MiMeDB: Showing metabocard for Acetoacetyl-CoA (MMDBc0029658)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:25 UTC

Update Date

2023-12-14 16:53:06 UTC

Metabolite ID

MMDBc0029658

Metabolite Identification

Common Name

Acetoacetyl-CoA

Description

Acetoacetyl-CoA is an intermediate in the metabolism of Butanoate. It is a substrate for Succinyl-CoA:3-ketoacid-coenzyme A transferase 1, Hydroxymethylglutaryl-CoA synthase , Short chain 3-hydroxyacyl-CoA dehydrogenase, Acetyl-CoA acetyltransferase, 3-hydroxyacyl-CoA dehydrogenase type , Succinyl-CoA:3-ketoacid-coenzyme A transferase 2, and 3-ketoacyl-CoA thiolase.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231219102D          

 54 56  0  0  1  0            999 V2000
    0.6808    3.0482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3366    1.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7602    3.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    3.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    0.8472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7602    3.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788    2.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    4.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    1.6300    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7489    0.8472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5749    0.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788    4.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1935    3.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813    1.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1724    0.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1935    3.8802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    5.1132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083    1.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460    0.2609    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2208    1.3274    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650    1.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8516    0.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -0.5636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2208   -0.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132    2.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0451    1.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -2.0914    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585   -2.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -3.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0414   -2.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6474   -1.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -2.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -2.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553   -1.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812   -0.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447   -1.7511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702   -2.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2555   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925   -1.7511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814   -2.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8182   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293   -2.1632    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -0.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6661   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3809   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6661   -0.9266    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  2  0  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 02231219102D          

 54 56  0  0  1  0            999 V2000
    0.6808    3.0482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3366    1.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7602    3.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    3.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    0.8472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7602    3.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788    2.6285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    4.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    1.6300    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7489    0.8472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5749    0.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4788    4.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1935    3.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7813    1.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1724    0.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1935    3.8802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    5.1132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083    1.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460    0.2609    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2208    1.3274    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0650    1.0438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8516    0.2420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -0.5636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2208   -0.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132    2.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0451    1.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -2.0914    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585   -2.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -3.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0414   -2.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6474   -1.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -2.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9439   -2.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553   -1.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812   -0.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447   -1.7511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702   -2.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2555   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3925   -1.7511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814   -2.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8182   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293   -2.1632    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -0.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6661   -1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3809   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6661   -0.9266    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  2  0  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>
MMDBc0029658

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=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/C25H40N7O18P3S/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/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20?,24-/m1/s1

> <INCHI_KEY>
OJFDKHTZOUZBOS-XBTRWLRFSA-N

> <FORMULA>
C25H40N7O18P3S

> <MOLECULAR_WEIGHT>
851.607

> <EXACT_MASS>
851.136337737

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
75.05438600033575

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <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-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.37

> <JCHEM_LOGP>
-6.75335690323495

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.83340451643227

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479625944367

> <JCHEM_PKA_STRONGEST_BASIC>
4.946045360882824

> <JCHEM_POLAR_SURFACE_AREA>
380.6999999999999

> <JCHEM_REFRACTIVITY>
182.10320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)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       1.271   5.690   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.628   3.022   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.419   5.690   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.271   7.243   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.635   3.939   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.170   1.581   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.419   7.243   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.760   4.906   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -0.071   8.027   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.885   3.043   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.398   1.581   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.073   0.339   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.760   8.013   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.095   5.690   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.325   3.495   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.189   0.480   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -4.095   7.243   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -2.767   9.545   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -5.429   2.506   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      -3.819   0.487   0.000  0.00  0.00           P+0
HETATM   21  P   UNK     0      -7.879   2.478   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      -3.855   1.948   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.323   0.452   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.833  -1.052   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -7.879  -0.777   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.865   4.031   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -9.418   2.506   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      -7.865  -3.904   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      -6.269  -3.876   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -7.893  -5.718   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -9.411  -3.876   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.942  -3.106   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.614  -3.876   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.645  -3.269   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.629  -5.238   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.650  -2.287   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.318  -4.038   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.645  -1.737   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0       1.017  -3.269   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0      -0.318  -5.570   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.344  -4.038   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.671  -3.269   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.005  -4.038   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       6.333  -3.269   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0       5.005  -5.570   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       7.667  -4.038   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.994  -3.269   0.000  0.00  0.00           C+0
HETATM   48  S   UNK     0      10.321  -4.038   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0      11.656  -3.269   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      12.983  -4.038   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      11.656  -1.730   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      14.310  -3.269   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      15.644  -4.038   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      14.310  -1.730   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
3-Acetoacetyl-CoA	HMDB
3-Acetoacetyl-coenzyme A	HMDB
3-Oxobutyryl-CoA	HMDB
3-Oxobutyryl-coenzyme A	HMDB
Acetoacetyl CoA	HMDB
Acetoacetyl coenzyme A	HMDB
Acetoacetyl-coenzyme A	HMDB
S-Acetoacetylcoenzyme A	HMDB

Molecular Formula

C₂₅H₄₀N₇O₁₈P₃S

Average Mass

851.607

Monoisotopic Mass

851.136337737

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-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)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-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

1420-36-6

SMILES

CC(=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/C25H40N7O18P3S/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/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20?,24-/m1/s1

InChI Key

OJFDKHTZOUZBOS-XBTRWLRFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

3-oxo-acyl 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
1,3-dicarbonyl compound
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Ketone
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
Amine
Alcohol
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	3.83 g/L	ALOGPS
logP	-0.37	ALOGPS
logP	-6.8	ChemAxon
logS	-2.4	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	9	ChemAxon
Polar Surface Area	380.7 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	182.1 m³·mol⁻¹	ChemAxon
Polarizability	75.05 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-1902000130-0c6e34cff5b58d8f1265	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1903000000-3bef9e83aef17f5606c2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1911000000-0baac4a38e6959329640	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9830140450-d224eb24f29b79b33c51	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5910110000-7eab06f15be38da08924	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-b0ad557e9c954b3efac6	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Feces
Fibroblasts

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
MMDBr0000150	Acetyl-CoA	Acetoacetyl-CoA	Acetyl-coa acetyltransferase 1	Acetyl Coenzyme A C-Acetyltransferase, Mitochondrial	VMH	30371894
MMDBr0000151	Acetyl-CoA	Acetoacetyl-CoA	Acetyl-coa acetyltransferase 2	Acetyl Coenzyme A C-Acetyltransferase	VMH	11108725
MMDBr0001413	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Hydroxyacyl-coa dehydrogenase	3-Hydroxyacyl Coenzyme A Dehydrogenase (Acetoacetyl Coenzyme A), Mitochondrial	VMH	30371894
MMDBr0001414	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Enoyl-coa, hydratase/3-hydroxyacyl coa dehydrogenase	3-Hydroxyacyl Coenzyme A Dehydrogenase (Acetoacetyl Coenzyme A), Peroxisomal	VMH	30371894
MMDBr0001447	Acetoacetyl-CoA	Coenzyme A	3-hydroxy-3-methylglutaryl-coa synthase 1 (soluble)	Hydroxymethylglutaryl Coenzyme A Synthase (Ir)	VMH	1358203
MMDBr0001448	Acetoacetyl-CoA	Coenzyme A	3-hydroxy-3-methylglutaryl-coa synthase 2 (mitochondrial)	Hydroxymethylglutaryl Coenzyme A Synthase (Ir)	VMH	7893153
MMDBr0001820	Acetoacetic acid	Acetoacetyl-CoA	3-oxoacid coa transferase 1	3-Oxoacid Coa-Transferase	VMH	30371894
MMDBr0002511	Acetoacetic acid	Acetoacetyl-CoA	Acetoacetyl-coa synthetase	Acetoacetate:Coa Ligase (AMP-Forming)	VMH	30371894
MMDBr0002566	Coenzyme A	Acetoacetyl-CoA	3-hydroxy-3-methylglutaryl-coa synthase 1 (soluble)	(S)-3-Hydroxy-3-Methylglutaryl Coenzyme A Acetoacetyl Coenzyme A-Lyase (Coa-Acetylating) Synthesis And Degradation of Ketone Bodies Valine, Leucine And Isoleucine Degradation	VMH	11087424 11108725 1358203 7893153
MMDBr0006907	Acetoacetic acid	Acetoacetyl-CoA	Not Available	Butyrate---acetoacetate CoA-transferase	VMH	30371894
MMDBr0006967	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Not Available	Acetoacetyl-CoA reductase	VMH	30371894
MMDBr0007231	Acetyl-CoA	Acetoacetyl-CoA	Not Available	Acetyl Coenzyme A C-Acetyltransferase	VMH	30371894
MMDBr0007513	Acetoacetic acid	Acetoacetyl-CoA	Not Available	3-oxoacid CoA-transferase (Succinyl-CoA: acetoacetate)	VMH	30371894
MMDBr0007691	Acetoacetyl-CoA	Acetoacetic acid	Not Available	Acetyl-CoA:acetoacetyl-CoA transferase, reversible	VMH	30371894
MMDBr0007854	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Not Available	3-hydroxyacyl-CoA dehydrogenase (acetoacetyl-CoA)	VMH	30371894
MMDBr0008103	Coenzyme A	Acetoacetyl-CoA	Not Available	Hydroxymethylglutaryl CoA synthase	VMH	30371894
MMDBr0008117	Acetoacetic acid	Acetoacetyl-CoA	Not Available	Acetoacetyl Coenzyme A:Acetate Coa-Transferase	VMH	30371894
MMDBr0008529	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Not Available	Acetoacetyl-CoA reductase reversible	VMH	30371894
MMDBr0010887	Acetoacetic acid	Acetoacetyl-CoA	Not Available	3-oxoacid CoA-transferase (Succinyl-CoA: acetoacetate)	VMH	30371894
MMDBr0010940	3-Hydroxybutyryl-CoA	Acetoacetyl-CoA	Not Available	(R)-3-Hydroxybutanoyl-CoA:NADP+ oxidoreductase	VMH	30371894
MMDBr0012864	Acetoacetyl-CoA	(3S)-hydroxy-3-methylglutaryl-CoA	Hydroxymethylglutaryl-CoA synthase erg13A	Synthesis	RHEA	34755880
MMDBr0012865	Acetoacetyl-CoA	(3S)-hydroxy-3-methylglutaryl-CoA	Hydroxymethylglutaryl-CoA synthase erg13A	Synthesis	RHEA	34755880
MMDBr0013169	Acetoacetic acid	Acetoacetyl-CoA	Butyrate--acetoacetate CoA-transferase subunit A	Transfer of CoA moiety	RHEA	34755880
MMDBr0013498	Acetoacetic acid	Acetoacetyl-CoA	Acetoacetyl-coenzyme A synthetase	Synthesis	RHEA	34755880
MMDBr0013505	(S)-3-Hydroxybutanoyl-CoA	Acetoacetyl-CoA	3-hydroxybutyryl-CoA dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0013506	Acetoacetyl-CoA	(S)-3-Hydroxybutanoyl-CoA	3-hydroxybutyryl-CoA dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0014062	Acetyl-CoA	Acetoacetyl-CoA	Acetyl-CoA acetyltransferase	Acylation; Acetylation	RHEA	34755880
MMDBr0014063	Acetyl-CoA	Acetoacetyl-CoA	Acetyl-CoA acetyltransferase erg10A, mitochondrial	N-Acetylation	RHEA	34755880
MMDBr0014064	Acetoacetyl-CoA	Acetyl-CoA	Acetyl-CoA acetyltransferase erg10A, mitochondrial	N-Acetylation	RHEA	34755880
MMDBr0014803	Acetyl-CoA	Acetoacetyl-CoA	Acetoacetyl CoA synthase NphT7	Synthesis	RHEA	34755880
MMDBr0015821	3-hydroxybutanoyl-CoA	Acetoacetyl-CoA	3-oxoacyl-[acyl-carrier-protein] reductase [NADH]	Dehydrogenation; Reduction	RHEA	34755880
MMDBr0015822	3-hydroxybutanoyl-CoA	Acetoacetyl-CoA	3-hydroxybutyryl-CoA dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0015823	Acetoacetyl-CoA	3-hydroxybutanoyl-CoA	3-oxoacyl-[acyl-carrier-protein] reductase [NADH]	Dehydrogenation; Reduction	RHEA	34755880
MMDBr0016152	(3R)-3-hydroxybutanoyl-CoA	Acetoacetyl-CoA	3-oxoacyl-[acyl-carrier-protein] reductase MabA	Reduction	RHEA	34755880
MMDBr0016153	Acetoacetyl-CoA	(3R)-3-hydroxybutanoyl-CoA	3-oxoacyl-[acyl-carrier-protein] reductase MabA	Reduction	RHEA	34755880
MMDBr0016530	(3S)-3-aminobutanoyl-CoA	Acetoacetyl-CoA	3-aminobutyryl-CoA aminotransferase	Amine group addition	RHEA	34755880
MMDBr0016629	Acetoacetyl-CoA	Adenosine monophosphate	Hybrid PKS-NRPS synthetase TAS1	Synthesis	RHEA	34755880
MMDBr0016630	Acetoacetyl-CoA	Adenosine monophosphate	Hybrid PKS-NRPS synthetase TAS1	Synthesis	RHEA	34755880
MMDBr0018705	NAD	Hydrogen Ion	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019345	Acetoacetyl-CoA	Acetyl-CoA	Acetyl-CoA acetyltransferase	N-Acetylation	PathBank	31602464
MMDBr0019347	Acetoacetic acid	Acetic acid	Acetate CoA-transferase subunit alpha	Transfer of CoA moiety	PathBank	31602464
MMDBr0019670	Acetyl-CoA	Coenzyme A	Acetyl-CoA acetyltransferase	N-Acetylation	PathBank	31602464
MMDBr0019728	Acetyl-CoA	Coenzyme A	3-ketoacyl-CoA thiolase, peroxisomal	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0019730	NAD	Hydrogen Ion	3-ketoacyl-CoA thiolase, peroxisomal	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0019902	Water	Coenzyme A	Hydroxymethylglutaryl-CoA synthase	Synthesis	PathBank	31602464
MMDBr0023299	Coenzyme A	Acetyl-CoA	3-ketoacyl-CoA thiolase FadA	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0038722	Acetoacetyl-CoA	Acetoacetic acid	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	Proteobacteria	181	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	Firmicutes	378	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; Goat feces; Sheep feces	Metabolic reconstruction
Bacteria	Actinobacteria	119	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	82	Human feces; Human appendix biopsy; Human ; Human stool; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	13	Human feces; Human saliva	Unknown
Eukaryota/Fungi	Basidiomycota	2
Archaea/Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Deinococcus-thermus	1
Bacteria	nah	1
Bacteria/NULL	Candidatus cloacimonetes	1

Exposure Sources

Source Type	Species	Data Source	Reference
Animal	Lota lota	FooDB	31437929
Animal	Porphyra umbilicalis	FooDB	31437929
Animal	Chondrus crispus	FooDB	31437929
Animal	Laminaria	FooDB	31437929
Animal	Haliotis	FooDB	31437929
Animal	Strombidae	FooDB	31437929
Animal	Clupea harengus harengus	FooDB	31437929
Animal	Undaria pinnatifida	FooDB	31437929
Animal	Peprilus triacanthus	FooDB	31437929
Animal	Rhodophyta	FooDB	31437929
Animal	Myoxocephalus	FooDB	31437929
Animal	Eucheuma	FooDB	31437929
Animal	Saccharina japonica	FooDB	31437929
Animal	Spirulina	FooDB	31437929
Plant	Apium graveolens	FooDB	31437929
Plant	Elaeis	FooDB	31437929
Plant	Cinnamomum	FooDB	31437929
Plant	Ribes uva-crispa	FooDB	31437929
Plant	Feijoa sellowiana	FooDB	31437929
Plant	Dysphania ambrosioides	FooDB	31437929
Plant	Raphanus sativus var. niger	FooDB	31437929
Plant	Photinia melanocarpa	FooDB	31437929
Plant	Salvia officinalis	FooDB	31437929
Plant	Rheum rhabarbarum	FooDB	31437929
Plant	Vaccinium	FooDB	31437929
Plant	Lablab purpureus	FooDB	31437929
Plant	Crocus sativus	FooDB	31437929
Plant	Citrus maxima	FooDB	31437929
Plant	Syzygium jambos	FooDB	31437929
Plant	Salix pulchra	FooDB	31437929
Plant	Castanea sativa	FooDB	31437929
Plant	Cydonia oblonga	FooDB	31437929
Plant	Annona muricata	FooDB	31437929
Plant	Fagus	FooDB	31437929
Plant	Cucurbita	FooDB	31437929
Plant	Opuntia cochenillifera	FooDB	31437929
Plant	Vaccinium ovatum	FooDB	31437929
Plant	Cocos nucifera	FooDB	31437929
Plant	Phaseolus coccineus	FooDB	31437929
Plant	Thymus pulegioides	FooDB	31437929
Plant	Tamarindus indica	FooDB	31437929
Plant	Mespilus germanica	FooDB	31437929
Plant	Brassica rapa var. perviridis	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Mentha aquatica	FooDB	31437929
Plant	Salvia elegans	FooDB	31437929
Plant	Mentha	FooDB	31437929
Plant	Sagittaria latifolia	FooDB	31437929
Plant	Solanum tuberosum	FooDB	31437929
Plant	Olea europaea	FooDB	31437929
Plant	Sambucus	FooDB	31437929
Plant	Pinus	FooDB	31437929
Plant	Psidium guajava	FooDB	31437929
Plant	Syzygium cumini	FooDB	31437929
Plant	Tilia tomentosa	FooDB	31437929
Plant	Typha angustifolia	FooDB	31437929
Plant	Daucus carota	FooDB	31437929
Plant	Empetrum nigrum	FooDB	31437929
Plant	Valerianella locusta	FooDB	31437929
Plant	Myrica rubra	FooDB	31437929
Plant	Vaccinium vitis-idaea	FooDB	31437929
Plant	Vaccinium angustifolium x vaccinium corymbosum	FooDB	31437929
Plant	Sisymbrium	FooDB	31437929
Plant	Vanilla	FooDB	31437929
Plant	Carya	FooDB	31437929
Plant	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant	Physalis philadelphica var. immaculata	FooDB	31437929
Plant	Vigna radiata	FooDB	31437929
Plant	Borago officinalis	FooDB	31437929
Plant	Raphanus sativus	FooDB	31437929
Plant	Prunus dulcis	FooDB	31437929
Plant	Hyssopus officinalis	FooDB	31437929
Plant	Manihot esculenta	FooDB	31437929
Plant	Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Scorzonera hispanica	FooDB	31437929
Plant	Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant	Angelica keiskei	FooDB	31437929
Plant	Ipomoea aquatica	FooDB	31437929
Plant	Musa x paradisiaca	FooDB	31437929
Plant	Cuminum cyminum	FooDB	31437929
Plant	Rubus spectabilis	FooDB	31437929
Plant	Allium sativum	FooDB	31437929
Plant	Arachis hypogaea	FooDB	31437929
Plant	Rubus idaeus	FooDB	31437929
Plant	Cantharellus cibarius	FooDB	31437929
Plant	Sinapis alba	FooDB	31437929
Plant	Fragaria x ananassa	FooDB	31437929
Plant	Pyrus communis	FooDB	31437929
Plant	Brassica ruvo	FooDB	31437929
Plant	Apium graveolens var. secalinum	FooDB	31437929
Plant	Morus nigra	FooDB	31437929
Plant	Solanum lycopersicum	FooDB	31437929
Plant	Abelmoschus esculentus	FooDB	31437929
Plant	Moringa oleifera	FooDB	31437929
Plant	Pinus edulis	FooDB	31437929
Plant	Passiflora edulis	FooDB	31437929
Plant	Opuntia macrorhiza	FooDB	31437929
Plant	Vigna angularis	FooDB	31437929
Plant	Manilkara zapota	FooDB	31437929
Plant	Cucurbita pepo var. clypeata	FooDB	31437929
Plant	Helianthus annuus	FooDB	31437929
Plant	Mentha spicata	FooDB	31437929
Plant	Corylus	FooDB	31437929
Plant	Malus	FooDB	31437929
Plant	Pisum sativum	FooDB	31437929
Plant	Sambucus nigra	FooDB	31437929
Plant	Allium cepa	FooDB	31437929
Plant	Juglans	FooDB	31437929
Plant	Mangifera indica	FooDB	31437929
Plant	Petroselinum crispum	FooDB	31437929
Plant	Ribes nigrum	FooDB	31437929
Plant	Zingiber officinale	FooDB	31437929
Plant	Chamaemelum nobile	FooDB	31437929
Plant	Illicium verum	FooDB	31437929
Plant		FooDB	31437929
Plant	Laurus nobilis	FooDB	31437929
Plant	Auricularia auricula-judae	FooDB	31437929
Plant	Attalea speciosa	FooDB	31437929
Plant	Juglans ailanthifolia	FooDB	31437929
Plant	Melissa officinalis	FooDB	31437929
Plant	Hippophae rhamnoides	FooDB	31437929
Plant	Polygonum alpinum	FooDB	31437929
Plant	Brassica juncea	FooDB	31437929
Plant	Pediomelum esculentum	FooDB	31437929
Plant	Spinacia oleracea	FooDB	31437929
Plant	Auricularia polytricha	FooDB	31437929
Plant	Camellia oleifera	FooDB	31437929
Plant	Vaccinium corymbosum	FooDB	31437929
Plant	Chrysanthemum coronarium	FooDB	31437929
Plant	Eleocharis dulcis	FooDB	31437929
Plant	Thymus vulgaris	FooDB	31437929
Plant	Actinidia chinensis	FooDB	31437929
Plant	Carica papaya	FooDB	31437929
Plant	Pimenta dioica	FooDB	31437929
Plant	Medicago sativa	FooDB	31437929
Plant	Vigna mungo	FooDB	31437929
Plant	Rubus arcticus	FooDB	31437929
Plant	Agaricus bisporus	FooDB	31437929
Plant	Cajanus cajan	FooDB	31437929
Plant	Rumex articus	FooDB	31437929
Plant	Origanum majorana	FooDB	31437929
Plant	Armoracia rusticana	FooDB	31437929
Plant	Hibiscus sabdariffa	FooDB	31437929
Plant	Benincasa hispida	FooDB	31437929
Plant	Prunus persica	FooDB	31437929
Plant	Canarium ovatum	FooDB	31437929
Plant	Ribes aureum var. villosum	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Foeniculum vulgare	FooDB	31437929
Plant	Phoenix dactylifera	FooDB	31437929
Plant	Vaccinium macrocarpon	FooDB	31437929
Plant		FooDB	31437929
Plant	Arctium lappa	FooDB	31437929
Plant	Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Juglans cinerea	FooDB	31437929
Plant	Prunus cerasus	FooDB	31437929
Plant	Eruca vesicaria ssp. sativa	FooDB	31437929
Plant	Rosmarinus officinalis	FooDB	31437929
Plant	Artocarpus altilis	FooDB	31437929
Plant	Citrus x paradisi	FooDB	31437929
Plant	Vigna unguiculata	FooDB	31437929
Plant	Cynara scolymus	FooDB	31437929
Plant	Cyathea	FooDB	31437929
Plant	Metroxylon sagu	FooDB	31437929
Plant	Vitis rotundifolia	FooDB	31437929
Plant	Brosimum alicastrum	FooDB	31437929
Plant	Ficus carica	FooDB	31437929
Plant	Lentinus edodes	FooDB	31437929
Plant	Psidium cattleianum	FooDB	31437929
Plant	Beta vulgaris var. rubra	FooDB	31437929
Plant	Castanea mollissima	FooDB	31437929
Plant	Lepidium sativum	FooDB	31437929
Plant	Morus	FooDB	31437929
Plant	Helianthus tuberosus	FooDB	31437929
Plant	Phytolacca americana	FooDB	31437929
Plant	Grifola frondosa	FooDB	31437929
Plant	Vitis labrusca	FooDB	31437929
Plant	Tetragonia tetragonioides	FooDB	31437929
Plant	Artemisia vulgaris	FooDB	31437929
Plant	Cucumis metuliferus	FooDB	31437929
Plant	Nephelium lappaceum	FooDB	31437929
Plant	Myrica	FooDB	31437929
Plant		FooDB	31437929
Plant	Corylus avellana	FooDB	31437929
Plant	Castanea crenata	FooDB	31437929
Plant	Litchi chinensis	FooDB	31437929
Plant	Juglans regia	FooDB	31437929
Plant	Quercus	FooDB	31437929
Plant	Trigonella foenum-graecum	FooDB	31437929
Plant	Vaccinium angustifolium	FooDB	31437929
Plant	Malpighia emarginata	FooDB	31437929
Plant	Physalis	FooDB	31437929
Plant	Brassica oleracea var. sabauda	FooDB	31437929
Plant	Thelesperma	FooDB	31437929
Plant	Brassica napus	FooDB	31437929
Plant	Asparagus officinalis	FooDB	31437929
Plant	Chamerion angustifolium	FooDB	31437929
Plant	Levisticum officinale	FooDB	31437929
Plant	Pimpinella anisum	FooDB	31437929
Plant	Vaccinium elliottii	FooDB	31437929
Plant	Artemisia dracunculus	FooDB	31437929
Plant	Matricaria recutita	FooDB	31437929
Plant	Citrus aurantiifolia	FooDB	31437929
Plant	Ziziphus zizyphus	FooDB	31437929
Plant	Lactuca sativa	FooDB	31437929
Plant	Dimocarpus longan	FooDB	31437929
Plant	Eragrostis tef	FooDB	31437929
Plant	Salvia hispanica	FooDB	31437929
Plant	Pistacia vera	FooDB	31437929
Plant	Cynara cardunculus	FooDB	31437929
Plant	Vitellaria paradoxa	FooDB	31437929
Plant	Pangium edule	FooDB	31437929
Plant	Malus pumila	FooDB	31437929
Plant	Allium	FooDB	31437929
Plant	Brassica oleracea var. viridis	FooDB	31437929
Plant	Punica granatum	FooDB	31437929
Plant	Agave	FooDB	31437929
Plant	Hedysarum alpinum	FooDB	31437929
Plant	Diospyros	FooDB	31437929
Plant		FooDB	31437929
Plant	Vigna aconitifolia	FooDB	31437929
Plant	Amaranthus	FooDB	31437929
Plant	Gossypium	FooDB	31437929
Plant	Beta vulgaris	FooDB	31437929
Plant	Mammea americana	FooDB	31437929
Plant	Brassica alboglabra	FooDB	31437929
Plant	Annona squamosa	FooDB	31437929
Plant	Apium graveolens var. dulce	FooDB	31437929
Plant	Vitis	FooDB	31437929
Plant	Xanthosoma sagittifolium	FooDB	31437929
Plant	Basella alba	FooDB	31437929
Plant	Cucumis sativus	FooDB	31437929
Plant	Citrus latifolia	FooDB	31437929
Plant	Carya illinoinensis	FooDB	31437929
Plant	Capsicum baccatum var. baccatum	FooDB	31437929
Plant	Byrsonima crassifolia	FooDB	31437929
Plant	Capsicum pubescens	FooDB	31437929
Plant	Cinnamomum aromaticum	FooDB	31437929
Plant	Ribes rubrum	FooDB	31437929
Plant	Crateva religiosa	FooDB	31437929
Plant		FooDB	31437929
Plant	Vitis aestivalis	FooDB	31437929
Plant	Brassica rapa var. chinensis	FooDB	31437929
Plant	Eugenia javanica	FooDB	31437929
Plant	Portulaca oleracea	FooDB	31437929
Plant	Ipomoea batatas	FooDB	31437929
Plant	Mentha arvensis	FooDB	31437929
Plant	Pastinaca sativa	FooDB	31437929
Plant	Cucurbita maxima	FooDB	31437929
Plant	Vaccinium stamineum	FooDB	31437929
Plant	Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant	Chenopodium album	FooDB	31437929
Plant	Psophocarpus tetragonolobus	FooDB	31437929
Plant	Allium ampeloprasum	FooDB	31437929
Plant	Brassica oleracea	FooDB	31437929
Plant	Sechium edule	FooDB	31437929
Plant	Lactuca sativa l. var. longifolia	FooDB	31437929
Plant	Grataegosorbus mitschurinii	FooDB	31437929
Plant	Diospyros virginiana	FooDB	31437929
Plant	Origanum x majoricum	FooDB	31437929
Plant	Rubus x loganobaccus	FooDB	31437929
Plant	Tragopogon porrifolius	FooDB	31437929
Plant	Taraxacum officinale	FooDB	31437929
Plant	Rumex	FooDB	31437929
Plant	Allium ascalonicum	FooDB	31437929
Plant	Curcuma longa	FooDB	31437929
Plant	Rubus chamaemorus	FooDB	31437929
Plant	Elettaria cardamomum	FooDB	31437929
Plant	Citrullus lanatus var. fistulosus	FooDB	31437929
Plant	Ananas comosus	FooDB	31437929
Plant	Persea americana	FooDB	31437929
Plant	Amelanchier alnifolia	FooDB	31437929
Plant	Eugenia uniflora	FooDB	31437929
Plant	Annona reticulata	FooDB	31437929
Plant	Cichorium intybus	FooDB	31437929
Plant	Sesbania bispinosa	FooDB	31437929
Plant	Chenopodium quinoa	FooDB	31437929
Plant	Brassica oleracea var. botrytis	FooDB	31437929
Plant	Ribes x nidigrolaria	FooDB	31437929
Plant	Garcinia mangostana	FooDB	31437929
Plant	Cucumis melo	FooDB	31437929
Plant	Dioscorea pentaphylla	FooDB	31437929
Plant	Corchorus olitorius	FooDB	31437929
Plant	Juglans nigra	FooDB	31437929
Plant	Lathyrus sativus	FooDB	31437929
Plant	Allium tuberosum	FooDB	31437929
Plant	Cinnamomum verum	FooDB	31437929
Plant	Glycine max	FooDB	31437929
Plant	Gaylussacia baccata	FooDB	31437929
Plant	Petasites japonicus	FooDB	31437929
Plant	Prunus tomentosa	FooDB	31437929
Plant	Ocimum basilicum	FooDB	31437929
Plant	Mentha x piperita	FooDB	31437929
Plant	Maranta arundinacea	FooDB	31437929
Plant	Matteuccia struthiopteris	FooDB	31437929
Plant	Cucurbita moschata	FooDB	31437929
Plant	Macadamia	FooDB	31437929
Plant	Tilia	FooDB	31437929
Plant	Citrus limon	FooDB	31437929
Plant	Vaccinium myrtilloides	FooDB	31437929
Plant	Capsicum annuum var. annuum	FooDB	31437929
Plant	Apium graveolens var. rapaceum	FooDB	31437929
Plant	Papaver	FooDB	31437929
Plant	Rosa	FooDB	31437929
Plant	Nelumbo	FooDB	31437929
Plant	Brassica oleracea var. conica	FooDB	31437929
Plant	Sesamum orientale	FooDB	31437929
Plant	Annona cherimola	FooDB	31437929
Plant	Brassica rapa var. pekinensis	FooDB	31437929
Plant	Brassica rapa	FooDB	31437929
Plant	Lippia graveolens	FooDB	31437929
Plant	Prunus	FooDB	31437929
Plant	Capparis spinosa	FooDB	31437929
Plant	Citrus sinensis	FooDB	31437929
Plant	Lens culinaris	FooDB	31437929
Plant	Vaccinium deliciosum	FooDB	31437929
Plant	Phaseolus lunatus	FooDB	31437929
Plant	Artocarpus heterophyllus	FooDB	31437929
Plant	Prunus virginiana	FooDB	31437929
Plant	Musa acuminata	FooDB	31437929
Plant	Citrullus lanatus	FooDB	31437929
Plant	Linum usitatissimum	FooDB	31437929
Plant	Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant	Macadamia tetraphylla	FooDB	31437929
Plant	Phyllostachys edulis	FooDB	31437929
Plant	Lagenaria siceraria	FooDB	31437929
Plant	Prunus domestica	FooDB	31437929
Plant	Prunus armeniaca	FooDB	31437929
Plant	Carum carvi	FooDB	31437929
Plant	Allium schoenoprasum	FooDB	31437929
Plant	Carissa macrocarpa	FooDB	31437929
Plant	Citrus reticulata	FooDB	31437929
Plant	Satureja hortensis	FooDB	31437929
Plant	Averrhoa carambola	FooDB	31437929
Plant	Brassica rapa var. rapa	FooDB	31437929
Plant	Sorbus aucuparia	FooDB	31437929
Plant	Anethum graveolens	FooDB	31437929
Plant	Nelumbo nucifera	FooDB	31437929
Plant	Coriandrum sativum	FooDB	31437929
Plant	Bertholletia excelsa	FooDB	31437929
Plant	Brassica oleracea var. costata	FooDB	31437929
Plant	Panax	FooDB	31437929
Plant	Ceratonia siliqua	FooDB	31437929
Plant	Cymbopogon citratus	FooDB	31437929
Plant	Luffa aegyptiaca	FooDB	31437929
Plant	Anacardium occidentale	FooDB	31437929
Plant	Carthamus tinctorius	FooDB	31437929
Plant	Rubus occidentalis	FooDB	31437929
Plant	Vigna umbellata	FooDB	31437929
Plant	Cicer arietinum	FooDB	31437929
Plant	Allium fistulosum	FooDB	31437929
Plant	Capsicum	FooDB	31437929
Plant	Vaccinium alaskaense	FooDB	31437929
Plant	Lupinus	FooDB	31437929
Plant	Tilia cordata	FooDB	31437929
Plant	Camellia sinensis	FooDB	31437929
Plant	Prunus persica var. nucipersica	FooDB	31437929
Plant	Durio zibethinus	FooDB	31437929
Plant	Eriobotrya japonica	FooDB	31437929
Plant	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Brassica napus var. pabularia	FooDB	31437929
Plant	Oenothera biennis	FooDB	31437929
Plant	Diospyros kaki	FooDB	31437929
Plant	Ribes glandulosum	FooDB	31437929
Plant	Phaseolus vulgaris	FooDB	31437929
Plant	Theobroma cacao	FooDB	31437929
Plant	Virola surinamensis	FooDB	31437929
Plant	Verbena officinalis	FooDB	31437929
Plant	Daucus carota ssp. sativus	FooDB	31437929
Plant	Vaccinium oxycoccos	FooDB	31437929
Plant	Rumex acetosa	FooDB	31437929
Plant	Syzygium aromaticum	FooDB	31437929
Plant	Pyrus pyrifolia	FooDB	31437929
Plant	Vaccinium myrtillus	FooDB	31437929
Plant	Vaccinium parvifolium	FooDB	31437929
Plant	Aloysia triphylla	FooDB	31437929
Plant	Brassica oleracea var. capitata	FooDB	31437929
Plant	Capsicum chinense	FooDB	31437929
Plant	Vicia faba	FooDB	31437929
Plant	Vaccinium reticulatum	FooDB	31437929
Plant	Solanum quitoense	FooDB	31437929
Plant	Ginkgo biloba	FooDB	31437929
Plant	Theobroma grandiflorum	FooDB	31437929
Plant	Vigna unguiculata ssp. cylindrica	FooDB	31437929
Plant	Flammulina velutipes	FooDB	31437929
Plant	Satureja montana	FooDB	31437929
Plant		FooDB	31437929
Plant	Vitis vinifera	FooDB	31437929
Plant	Citrus japonica	FooDB	31437929
Plant	Prunus avium	FooDB	31437929
Plant	Perideridia oregana	FooDB	31437929
Plant	Vaccinium arboreum	FooDB	31437929
Plant	Pouteria sapota	FooDB	31437929
Plant	Wasabia japonica	FooDB	31437929
Plant	Piper nigrum	FooDB	31437929
Plant	Origanum onites	FooDB	31437929
Plant	Capsicum annuum	FooDB	31437929
Plant	Origanum vulgare	FooDB	31437929
Plant	Viburnum edule	FooDB	31437929
Plant	Dioscorea	FooDB	31437929
Plant	Brassica oleracea var. italica	FooDB	31437929
Plant	Momordica charantia	FooDB	31437929
Plant	Vaccinium uliginosum	FooDB	31437929
Plant	Castanea	FooDB	31437929
Plant	Rubus ursinus x idaeus	FooDB	31437929
Plant	Pleurotus ostreatus	FooDB	31437929
Plant	Cirsium	FooDB	31437929
Plant	Solanum melongena	FooDB	31437929
Plant	Opuntia	FooDB	31437929
Plant	Raphanus sativus var. sativus	FooDB	31437929
Plant	Colocasia esculenta	FooDB	31437929
Plant	Prunus persica var. persica	FooDB	31437929
Plant	Anthriscus cerefolium	FooDB	31437929
Plant	Nuphar lutea	FooDB	31437929
Plant	Lupinus albus	FooDB	31437929
Plant	Myristica fragrans	FooDB	31437929
Plant	Pachyrhizus erosus	FooDB	31437929
Plant	Cichorium endivia	FooDB	31437929

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
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001484

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022648

KNApSAcK ID

Not Available

Chemspider ID

388353

KEGG Compound ID

C00332

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15345

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Clayton PT, Eaton S, Aynsley-Green A, Edginton M, Hussain K, Krywawych S, Datta V, Malingre HE, Berger R, van den Berg IE: Hyperinsulinism in short-chain L-3-hydroxyacyl-CoA dehydrogenase deficiency reveals the importance of beta-oxidation in insulin secretion. J Clin Invest. 2001 Aug;108(3):457-65. doi: 10.1172/JCI11294. [PubMed:11489939 ]

Showing metabocard for Acetoacetyl-CoA (MMDBc0029658)

MOL for #<Metabolite:0x00007f5a94018920>

3D MOL for #<Metabolite:0x00007f5a94018920>

3D SDF for #<Metabolite:0x00007f5a94018920>

3D-SDF for #<Metabolite:0x00007f5a94018920>

PDB for #<Metabolite:0x00007f5a94018920>

3D PDB for #<Metabolite:0x00007f5a94018920>

SMILES for #<Metabolite:0x00007f5a94018920>

INCHI for #<Metabolite:0x00007f5a94018920>

Structure for #<Metabolite:0x00007f5a94018920>

3D Structure for #<Metabolite:0x00007f5a94018920>