MiMeDB: Showing metabocard for Tiglyl-CoA (MMDBc0029679)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:37:14 UTC

Update Date

2024-04-30 19:40:33 UTC

Metabolite ID

MMDBc0029679

Metabolite Identification

Common Name

Tiglyl-CoA

Description

Tiglyl-CoA is a metabolite in the degradation of isoleucine to propionic acid pathway. It is a substrate of enoyl-CoA hydratase-isomerase [EC:4.2.1.17] and converted to (2S,3S)-3-Hydroxy-2-methylbutanoyl-CoA.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023452D          

 60 62  0  0  1  0            999 V2000
    1.5749   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   15.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5383   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8883   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    8.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   12.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0280    6.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3874    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5711    8.2834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1409   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6931    5.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8768    8.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.3248    8.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4468    5.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6069    6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4643    7.2914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5685   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5330    4.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2843   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1142    5.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2743    6.8511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9394    5.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7999    6.5377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6973    8.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   14.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   13.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3312    9.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4353   10.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2701   10.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5547   10.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7297    9.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2527   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6027   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    9.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6574    7.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4963    9.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   10.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8832    9.9779    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1422    9.9334    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.1709    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   14.4709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6143    9.1072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1725    8.7760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1533    7.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   13.6459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2882    7.2482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15 10  1  1  0  0  0
 16  6  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 11  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  8  1  4  0  0  0
 28 16  2  0  0  0  0
 29  7  1  4  0  0  0
 29 23  2  0  0  0  0
 30 12  2  0  0  0  0
 30 21  1  0  0  0  0
 31 12  1  0  0  0  0
 31 22  2  0  0  0  0
 32 13  2  0  0  0  0
 32 17  1  0  0  0  0
 33 13  1  0  0  0  0
 33 22  1  0  0  0  0
 24 33  1  1  0  0  0
 34 16  1  0  0  0  0
 18 35  1  6  0  0  0
 36 20  1  0  0  0  0
 37 23  1  0  0  0  0
 38 25  2  0  0  0  0
 46 10  1  0  0  0  0
 47 11  1  0  0  0  0
 48 15  1  0  0  0  0
 48 24  1  0  0  0  0
 19 49  1  1  0  0  0
 51 39  1  0  0  0  0
 51 40  1  0  0  0  0
 51 41  2  0  0  0  0
 51 49  1  0  0  0  0
 52 42  1  0  0  0  0
 52 43  2  0  0  0  0
 52 46  1  0  0  0  0
 52 50  1  0  0  0  0
 53 44  1  0  0  0  0
 53 45  2  0  0  0  0
 53 47  1  0  0  0  0
 53 50  1  0  0  0  0
 54  9  1  0  0  0  0
 54 25  1  0  0  0  0
 55  5  1  0  0  0  0
 15 56  1  6  0  0  0
 18 57  1  1  0  0  0
 19 58  1  1  0  0  0
 59 20  1  0  0  0  0
 24 60  1  6  0  0  0
M  END


  Mrv1652306222023452D          

 60 62  0  0  1  0            999 V2000
    1.5749   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   15.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5383   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8883   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    8.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   12.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0280    6.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3874    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5711    8.2834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1409   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6931    5.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8768    8.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.3248    8.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4468    5.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6069    6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4643    7.2914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5685   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5330    4.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2843   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1142    5.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2743    6.8511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9394    5.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7999    6.5377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6973    8.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   14.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   13.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3312    9.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4353   10.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2701   10.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5547   10.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7297    9.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2527   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6027   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    9.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6574    7.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4963    9.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   10.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8832    9.9779    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1422    9.9334    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.1709    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   14.4709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6143    9.1072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1725    8.7760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1533    7.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   13.6459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2882    7.2482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15 10  1  1  0  0  0
 16  6  1  0  0  0  0
 19 15  1  0  0  0  0
 19 18  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 18  1  0  0  0  0
 25 14  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 11  1  0  0  0  0
 26 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  8  1  4  0  0  0
 28 16  2  0  0  0  0
 29  7  1  4  0  0  0
 29 23  2  0  0  0  0
 30 12  2  0  0  0  0
 30 21  1  0  0  0  0
 31 12  1  0  0  0  0
 31 22  2  0  0  0  0
 32 13  2  0  0  0  0
 32 17  1  0  0  0  0
 33 13  1  0  0  0  0
 33 22  1  0  0  0  0
 24 33  1  1  0  0  0
 34 16  1  0  0  0  0
 18 35  1  6  0  0  0
 36 20  1  0  0  0  0
 37 23  1  0  0  0  0
 38 25  2  0  0  0  0
 46 10  1  0  0  0  0
 47 11  1  0  0  0  0
 48 15  1  0  0  0  0
 48 24  1  0  0  0  0
 19 49  1  1  0  0  0
 51 39  1  0  0  0  0
 51 40  1  0  0  0  0
 51 41  2  0  0  0  0
 51 49  1  0  0  0  0
 52 42  1  0  0  0  0
 52 43  2  0  0  0  0
 52 46  1  0  0  0  0
 52 50  1  0  0  0  0
 53 44  1  0  0  0  0
 53 45  2  0  0  0  0
 53 47  1  0  0  0  0
 53 50  1  0  0  0  0
 54  9  1  0  0  0  0
 54 25  1  0  0  0  0
 55  5  1  0  0  0  0
 15 56  1  6  0  0  0
 18 57  1  1  0  0  0
 19 58  1  1  0  0  0
 59 20  1  0  0  0  0
 24 60  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029679

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H42N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h5,12-13,15,18-20,24,35-36H,6-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/b14-5+/t15-,18-,19-,20?,24-/m1/s1

> <INCHI_KEY>
PMWATMXOQQZNBX-APMDNKNFSA-N

> <FORMULA>
C26H42N7O17P3S

> <MOLECULAR_WEIGHT>
849.635

> <EXACT_MASS>
849.157073179

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
76.73841665619983

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <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-2,2-dimethyl-3-({2-[(2-{[(2E)-2-methylbut-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
-4.109807288814626

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776185

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398224

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
186.8863

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.48e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0       2.940  27.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.272  28.552   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.938  24.702   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.858  24.702   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.606  26.242   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.063  26.242   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.397  27.012   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.062  27.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.729  26.242   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -18.399  16.232   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.398  23.162   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -26.186  12.162   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -21.256  10.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.272  27.012   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -19.733  15.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.730  27.012   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -23.694  10.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -22.170  14.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -21.140  16.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.398  26.242   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -25.101   9.726   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -23.533  11.884   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.064  27.012   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -21.400  13.611   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.061  26.242   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.398  24.702   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0     -25.262   8.194   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      -6.396  26.242   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0     -11.731  26.242   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0     -26.347  10.631   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0     -24.779  12.789   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0     -22.287   9.726   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0     -22.026  12.204   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0      -7.730  28.552   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -23.702  15.105   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -15.732  27.012   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -13.064  28.552   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.061  24.702   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -19.285  17.481   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -21.346  19.770   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -19.171  19.656   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -17.835  19.876   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -16.295  17.209   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -17.272  20.852   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0     -14.192  20.852   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0     -18.399  17.772   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -15.732  22.392   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -19.894  13.931   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -21.460  17.595   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -15.732  19.312   0.000  0.00  0.00           O+0
HETATM   51  P   UNK     0     -20.315  18.625   0.000  0.00  0.00           P+0
HETATM   52  P   UNK     0     -17.065  18.542   0.000  0.00  0.00           P+0
HETATM   53  P   UNK     0     -15.732  20.852   0.000  0.00  0.00           P+0
HETATM   54  S   UNK     0      -2.395  27.012   0.000  0.00  0.00           S+0
HETATM   55  H   UNK     0       1.606  24.702   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0     -19.813  17.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0     -22.722  16.382   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0     -20.819  14.582   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0     -13.064  25.472   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0     -22.938  13.530   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   14                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5    1   14   55                                                  
CONECT    6    7   16                                                       
CONECT    7    6   29                                                       
CONECT    8    9   28                                                       
CONECT    9    8   54                                                       
CONECT   10   15   46                                                       
CONECT   11   26   47                                                       
CONECT   12   30   31                                                       
CONECT   13   32   33                                                       
CONECT   14    2    5   25                                                  
CONECT   15   10   19   48   56                                             
CONECT   16    6   28   34                                                  
CONECT   17   21   22   32                                                  
CONECT   18   19   24   35   57                                             
CONECT   19   15   18   49   58                                             
CONECT   20   23   26   36   59                                             
CONECT   21   17   27   30                                                  
CONECT   22   17   31   33                                                  
CONECT   23   20   29   37                                                  
CONECT   24   18   33   48   60                                             
CONECT   25   14   38   54                                                  
CONECT   26    3    4   11   20                                             
CONECT   27   21                                                            
CONECT   28    8   16                                                       
CONECT   29    7   23                                                       
CONECT   30   12   21                                                       
CONECT   31   12   22                                                       
CONECT   32   13   17                                                       
CONECT   33   13   22   24                                                  
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
CONECT   37   23                                                            
CONECT   38   25                                                            
CONECT   39   51                                                            
CONECT   40   51                                                            
CONECT   41   51                                                            
CONECT   42   52                                                            
CONECT   43   52                                                            
CONECT   44   53                                                            
CONECT   45   53                                                            
CONECT   46   10   52                                                       
CONECT   47   11   53                                                       
CONECT   48   15   24                                                       
CONECT   49   19   51                                                       
CONECT   50   52   53                                                       
CONECT   51   39   40   41   49                                             
CONECT   52   42   43   46   50                                             
CONECT   53   44   45   47   50                                             
CONECT   54    9   25                                                       
CONECT   55    5                                                            
CONECT   56   15                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   20                                                            
CONECT   60   24                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

Synonyms

Value	Source
(e)-2-Methylcrotonoyl-CoA	HMDB
(e)-2-Methylcrotonoyl-coenzyme A	HMDB
2-Methylbut-2-enoyl-CoA	HMDB
2-Methylbut-2-enoyl-coenzyme A	HMDB
2-Methylcrotanoyl-CoA	HMDB
2-Methylcrotanoyl-coenzyme A	HMDB
2-Methylcrotonoyl-CoA	HMDB
2-Methylcrotonoyl-coenzyme A	HMDB
2-Methylcrotonyl-CoA	HMDB
2-Methylcrotonyl-coenzyme A	HMDB
Methylcrotonoyl-CoA	HMDB
Methylcrotonoyl-coenzyme A	HMDB
Methylcrotonyl-CoA	HMDB
Methylcrotonyl-coenzyme A	HMDB
Tigloyl-CoA	HMDB
Tigloyl-coenzyme A	HMDB
Tiglyl-coenzyme A	HMDB
trans-2-Methylbut-2-enoyl-CoA	HMDB
trans-2-Methylbut-2-enoyl-coenzyme A	HMDB

Molecular Formula

C₂₆H₄₂N₇O₁₇P₃S

Average Mass

849.635

Monoisotopic Mass

849.157073179

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2E)-2-methylbut-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]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-2,2-dimethyl-3-({2-[(2-{[(2E)-2-methylbut-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H42N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h5,12-13,15,18-20,24,35-36H,6-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/b14-5+/t15-,18-,19-,20?,24-/m1/s1

InChI Key

PMWATMXOQQZNBX-APMDNKNFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cresol (CHEBI:28054 )
a methylphenol (CPD-109 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.48 g/L	ALOGPS
logP	0.12	ALOGPS
logP	-4.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	186.89 m³·mol⁻¹	ChemAxon
Polarizability	76.74 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-1912000120-81b21095705a1243f37e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1912000000-62328cd733089510fd34	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-95f748a6c71560aeb958	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-9830140640-81896860f616d5db847b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-5910010010-e384bb18aba2816a9a63	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-a10b6138b97c5a8d8893	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

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000193	2-Methylbutyryl-CoA	Tiglyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	11013134
MMDBr0000852	Tiglyl-CoA	2-Methyl-3-hydroxybutyryl-CoA	enoyl CoA hydratase, short chain, 1, mitochondrial	VMH; KEGG	9073515
MMDBr0002618	2-Methylbutyryl-CoA	Tiglyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	6401712
MMDBr0004272	Tiglyl-CoA	2-Methylglutaconyl Coenzyme A	methylcrotonoyl-CoA carboxylase 1 (alpha)	VMH	7059658
MMDBr0005058	Tiglyl-CoA	Tiglyl-CoA	diazepam binding inhibitor (GABA receptor modulator, acyl-CoA binding protein)	VMH	20511713 11859412 16908521 8001684
MMDBr0005105	Tiglyl-CoA	Tiglylcarnitine	carnitine palmitoyltransferase 1A (liver)	VMH	8930414 14518824
MMDBr0006896	2-Methylbutyryl-CoA	Tiglyl-CoA	Not Available	VMH	30371894
MMDBr0007763	Tiglyl-CoA	2-Methyl-3-hydroxybutyryl-CoA	Not Available	VMH	30371894
MMDBr0008488	2-Methylbutyryl-CoA	Tiglyl-CoA	Not Available	VMH	30371894
MMDBr0008606	Tiglyl-CoA	Tiglyl Glycine	glycine-N-acyltransferase	VMH	30371894

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	150	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	218	Pig ; Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa	Metabolic reconstruction
Bacteria	Actinobacteria	61	Human feces; Human ; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	22	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

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

HMDB0002054

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022819

KNApSAcK ID

Not Available

Chemspider ID

4444187

KEGG Compound ID

C03345

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15478

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Duran M, Bruinvis L, Ketting D, Kamerling JP, Wadman SK, Schutgens RB: The identification of (E)-2-methylglutaconic acid, a new isoleucine metabolite, in the urine of patients with beta-ketothiolase deficiency, propionic acidaemia and methylmalonic acidaemia. Biomed Mass Spectrom. 1982 Jan;9(1):1-5. doi: 10.1002/bms.1200090102. [PubMed:7059658 ]

Showing metabocard for Tiglyl-CoA (MMDBc0029679)

MOL for #<Metabolite:0x00007fdb112228d0>

3D MOL for #<Metabolite:0x00007fdb112228d0>

3D SDF for #<Metabolite:0x00007fdb112228d0>

3D-SDF for #<Metabolite:0x00007fdb112228d0>

PDB for #<Metabolite:0x00007fdb112228d0>

3D PDB for #<Metabolite:0x00007fdb112228d0>

SMILES for #<Metabolite:0x00007fdb112228d0>

INCHI for #<Metabolite:0x00007fdb112228d0>

Structure for #<Metabolite:0x00007fdb112228d0>

3D Structure for #<Metabolite:0x00007fdb112228d0>