MiMeDB: Showing metabocard for [(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA (MMDBc0055082)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:41:32 UTC

Update Date

2022-08-12 20:09:13 UTC

Metabolite ID

MMDBc0055082

Metabolite Identification

Common Name

[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA

Description

[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA(4-), also known as 2-oxo-Delta(3)-4,5,5-trimethylcyclopentenylacetyl-CoA, 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. Based on a literature review a significant number of articles have been published on [(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA(4-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221412D          

 66 69  0  0  1  0            999 V2000
    3.0336   12.9696    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
    2.3285   13.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   14.2110    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
    1.8006   12.1689    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
   -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
    2.2131   12.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9074   13.1609    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9937   12.3405    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
   -0.5215   13.1609    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  1  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
   -7.6662   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   13.4965    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
    0.3806   11.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0939   14.3984    0.0000 O   0  5  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
  -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  5  0  0  0  0  0  0  0  0  0  0
  -10.2842    8.4674    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -11.3882    9.6936    0.0000 O   0  5  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
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   -8.3807    9.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
    0.9506   13.9848    0.0000 H   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
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  -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
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 16  1  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  1  6  0  0  0
 18 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  1  0  0  0
 20  6  1  0  0  0  0
 21 11  1  0  0  0  0
 24 19  1  0  0  0  0
 24 23  1  0  0  0  0
 26 22  2  0  0  0  0
 27 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29 23  1  0  0  0  0
 30  2  1  0  0  0  0
 30  3  1  0  0  0  0
 30 13  1  0  0  0  0
 30 25  1  0  0  0  0
 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 16  1  0  0  0  0
 31 17  1  0  0  0  0
 32 26  1  0  0  0  0
 33  8  1  4  0  0  0
 33 20  2  0  0  0  0
 34  7  1  4  0  0  0
 34 28  2  0  0  0  0
 35 14  2  0  0  0  0
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 38 27  1  0  0  0  0
 29 38  1  1  0  0  0
 39 18  2  0  0  0  0
 40 20  1  0  0  0  0
 41 21  2  0  0  0  0
 23 42  1  6  0  0  0
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 44 28  1  0  0  0  0
 52 12  1  0  0  0  0
 53 13  1  0  0  0  0
 54 19  1  0  0  0  0
 54 29  1  0  0  0  0
 24 55  1  1  0  0  0
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 57 46  1  0  0  0  0
 57 47  2  0  0  0  0
 57 55  1  0  0  0  0
 58 48  1  0  0  0  0
 58 49  2  0  0  0  0
 58 52  1  0  0  0  0
 58 56  1  0  0  0  0
 59 50  1  0  0  0  0
 59 51  2  0  0  0  0
 59 53  1  0  0  0  0
 59 56  1  0  0  0  0
 60  9  1  0  0  0  0
 60 21  1  0  0  0  0
 17 61  1  1  0  0  0
 19 62  1  6  0  0  0
 23 63  1  1  0  0  0
 24 64  1  1  0  0  0
 25 65  1  6  0  0  0
 29 66  1  6  0  0  0
M  CHG  4  40  -1  44  -1  45  -1  46  -1
M  END


  Mrv1652306172221412D          

 66 69  0  0  1  0            999 V2000
    3.0336   12.9696    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
    2.3285   13.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   14.2110    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
    1.8006   12.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2131   12.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.6461    4.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6662   12.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   13.4965    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
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   -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  5  0  0  0  0  0  0  0  0  0  0
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   -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
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   -8.3807   11.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.3807    9.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
    0.9506   13.9848    0.0000 H   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
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  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 16  1  1  0  0  0  0
 16 10  2  0  0  0  0
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 30 25  1  0  0  0  0
 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 16  1  0  0  0  0
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 52 12  1  0  0  0  0
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 58 52  1  0  0  0  0
 58 56  1  0  0  0  0
 59 50  1  0  0  0  0
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 59 53  1  0  0  0  0
 59 56  1  0  0  0  0
 60  9  1  0  0  0  0
 60 21  1  0  0  0  0
 17 61  1  1  0  0  0
 19 62  1  6  0  0  0
 23 63  1  1  0  0  0
 24 64  1  1  0  0  0
 25 65  1  6  0  0  0
 29 66  1  6  0  0  0
M  CHG  4  40  -1  44  -1  45  -1  46  -1
M  END
> <DATABASE_ID>
MMDBc0055082

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C[C@@]1([H])C(=O)C=C(C)C1(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/C31H48N7O18P3S/c1-16-10-18(39)17(31(16,4)5)11-21(41)60-9-8-33-20(40)6-7-34-28(44)25(43)30(2,3)13-53-59(50,51)56-58(48,49)52-12-19-24(55-57(45,46)47)23(42)29(54-19)38-15-37-22-26(32)35-14-36-27(22)38/h10,14-15,17,19,23-25,29,42-43H,6-9,11-13H2,1-5H3,(H,33,40)(H,34,44)(H,48,49)(H,50,51)(H2,32,35,36)(H2,45,46,47)/p-4/t17-,19+,23+,24+,25-,29+/m0/s1

> <INCHI_KEY>
QRPFCCJPSQOMPY-WNZSEHGDSA-J

> <FORMULA>
C31H44N7O18P3S

> <MOLECULAR_WEIGHT>
927.71

> <EXACT_MASS>
927.169834092

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
83.63207286833644

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({2-[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-en-1-yl]acetyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanecarboximidate

> <JCHEM_LOGP>
-3.8589461571722277

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8846783539997332

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8189911176900071

> <JCHEM_PKA_STRONGEST_BASIC>
6.378957161670403

> <JCHEM_POLAR_SURFACE_AREA>
399.00000000000006

> <JCHEM_REFRACTIVITY>
228.35120000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-({2-[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-en-1-yl]acetyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       5.663  24.210   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.850  23.027   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.770  23.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.347  26.099   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.331  26.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.976  24.567   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.309  25.337   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.975  25.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.641  24.567   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.361  22.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.360  25.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -18.311  14.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.310  21.487   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -26.098  10.487   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -21.169   9.195   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.131  24.049   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.694  24.567   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.855  23.036   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -19.645  13.787   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.642  25.337   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.973  24.567   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -23.606   8.677   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -22.082  13.269   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -21.052  14.413   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.310  24.567   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -25.013   8.050   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -23.445  10.208   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.977  25.337   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.312  11.935   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -14.310  23.027   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.101  25.193   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0     -25.174   6.519   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0      -6.308  24.567   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0     -11.643  24.567   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0     -26.259   8.956   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0     -24.691  11.113   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0     -22.199   8.050   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0     -21.939  10.528   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0       0.710  22.005   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -7.642  26.877   0.000  0.00  0.00           O-1
HETATM   41  O   UNK     0      -0.973  23.027   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -23.614  13.430   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -15.644  25.337   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -12.977  26.877   0.000  0.00  0.00           O-1
HETATM   45  O   UNK     0     -19.197  15.806   0.000  0.00  0.00           O-1
HETATM   46  O   UNK     0     -21.258  18.095   0.000  0.00  0.00           O-1
HETATM   47  O   UNK     0     -19.083  17.981   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -17.748  18.201   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -16.208  15.533   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -17.184  19.177   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0     -14.104  19.177   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -18.311  16.097   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0     -15.644  20.717   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0     -19.806  12.256   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0     -21.372  15.920   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0     -15.644  17.637   0.000  0.00  0.00           O+0
HETATM   57  P   UNK     0     -20.228  16.950   0.000  0.00  0.00           P+0
HETATM   58  P   UNK     0     -16.978  16.867   0.000  0.00  0.00           P+0
HETATM   59  P   UNK     0     -15.644  19.177   0.000  0.00  0.00           P+0
HETATM   60  S   UNK     0      -2.307  25.337   0.000  0.00  0.00           S+0
HETATM   61  H   UNK     0       1.774  26.105   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0     -19.726  15.325   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0     -22.634  14.707   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0     -20.732  12.907   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0     -12.977  23.797   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0     -22.850  11.855   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   30                                                            
CONECT    3   30                                                            
CONECT    4   31                                                            
CONECT    5   31                                                            
CONECT    6    7   20                                                       
CONECT    7    6   34                                                       
CONECT    8    9   33                                                       
CONECT    9    8   60                                                       
CONECT   10   16   18                                                       
CONECT   11   17   21                                                       
CONECT   12   19   52                                                       
CONECT   13   30   53                                                       
CONECT   14   35   36                                                       
CONECT   15   37   38                                                       
CONECT   16    1   10   31                                                  
CONECT   17   11   18   31   61                                             
CONECT   18   10   17   39                                                  
CONECT   19   12   24   54   62                                             
CONECT   20    6   33   40                                                  
CONECT   21   11   41   60                                                  
CONECT   22   26   27   37                                                  
CONECT   23   24   29   42   63                                             
CONECT   24   19   23   55   64                                             
CONECT   25   28   30   43   65                                             
CONECT   26   22   32   35                                                  
CONECT   27   22   36   38                                                  
CONECT   28   25   34   44                                                  
CONECT   29   23   38   54   66                                             
CONECT   30    2    3   13   25                                             
CONECT   31    4    5   16   17                                             
CONECT   32   26                                                            
CONECT   33    8   20                                                       
CONECT   34    7   28                                                       
CONECT   35   14   26                                                       
CONECT   36   14   27                                                       
CONECT   37   15   22                                                       
CONECT   38   15   27   29                                                  
CONECT   39   18                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   23                                                            
CONECT   43   25                                                            
CONECT   44   28                                                            
CONECT   45   57                                                            
CONECT   46   57                                                            
CONECT   47   57                                                            
CONECT   48   58                                                            
CONECT   49   58                                                            
CONECT   50   59                                                            
CONECT   51   59                                                            
CONECT   52   12   58                                                       
CONECT   53   13   59                                                       
CONECT   54   19   29                                                       
CONECT   55   24   57                                                       
CONECT   56   58   59                                                       
CONECT   57   45   46   47   55                                             
CONECT   58   48   49   52   56                                             
CONECT   59   50   51   53   56                                             
CONECT   60    9   21                                                       
CONECT   61   17                                                            
CONECT   62   19                                                            
CONECT   63   23                                                            
CONECT   64   24                                                            
CONECT   65   25                                                            
CONECT   66   29                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  138    0
END

Synonyms

Value	Source
2-oxo-Delta(3)-4,5,5-Trimethylcyclopentenylacetyl-CoA	ChEBI
2-oxo-Delta(3)-4,5,5-Trimethylcyclopentenylacetyl-coenzyme A	ChEBI
[(1R)-2,2,3-Trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA	ChEBI
[(R)-2,2,3-Trimethyl-2-oxocyclopent-3-en-1-yl]acetyl-coenzyme A(4-)	ChEBI
2-oxo-Δ(3)-4,5,5-trimethylcyclopentenylacetyl-CoA	Generator
2-oxo-Δ(3)-4,5,5-trimethylcyclopentenylacetyl-coenzyme A	Generator

Molecular Formula

C₃₁H₄₄N₇O₁₈P₃S

Average Mass

927.71

Monoisotopic Mass

927.169834092

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({2-[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-en-1-yl]acetyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanecarboximidate

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-({2-[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-en-1-yl]acetyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanecarboximidate

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C[C@@]1([H])C(=O)C=C(C)C1(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/C31H48N7O18P3S/c1-16-10-18(39)17(31(16,4)5)11-21(41)60-9-8-33-20(40)6-7-34-28(44)25(43)30(2,3)13-53-59(50,51)56-58(48,49)52-12-19-24(55-57(45,46)47)23(42)29(54-19)38-15-37-22-26(32)35-14-36-27(22)38/h10,14-15,17,19,23-25,29,42-43H,6-9,11-13H2,1-5H3,(H,33,40)(H,34,44)(H,48,49)(H,50,51)(H2,32,35,36)(H2,45,46,47)/p-4/t17-,19+,23+,24+,25-,29+/m0/s1

InChI Key

QRPFCCJPSQOMPY-WNZSEHGDSA-J

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl-CoA(4-) (CHEBI:64784 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.9	ChemAxon
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.38	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	399 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	228.35 m³·mol⁻¹	ChemAxon
Polarizability	83.63 Å³	ChemAxon
Number of Rings	4	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	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0015187	[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA	[(2R)-3,3,4-trimethyl-6-oxo-3,6-dihydro-1H-pyran-2-yl]acetyl-CoA	2-oxo-Delta(3)-4,5,5-trimethylcyclopentenylacetyl-CoA monooxygenase	Oxygenation	RHEA	34755880

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28184598

KEGG Compound ID

Not Available

BioCyc ID

CPD-867

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57339184

PDB ID

Not Available

ChEBI ID

64784

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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

Showing metabocard for [(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA (MMDBc0055082)

MOL for #<Metabolite:0x000055c79a8e0320>

3D MOL for #<Metabolite:0x000055c79a8e0320>

3D SDF for #<Metabolite:0x000055c79a8e0320>

3D-SDF for #<Metabolite:0x000055c79a8e0320>

PDB for #<Metabolite:0x000055c79a8e0320>

3D PDB for #<Metabolite:0x000055c79a8e0320>

SMILES for #<Metabolite:0x000055c79a8e0320>

INCHI for #<Metabolite:0x000055c79a8e0320>

Structure for #<Metabolite:0x000055c79a8e0320>

3D Structure for #<Metabolite:0x000055c79a8e0320>