Acetoacetyl-CoA (ECMDB01484) (M2MDB000397)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:53:16 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-17 15:41:12 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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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 |
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Molecular Framework | Aliphatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Acetoacetic acid + Acetyl-CoA > Acetoacetyl-CoA + Acetic acid 2 Acetyl-CoA <> Acetoacetyl-CoA + Coenzyme A Acetoacetyl-CoA + Hydrogen ion + NADH <> 3-Hydroxybutyryl-CoA + NAD Acetoacetyl-CoA + Acetic acid <> Acetoacetic acid + Acetyl-CoA (S)-3-Hydroxybutanoyl-CoA + NAD <> Acetoacetyl-CoA + NADH + Hydrogen ion (S)-3-Hydroxybutanoyl-CoA + NADP + 3-Hydroxybutyryl-CoA <> Acetoacetyl-CoA + NADPH + Hydrogen ion 3-Hydroxybutanoyl-CoA + NADP <> Acetoacetyl-CoA + NADPH + Hydrogen ion Acetoacetic acid + Acetyl-CoA <> Acetoacetyl-CoA + Acetic acid Acetyl-CoA <> Acetoacetyl-CoA + Coenzyme A 2 Acetyl-CoA > CoA + Acetoacetyl-CoA 3-Hydroxybutyryl-CoA + NADP > Acetoacetyl-CoA + NADPH 3-Hydroxybutyryl-CoA + NAD + 3-Hydroxybutyryl-CoA > NADH + Hydrogen ion + Acetoacetyl-CoA + Acetoacetyl-CoA Acetoacetyl-CoA + Coenzyme A + Acetoacetyl-CoA > Acetyl-CoA + Succinyl-CoA + Succinyl-CoA 3-Hydroxybutyryl-CoA + NAD + 3-Hydroxybutyryl-CoA <> Acetoacetyl-CoA + NADH + Hydrogen ion + Acetoacetyl-CoA 2 Acetyl-CoA <> Acetoacetyl-CoA + Coenzyme A + Acetoacetyl-CoA Acetoacetyl-CoA > Coenzyme A + Acetyl-CoA 2 Acetyl-CoA <> Acetoacetyl-CoA + Coenzyme A 2 Acetyl-CoA <> Acetoacetyl-CoA + Coenzyme A | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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. |
- 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
- 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. |