CONECT   47   48   94
CONECT   48   49
CONECT   49   50   50   51   52
CONECT   51   95
CONECT   52   96
CONECT   53   54   55   97
CONECT   54   98
CONECT   55   56   56   57
CONECT   57   99
END

HMDB0300833
     RDKit          3D
2-hydroxy-3-methylbutanedioyl-CoA
 99101  0  0  0  0  0  0  0  0999 V2000
   11.6126    0.7550    2.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6700   -0.4994    1.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4637   -1.3048    1.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6060   -2.4991    2.0469 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7835   -0.7636    1.6030 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5721    0.9036    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0126    0.8973   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1755    0.0035   -1.1985 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7419    0.2119   -1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3241    1.2548   -0.8976 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566   -0.7478   -2.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6533   -0.4644   -2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5825   -0.0747   -1.8385 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.0576   -1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    2.1572   -1.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9373    1.0879   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3446   -0.1614   -0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9940    2.1142   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7111    1.6579   -2.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437    3.4667   -0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    2.1407   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867    3.0574   -0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593    3.0418    0.4203 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.4741    4.1903    0.0787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889    3.1484    2.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    1.6016    0.2409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721    1.9293   -0.5440 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.5447    3.0297    0.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5261    2.4876   -2.0965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9101    0.6282   -0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590   -0.5772   -0.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -1.6831   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8812   -1.7671    0.4147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0946   -1.1269    0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8752   -1.2461    1.5969 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4735   -0.7028    2.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3726   -0.9426    3.7114 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3882   -1.6441    3.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5634   -2.1455    3.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8200   -1.9102    5.0564 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3697   -2.8124    2.8594 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0442   -2.9887    1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8818   -2.4886    1.0663 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0507   -1.8214    1.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7406   -1.6389   -0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0174   -2.9841   -0.8412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5533   -1.4527   -1.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6425   -2.4056   -2.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8337   -1.5894   -4.2891 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.5170   -1.5378   -5.0461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0034   -2.4485   -5.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3723    0.0006   -4.0698 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9102   -1.3213    1.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0416   -0.5056    1.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9388   -1.6064    3.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8297   -1.0629    4.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0607   -2.4357    4.1024 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6949    0.6990    3.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5564    1.6827    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4938    0.7447    3.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8676   -0.2355    0.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125    1.6699    1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5135    1.1483    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0621    0.6397   -0.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9057    1.9342   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5615   -0.8511   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213   -1.7026   -1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6304   -1.1886   -2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -1.2790   -3.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8245    0.3906   -3.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.8992   -1.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386    1.3910    0.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -0.4443    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    2.1275   -3.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    1.9151   -2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915    0.5486   -2.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    4.2618   -1.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143    3.6652   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665    3.5770   -1.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374    2.5379    0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806    1.1479    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9262    4.1237    2.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4027    2.8039   -2.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0403   -0.4912   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4739   -0.8108   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8677   -2.6419   -1.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9628   -0.0138    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5436   -0.1404    2.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7905   -1.7760    5.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0444   -1.8685    5.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6995   -3.5338    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5495   -1.0071   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2428   -3.5653   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5750   -0.4246   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7379   -1.8446   -5.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0855    0.2544   -4.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0165   -2.2232    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7492    0.4237    1.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3662   -3.1733    4.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 39 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 34 45  1  0
 45 46  1  0
 45 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  2  0
 49 51  1  0
 49 52  1  0
  2 53  1  0
 53 54  1  0
 53 55  1  0
 55 56  2  0
 55 57  1  0
 47 32  1  0
 44 35  1  0
 44 38  1  0
  1 58  1  0
  1 59  1  0
  1 60  1  0
  2 61  1  0
  6 62  1  0
  6 63  1  0
  7 64  1  0
  7 65  1  0
  8 66  1  0
 11 67  1  0
 11 68  1  0
 12 69  1  0
 12 70  1  0
 13 71  1  0
 16 72  1  0
 17 73  1  0
 19 74  1  0
 19 75  1  0
 19 76  1  0
 20 77  1  0
 20 78  1  0
 20 79  1  0
 21 80  1  0
 21 81  1  0
 25 82  1  0
 29 83  1  0
 31 84  1  0
 31 85  1  0
 32 86  1  0
 34 87  1  0
 36 88  1  0
 40 89  1  0
 40 90  1  0
 42 91  1  0
 45 92  1  0
 46 93  1  0
 47 94  1  0
 51 95  1  0
 52 96  1  0
 53 97  1  0
 54 98  1  0
 57 99  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-hydroxy-3-methyl-4-oxobutanoate	HMDB
4-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-hydroxy-3-methyl-4-oxobutanoate	HMDB
4-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-hydroxy-3-methyl-4-oxobutanoic acid	HMDB

Chemical Formula

C₂₆H₄₂N₇O₂₀P₃S

Average Molecular Weight

897.63

Monoisotopic Molecular Weight

897.141818948

IUPAC Name

4-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-hydroxy-3-methyl-4-oxobutanoic acid

Traditional Name

4-({2-[3-(3-{[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-hydroxy-3-methyl-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

CC(C(O)C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C26H42N7O20P3S/c1-12(16(35)24(39)40)25(41)57-7-6-28-14(34)4-5-29-22(38)19(37)26(2,3)9-50-56(47,48)53-55(45,46)49-8-13-18(52-54(42,43)44)17(36)23(51-13)33-11-32-15-20(27)30-10-31-21(15)33/h10-13,16-19,23,35-37H,4-9H2,1-3H3,(H,28,34)(H,29,38)(H,39,40)(H,45,46)(H,47,48)(H2,27,30,31)(H2,42,43,44)

InChI Key

OTENCPQKSBPYCM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

3-hydroxyacyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Pentose phosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Hydroxy fatty acid
Monoalkyl phosphate
Aminopyrimidine
Thia fatty acid
Hydroxy acid
Imidolactam
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Alpha-hydroxy acid
Phosphoric acid ester
Pyrimidine
Imidazole
Oxolane
Azole
Heteroaromatic compound
Secondary alcohol
Amino acid or derivatives
Thiocarboxylic acid ester
Amino acid
Carbothioic s-ester
Carboximidic acid derivative
Organoheterocyclic compound
Organic 1,3-dipolar compound
Carboxylic acid
Azacycle
Propargyl-type 1,3-dipolar organic compound
Oxacycle
Carboximidic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Amine
Organic oxide
Primary 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	-0.64	ALOGPS
logP	-6.2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.1	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	421.16 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	189.01 m³·mol⁻¹	ChemAxon
Polarizability	79.07 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]+	260.792	32859911
AllCCS	[M+H-H2O]+	261.365	32859911
AllCCS	[M+Na]+	260.031	32859911
AllCCS	[M+NH4]+	260.208	32859911
AllCCS	[M-H]-	262.567	32859911
AllCCS	[M+Na-2H]-	266.867	32859911
AllCCS	[M+HCOO]-	271.621	32859911
DeepCCS	[M+H]+	237.066	30932474
DeepCCS	[M-H]-	235.17	30932474
DeepCCS	[M-2H]-	268.406	30932474
DeepCCS	[M+Na]+	243.05	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxy-3-methylbutanedioyl-CoA 10V, Positive-QTOF	splash10-001i-0000000190-d02cb7ecba85b2a13b7c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxy-3-methylbutanedioyl-CoA 20V, Positive-QTOF	splash10-03ei-0500000290-29c5626afafe49bb5825	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxy-3-methylbutanedioyl-CoA 40V, Positive-QTOF	splash10-0006-0039000000-ec1cb758bff0ee0e4890	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxy-3-methylbutanedioyl-CoA 10V, Negative-QTOF	splash10-0002-0000000190-a387885acc8e49e4efd2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxy-3-methylbutanedioyl-CoA 20V, Negative-QTOF	splash10-0170-9300001330-b39ffb2c91e47198c5a3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxy-3-methylbutanedioyl-CoA 40V, Negative-QTOF	splash10-004j-2101301900-f9c6b4fdd61f0d456417	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25246206

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 2-hydroxy-3-methylbutanedioyl-CoA (HMDB0300833)

MOL for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

3D MOL for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

3D SDF for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

3D-SDF for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

PDB for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

3D PDB for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

SMILES for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

INCHI for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

Structure for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

3D Structure for HMDB0300833 (2-hydroxy-3-methylbutanedioyl-CoA)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra