MiMeDB: Showing metabocard for (3S)-hydroxy-3-methylglutaryl-CoA (MMDBc0054068)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:50:31 UTC

Update Date

2022-09-01 02:26:55 UTC

Metabolite ID

MMDBc0054068

Metabolite Identification

Common Name

(3S)-hydroxy-3-methylglutaryl-CoA

Description

(S)-Hmg-Coa belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration (S)-Hmg-Coa is a strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041405192D          

 63 65  0  0  1  0            999 V2000
   -5.2497   -0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -2.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5254   -5.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1812   -1.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4275   -1.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2698   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1835   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2597   -6.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4322   -4.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8486   -2.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9271   -6.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7647   -4.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3390   -1.2710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0064   -1.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5853   -1.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3459   -5.6353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6023   -1.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601   -1.4203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7624   -2.8751    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -12.8409   -7.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6808   -6.6051    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -11.0110   -4.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4252   -0.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -2.5764    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -13.1664   -5.7215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.2137    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -2.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -2.6617    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8510   -3.5094    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -1.7306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -2.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -2.0914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
 14 10  1  1  0  0  0
 15  4  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 20 14  1  0  0  0  0
 20 19  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 24 21  1  0  0  0  0
 25 19  1  0  0  0  0
 26  1  1  0  0  0  0
 26  2  1  0  0  0  0
 26 11  1  0  0  0  0
 26 21  1  0  0  0  0
 27  3  1  1  0  0  0
 27  8  1  0  0  0  0
 27  9  1  0  0  0  0
 28 22  1  0  0  0  0
 29  6  1  4  0  0  0
 29 15  2  0  0  0  0
 30  5  1  4  0  0  0
 30 24  2  0  0  0  0
 31 12  2  0  0  0  0
 31 22  1  0  0  0  0
 32 12  1  0  0  0  0
 32 23  2  0  0  0  0
 33 13  2  0  0  0  0
 33 18  1  0  0  0  0
 34 13  1  0  0  0  0
 34 23  1  0  0  0  0
 25 34  1  1  0  0  0
 35 15  1  0  0  0  0
 36 16  2  0  0  0  0
 37 16  1  0  0  0  0
 38 17  2  0  0  0  0
 19 39  1  6  0  0  0
 21 40  1  1  0  0  0
 41 24  1  0  0  0  0
 27 42  1  1  0  0  0
 50 10  1  0  0  0  0
 51 11  1  0  0  0  0
 52 14  1  0  0  0  0
 52 25  1  0  0  0  0
 20 53  1  6  0  0  0
 55 43  1  0  0  0  0
 55 44  1  0  0  0  0
 55 45  2  0  0  0  0
 55 53  1  0  0  0  0
 56 46  1  0  0  0  0
 56 47  2  0  0  0  0
 56 50  1  0  0  0  0
 56 54  1  0  0  0  0
 57 48  1  0  0  0  0
 57 49  2  0  0  0  0
 57 51  1  0  0  0  0
 57 54  1  0  0  0  0
 58  7  1  0  0  0  0
 58 17  1  0  0  0  0
 14 59  1  6  0  0  0
 19 60  1  1  0  0  0
 20 61  1  1  0  0  0
 21 62  1  1  0  0  0
 25 63  1  6  0  0  0
M  CHG  5  35  -1  37  -1  41  -1  43  -1  44  -1
M  END


  Mrv0541 05041405192D          

 63 65  0  0  1  0            999 V2000
   -5.2497   -0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -2.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5254   -5.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1812   -1.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4275   -1.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2698   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1835   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2597   -6.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4322   -4.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8486   -2.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9271   -6.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7647   -4.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3390   -1.2710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0064   -1.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5853   -1.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3459   -5.6353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6023   -1.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601   -1.4203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7624   -2.8751    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -12.8409   -7.7611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6808   -6.6051    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -11.0110   -4.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4252   -0.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -2.5764    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -13.1664   -5.7215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.2137    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -2.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -2.6617    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8510   -3.5094    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -1.7306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -2.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -2.0914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
 14 10  1  1  0  0  0
 15  4  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 20 14  1  0  0  0  0
 20 19  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 24 21  1  0  0  0  0
 25 19  1  0  0  0  0
 26  1  1  0  0  0  0
 26  2  1  0  0  0  0
 26 11  1  0  0  0  0
 26 21  1  0  0  0  0
 27  3  1  1  0  0  0
 27  8  1  0  0  0  0
 27  9  1  0  0  0  0
 28 22  1  0  0  0  0
 29  6  1  4  0  0  0
 29 15  2  0  0  0  0
 30  5  1  4  0  0  0
 30 24  2  0  0  0  0
 31 12  2  0  0  0  0
 31 22  1  0  0  0  0
 32 12  1  0  0  0  0
 32 23  2  0  0  0  0
 33 13  2  0  0  0  0
 33 18  1  0  0  0  0
 34 13  1  0  0  0  0
 34 23  1  0  0  0  0
 25 34  1  1  0  0  0
 35 15  1  0  0  0  0
 36 16  2  0  0  0  0
 37 16  1  0  0  0  0
 38 17  2  0  0  0  0
 19 39  1  6  0  0  0
 21 40  1  1  0  0  0
 41 24  1  0  0  0  0
 27 42  1  1  0  0  0
 50 10  1  0  0  0  0
 51 11  1  0  0  0  0
 52 14  1  0  0  0  0
 52 25  1  0  0  0  0
 20 53  1  6  0  0  0
 55 43  1  0  0  0  0
 55 44  1  0  0  0  0
 55 45  2  0  0  0  0
 55 53  1  0  0  0  0
 56 46  1  0  0  0  0
 56 47  2  0  0  0  0
 56 50  1  0  0  0  0
 56 54  1  0  0  0  0
 57 48  1  0  0  0  0
 57 49  2  0  0  0  0
 57 51  1  0  0  0  0
 57 54  1  0  0  0  0
 58  7  1  0  0  0  0
 58 17  1  0  0  0  0
 14 59  1  6  0  0  0
 19 60  1  1  0  0  0
 20 61  1  1  0  0  0
 21 62  1  1  0  0  0
 25 63  1  6  0  0  0
M  CHG  5  35  -1  37  -1  41  -1  43  -1  44  -1
M  END
> <DATABASE_ID>
MMDBc0054068

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C[C@@](C)(O)CC([O-])=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/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/p-5/t14-,19-,20-,21+,25-,27+/m1/s1

> <INCHI_KEY>
CABVTRNMFUVUDM-VRHQGPGLSA-I

> <FORMULA>
C27H39N7O20P3S

> <MOLECULAR_WEIGHT>
906.62

> <EXACT_MASS>
906.118341949

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
78.82929105376583

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-5

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-3-hydroxy-3-methyl-5-oxopentanoate

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-4.81081521960255

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001409853139961

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8204322378420241

> <JCHEM_PKA_STRONGEST_BASIC>
4.839550529913015

> <JCHEM_POLAR_SURFACE_AREA>
442.2900000000001

> <JCHEM_REFRACTIVITY>
224.4397000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-3-hydroxy-3-methyl-5-oxopentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   55  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   56  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   57  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   58  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   59  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   26                                                            
CONECT    2   26                                                            
CONECT    3   27                                                            
CONECT    4    5   15                                                       
CONECT    5    4   30                                                       
CONECT    6    7   29                                                       
CONECT    7    6   58                                                       
CONECT    8   16   27                                                       
CONECT    9   17   27                                                       
CONECT   10   14   50                                                       
CONECT   11   26   51                                                       
CONECT   12   31   32                                                       
CONECT   13   33   34                                                       
CONECT   14   10   20   52   59                                             
CONECT   15    4   29   35                                                  
CONECT   16    8   36   37                                                  
CONECT   17    9   38   58                                                  
CONECT   18   22   23   33                                                  
CONECT   19   20   25   39   60                                             
CONECT   20   14   19   53   61                                             
CONECT   21   24   26   40   62                                             
CONECT   22   18   28   31                                                  
CONECT   23   18   32   34                                                  
CONECT   24   21   30   41                                                  
CONECT   25   19   34   52   63                                             
CONECT   26    1    2   11   21                                             
CONECT   27    3    8    9   42                                             
CONECT   28   22                                                            
CONECT   29    6   15                                                       
CONECT   30    5   24                                                       
CONECT   31   12   22                                                       
CONECT   32   12   23                                                       
CONECT   33   13   18                                                       
CONECT   34   13   23   25                                                  
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   17                                                            
CONECT   39   19                                                            
CONECT   40   21                                                            
CONECT   41   24                                                            
CONECT   42   27                                                            
CONECT   43   55                                                            
CONECT   44   55                                                            
CONECT   45   55                                                            
CONECT   46   56                                                            
CONECT   47   56                                                            
CONECT   48   57                                                            
CONECT   49   57                                                            
CONECT   50   10   56                                                       
CONECT   51   11   57                                                       
CONECT   52   14   25                                                       
CONECT   53   20   55                                                       
CONECT   54   56   57                                                       
CONECT   55   43   44   45   53                                             
CONECT   56   46   47   50   54                                             
CONECT   57   48   49   51   54                                             
CONECT   58    7   17                                                       
CONECT   59   14                                                            
CONECT   60   19                                                            
CONECT   61   20                                                            
CONECT   62   21                                                            
CONECT   63   25                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

Synonyms

Value	Source
(3S)-Hydroxy-3-methylglutaryl-CoA	ChEBI
3-HYDROXY-3-methylglutaryl-coenzyme A	ChEBI
(S)-3-Hydroxy-3-methylglutaryl-CoA	ChEBI
3-Hydroxy-3-methylglutaryl-CoA	MeSH
HMG-CoA	MeSH
Hydroxymethylglutaryl-CoA	MeSH
3-Hydroxy-3-methylglutaryl-coenzyme A, mono(3-oxobutanoate)	MeSH
3-Hydroxy-3-methylglutaryl-coenzyme A, (S)-isomer	MeSH

Molecular Formula

C₂₇H₃₉N₇O₂₀P₃S

Average Mass

906.62

Monoisotopic Mass

906.118341949

IUPAC Name

(3S)-5-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-3-hydroxy-3-methyl-5-oxopentanoate

Traditional Name

(3S)-5-({2-[(3-{[(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-3-hydroxy-3-methyl-5-oxopentanoate

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C[C@@](C)(O)CC([O-])=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/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/p-5/t14-,19-,20-,21+,25-,27+/m1/s1

InChI Key

CABVTRNMFUVUDM-VRHQGPGLSA-I

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

(S)-3-hydroxy-3-alkylglutaryl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxylic acid anion (CHEBI:43074 )
acyl-CoA oxoanion (CHEBI:43074 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	9 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-4.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.84	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	442.29 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	224.44 m³·mol⁻¹	ChemAxon
Polarizability	78.83 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	splash10-066r-0000001019-e2101c36e3d7b0c34f28	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0001000093-3c329cb7cc57088d72ce	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9510808020-d45c1298ad69a2a8a741	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-4400000009-74248f5c2c9b5809f21b	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9600000015-efcb95c79c228a7c2a75	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01u1-9500000000-b3bdce5fd8db670e106f	2017-07-26	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Eukaryota/Fungi	Ascomycota	15	Human feces
Eukaryota/Fungi	Basidiomycota	2
Bacteria	Firmicutes	2	Human ; Human feces
Archaea/Archaea	Euryarchaeota	7
Bacteria	Spirochaetes	1	Human
Bacteria	Proteobacteria	2	Human
Archaea/Archaea	Crenarchaeota	1
Eukaryota/Fungi	Mucoromycota	1
Archaea	Crenarchaeota	1

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

External Links

HMDB ID

Not Available

DrugBank ID

DB03169

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

3-HYDROXY-3-METHYL-GLUTARYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5288565

PDB ID

Not Available

ChEBI ID

43074

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (3S)-hydroxy-3-methylglutaryl-CoA (MMDBc0054068)

MOL for #<Metabolite:0x00007fed14ba23c8>

3D MOL for #<Metabolite:0x00007fed14ba23c8>

3D SDF for #<Metabolite:0x00007fed14ba23c8>

3D-SDF for #<Metabolite:0x00007fed14ba23c8>

PDB for #<Metabolite:0x00007fed14ba23c8>

3D PDB for #<Metabolite:0x00007fed14ba23c8>

SMILES for #<Metabolite:0x00007fed14ba23c8>

INCHI for #<Metabolite:0x00007fed14ba23c8>

Structure for #<Metabolite:0x00007fed14ba23c8>

3D Structure for #<Metabolite:0x00007fed14ba23c8>