MiMeDB: Showing metabocard for 3-Methylcrotonyl-CoA (MMDBc0029661)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:31 UTC

Update Date

2024-04-30 19:40:14 UTC

Metabolite ID

MMDBc0029661

Metabolite Identification

Common Name

3-Methylcrotonyl-CoA

Description

3-Methylcrotonyl-CoA is an essential metabolite for leucine metabolism.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023452D          

 59 61  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
    0.8604   13.2334    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
   -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
    0.1459   14.4709    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
    0.8604   14.0584    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
   -0.5685   14.0584    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
   -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
   -0.5685   13.2334    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
  -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
  -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
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  1  1  0  0  0
 16  5  1  0  0  0  0
 17  9  1  0  0  0  0
 20 15  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  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 11  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28  7  1  4  0  0  0
 28 16  2  0  0  0  0
 29  6  1  4  0  0  0
 29 24  2  0  0  0  0
 30 12  2  0  0  0  0
 30 22  1  0  0  0  0
 31 12  1  0  0  0  0
 31 23  2  0  0  0  0
 32 13  2  0  0  0  0
 32 18  1  0  0  0  0
 33 13  1  0  0  0  0
 33 23  1  0  0  0  0
 25 33  1  1  0  0  0
 34 16  1  0  0  0  0
 35 17  2  0  0  0  0
 19 36  1  6  0  0  0
 37 21  1  0  0  0  0
 38 24  1  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 25  1  0  0  0  0
 20 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  8  1  0  0  0  0
 54 17  1  0  0  0  0
 15 55  1  6  0  0  0
 19 56  1  1  0  0  0
 20 57  1  1  0  0  0
 58 21  1  0  0  0  0
 25 59  1  6  0  0  0
M  END


  Mrv1652306222023452D          

 59 61  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
    0.8604   13.2334    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
   -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
    0.1459   14.4709    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
    0.8604   14.0584    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
   -0.5685   14.0584    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
   -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
   -0.5685   13.2334    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
  -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
  -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
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  1  1  0  0  0
 16  5  1  0  0  0  0
 17  9  1  0  0  0  0
 20 15  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  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 11  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28  7  1  4  0  0  0
 28 16  2  0  0  0  0
 29  6  1  4  0  0  0
 29 24  2  0  0  0  0
 30 12  2  0  0  0  0
 30 22  1  0  0  0  0
 31 12  1  0  0  0  0
 31 23  2  0  0  0  0
 32 13  2  0  0  0  0
 32 18  1  0  0  0  0
 33 13  1  0  0  0  0
 33 23  1  0  0  0  0
 25 33  1  1  0  0  0
 34 16  1  0  0  0  0
 35 17  2  0  0  0  0
 19 36  1  6  0  0  0
 37 21  1  0  0  0  0
 38 24  1  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 25  1  0  0  0  0
 20 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  8  1  0  0  0  0
 54 17  1  0  0  0  0
 15 55  1  6  0  0  0
 19 56  1  1  0  0  0
 20 57  1  1  0  0  0
 58 21  1  0  0  0  0
 25 59  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029661

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)C=C(C)C)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/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1

> <INCHI_KEY>
BXIPALATIYNHJN-TVCSPYKZSA-N

> <FORMULA>
C26H42N7O17P3S

> <MOLECULAR_WEIGHT>
849.635

> <EXACT_MASS>
849.157073179

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
75.86930950852853

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

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
-4.261996506481293

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207347761846

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398228

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
186.81120000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.51e+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-[(3-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       1.606  24.702   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      -9.063  26.242   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.397  27.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.062  27.012   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.729  26.242   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.272  27.012   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       1.606  26.242   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      -1.061  26.242   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -23.694  10.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -22.170  14.944   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -21.140  16.089   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.398  26.242   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -25.101   9.726   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -23.533  11.884   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.064  27.012   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -21.400  13.611   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      -1.061  24.702   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -23.702  15.105   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -15.732  27.012   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -13.064  28.552   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     -19.813  17.000   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0     -22.722  16.382   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0     -20.819  14.582   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0     -13.064  25.472   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0     -22.938  13.530   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5    6   16                                                       
CONECT    6    5   29                                                       
CONECT    7    8   28                                                       
CONECT    8    7   54                                                       
CONECT    9   14   17                                                       
CONECT   10   15   46                                                       
CONECT   11   26   47                                                       
CONECT   12   30   31                                                       
CONECT   13   32   33                                                       
CONECT   14    1    2    9                                                  
CONECT   15   10   20   48   55                                             
CONECT   16    5   28   34                                                  
CONECT   17    9   35   54                                                  
CONECT   18   22   23   32                                                  
CONECT   19   20   25   36   56                                             
CONECT   20   15   19   49   57                                             
CONECT   21   24   26   37   58                                             
CONECT   22   18   27   30                                                  
CONECT   23   18   31   33                                                  
CONECT   24   21   29   38                                                  
CONECT   25   19   33   48   59                                             
CONECT   26    3    4   11   21                                             
CONECT   27   22                                                            
CONECT   28    7   16                                                       
CONECT   29    6   24                                                       
CONECT   30   12   22                                                       
CONECT   31   12   23                                                       
CONECT   32   13   18                                                       
CONECT   33   13   23   25                                                  
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   19                                                            
CONECT   37   21                                                            
CONECT   38   24                                                            
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   25                                                       
CONECT   49   20   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    8   17                                                       
CONECT   55   15                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   21                                                            
CONECT   59   25                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

Synonyms

Value	Source
3-Methylbut-2-enoyl-CoA	HMDB
3-Methylbut-2-enoyl-coenzyme A	HMDB
3-Methylcrotonoyl-CoA	HMDB
3-Methylcrotonoyl-coenzyme A	HMDB
3-Methylcrotonyl-coenzyme A	HMDB
b-Methylcrotonyl-CoA (HMDB01493	HMDB
b-Methylcrotonyl-coenzyme A (HMDB01493	HMDB
beta-Methylcrotonoyl-CoA	HMDB
beta-Methylcrotonoyl-coenzyme A	HMDB
beta-Methylcrotonyl-CoA (HMDB01493	HMDB
beta-Methylcrotonyl-coenzyme A (HMDB01493	HMDB
Dimethylacryloyl-CoA	HMDB
Dimethylacryloyl-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-[(3-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-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

793193-48-3

SMILES

[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)C=C(C)C)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/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1

InChI Key

BXIPALATIYNHJN-TVCSPYKZSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.51 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	-4.3	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	186.81 m³·mol⁻¹	ChemAxon
Polarizability	75.87 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-1912000120-6c047fea21fac24e0423	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1912000000-1e69b9a4b44e8aac26c2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-e356c983f19414fbc82c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-8930140450-c6626636d28643a91eac	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-6910010010-8348d44355d1e2c70b46	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-0bfd3b35a59a8c971903	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)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	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
MMDBr0000195	Isovaleryl-CoA	3-Methylcrotonyl-CoA	isovaleryl-CoA dehydrogenase	VMH; KEGG	9214289
MMDBr0001621	3-Methylcrotonyl-CoA	3-Methylglutaconyl-CoA	methylcrotonoyl-CoA carboxylase 1 (alpha)	VMH; KEGG	30371894
MMDBr0002651	Isovaleryl-CoA	3-Methylcrotonyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	3597357 9214289
MMDBr0004171	3-Methylcrotonyl-CoA	3-Methylcrotonoylglycine	glycine-N-acyltransferase	VMH	11406611 657530
MMDBr0005293	3-Methylcrotonyl-CoA	3-Hydroxyisovaleryl-CoA	Not Available	VMH	8582058
MMDBr0008316	Isovaleryl-CoA	3-Methylcrotonyl-CoA	Not Available	VMH	30371894
MMDBr0008329	3-Methylcrotonyl-CoA	3-Methylglutaconyl-CoA	Not Available	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/Eubacteria	Proteobacteria	55	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Human pleural fluid plaque	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	56	Human feces; Human pleural fluid plaque; Human ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	23	Human feces; Human	Metabolic reconstruction
Bacteria	Actinobacteria	6	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	10	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Firmicutes	6	Human feces; Human pleural fluid plaque; Human ; Human stool	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Human pleural fluid plaque	Unknown; Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	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

HMDB0001493

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022652

KNApSAcK ID

Not Available

Chemspider ID

388909

KEGG Compound ID

C03069

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15486

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wysocki SJ, Hahnel R: 3-Methylcrotonylglycine excretion in 3-hydroxy-3-methylglutaric aciduria. Clin Chim Acta. 1978 May 16;86(1):101-8. doi: 10.1016/0009-8981(78)90464-3. [PubMed:657530 ]

Showing metabocard for 3-Methylcrotonyl-CoA (MMDBc0029661)

MOL for #<Metabolite:0x00007f3e144c5550>

3D MOL for #<Metabolite:0x00007f3e144c5550>

3D SDF for #<Metabolite:0x00007f3e144c5550>

3D-SDF for #<Metabolite:0x00007f3e144c5550>

PDB for #<Metabolite:0x00007f3e144c5550>

3D PDB for #<Metabolite:0x00007f3e144c5550>

SMILES for #<Metabolite:0x00007f3e144c5550>

INCHI for #<Metabolite:0x00007f3e144c5550>

Structure for #<Metabolite:0x00007f3e144c5550>

3D Structure for #<Metabolite:0x00007f3e144c5550>