MiMeDB: Showing metabocard for (S)-Hydroxyhexanoyl-CoA (MMDBc0029743)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:39:49 UTC

Update Date

2022-08-31 17:16:33 UTC

Metabolite ID

MMDBc0029743

Metabolite Identification

Common Name

(S)-Hydroxyhexanoyl-CoA

Description

(S)-Hydroxyhexanoyl-CoA is an intermediate in fatty acid metabolism, being the substrate of the enzymes beta-hydroxyacyl-CoA dehydrogenase and 3-hydroxyacyl-CoA dehydrogenase [EC 1.1.1.211-1.1.1.35]; (S)-Hydroxyhexanoyl-CoA is an intermediate in fatty acid elongation, the substrate of the enzymes enoyl-CoA hydratase and long-chain-enoyl-CoA hydratase [EC 4.2.1.17-4.2.1.74]. (KEGG)

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221921022D          

 62 64  0  0  1  0            999 V2000
   -2.3503   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1918   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5418   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2234   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5076   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   23.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3668   19.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6815   25.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0410   26.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   17.9021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2247   23.6771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7945   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3467   26.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5304   23.9547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9784   23.3416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1003   26.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2604   25.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1179   24.6692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1866   27.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9379   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7678   26.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9279   25.1094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5930   26.7504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4535   25.4228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7945   16.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3509   23.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   17.4896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   16.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9848   22.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0888   21.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9237   21.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2082   21.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3832   22.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9063   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2563   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   22.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   19.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3109   24.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1499   22.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   21.6146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5368   21.9826    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7957   22.0271    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   20.7896    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   17.4896    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   17.0771    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2679   22.8533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8261   23.1845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8068   24.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   18.3146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9418   24.7123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  1  0  0  0
 17  6  1  0  0  0  0
 18 10  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 27  2  1  0  0  0  0
 27  3  1  0  0  0  0
 27 12  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  8  1  4  0  0  0
 29 17  2  0  0  0  0
 30  7  1  4  0  0  0
 30 25  2  0  0  0  0
 31 13  2  0  0  0  0
 31 23  1  0  0  0  0
 32 13  1  0  0  0  0
 32 24  2  0  0  0  0
 33 14  2  0  0  0  0
 33 19  1  0  0  0  0
 34 14  1  0  0  0  0
 34 24  1  0  0  0  0
 26 34  1  1  0  0  0
 15 35  1  1  0  0  0
 36 17  1  0  0  0  0
 37 18  2  0  0  0  0
 20 38  1  6  0  0  0
 39 22  1  0  0  0  0
 40 25  1  0  0  0  0
 48 11  1  0  0  0  0
 49 12  1  0  0  0  0
 50 16  1  0  0  0  0
 50 26  1  0  0  0  0
 21 51  1  1  0  0  0
 53 41  1  0  0  0  0
 53 42  1  0  0  0  0
 53 43  2  0  0  0  0
 53 51  1  0  0  0  0
 54 44  1  0  0  0  0
 54 45  2  0  0  0  0
 54 48  1  0  0  0  0
 54 52  1  0  0  0  0
 55 46  1  0  0  0  0
 55 47  2  0  0  0  0
 55 49  1  0  0  0  0
 55 52  1  0  0  0  0
 56  9  1  0  0  0  0
 56 18  1  0  0  0  0
 15 57  1  1  0  0  0
 16 58  1  6  0  0  0
 20 59  1  1  0  0  0
 21 60  1  1  0  0  0
 61 22  1  0  0  0  0
 26 62  1  6  0  0  0
M  END


  Mrv1652305221921022D          

 62 64  0  0  1  0            999 V2000
   -2.3503   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1918   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5418   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5089   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2234   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5076   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   23.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3668   19.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6815   25.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0410   26.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   17.9021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2247   23.6771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7945   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3467   26.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5304   23.9547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9784   23.3416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   17.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1003   26.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2604   25.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   17.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1179   24.6692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3668   18.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1866   27.5709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9379   17.9021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7678   26.2655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9279   25.1094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5930   26.7504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4535   25.4228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7945   16.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   18.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3509   23.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   17.4896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   16.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9848   22.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0888   21.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9237   21.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2082   21.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3832   22.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9063   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2563   20.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   22.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   19.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3109   24.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1499   22.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   21.6146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5368   21.9826    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7957   22.0271    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.0813   20.7896    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   17.4896    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   17.0771    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2679   22.8533    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8261   23.1845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8068   24.1486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6523   18.3146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9418   24.7123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  1  0  0  0
 17  6  1  0  0  0  0
 18 10  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 27  2  1  0  0  0  0
 27  3  1  0  0  0  0
 27 12  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  8  1  4  0  0  0
 29 17  2  0  0  0  0
 30  7  1  4  0  0  0
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 31 13  2  0  0  0  0
 31 23  1  0  0  0  0
 32 13  1  0  0  0  0
 32 24  2  0  0  0  0
 33 14  2  0  0  0  0
 33 19  1  0  0  0  0
 34 14  1  0  0  0  0
 34 24  1  0  0  0  0
 26 34  1  1  0  0  0
 15 35  1  1  0  0  0
 36 17  1  0  0  0  0
 37 18  2  0  0  0  0
 20 38  1  6  0  0  0
 39 22  1  0  0  0  0
 40 25  1  0  0  0  0
 48 11  1  0  0  0  0
 49 12  1  0  0  0  0
 50 16  1  0  0  0  0
 50 26  1  0  0  0  0
 21 51  1  1  0  0  0
 53 41  1  0  0  0  0
 53 42  1  0  0  0  0
 53 43  2  0  0  0  0
 53 51  1  0  0  0  0
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 54 48  1  0  0  0  0
 54 52  1  0  0  0  0
 55 46  1  0  0  0  0
 55 47  2  0  0  0  0
 55 49  1  0  0  0  0
 55 52  1  0  0  0  0
 56  9  1  0  0  0  0
 56 18  1  0  0  0  0
 15 57  1  1  0  0  0
 16 58  1  6  0  0  0
 20 59  1  1  0  0  0
 21 60  1  1  0  0  0
 61 22  1  0  0  0  0
 26 62  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029743

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(CCC)CC(=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/C27H46N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-16,20-22,26,35,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t15-,16+,20+,21+,22?,26+/m0/s1

> <INCHI_KEY>
VAAHKRMGOFIORX-DWUFXMDISA-N

> <FORMULA>
C27H46N7O18P3S

> <MOLECULAR_WEIGHT>
881.677

> <EXACT_MASS>
881.183287929

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
80.03213315390337

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-5.078188338147962

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776185

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398193

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
383.85999999999984

> <JCHEM_REFRACTIVITY>
192.15340000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.387  32.647   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.158  34.957   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.078  34.957   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.053  33.417   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.720  32.647   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.283  33.417   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.617  32.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.282  32.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.949  33.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.948  32.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.619  43.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.618  36.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.406  47.497   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.476  48.790   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.386  33.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.953  44.197   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.950  32.647   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.281  33.417   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.914  49.308   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.390  44.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.360  43.571   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.618  33.417   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.321  49.934   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.753  47.776   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.284  32.647   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.620  46.049   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.618  34.957   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      26.482  51.466   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       7.616  33.417   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      12.951  33.417   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      27.567  49.029   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      25.999  46.871   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0      23.507  49.934   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0      23.246  47.456   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0      -0.386  34.957   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.950  31.107   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.281  34.957   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      24.922  44.554   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      16.952  32.647   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      14.284  31.107   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      20.505  42.179   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      22.566  39.890   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      20.391  40.004   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      19.055  39.784   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      17.515  42.451   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      18.492  38.807   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      15.412  38.807   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      19.619  41.887   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      16.952  37.267   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      21.114  45.729   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      22.680  42.065   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      16.952  40.347   0.000  0.00  0.00           O+0
HETATM   53  P   UNK     0      21.535  41.034   0.000  0.00  0.00           P+0
HETATM   54  P   UNK     0      18.285  41.117   0.000  0.00  0.00           P+0
HETATM   55  P   UNK     0      16.952  38.807   0.000  0.00  0.00           P+0
HETATM   56  S   UNK     0       3.615  32.647   0.000  0.00  0.00           S+0
HETATM   57  H   UNK     0      -0.386  31.877   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      21.033  42.659   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      23.942  43.278   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      22.039  45.077   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      14.284  34.187   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      24.158  46.130   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   27                                                            
CONECT    3   27                                                            
CONECT    4    1    5                                                       
CONECT    5    4   15                                                       
CONECT    6    7   17                                                       
CONECT    7    6   30                                                       
CONECT    8    9   29                                                       
CONECT    9    8   56                                                       
CONECT   10   15   18                                                       
CONECT   11   16   48                                                       
CONECT   12   27   49                                                       
CONECT   13   31   32                                                       
CONECT   14   33   34                                                       
CONECT   15    5   10   35   57                                             
CONECT   16   11   21   50   58                                             
CONECT   17    6   29   36                                                  
CONECT   18   10   37   56                                                  
CONECT   19   23   24   33                                                  
CONECT   20   21   26   38   59                                             
CONECT   21   16   20   51   60                                             
CONECT   22   25   27   39   61                                             
CONECT   23   19   28   31                                                  
CONECT   24   19   32   34                                                  
CONECT   25   22   30   40                                                  
CONECT   26   20   34   50   62                                             
CONECT   27    2    3   12   22                                             
CONECT   28   23                                                            
CONECT   29    8   17                                                       
CONECT   30    7   25                                                       
CONECT   31   13   23                                                       
CONECT   32   13   24                                                       
CONECT   33   14   19                                                       
CONECT   34   14   24   26                                                  
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   20                                                            
CONECT   39   22                                                            
CONECT   40   25                                                            
CONECT   41   53                                                            
CONECT   42   53                                                            
CONECT   43   53                                                            
CONECT   44   54                                                            
CONECT   45   54                                                            
CONECT   46   55                                                            
CONECT   47   55                                                            
CONECT   48   11   54                                                       
CONECT   49   12   55                                                       
CONECT   50   16   26                                                       
CONECT   51   21   53                                                       
CONECT   52   54   55                                                       
CONECT   53   41   42   43   51                                             
CONECT   54   44   45   48   52                                             
CONECT   55   46   47   49   52                                             
CONECT   56    9   18                                                       
CONECT   57   15                                                            
CONECT   58   16                                                            
CONECT   59   20                                                            
CONECT   60   21                                                            
CONECT   61   22                                                            
CONECT   62   26                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  128    0
END

Synonyms

Value	Source
(S)-3-Hydroxyhexanoyl-CoA	HMDB
(S)-3-Hydroxyhexanoyl-coenzyme A	HMDB
S-(3-Hydroxyhexanoate	HMDB
S-(3-Hydroxyhexanoate)CoA	HMDB
S-(3-Hydroxyhexanoate)coenzyme A	HMDB
S-(3-Hydroxyhexanoic acid	HMDB
[R,S]-Lactyl CoA	HMDB
[R,S]-Lactyl coenzyme A	HMDB

Molecular Formula

C₂₇H₄₆N₇O₁₈P₃S

Average Mass

881.677

Monoisotopic Mass

881.183287929

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

74875-70-0

SMILES

[H][C@](O)(CCC)CC(=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/C27H46N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-16,20-22,26,35,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t15-,16+,20+,21+,22?,26+/m0/s1

InChI Key

VAAHKRMGOFIORX-DWUFXMDISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-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

(S)-3-hydroxyacyl 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

Fatty acyl CoAs (C05268 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.52 g/L	ALOGPS
logP	-0.21	ALOGPS
logP	-5.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	192.15 m³·mol⁻¹	ChemAxon
Polarizability	80.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1912000130-757a06d65095dfcd1109	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0913000000-3fa51d2d6e52aef25807	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1911000000-1d079f0830ffba4a4703	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-6911140360-f5b174e02338cd1237c2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3910110010-d4f8e7e5b133ff16545a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-4cc298a4369bf1766fbb	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0002689	(S)-Hydroxyhexanoyl-CoA	Hydrogen Ion	Enoyl-coa, hydratase/3-hydroxyacyl coa dehydrogenase	(S)-Hydroxyhexanoyl Coenzyme A:NAD+ Oxidoreductase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002690	Water	(S)-Hydroxyhexanoyl-CoA	Enoyl coa hydratase, short chain, 1, mitochondrial	(S)-Hydroxyhexanoyl Coenzyme A Hydro-Lyase	VMH	8012501 8188243
MMDBr0010035	Water	(S)-Hydroxyhexanoyl-CoA	Enoyl-coa, hydratase/3-hydroxyacyl coa dehydrogenase	Enoyl Coenzyme A Hydratase	VMH	30371894
MMDBr0010036	(S)-Hydroxyhexanoyl-CoA	Hydrogen Ion	Enoyl-coa, hydratase/3-hydroxyacyl coa dehydrogenase	3-Hydroxyacyl Coenzyme A Dehydrogenase	VMH	30371894
MMDBr0018708	(2E)-hexenoyl-CoA	Water	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018709	NAD	Hydrogen Ion	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019723	(S)-Hydroxyhexanoyl-CoA	Water	3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Hydrolysis of bond	PathBank	31602464
MMDBr0019724	NAD	Hydrogen Ion	3-ketoacyl-CoA thiolase, peroxisomal	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0023309	(S)-Hydroxyhexanoyl-CoA	(2E)-hexenoyl-CoA	Fatty acid oxidation complex subunit alpha	Aerobic and anaerobic degradation of long-chain fatty acids	PathBank	31602464
MMDBr0023310	(S)-Hydroxyhexanoyl-CoA	(2E)-hexenoyl-CoA	Fatty acid oxidation complex subunit alpha	Aerobic and anaerobic degradation of long-chain fatty acids	PathBank	31602464
MMDBr0038743	(S)-Hydroxyhexanoyl-CoA	(S)-Hydroxyhexanoic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023261

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

440609

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
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 (S)-Hydroxyhexanoyl-CoA (MMDBc0029743)

MOL for #<Metabolite:0x00007f5abc2aeb58>

3D MOL for #<Metabolite:0x00007f5abc2aeb58>

3D SDF for #<Metabolite:0x00007f5abc2aeb58>

3D-SDF for #<Metabolite:0x00007f5abc2aeb58>

PDB for #<Metabolite:0x00007f5abc2aeb58>

3D PDB for #<Metabolite:0x00007f5abc2aeb58>

SMILES for #<Metabolite:0x00007f5abc2aeb58>

INCHI for #<Metabolite:0x00007f5abc2aeb58>

Structure for #<Metabolite:0x00007f5abc2aeb58>

3D Structure for #<Metabolite:0x00007f5abc2aeb58>