MiMeDB: Showing metabocard for Coenzyme A (MMDBc0029649)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:04 UTC

Update Date

2024-10-10 00:08:54 UTC

Metabolite ID

MMDBc0029649

Metabolite Identification

Common Name

Coenzyme A

Description

Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate and adenosine triphosphate. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine, in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. -- Wikipedia

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920542D          

 53 55  0  0  1  0            999 V2000
   -5.2497   -0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -2.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1812   -1.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4275   -1.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2698   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0234   -1.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8486   -2.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3390   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0064   -1.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5853   -1.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6023   -1.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601   -1.4203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7624   -2.8751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4252   -0.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -2.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -2.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -2.6617    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6909   -2.3533    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -1.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.4794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -2.0914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
 11  7  1  1  0  0  0
 12  3  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21  8  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  5  1  4  0  0  0
 23 12  2  0  0  0  0
 24  4  1  4  0  0  0
 24 19  2  0  0  0  0
 25  9  2  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 26 18  2  0  0  0  0
 27 10  2  0  0  0  0
 27 13  1  0  0  0  0
 28 10  1  0  0  0  0
 28 18  1  0  0  0  0
 20 28  1  1  0  0  0
 29 12  1  0  0  0  0
 14 30  1  6  0  0  0
 31 16  1  0  0  0  0
 32 19  1  0  0  0  0
 40  7  1  0  0  0  0
 41  8  1  0  0  0  0
 42 11  1  0  0  0  0
 42 20  1  0  0  0  0
 15 43  1  1  0  0  0
 45 33  1  0  0  0  0
 45 34  1  0  0  0  0
 45 35  2  0  0  0  0
 45 43  1  0  0  0  0
 46 36  1  0  0  0  0
 46 37  2  0  0  0  0
 46 40  1  0  0  0  0
 46 44  1  0  0  0  0
 47 38  1  0  0  0  0
 47 39  2  0  0  0  0
 47 41  1  0  0  0  0
 47 44  1  0  0  0  0
 48  6  1  0  0  0  0
 11 49  1  6  0  0  0
 14 50  1  1  0  0  0
 15 51  1  1  0  0  0
 52 16  1  0  0  0  0
 20 53  1  6  0  0  0
M  END


  Mrv1652305221920542D          

 53 55  0  0  1  0            999 V2000
   -5.2497   -0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -2.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1812   -1.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4275   -1.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2698   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0234   -1.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.8486   -2.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3390   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0064   -1.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5853   -1.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6023   -1.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601   -1.4203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7624   -2.8751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4252   -0.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -2.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -2.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -2.6617    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6909   -2.3533    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -1.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.4794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527   -2.0914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
 11  7  1  1  0  0  0
 12  3  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 19 16  1  0  0  0  0
 20 14  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21  8  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  5  1  4  0  0  0
 23 12  2  0  0  0  0
 24  4  1  4  0  0  0
 24 19  2  0  0  0  0
 25  9  2  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 26 18  2  0  0  0  0
 27 10  2  0  0  0  0
 27 13  1  0  0  0  0
 28 10  1  0  0  0  0
 28 18  1  0  0  0  0
 20 28  1  1  0  0  0
 29 12  1  0  0  0  0
 14 30  1  6  0  0  0
 31 16  1  0  0  0  0
 32 19  1  0  0  0  0
 40  7  1  0  0  0  0
 41  8  1  0  0  0  0
 42 11  1  0  0  0  0
 42 20  1  0  0  0  0
 15 43  1  1  0  0  0
 45 33  1  0  0  0  0
 45 34  1  0  0  0  0
 45 35  2  0  0  0  0
 45 43  1  0  0  0  0
 46 36  1  0  0  0  0
 46 37  2  0  0  0  0
 46 40  1  0  0  0  0
 46 44  1  0  0  0  0
 47 38  1  0  0  0  0
 47 39  2  0  0  0  0
 47 41  1  0  0  0  0
 47 44  1  0  0  0  0
 48  6  1  0  0  0  0
 11 49  1  6  0  0  0
 14 50  1  1  0  0  0
 15 51  1  1  0  0  0
 52 16  1  0  0  0  0
 20 53  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029649

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(O)(C(O)=NCCC(O)=NCCS)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/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1

> <INCHI_KEY>
RGJOEKWQDUBAIZ-DRCCLKDXSA-N

> <FORMULA>
C21H36N7O16P3S

> <MOLECULAR_WEIGHT>
767.534

> <EXACT_MASS>
767.115208365

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
66.81625080704382

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <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-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.63

> <JCHEM_LOGP>
-5.722226670490722

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207321011595

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787810970068

> <JCHEM_PKA_STRONGEST_BASIC>
4.006052953653216

> <JCHEM_POLAR_SURFACE_AREA>
346.5599999999999

> <JCHEM_REFRACTIVITY>
162.7402

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coenzyme A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -9.800  -1.592   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.052  -4.406   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.138  -2.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -15.731  -3.556   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -21.037  -4.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -22.444  -3.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.061  -2.789   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.019  -3.625   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.185  -1.884   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -18.384  -3.835   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.555  -1.114   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.650  -2.359   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -11.833  -2.372   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.079  -3.278   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.426  -2.999   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.924   5.923   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0     -19.791  -3.209   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0     -14.485  -2.651   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0     -18.223  -5.367   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.095  -1.114   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -11.994  -0.841   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -12.918  -4.809   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.049  -3.938   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.240  -5.999   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.065  -6.113   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -4.619  -1.822   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.808  -4.313   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -5.740  -1.940   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -6.993  -4.753   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.468  -2.162   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -7.773  -2.720   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.185  -0.344   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.126  -3.824   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -4.959  -3.973   0.000  0.00  0.00           O+0
HETATM   45  P   UNK     0       1.095  -4.969   0.000  0.00  0.00           P+0
HETATM   46  P   UNK     0      -3.714  -3.068   0.000  0.00  0.00           P+0
HETATM   47  P   UNK     0      -6.366  -3.346   0.000  0.00  0.00           P+0
HETATM   48  S   UNK     0     -23.690  -4.393   0.000  0.00  0.00           S+0
HETATM   49  H   UNK     0       0.426  -3.405   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.254  -2.486   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.174  -0.895   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0     -11.672  -3.904   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.171   0.373   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3    4   12                                                       
CONECT    4    3   24                                                       
CONECT    5    6   23                                                       
CONECT    6    5   48                                                       
CONECT    7   11   40                                                       
CONECT    8   21   41                                                       
CONECT    9   25   26                                                       
CONECT   10   27   28                                                       
CONECT   11    7   15   42   49                                             
CONECT   12    3   23   29                                                  
CONECT   13   17   18   27                                                  
CONECT   14   15   20   30   50                                             
CONECT   15   11   14   43   51                                             
CONECT   16   19   21   31   52                                             
CONECT   17   13   22   25                                                  
CONECT   18   13   26   28                                                  
CONECT   19   16   24   32                                                  
CONECT   20   14   28   42   53                                             
CONECT   21    1    2    8   16                                             
CONECT   22   17                                                            
CONECT   23    5   12                                                       
CONECT   24    4   19                                                       
CONECT   25    9   17                                                       
CONECT   26    9   18                                                       
CONECT   27   10   13                                                       
CONECT   28   10   18   20                                                  
CONECT   29   12                                                            
CONECT   30   14                                                            
CONECT   31   16                                                            
CONECT   32   19                                                            
CONECT   33   45                                                            
CONECT   34   45                                                            
CONECT   35   45                                                            
CONECT   36   46                                                            
CONECT   37   46                                                            
CONECT   38   47                                                            
CONECT   39   47                                                            
CONECT   40    7   46                                                       
CONECT   41    8   47                                                       
CONECT   42   11   20                                                       
CONECT   43   15   45                                                       
CONECT   44   46   47                                                       
CONECT   45   33   34   35   43                                             
CONECT   46   36   37   40   44                                             
CONECT   47   38   39   41   44                                             
CONECT   48    6                                                            
CONECT   49   11                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   20                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

Synonyms

Value	Source
CoA	MeSH
CoASH	MeSH
Acetoacetyl coenzyme A sodium salt	HMDB
CoA Hydrate	HMDB
CoA-SH	HMDB
coenzyme A Hydrate	HMDB
coenzyme A-SH	HMDB
coenzyme ASH	HMDB
Coenzymes a	HMDB
Depot-zeel	HMDB
Propionyl CoA	HMDB
Propionyl coenzyme A	HMDB
S-Propanoate	HMDB
S-Propanoate CoA	HMDB
S-Propanoate coenzyme A	HMDB
S-Propanoic acid	HMDB
S-Propionate CoA	HMDB
S-Propionate coenzyme A	HMDB
Zeel	HMDB
[(2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate	HMDB
a, Coenzyme	MeSH

Molecular Formula

C₂₁H₃₆N₇O₁₆P₃S

Average Mass

767.534

Monoisotopic Mass

767.115208365

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-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

coenzyme A

CAS Registry Number

85-61-0

SMILES

[H]C(O)(C(O)=NCCC(O)=NCCS)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/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1

InChI Key

RGJOEKWQDUBAIZ-DRCCLKDXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Coenzyme A and derivatives

Alternative Parents

Substituents

Coenzyme a or derivatives
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
Aminopyrimidine
Monoalkyl phosphate
Fatty amide
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Fatty acyl
Imidolactam
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Alkylthiol
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Alcohol
Amine
Organopnictogen compound
Primary amine
Organic oxygen compound
Organonitrogen compound
Carbonyl group
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	5.35 g/L	ALOGPS
logP	-0.63	ALOGPS
logP	-5.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	346.56 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	162.74 m³·mol⁻¹	ChemAxon
Polarizability	66.82 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

Not Available

Biological Properties

Cellular Locations

Endoplasmic reticulum
Golgi apparatus
Lysosome
Mitochondria
Nucleus
Peroxisome

Biospecimen Locations

Adipose Tissue
Feces
Fibroblasts
Skeletal Muscle

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	Reaction Type	Data Source	Reference
MMDBr0018082	Pyruvic acid	Carbon dioxide	Unknown Protein		PathBank	31602464
MMDBr0018184	Hydrogen Ion	Carbon dioxide	3-oxoacyl-[acyl-carrier-protein] synthase 3	Synthesis	PathBank	31602464
MMDBr0018286	Adenosine triphosphate	Adenosine monophosphate	Medium-chain fatty-acid--CoA ligase	Ligation	PathBank	31602464
MMDBr0018289	Coenzyme A	Acetyl-CoA	3-ketoacyl-CoA thiolase FadA	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0018362	Dephospho-CoA	Hydrogen Ion	Dephospho-CoA kinase	Phosphorylation	PathBank	31602464
MMDBr0018420	Pyruvic acid	Carbon dioxide	Pyruvate dehydrogenase complex protein X component, mitochondrial	Dehydrogenation	PathBank	31602464
MMDBr0018483	Malonyl-CoA	Coenzyme A	Malonyl CoA-acyl carrier protein transacylase	Deacylation	PathBank	31602464
MMDBr0018484	Hydrogen Ion	Carbon dioxide	3-oxoacyl-[acyl-carrier-protein] synthase 3	Synthesis	PathBank	31602464
MMDBr0018485	Acetyl-CoA	Coenzyme A	3-oxoacyl-[acyl-carrier-protein] synthase 3	Synthesis	PathBank	31602464
MMDBr0019329	Coenzyme A	Acetyl-CoA	Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex	Dehydrogenation	PathBank	31602464
MMDBr0019345	Acetoacetyl-CoA	Acetyl-CoA	Acetyl-CoA acetyltransferase	N-Acetylation	PathBank	31602464
MMDBr0019377	Succinyl-CoA	Coenzyme A	Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex	Dehydrogenation	PathBank	31602464
MMDBr0019435	Dephospho-CoA	Hydrogen Ion	Dephospho-CoA kinase CAB5	Phosphorylation	PathBank	31602464
MMDBr0019665	Coenzyme A	Acetyl-CoA	Pyruvate dehydrogenase complex protein X component, mitochondrial	Dehydrogenation	PathBank	31602464
MMDBr0020655	Glycerol 3-phosphate	Coenzyme A	Glycerol-3-phosphate acyltransferase	Acylation	PathBank	31602464
MMDBr0020662	Glycerol 3-phosphate	Coenzyme A	Glycerol-3-phosphate O-acyltransferase 1	Acylation	PathBank	31602464
MMDBr0024337	Glycerol 3-phosphate	Coenzyme A	Glycerol-3-phosphate O-acyltransferase 1	Acylation	PathBank	31602464

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	8	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	363	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	174	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	15	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	114	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human subgingival plaque; Human supragingival plaque; Human urine	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	28	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	6	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Adipose tissue	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022614

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coenzyme A

METLIN ID

Not Available

PubChem Compound

6816

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Osmundsen H, Bremer J, Pedersen JI: Metabolic aspects of peroxisomal beta-oxidation. Biochim Biophys Acta. 1991 Sep 11;1085(2):141-58. doi: 10.1016/0005-2760(91)90089-z. [PubMed:1892883 ]
Reihner E, Angelin B, Rudling M, Ewerth S, Bjorkhem I, Einarsson K: Regulation of hepatic cholesterol metabolism in humans: stimulatory effects of cholestyramine on HMG-CoA reductase activity and low density lipoprotein receptor expression in gallstone patients. J Lipid Res. 1990 Dec;31(12):2219-26. [PubMed:2090716 ]
Kretschmer RE, Bachmann C: Methylcitric acid determination in amniotic fluid by electron-impact mass fragmentography. J Clin Chem Clin Biochem. 1988 May;26(5):345-8. doi: 10.1515/cclm.1988.26.5.345. [PubMed:3404093 ]
Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. doi: 10.3109/00365518109092023. [PubMed:7313494 ]
Lehnert W, Junker A: [2-Methyl-3-oxovaleric acid: a characteristic metabolite in propionic acidemia]. Clin Chim Acta. 1980 May 21;104(1):47-51. doi: 10.1016/0009-8981(80)90133-3. [PubMed:7389125 ]
Salen G, Batta AK, Tint GS, Shefer S: Comparative effects of lovastatin and chenodeoxycholic acid on plasma cholestanol levels and abnormal bile acid metabolism in cerebrotendinous xanthomatosis. Metabolism. 1994 Aug;43(8):1018-22. doi: 10.1016/0026-0495(94)90183-x. [PubMed:8052141 ]
Wendel U, Zass R, Leupold D: Contribution of odd-numbered fatty acid oxidation to propionate production in neonates with methylmalonic and propionic acidaemias. Eur J Pediatr. 1993 Dec;152(12):1021-3. doi: 10.1007/BF01957229. [PubMed:8131803 ]
Roe CR, Sweetman L, Roe DS, David F, Brunengraber H: Treatment of cardiomyopathy and rhabdomyolysis in long-chain fat oxidation disorders using an anaplerotic odd-chain triglyceride. J Clin Invest. 2002 Jul;110(2):259-69. doi: 10.1172/JCI15311. [PubMed:12122118 ]
Yano S, Li L, Le TP, Moseley K, Guedalia A, Lee J, Gonzalez I, Boles RG: Infantile mitochondrial DNA depletion syndrome associated with methylmalonic aciduria and 3-methylcrotonyl-CoA and propionyl-CoA carboxylase deficiencies in two unrelated patients: a new phenotype of mtDNA depletion syndrome. J Inherit Metab Dis. 2003;26(5):481-8. doi: 10.1023/a:1025125427868. [PubMed:14518828 ]

Showing metabocard for Coenzyme A (MMDBc0029649)

MOL for #<Metabolite:0x00007f923e7a2588>

3D MOL for #<Metabolite:0x00007f923e7a2588>

3D SDF for #<Metabolite:0x00007f923e7a2588>

3D-SDF for #<Metabolite:0x00007f923e7a2588>

PDB for #<Metabolite:0x00007f923e7a2588>

3D PDB for #<Metabolite:0x00007f923e7a2588>

SMILES for #<Metabolite:0x00007f923e7a2588>

INCHI for #<Metabolite:0x00007f923e7a2588>

Structure for #<Metabolite:0x00007f923e7a2588>

3D Structure for #<Metabolite:0x00007f923e7a2588>