ECMDB: Acetoacetyl-CoA (ECMDB01484) (M2MDB000397)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (10)Transporters (1)XML

Proteins (2433)

Record Information

Version

2.0

Creation Date

2012-05-31 13:53:16 -0600

Update Date

2015-09-17 15:41:12 -0600

Secondary Accession Numbers

ECMDB01484

Identification

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

Synonyms:

3-Acetoacetyl-CoA
3-Acetoacetyl-Coenzyme A
3-Oxobutyryl-CoA
3-Oxobutyryl-Coenzyme A
Acetoacetyl coa
Acetoacetyl coenzyme A
Acetoacetyl-S-CoA
Acetoacetyl-CoA
Acetoacetyl-Coenzyme A
Acetoacetyl-S-CoA
S-Acetoacetylcoenzyme A

Chemical Formula:

C₂₅H₄₀N₇O₁₈P₃S

Weight:

Average: 851.607
Monoisotopic: 851.136337737

InChI Key:

OJFDKHTZOUZBOS-XBTRWLRFSA-N

InChI:

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

CAS number:

1420-36-6

IUPAC Name:

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-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 IUPAC Name:

acetoacetyl-coa

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Aminopiperidines

Direct Parent

Aminopiperidines

Alternative Parents

Substituents

4-aminopiperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

bipiperidine (CHEBI:40117 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.84 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-5.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	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	76.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Acetate metabolism	PW002090
Fatty acid metabolism	PW000796
Phenylalanine metabolism	PW000921
Propanoate metabolism	PW000940
Tryptophan metabolism	PW000815
fatty acid oxidation (Butanoate)	PW001017

KEGG Pathways:

Benzoate degradation via CoA ligation ec00632
Benzoate degradation via hydroxylation ec00362
Butanoate metabolism ec00650
Fatty acid metabolism ec00071
Glyoxylate and dicarboxylate metabolism ec00630
Lysine degradation ec00310
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Phenylalanine metabolism ec00360
Propanoate metabolism ec00640
Pyruvate metabolism ec00620
Reductive carboxylate cycle (CO2 fixation) ec00720
Synthesis and degradation of ketone bodies ec00072
Terpenoid backbone biosynthesis ec00900
Tryptophan metabolism ec00380
Valine, leucine and isoleucine degradation ec00280

EcoCyc Pathways:

acetoacetate degradation (to acetyl CoA) ACETOACETATE-DEG-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
22± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-000i-0004009000-9559fa356f1bae03b7ca	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0a4i-0269300000-d5574d3fd84812c0057d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-05n1-0009600000-a29b94fc4d454c655bab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-000i-0001209000-21979fdba010c3871c5a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0udi-0000000090-aa1f97ad009df4ad9439	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 57V, negative	splash10-0udi-0000100490-97b56edeb43a5d82ba85	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 71V, negative	splash10-014i-0000910830-9d7a9bb5d2817f98fbf1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 93V, negative	splash10-0ar9-0101901000-ee3c1d5ebb3142f3c5af	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 115V, negative	splash10-0a6r-5524900000-2d745cfa452462059e2c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 136V, negative	splash10-056r-9513200000-037d88669e973d0dff1c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 158V, negative	splash10-004i-9400000000-fca9f3020e4e007e8164	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 187V, negative	splash10-004i-9300000000-13ad94b2682d99b6234d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 216V, negative	splash10-004i-9200000000-32dfa0b8d343e2eb7b7b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 260V, negative	splash10-004i-9100000000-6461ef6280ce0db781b2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-014i-0000000900-727bb0c3c925e7bbeba4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-00di-0190000000-0e093fb5398057b2093d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0a4i-0900000000-b4c90f8c858e783159b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0udl-0018900000-91aaf6888a10aac16f57	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-00xr-0092000000-2dd3c44dfb7a39ee9a59	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0670-0000904200-f3bcbcab3db17ae6a02a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-00di-0190000000-3a982abdcfdcfe6b0420	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0udr-0027900000-0d41e18ae4bea1b5b7eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, positive	splash10-0002-6900000000-959cba779002108c94cc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, positive	splash10-00di-9000000000-9fd58d8b09e3b71e5e6f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 59V, positive	splash10-03di-0190000000-aa6e0456b3c35ec78a6a	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15345
HMDB ID	HMDB01484
Pubchem Compound ID	439214
Kegg ID	C00332
ChemSpider ID	388353
Wikipedia	Acetoacetyl-CoA
BioCyc ID	ACETOACETYL-COA
EcoCyc ID	ACETOACETYL-COA
Ligand Expo	CAA

Enzymes

Protein Details

1. 3-ketoacyl-CoA thiolase

General function:: Involved in acetyl-CoA C-acyltransferase activity
Specific function:: Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadA
Uniprot ID:: P21151
Molecular weight:: 40876

Reactions

Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.

Protein Details

2. Fatty acid oxidation complex subunit alpha

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadB
Uniprot ID:: P21177
Molecular weight:: 79593

Reactions

(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.

Protein Details

3. Probable enoyl-CoA hydratase paaF

General function:: Involved in catalytic activity
Specific function:: Could possibly oxidize fatty acids using specific components
Gene Name:: paaF
Uniprot ID:: P76082
Molecular weight:: 27237

Reactions

(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.

Protein Details

4. Probable 3-hydroxybutyryl-CoA dehydrogenase

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: (S)-3-hydroxybutanoyl-CoA + NADP(+) = 3- acetoacetyl-CoA + NADPH
Gene Name:: paaH
Uniprot ID:: P76083
Molecular weight:: 51732

Reactions

(S)-3-hydroxybutanoyl-CoA + NADP(+) = 3-acetoacetyl-CoA + NADPH.

Protein Details

5. Acetate CoA-transferase subunit alpha

General function:: Involved in CoA-transferase activity
Specific function:: Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:: atoD
Uniprot ID:: P76458
Molecular weight:: 23526

Reactions

Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.

Protein Details

6. Acetate CoA-transferase subunit beta

General function:: Involved in CoA-transferase activity
Specific function:: Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:: atoA
Uniprot ID:: P76459
Molecular weight:: 22960

Reactions

Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.

Protein Details

7. Acetyl-CoA acetyltransferase

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: 2 acetyl-CoA = CoA + acetoacetyl-CoA
Gene Name:: atoB
Uniprot ID:: P76461
Molecular weight:: 40352

Reactions

2 acetyl-CoA = CoA + acetoacetyl-CoA.

Protein Details

8. 3-ketoacyl-CoA thiolase_

General function:: Involved in transferase activity
Specific function:: Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:: fadI
Uniprot ID:: P76503
Molecular weight:: 46530

Reactions

Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.

Protein Details

9. Fatty acid oxidation complex subunit alpha_

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long-chain fatty acids
Gene Name:: fadJ
Uniprot ID:: P77399
Molecular weight:: 77072

Reactions

(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.

Protein Details

10. Probable acetyl-CoA acetyltransferase

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: 2 acetyl-CoA = CoA + acetoacetyl-CoA
Gene Name:: yqeF
Uniprot ID:: Q46939
Molecular weight:: 41018

Reactions

2 acetyl-CoA = CoA + acetoacetyl-CoA.

Transporters

Protein Details

1. Fatty acid oxidation complex subunit alpha

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:: fadB
Uniprot ID:: P21177
Molecular weight:: 79593

Reactions

(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.

Acetoacetyl-CoA (ECMDB01484) (M2MDB000397)

Structure for #<Compound:0xa2de2fcc>

Enzymes

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Transporters

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