MiMeDB: Showing metabocard for 3-Hydroxybutyryl-CoA (MMDBc0029576)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:32:56 UTC

Update Date

2024-04-30 19:38:15 UTC

Metabolite ID

MMDBc0029576

Metabolite Identification

Common Name

3-Hydroxybutyryl-CoA

Description

3-Hydroxybutyryl-CoA or 3-hydroxybutyryl-coenzyme A is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231218572D          

 54 56  0  0  1  0            999 V2000
    0.7191    2.3842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384    1.7371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1610    2.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    3.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9159    2.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    0.9613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1610    3.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    1.9642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4381    3.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.7484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3246    0.9613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    3.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953    2.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578    1.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    0.2952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953    3.2168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    4.4506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856    1.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6189    0.2914    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7988    1.4419    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    1.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287    0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6303   -0.4503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8026   -0.3481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8102    2.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6238    1.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7988   -1.9491    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9435   -1.9604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950   -2.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313   -1.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2358   -1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090   -1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -2.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090   -0.7267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -1.5478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975   -2.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0408   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675   -1.5478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -2.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1791   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -1.9604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3172   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0326   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3172   -0.7267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440   -1.5478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4592   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440   -0.7267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  6  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  1  0  0  0
 11 16  1  6  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 21 26  1  0  0  0  0
 21 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  6  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 14 17  1  0  0  0  0
M  END


  Mrv0541 02231218572D          

 54 56  0  0  1  0            999 V2000
    0.7191    2.3842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2384    1.7371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1610    2.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    3.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9159    2.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    0.9613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1610    3.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    1.9642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4381    3.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.7484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3246    0.9613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    3.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953    2.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578    1.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    0.2952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5953    3.2168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8724    4.4506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856    1.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6189    0.2914    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7988    1.4419    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    1.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287    0.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6303   -0.4503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8026   -0.3481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8102    2.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6238    1.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7988   -1.9491    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9435   -1.9604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950   -2.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313   -1.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2358   -1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090   -1.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -2.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -1.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090   -0.7267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3823   -1.5478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975   -2.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0408   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675   -1.5478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7560   -2.7854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1791   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -1.9604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3172   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0326   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3172   -0.7267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440   -1.5478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4592   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440   -0.7267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  6  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  1  0  0  0
 11 16  1  6  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 25  1  0  0  0  0
 21 26  1  0  0  0  0
 21 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  6  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029576

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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

> <INCHI_IDENTIFIER>
InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20?,24-/m1/s1

> <INCHI_KEY>
QHHKKMYHDBRONY-JYMPOPDUSA-N

> <FORMULA>
C25H42N7O18P3S

> <MOLECULAR_WEIGHT>
853.623

> <EXACT_MASS>
853.151987801

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
75.89195922576226

> <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-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.62

> <JCHEM_LOGP>
-7.138871154966353

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8334045176178444

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
383.8599999999999

> <JCHEM_REFRACTIVITY>
183.02840000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       1.342   4.451   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.445   3.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.034   4.451   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.342   6.005   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.710   4.161   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.904   1.794   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.034   6.005   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.362   3.667   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       2.684   6.789   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.967   3.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.473   1.794   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.558   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.362   6.775   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.711   4.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.401   3.716   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.377   0.551   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       6.711   6.005   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       5.362   8.308   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -6.506   2.720   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      -4.889   0.544   0.000  0.00  0.00           P+0
HETATM   21  P   UNK     0      -8.958   2.692   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      -4.783   2.169   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.400   0.671   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.910  -0.841   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -8.965  -0.650   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -8.979   4.196   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -10.498   2.720   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      -8.958  -3.638   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      -7.361  -3.659   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -8.951  -5.199   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -10.512  -3.667   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.040  -2.897   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.705  -3.659   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.377  -2.897   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.705  -5.199   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.726  -1.964   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.049  -3.659   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.377  -1.357   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0      -0.714  -2.889   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0      -2.049  -5.199   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.615  -3.659   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.943  -2.889   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.278  -3.659   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       4.606  -2.889   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0       3.278  -5.199   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       5.934  -3.659   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.269  -2.889   0.000  0.00  0.00           C+0
HETATM   48  S   UNK     0       8.597  -3.659   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0       9.925  -2.889   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      11.261  -3.659   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.925  -1.357   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      12.589  -2.889   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      13.924  -3.659   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      12.589  -1.357   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11   12                                                  
CONECT    7    3   13    9                                                  
CONECT    8    3   14                                                       
CONECT    9    4    7                                                       
CONECT   10    5   15   11                                                  
CONECT   11    6   16   10                                                  
CONECT   12    6                                                            
CONECT   13    7   17   18                                                  
CONECT   14    8   17                                                       
CONECT   15   10   19                                                       
CONECT   16   11   20                                                       
CONECT   17   13   14                                                       
CONECT   18   13                                                            
CONECT   19   15   21                                                       
CONECT   20   16   22   23   24                                             
CONECT   21   19   25   26   27                                             
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   20                                                            
CONECT   25   21   28                                                       
CONECT   26   21                                                            
CONECT   27   21                                                            
CONECT   28   25   29   30   31                                             
CONECT   29   28   32                                                       
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33   37   38                                                  
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   34   39   40                                                  
CONECT   38   34                                                            
CONECT   39   37   41                                                       
CONECT   40   37                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43   46                                                       
CONECT   45   43                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49   52                                                       
CONECT   51   49                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

Synonyms

Value	Source
(3R)-3-Hydroxybutanoyl-CoA	HMDB
(3R)-3-Hydroxybutanoyl-coenzyme A	HMDB
(R)-3-Hydroxybutanoyl-CoA	HMDB
(R)-3-Hydroxybutanoyl-coenzyme A	HMDB
(S)-3-Hydroxybutanoyl-CoA	HMDB
(S)-3-Hydroxybutanoyl-coenzyme A	HMDB
3-Hydroxybutanoyl-CoA	HMDB
3-Hydroxybutanoyl-coenzyme A	HMDB
3-Hydroxybutyryl-coenzyme A	HMDB
3-OH-Butyryl-CoA	HMDB
3-OH-Butyryl-coenzyme A	HMDB
beta-Hydroxybutyryl-CoA	HMDB
beta-Hydroxybutyryl-coenzyme A	HMDB
beta-Hydroxybutyryl-S-CoA	HMDB
beta-Hydroxybutyryl-S-coenzyme A	HMDB
Hydroxy-butyryl-CoA	HMDB
Hydroxy-butyryl-coenzyme A	HMDB
3-Hydroxybutyryl-coenzyme A, (R)-isomer	HMDB
3-Hydroxybutyryl-coenzyme A, (S)-isomer	HMDB

Molecular Formula

C₂₅H₄₂N₇O₁₈P₃S

Average Mass

853.623

Monoisotopic Mass

853.151987801

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

2871-66-1

SMILES

C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(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

InChI Identifier

InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20?,24-/m1/s1

InChI Key

QHHKKMYHDBRONY-JYMPOPDUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (r)-3-hydroxyacyl coas. These are organic compounds containing a (R)-3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

(R)-3-hydroxyacyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.07 g/L	ALOGPS
logP	-0.62	ALOGPS
logP	-7.1	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	183.03 m³·mol⁻¹	ChemAxon
Polarizability	75.89 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-0931000130-d924499294c56a627b62	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-1912000000-416f64a8b75913d6ee9c	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1920000000-137c383401c378170f3d	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-9720041570-1667d7f76a22ea47025f	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5910220010-688de5c2366fa2409e73	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-7900100000-b81dd46468dec5a6d312	2016-09-14	View Spectrum
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

Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000064	Crotonoyl-CoA	3-Hydroxybutyryl-CoA	enoyl CoA hydratase domain containing 2	VMH	9073515
MMDBr0000850	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	AU RNA binding protein/enoyl-CoA hydratase	VMH; KEGG	7558027
MMDBr0000851	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	enoyl CoA hydratase 1, peroxisomal	VMH; KEGG	7558027
MMDBr0001413	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	hydroxyacyl-CoA dehydrogenase	VMH; KEGG	30371894
MMDBr0001414	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH; KEGG	30371894
MMDBr0005059	3-Hydroxybutyryl-CoA	3-Hydroxybutyryl-CoA	diazepam binding inhibitor (GABA receptor modulator, acyl-CoA binding protein)	VMH	20511713 11859412 16908521 8001684
MMDBr0005100	3-Hydroxybutyryl-CoA	3-Hydroxy Butyryl Carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	17442642
MMDBr0006927	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	Not Available	VMH	30371894
MMDBr0006967	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Not Available	VMH	30371894
MMDBr0007033	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	Not Available	VMH	30371894
MMDBr0007679	3-Hydroxybutyryl-CoA	3-Hydroxybutyryl-CoA	Not Available	VMH	30371894
MMDBr0007854	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Not Available	VMH	30371894
MMDBr0008529	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Not Available	VMH	30371894
MMDBr0010940	3-Hydroxybutyryl-CoA	Acetoacetyl-CoA	Not Available	VMH	30371894

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	140	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	238	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	69	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	19	Human feces; Human ; Human stool	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0001166

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022460

KNApSAcK ID

Not Available

Chemspider ID

389056

KEGG Compound ID

C03561

BioCyc ID

Not Available

BiGG ID

36912

Wikipedia Link

Not Available

METLIN ID

456

PubChem Compound

440045

PDB ID

Not Available

ChEBI ID

15452

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Emmett B, Hochachka PW: Scaling of oxidative and glycolytic enzymes in mammals. Respir Physiol. 1981 Sep;45(3):261-72. doi: 10.1016/0034-5687(81)90010-4. [PubMed:7036306 ]
Gerngross TU, Snell KD, Peoples OP, Sinskey AJ, Csuhai E, Masamune S, Stubbe J: Overexpression and purification of the soluble polyhydroxyalkanoate synthase from Alcaligenes eutrophus: evidence for a required posttranslational modification for catalytic activity. Biochemistry. 1994 Aug 9;33(31):9311-20. doi: 10.1021/bi00197a035. [PubMed:8049232 ]
Kraak MN, Kessler B, Witholt B: In vitro activities of granule-bound poly[(R)-3-hydroxyalkanoate]polymerase C1 of Pseudomonas oleovorans--development of an activity test for medium-chain-length-poly(3-hydroxyalkanoate) polymerases. Eur J Biochem. 1997 Dec 1;250(2):432-9. doi: 10.1111/j.1432-1033.1997.0432a.x. [PubMed:9428695 ]

Showing metabocard for 3-Hydroxybutyryl-CoA (MMDBc0029576)

MOL for #<Metabolite:0x00007fdb4cf0c1a0>

3D MOL for #<Metabolite:0x00007fdb4cf0c1a0>

3D SDF for #<Metabolite:0x00007fdb4cf0c1a0>

3D-SDF for #<Metabolite:0x00007fdb4cf0c1a0>

PDB for #<Metabolite:0x00007fdb4cf0c1a0>

3D PDB for #<Metabolite:0x00007fdb4cf0c1a0>

SMILES for #<Metabolite:0x00007fdb4cf0c1a0>

INCHI for #<Metabolite:0x00007fdb4cf0c1a0>

Structure for #<Metabolite:0x00007fdb4cf0c1a0>

3D Structure for #<Metabolite:0x00007fdb4cf0c1a0>