MiMeDB: Showing metabocard for 4-Hydroxybutyryl-CoA (MMDBc0049881)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:45:27 UTC

Update Date

2022-09-01 02:16:51 UTC

Metabolite ID

MMDBc0049881

Metabolite Identification

Common Name

4-Hydroxybutyryl-CoA

Description

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006051512412D          
 
 54 56  0  0  1  0            999 V2000
    5.9400  -12.2925    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0850  -11.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7863  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5288  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2300  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9313  -11.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6738  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750  -11.8800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0763  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7775  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5200  -12.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7863  -13.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6738  -13.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750  -11.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0763  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0763  -13.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -12.2925    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.1700  -12.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -13.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5088   -9.3638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3338   -9.3638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5813   -8.5800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9213   -8.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2613   -8.5800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3650   -8.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0138  -10.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8288  -10.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6538  -10.0238    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6538   -9.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4788  -10.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6538  -10.8488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8275   -7.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8275   -8.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2713   -8.3325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2713   -7.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5288   -7.0950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1263   -7.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838   -7.5075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838   -8.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1263   -8.7450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1263   -6.2700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5200   -8.5800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450   -8.5800    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450   -7.7550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1700   -8.5800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -10.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800  -11.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9600  -11.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6400  -11.9213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  2  0  0  0  0
  9 15  2  0  0  0  0
 10 16  1  6  0  0  0
 11 17  1  0  0  0  0
 11 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 24 27  1  6  0  0  0
 22 28  1  1  0  0  0
 23 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  2  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 35 42  1  0  0  0  0
 39 43  1  0  0  0  0
 26 36  1  6  0  0  0
 27 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 45 48  1  0  0  0  0
 19 48  1  0  0  0  0
  1 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
 53 54  1  0  0  0  0
M  END

 
  Mrv1533006051512412D          
 
 54 56  0  0  1  0            999 V2000
    5.9400  -12.2925    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0850  -11.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7863  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5288  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2300  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9313  -11.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6738  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750  -11.8800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0763  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7775  -11.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5200  -12.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7863  -13.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6738  -13.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750  -11.0550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0763  -11.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0763  -13.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -12.2925    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.1700  -12.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -13.1175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5088   -9.3638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3338   -9.3638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5813   -8.5800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9213   -8.0850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2613   -8.5800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3650   -8.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0138  -10.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8288  -10.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6538  -10.0238    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6538   -9.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4788  -10.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6538  -10.8488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8275   -7.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8275   -8.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2713   -8.3325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2713   -7.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5288   -7.0950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1263   -7.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838   -7.5075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3838   -8.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1263   -8.7450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1263   -6.2700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5200   -8.5800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450   -8.5800    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450   -7.7550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1700   -8.5800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -10.4775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800  -11.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9600  -11.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000  -12.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6400  -11.9213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  2  0  0  0  0
  9 15  2  0  0  0  0
 10 16  1  6  0  0  0
 11 17  1  0  0  0  0
 11 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 24 27  1  6  0  0  0
 22 28  1  1  0  0  0
 23 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  2  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 38  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 35 42  1  0  0  0  0
 39 43  1  0  0  0  0
 26 36  1  6  0  0  0
 27 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 45 48  1  0  0  0  0
 19 48  1  0  0  0  0
  1 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
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049881

> <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)CCCO

> <INCHI_IDENTIFIER>
InChI=1S/C25H42N7O18P3S/c1-25(2,20(37)23(38)28-6-5-15(34)27-7-9-54-16(35)4-3-8-33)11-47-53(44,45)50-52(42,43)46-10-14-19(49-51(39,40)41)18(36)24(48-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,33,36-37H,3-11H2,1-2H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1

> <INCHI_KEY>
BAMBWCGEVIAQBF-CITAKDKDSA-N

> <FORMULA>
C25H42N7O18P3S

> <MOLECULAR_WEIGHT>
853.62

> <EXACT_MASS>
853.151989708

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
75.09144527045468

> <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[(3R)-3-hydroxy-3-{[2-({2-[(4-hydroxybutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.52

> <JCHEM_LOGP>
-6.216318526499258

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9035538370263239

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8207476508908789

> <JCHEM_PKA_STRONGEST_BASIC>
4.945907435196925

> <JCHEM_POLAR_SURFACE_AREA>
383.86

> <JCHEM_REFRACTIVITY>
183.36460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxybutyryl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  S   UNK     0      11.088 -22.946   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0      12.397 -22.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.783 -22.946   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      15.092 -22.176   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      16.401 -22.946   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.787 -22.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.096 -22.946   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      20.405 -22.176   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      21.791 -22.946   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.100 -22.176   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.409 -22.946   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.718 -22.176   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      27.104 -22.946   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      16.401 -24.486   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      21.791 -24.486   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.100 -20.636   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      24.409 -21.406   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.409 -24.486   0.000  0.00  0.00           C+0
HETATM   19  P   UNK     0      28.644 -22.946   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0      30.184 -22.946   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      28.644 -24.486   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.483 -17.479   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.023 -17.479   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.485 -16.016   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      22.253 -15.092   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      21.021 -16.016   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.948 -15.554   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.559 -18.711   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      23.947 -18.711   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      25.487 -18.711   0.000  0.00  0.00           P+0
HETATM   31  O   UNK     0      25.487 -17.171   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      27.027 -18.711   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      25.487 -20.251   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.478 -14.014   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.478 -15.554   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      19.173 -15.554   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      19.173 -14.014   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      17.787 -13.244   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      15.169 -13.244   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      13.783 -14.014   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      13.783 -15.554   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      15.169 -16.324   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      15.169 -11.704   0.000  0.00  0.00           N+0
HETATM   44  O   UNK     0      27.104 -16.016   0.000  0.00  0.00           O+0
HETATM   45  P   UNK     0      28.644 -16.016   0.000  0.00  0.00           P+0
HETATM   46  O   UNK     0      28.644 -14.476   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      30.184 -16.016   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      28.644 -19.558   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       9.856 -22.253   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.624 -22.946   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.856 -20.790   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       7.392 -22.253   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       6.160 -22.946   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       4.928 -22.253   0.000  0.00  0.00           O+0
CONECT    1    2   49                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12   17   18                                             
CONECT   12   11   13                                                       
CONECT   13   12   19                                                       
CONECT   14    5                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   11                                                            
CONECT   19   13   20   21   48                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   23   26   28                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   22   36                                                  
CONECT   27   24   44                                                       
CONECT   28   22                                                            
CONECT   29   23   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   35   38   39                                                  
CONECT   35   34   36   42                                                  
CONECT   36   35   37   26                                                  
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
CONECT   39   34   40   43                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   35                                                       
CONECT   43   39                                                            
CONECT   44   27   45                                                       
CONECT   45   44   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45   19                                                       
CONECT   49    1   50   51                                                  
CONECT   50   49   52                                                       
CONECT   51   49                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

Synonyms

Value	Source
4-Hydroxybutanoyl-CoA	ChEBI
4-Hydroxybutanoyl-coenzyme A	ChEBI
4-Hydroxybutyryl-coenzyme A	ChEBI
gamma-Hydroxybutanoyl-CoA	ChEBI
gamma-Hydroxybutyryl-CoA	ChEBI
gamma-Hydroxybutyryl-coenzyme A	ChEBI
g-Hydroxybutanoyl-CoA	Generator
Γ-hydroxybutanoyl-CoA	Generator
g-Hydroxybutyryl-CoA	Generator
Γ-hydroxybutyryl-CoA	Generator
g-Hydroxybutyryl-coenzyme A	Generator
Γ-hydroxybutyryl-coenzyme A	Generator

Molecular Formula

C₂₅H₄₂N₇O₁₈P₃S

Average Mass

853.62

Monoisotopic Mass

853.151989708

IUPAC Name

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

Traditional Name

4-hydroxybutyryl-coa

CAS Registry Number

Not Available

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)CCCO

InChI Identifier

InChI=1S/C25H42N7O18P3S/c1-25(2,20(37)23(38)28-6-5-15(34)27-7-9-54-16(35)4-3-8-33)11-47-53(44,45)50-52(42,43)46-10-14-19(49-51(39,40)41)18(36)24(48-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,33,36-37H,3-11H2,1-2H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1

InChI Key

BAMBWCGEVIAQBF-CITAKDKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Monosaccharide phosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Phosphonic acid ester
Alkyl phosphate
Organophosphonic acid derivative
Organophosphonic acid
Tetrahydrofuran
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organophosphorus compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ribose monophosphate (CHEBI:68820 )
organic phosphonate (CHEBI:68820 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.2 g/L	ALOGPS
logP	-0.52	ALOGPS
logP	-6.2	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	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	23	ChemAxon
Refractivity	183.36 m³·mol⁻¹	ChemAxon
Polarizability	75.09 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-1912000130-dbd427923a89485e1b33	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1913000000-8a8111dc379b1916dc86	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1911000000-271330947183ec2b27e9	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-7930140560-1eb63491c176a81508cb	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5920020010-325087e0928291aea312	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-6bbc15ec4ebbd696ca97	2019-02-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0006892	gamma-Hydroxybutyrate	4-Hydroxybutyryl-CoA	Not Available	Acetyl-CoA: 4-hydroxybutanoate CoA transferase	VMH	30371894
MMDBr0014296	gamma-Hydroxybutyrate	4-Hydroxybutyryl-CoA	4-hydroxybutyrate--CoA ligase 1	Ligation	RHEA	34755880
MMDBr0014653	4-Hydroxybutyryl-CoA	Crotonoyl-CoA	4-hydroxybutyryl-CoA dehydratase/vinylacetyl-CoA-Delta-isomerase	Isomerization	RHEA	34755880
MMDBr0016957	gamma-Hydroxybutyrate	4-Hydroxybutyryl-CoA	4-hydroxybutyrate--CoA ligase [ADP-forming]	Ligation	RHEA	34755880
MMDBr0038842	4-Hydroxybutyryl-CoA	gamma-Hydroxybutyrate	Thioesterase TesA	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	32	Pig ; Human feces; Human	Metabolic reconstruction
Bacteria	Proteobacteria	3	Human feces; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	10	Human feces; Human	Metabolic reconstruction
Bacteria	Fusobacteria	16	Human feces; Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	1
Bacteria/NULL	Firmicutes	1	Pig ; Human feces; Human	Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

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

C11062

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966192

PDB ID

Not Available

ChEBI ID

28522

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 4-Hydroxybutyryl-CoA (MMDBc0049881)

MOL for #<Metabolite:0x00007fe2b83616e8>

3D MOL for #<Metabolite:0x00007fe2b83616e8>

3D SDF for #<Metabolite:0x00007fe2b83616e8>

3D-SDF for #<Metabolite:0x00007fe2b83616e8>

PDB for #<Metabolite:0x00007fe2b83616e8>

3D PDB for #<Metabolite:0x00007fe2b83616e8>

SMILES for #<Metabolite:0x00007fe2b83616e8>

INCHI for #<Metabolite:0x00007fe2b83616e8>

Structure for #<Metabolite:0x00007fe2b83616e8>

3D Structure for #<Metabolite:0x00007fe2b83616e8>