MiMeDB: Showing metabocard for itaconyl-CoA (MMDBc0033097)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:34:39 UTC

Update Date

2022-12-15 22:51:53 UTC

MiMeDB ID

MMDBc0033097

Metabolite Identification

Common Name

itaconyl-CoA

Description

Itaconyl-CoA is an intermediate metabolite in the degradation pathway of itaconic acid, an unsaturated dicarbonic organic acid. Citramalyl coenzyme A (CoA) is found to be the intermediate in the conversion of itaconyl-Co-A to acetyl-CoA and pyruvate, catalyzed by methylglutaconase. Methylglutaconase catalyzes the interconversion of itaconyl-, mesaconyl-, and citramalyl-CoA. In liver mitochondria, methylglutaconase converts itaconate to pyruvate and acetyl coenzyme A. In this metabolic process, itaconate is first activated to itaconyl-CoA by a succinate activating enzyme, and a CoA derivative is cleaved to acetyl-CoA and pyruvate. (PMID: 13783048 , 11548996 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222332D          

 56 58  0  0  1  0            999 V2000
   26.4894   -2.1919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.8220   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2345   -2.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.1545   -2.1919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.4095   -2.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.7194   -3.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7437   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4865   -6.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0292   -6.6454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3148   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6003   -6.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0576   -4.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3148   -5.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0576   -4.1704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6287   -4.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3431   -3.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7721   -2.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6451   -1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0576   -2.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4701   -1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3431   -2.9328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6286   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4865   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1365   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7865   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3115   -1.6953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3115   -3.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9615   -1.6953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9615   -3.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3115   -2.5203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9615   -2.5203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.3699   -1.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9245   -3.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0995   -4.4690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7495   -4.4690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9245   -4.4690    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.9245   -5.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2740   -1.9370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8872   -2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6096   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6016   -2.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8872   -3.3140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4301   -1.2695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3161   -2.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6017   -3.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3161   -3.3139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0305   -2.0764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2010   -6.2329    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9154   -7.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9154   -6.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6299   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3444   -7.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3444   -6.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0588   -5.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0588   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7733   -6.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 53  1  0  0  0  0
 53 52  2  0  0  0  0
 53 55  1  0  0  0  0
 55 54  2  0  0  0  0
 55 56  1  0  0  0  0
M  END


  Mrv0541 02241222332D          

 56 58  0  0  1  0            999 V2000
   26.4894   -2.1919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.8220   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2345   -2.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.1545   -2.1919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.4095   -2.9765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.7194   -3.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7437   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4865   -6.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0292   -6.6454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3148   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6003   -6.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0576   -4.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3148   -5.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0576   -4.1704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6287   -4.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3431   -3.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7721   -2.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6451   -1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0576   -2.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4701   -1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3431   -2.9328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6286   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4865   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1365   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7865   -2.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3115   -1.6953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3115   -3.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9615   -1.6953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9615   -3.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3115   -2.5203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9615   -2.5203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.3699   -1.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9245   -3.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0995   -4.4690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7495   -4.4690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9245   -4.4690    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.9245   -5.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2740   -1.9370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8872   -2.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6096   -1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6016   -2.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8872   -3.3140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4301   -1.2695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3161   -2.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6017   -3.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3161   -3.3139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0305   -2.0764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2010   -6.2329    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9154   -7.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9154   -6.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6299   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3444   -7.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3444   -6.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0588   -5.4079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0588   -6.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7733   -6.6454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 51  1  0  0  0  0
 51 53  1  0  0  0  0
 53 52  2  0  0  0  0
 53 55  1  0  0  0  0
 55 54  2  0  0  0  0
 55 56  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033097

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40N7O19P3S/c1-13(25(39)40)8-16(35)56-7-6-28-15(34)4-5-29-23(38)20(37)26(2,3)10-49-55(46,47)52-54(44,45)48-9-14-19(51-53(41,42)43)18(36)24(50-14)33-12-32-17-21(27)30-11-31-22(17)33/h11-12,14,18-20,24,36-37H,1,4-10H2,2-3H3,(H,28,34)(H,29,38)(H,39,40)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,18-,19-,20+,24-/m1/s1

> <INCHI_KEY>
NFVGYLGSSJPRKW-CITAKDKDSA-N

> <FORMULA>
C26H40N7O19P3S

> <MOLECULAR_WEIGHT>
879.618

> <EXACT_MASS>
879.131252359

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
77.61848625310338

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2-{3-[(2R)-3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-2-methylidene-4-oxobutanoic acid

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-6.702056925205317

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.8307159860430309

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8249584973577533

> <JCHEM_PKA_STRONGEST_BASIC>
4.987411744502679

> <JCHEM_POLAR_SURFACE_AREA>
400.9299999999999

> <JCHEM_REFRACTIVITY>
187.47920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
itaconyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      49.447  -4.092   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      48.201  -3.186   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      48.971  -5.556   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      46.955  -4.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.431  -5.556   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      49.876  -6.802   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      36.855 -11.635   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.241 -12.405   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      35.521 -12.405   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      34.188 -11.635   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      32.854 -12.405   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      35.574  -9.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.188 -10.095   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      35.574  -7.785   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      32.907  -7.785   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      34.240  -7.015   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.908  -5.475   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.804  -3.371   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.574  -4.705   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.344  -3.371   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.240  -5.475   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      32.907  -4.705   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      38.241  -4.705   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      41.321  -4.705   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      44.401  -4.705   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      39.781  -3.165   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      39.781  -6.245   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      42.861  -3.165   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      42.861  -6.245   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      39.781  -4.705   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      42.861  -4.705   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      45.490  -3.616   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      46.526  -6.802   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      44.986  -8.342   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      48.066  -8.342   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      46.526  -8.342   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      46.526  -9.882   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      50.911  -3.616   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      52.056  -4.646   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      51.538  -2.209   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      53.390  -3.876   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      52.056  -6.186   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      53.070  -2.370   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      54.723  -4.646   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      53.390  -6.956   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      54.723  -6.186   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      56.057  -3.876   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      39.575 -11.635   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      40.909 -13.945   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      40.909 -12.405   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      42.242 -11.635   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      43.576 -13.945   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      43.576 -12.405   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      44.910 -10.095   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      44.910 -11.635   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      46.243 -12.405   0.000  0.00  0.00           O+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   50                                                       
CONECT   49   50                                                            
CONECT   50   48   49   51                                                  
CONECT   51   50   53                                                       
CONECT   52   53                                                            
CONECT   53   51   52   55                                                  
CONECT   54   55                                                            
CONECT   55   53   54   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀N₇O₁₉P₃S

Average Molecular Weight

879.618

Monoisotopic Molecular Weight

879.131252359

IUPAC Name

4-[(2-{3-[(2R)-3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-2-methylidene-4-oxobutanoic acid

Traditional Name

itaconyl-coa

CAS Registry Number

6008-93-1

SMILES

CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(=C)C(O)=O

InChI Identifier

InChI=1S/C26H40N7O19P3S/c1-13(25(39)40)8-16(35)56-7-6-28-15(34)4-5-29-23(38)20(37)26(2,3)10-49-55(46,47)52-54(44,45)48-9-14-19(51-53(41,42)43)18(36)24(50-14)33-12-32-17-21(27)30-11-31-22(17)33/h11-12,14,18-20,24,36-37H,1,4-10H2,2-3H3,(H,28,34)(H,29,38)(H,39,40)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,18-,19-,20+,24-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3-enoyl-CoA (CHEBI:15528 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.71 g/L	ALOGPS
logP	-0.44	ALOGPS
logP	-6.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	400.93 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	187.48 m³·mol⁻¹	ChemAxon
Polarizability	77.62 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-1931000120-f21841089f37885c3922	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-8ec468defd81f216ea08	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1910000000-65860a5be97c754ec879	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01u0-3911031350-198a08bda9e5a9f75079	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2901110000-f5bb92914564dd7cc2c8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-7ea30ba57ca8598189f7	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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		details

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

Not Available

KEGG Compound ID

C00531

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966125

PDB ID

Not Available

ChEBI ID

15528

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Willke T, Vorlop KD: Biotechnological production of itaconic acid. Appl Microbiol Biotechnol. 2001 Aug;56(3-4):289-95. doi: 10.1007/s002530100685. [PubMed:11548996 ]
WANG SF, ADLER J, LARDY HA: The pathway of itaconate metabolism by liver mitochondria. J Biol Chem. 1961 Jan;236:26-30. [PubMed:13783048 ]

Showing metabocard for itaconyl-CoA (MMDBc0033097)

MOL for #<Metabolite:0x000055b76beb2e90>

3D MOL for #<Metabolite:0x000055b76beb2e90>

3D SDF for #<Metabolite:0x000055b76beb2e90>

3D-SDF for #<Metabolite:0x000055b76beb2e90>

PDB for #<Metabolite:0x000055b76beb2e90>

3D PDB for #<Metabolite:0x000055b76beb2e90>

SMILES for #<Metabolite:0x000055b76beb2e90>

INCHI for #<Metabolite:0x000055b76beb2e90>

Structure for #<Metabolite:0x000055b76beb2e90>

3D Structure for #<Metabolite:0x000055b76beb2e90>