MiMeDB: Showing metabocard for Methacrylyl-CoA (MMDBc0029529)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:31:09 UTC

Update Date

2024-04-30 19:37:16 UTC

Metabolite ID

MMDBc0029529

Metabolite Identification

Common Name

Methacrylyl-CoA

Description

Methacrylyl-CoA is a metabolite in the valine, leucine and isoleucine degradation pathway and is highly reactive with free thiol compounds (PMID 14684172 ; KEGG).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306222023472D          

 58 60  0  0  1  0            999 V2000
    0.9074   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   14.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4912   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8412   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5228   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6649   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9505   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8096    7.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6662   11.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9810    5.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3404    4.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5241    7.3859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0939   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6461    4.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8298    7.1084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.2778    7.7215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6662   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3998    4.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5598    5.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9518   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4173    6.3939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5215   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6662   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4860    3.4922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3794   13.1609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2373   13.1609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0672    4.7976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2273    5.9537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8924    4.3127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7529    5.6403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0939   14.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6503    7.1946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807   13.5734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9518   14.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   12.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2842    8.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3882    9.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2231    9.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5077    9.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6827    8.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2057   10.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5557   10.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8096    8.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807   11.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6103    6.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4493    8.5285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807    9.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8362    9.0805    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0952    9.0359    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807   10.2734    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2360   13.5734    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5673    8.2098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1255    7.8786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1063    6.9145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9518   12.7484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2412    6.3508    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
 13  1  2  0  0  0  0
 13  2  1  0  0  0  0
 14  9  1  1  0  0  0
 15  5  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 20 16  2  0  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 24 13  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27  7  1  4  0  0  0
 27 15  2  0  0  0  0
 28  6  1  4  0  0  0
 28 22  2  0  0  0  0
 29 11  2  0  0  0  0
 29 20  1  0  0  0  0
 30 11  1  0  0  0  0
 30 21  2  0  0  0  0
 31 12  2  0  0  0  0
 31 16  1  0  0  0  0
 32 12  1  0  0  0  0
 32 21  1  0  0  0  0
 23 32  1  1  0  0  0
 33 15  1  0  0  0  0
 17 34  1  6  0  0  0
 35 19  1  0  0  0  0
 36 22  1  0  0  0  0
 37 24  2  0  0  0  0
 45  9  1  0  0  0  0
 46 10  1  0  0  0  0
 47 14  1  0  0  0  0
 47 23  1  0  0  0  0
 18 48  1  1  0  0  0
 50 38  1  0  0  0  0
 50 39  1  0  0  0  0
 50 40  2  0  0  0  0
 50 48  1  0  0  0  0
 51 41  1  0  0  0  0
 51 42  2  0  0  0  0
 51 45  1  0  0  0  0
 51 49  1  0  0  0  0
 52 43  1  0  0  0  0
 52 44  2  0  0  0  0
 52 46  1  0  0  0  0
 52 49  1  0  0  0  0
 53  8  1  0  0  0  0
 53 24  1  0  0  0  0
 14 54  1  6  0  0  0
 17 55  1  1  0  0  0
 18 56  1  1  0  0  0
 57 19  1  0  0  0  0
 23 58  1  6  0  0  0
M  END


  Mrv1652306222023472D          

 58 60  0  0  1  0            999 V2000
    0.9074   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   14.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4912   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8412   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5228   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6649   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9505   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8096    7.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6662   11.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9810    5.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3404    4.9258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5241    7.3859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0939   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6461    4.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8298    7.1084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.2778    7.7215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6662   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3998    4.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5598    5.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9518   13.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4173    6.3939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5215   13.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6662   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4860    3.4922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3794   13.1609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2373   13.1609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0672    4.7976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2273    5.9537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8924    4.3127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7529    5.6403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0939   14.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6503    7.1946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807   13.5734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9518   14.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   12.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2842    8.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3882    9.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2231    9.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5077    9.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6827    8.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2057   10.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5557   10.2734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8096    8.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807   11.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6103    6.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4493    8.5285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807    9.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8362    9.0805    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0952    9.0359    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3807   10.2734    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2360   13.5734    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5673    8.2098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1255    7.8786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1063    6.9145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9518   12.7484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2412    6.3508    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
 13  1  2  0  0  0  0
 13  2  1  0  0  0  0
 14  9  1  1  0  0  0
 15  5  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 20 16  2  0  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 24 13  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 19  1  0  0  0  0
 26 20  1  0  0  0  0
 27  7  1  4  0  0  0
 27 15  2  0  0  0  0
 28  6  1  4  0  0  0
 28 22  2  0  0  0  0
 29 11  2  0  0  0  0
 29 20  1  0  0  0  0
 30 11  1  0  0  0  0
 30 21  2  0  0  0  0
 31 12  2  0  0  0  0
 31 16  1  0  0  0  0
 32 12  1  0  0  0  0
 32 21  1  0  0  0  0
 23 32  1  1  0  0  0
 33 15  1  0  0  0  0
 17 34  1  6  0  0  0
 35 19  1  0  0  0  0
 36 22  1  0  0  0  0
 37 24  2  0  0  0  0
 45  9  1  0  0  0  0
 46 10  1  0  0  0  0
 47 14  1  0  0  0  0
 47 23  1  0  0  0  0
 18 48  1  1  0  0  0
 50 38  1  0  0  0  0
 50 39  1  0  0  0  0
 50 40  2  0  0  0  0
 50 48  1  0  0  0  0
 51 41  1  0  0  0  0
 51 42  2  0  0  0  0
 51 45  1  0  0  0  0
 51 49  1  0  0  0  0
 52 43  1  0  0  0  0
 52 44  2  0  0  0  0
 52 46  1  0  0  0  0
 52 49  1  0  0  0  0
 53  8  1  0  0  0  0
 53 24  1  0  0  0  0
 14 54  1  6  0  0  0
 17 55  1  1  0  0  0
 18 56  1  1  0  0  0
 57 19  1  0  0  0  0
 23 58  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029529

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)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/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19?,23-/m1/s1

> <INCHI_KEY>
NPALUEYCDZWBOV-NNYIDDMCSA-N

> <FORMULA>
C25H40N7O17P3S

> <MOLECULAR_WEIGHT>
835.608

> <EXACT_MASS>
835.141423115

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
73.72352173013282

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

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
-4.496442283481292

> <ALOGPS_LOGS>
-2.16

> <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>
363.62999999999994

> <JCHEM_REFRACTIVITY>
181.21280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.82e+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-[(2-methylprop-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       1.694  24.567   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.360  26.877   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.850  23.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.770  23.027   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.975  24.567   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.309  25.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.974  25.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.641  24.567   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -18.311  14.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.310  21.487   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -26.098  10.487   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -21.169   9.195   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.360  25.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -19.645  13.787   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.642  25.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -23.606   8.677   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -22.082  13.269   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -21.052  14.413   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -14.310  24.567   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -25.013   8.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -23.445  10.208   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.977  25.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -21.312  11.935   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.973  24.567   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.310  23.027   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0     -25.174   6.519   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      -6.308  24.567   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0     -11.643  24.567   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0     -26.259   8.956   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0     -24.691  11.114   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0     -22.199   8.050   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0     -21.939  10.529   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      -7.642  26.877   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0     -23.614  13.430   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -15.644  25.337   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -12.977  26.877   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.973  23.027   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -19.197  15.806   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -21.258  18.095   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -19.083  17.981   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -17.748  18.201   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -16.208  15.533   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -17.184  19.177   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -14.104  19.177   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0     -18.311  16.097   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0     -15.644  20.717   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -19.806  12.256   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -21.372  15.920   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -15.644  17.637   0.000  0.00  0.00           O+0
HETATM   50  P   UNK     0     -20.228  16.950   0.000  0.00  0.00           P+0
HETATM   51  P   UNK     0     -16.978  16.867   0.000  0.00  0.00           P+0
HETATM   52  P   UNK     0     -15.644  19.177   0.000  0.00  0.00           P+0
HETATM   53  S   UNK     0      -2.307  25.337   0.000  0.00  0.00           S+0
HETATM   54  H   UNK     0     -19.726  15.325   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0     -22.634  14.707   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0     -20.732  12.907   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0     -12.977  23.797   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0     -22.850  11.855   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    6   15                                                       
CONECT    6    5   28                                                       
CONECT    7    8   27                                                       
CONECT    8    7   53                                                       
CONECT    9   14   45                                                       
CONECT   10   25   46                                                       
CONECT   11   29   30                                                       
CONECT   12   31   32                                                       
CONECT   13    1    2   24                                                  
CONECT   14    9   18   47   54                                             
CONECT   15    5   27   33                                                  
CONECT   16   20   21   31                                                  
CONECT   17   18   23   34   55                                             
CONECT   18   14   17   48   56                                             
CONECT   19   22   25   35   57                                             
CONECT   20   16   26   29                                                  
CONECT   21   16   30   32                                                  
CONECT   22   19   28   36                                                  
CONECT   23   17   32   47   58                                             
CONECT   24   13   37   53                                                  
CONECT   25    3    4   10   19                                             
CONECT   26   20                                                            
CONECT   27    7   15                                                       
CONECT   28    6   22                                                       
CONECT   29   11   20                                                       
CONECT   30   11   21                                                       
CONECT   31   12   16                                                       
CONECT   32   12   21   23                                                  
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   19                                                            
CONECT   36   22                                                            
CONECT   37   24                                                            
CONECT   38   50                                                            
CONECT   39   50                                                            
CONECT   40   50                                                            
CONECT   41   51                                                            
CONECT   42   51                                                            
CONECT   43   52                                                            
CONECT   44   52                                                            
CONECT   45    9   51                                                       
CONECT   46   10   52                                                       
CONECT   47   14   23                                                       
CONECT   48   18   50                                                       
CONECT   49   51   52                                                       
CONECT   50   38   39   40   48                                             
CONECT   51   41   42   45   49                                             
CONECT   52   43   44   46   49                                             
CONECT   53    8   24                                                       
CONECT   54   14                                                            
CONECT   55   17                                                            
CONECT   56   18                                                            
CONECT   57   19                                                            
CONECT   58   23                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

Synonyms

Value	Source
2-Methylprop-2-enoyl-CoA	HMDB
2-Methylprop-2-enoyl-coenzyme A	HMDB
Methacrylyl CoA	HMDB
Methacrylyl coenzyme A	HMDB
Methacrylyl-coenzyme A	HMDB
Methylacrylyl-CoA	HMDB
Methylacrylyl-coenzyme A	HMDB
S-(2-Methyl-2-propenoate	HMDB
S-(2-Methyl-2-propenoate) CoA	HMDB
S-(2-Methyl-2-propenoate) coenzyme A	HMDB
S-(2-Methyl-2-propenoic acid	HMDB

Molecular Formula

C₂₅H₄₀N₇O₁₇P₃S

Average Mass

835.608

Monoisotopic Mass

835.141423115

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-[(2-methylprop-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-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

6008-91-9

SMILES

[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)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/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19?,23-/m1/s1

InChI Key

NPALUEYCDZWBOV-NNYIDDMCSA-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	5.82 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-4.5	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	181.21 m³·mol⁻¹	ChemAxon
Polarizability	73.72 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-1912000120-43e6bafbba6b6bab0398	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0912000000-599320c41cce75641963	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-53ae9df4445dfd4eb7d6	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4930131150-65deb538cb1e798afaa9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-3910100000-5913bc83b63ee9f0b2b9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-806bd274223a7dc2c783	2015-09-15	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
MMDBr0000196	Isobutyryl-CoA	Methacrylyl-CoA	acyl-CoA dehydrogenase family, member 8	VMH	11013134
MMDBr0000849	Methacrylyl-CoA	(S)-3-Hydroxyisobutyryl-CoA	enoyl CoA hydratase, short chain, 1, mitochondrial	VMH; KEGG	9073515
MMDBr0002601	Isobutyryl-CoA	Methacrylyl-CoA	acyl-CoA dehydrogenase, C-2 to C-3 short chain	VMH	12855692 3597357 6401712 6874697
MMDBr0002657	Methacrylyl-CoA	(S)-3-Hydroxyisobutyryl-CoA	enoyl CoA hydratase, short chain, 1, mitochondrial	VMH	10671535 12467702
MMDBr0006897	Isobutyryl-CoA	Methacrylyl-CoA	Not Available	VMH	30371894
MMDBr0007758	Methacrylyl-CoA	(S)-3-Hydroxyisobutyryl-CoA	Not Available	VMH	30371894
MMDBr0008489	Isobutyryl-CoA	Methacrylyl-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	Proteobacteria	145	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	211	Pig ; Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa	Metabolic reconstruction
Bacteria	Actinobacteria	56	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	21	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0001011

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022369

KNApSAcK ID

Not Available

Chemspider ID

389035

KEGG Compound ID

C03460

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

27754

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Taniguchi K, Nonami T, Nakao A, Harada A, Kurokawa T, Sugiyama S, Fujitsuka N, Shimomura Y, Hutson SM, Harris RA, Takagi H: The valine catabolic pathway in human liver: effect of cirrhosis on enzyme activities. Hepatology. 1996 Dec;24(6):1395-8. doi: 10.1002/hep.510240614. [PubMed:8938168 ]
Shimomura Y, Honda T, Goto H, Nonami T, Kurokawa T, Nagasaki M, Murakami T: Effects of liver failure on the enzymes in the branched-chain amino acid catabolic pathway. Biochem Biophys Res Commun. 2004 Jan 9;313(2):381-5. doi: 10.1016/j.bbrc.2003.07.022. [PubMed:14684172 ]
Lehnert W, Sass JO: Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I). Med Hypotheses. 2005;65(2):330-3. doi: 10.1016/j.mehy.2005.02.021. [PubMed:15922108 ]

Showing metabocard for Methacrylyl-CoA (MMDBc0029529)

MOL for #<Metabolite:0x00007f666df0ad18>

3D MOL for #<Metabolite:0x00007f666df0ad18>

3D SDF for #<Metabolite:0x00007f666df0ad18>

3D-SDF for #<Metabolite:0x00007f666df0ad18>

PDB for #<Metabolite:0x00007f666df0ad18>

3D PDB for #<Metabolite:0x00007f666df0ad18>

SMILES for #<Metabolite:0x00007f666df0ad18>

INCHI for #<Metabolite:0x00007f666df0ad18>

Structure for #<Metabolite:0x00007f666df0ad18>

3D Structure for #<Metabolite:0x00007f666df0ad18>