acetoacetyl-CoA (CHEBI:15345)

ChEBI > Main

CHEBI:15345 - acetoacetyl-CoA

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

ChEBI Name	acetoacetyl-CoA

ChEBI ID	CHEBI:15345

Definition	A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41333, CHEBI:2392, CHEBI:11756, CHEBI:13706, CHEBI:22173

Supplier Information	ChemicalBook:CB6320803, eMolecules:515159, ZINC000003830891

Download	Molfile XML SDF

more structures >>

call loadScript javascripts\jsmol\core\package.js

call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode

call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js

Jmol JavaScript applet jmolApplet0_object__172215931493807__ initializing

getValue debug = null

getValue logLevel = null

getValue allowjavascript = null

AppletRegistry.checkIn(jmolApplet0_object__172215931493807__)

call loadScript javascripts\jsmol\core\corestate.z.js

viewerOptions:

{ "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15345","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__172215931493807__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"172215931493807","bgcolor":"#000" }

Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $

java.vendor: j2s

java.version: 0.0

os.name: j2s

Access: ALL

memory: 0.0/0.0

processors available: 1

useCommandThread: false

appletId:jmolApplet0_object (signed)

starting HoverWatcher_1

getValue emulate = null

defaults = "Jmol"

getValue boxbgcolor = null

getValue bgcolor = #000

backgroundColor = "#000"

getValue ANIMFRAMECallback = null

getValue APPLETREADYCallback = Jmol._readyCallback

APPLETREADYCallback = "Jmol._readyCallback"

getValue ATOMMOVEDCallback = null

getValue CLICKCallback = null

getValue ECHOCallback = null

getValue ERRORCallback = null

getValue EVALCallback = null

getValue HOVERCallback = null

getValue LOADSTRUCTCallback = null

getValue MEASURECallback = null

getValue MESSAGECallback = null

getValue MINIMIZATIONCallback = null

getValue PICKCallback = null

getValue RESIZECallback = null

getValue SCRIPTCallback = null

getValue SYNCCallback = null

getValue STRUCTUREMODIFIEDCallback = null

getValue doTranslate = null

language=en_US

getValue popupMenu = null

getValue script = null

Jmol applet jmolApplet0_object__172215931493807__ ready

call loadScript javascripts\jsmol\core\corescript.z.js

call loadScript javascripts\jsmol\J\script\FileLoadThread.js

starting QueueThread0_2

script 1 started

starting HoverWatcher_3

starting HoverWatcher_4

The Resolver thinks Mol

CAA - Ideal conformer

Mrv1927 06082115473D

starting HoverWatcher_5

Time for openFile(CAA - Ideal conformer

Mrv1927 06082115473D

94 96 0 0 0 0 999 V2000

5.0080 1.1060 -11.4150 N 0 0 0 0 0 0 0 0 0 0 0 0

4.0720 2.0300 -11.3010 C 0 0 0 0 0 0 0 0 0 0 0 0

3.1000 1.9460 -10.4170 N 0 0 0 0 0 0 0 0 0 0 0 0

3.0200 0.9050 -9.5950 C 0 0 0 0 0 0 0 0 0 0 0 0

3.9970 -0.1020 -9.6720 C 0 0 0 0 0 0 0 0 0 0 0 0

5.0140 0.0320 -10.6320 C 0 0 0 0 0 0 0 0 0 0 0 0

6.0000 -0.9300 -10.7590 N 0 0 0 0 0 0 0 0 0 0 0 0

3.6900 -1.0280 -8.7330 N 0 0 0 0 0 0 0 0 0 0 0 0

2.6160 -0.6600 -8.0960 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1670 0.5280 -8.5880 N 0 0 0 0 0 0 0 0 0 0 0 0

0.9860 1.2650 -8.1310 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.2890 0.7560 -8.8470 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.4750 1.4250 -10.0960 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.4040 1.1440 -7.8410 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.0230 2.3720 -8.2290 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.5890 2.0600 -8.4310 P 0 0 1 0 0 5 0 0 0 0 0 0

-4.1610 1.5630 -7.1600 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.3520 3.4080 -8.8720 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.7710 0.9420 -9.5750 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.6580 1.3080 -6.5020 C 0 0 2 0 0 0 0 0 0 0 0 0

0.7240 0.9910 -6.7390 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.2400 0.3490 -5.4620 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.5380 0.5030 -4.2270 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.1990 -0.5290 -3.1840 P 0 0 1 0 0 5 0 0 0 0 0 0

-2.6340 -0.2090 -3.0150 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.0470 -2.0310 -3.7450 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.4520 -0.4090 -1.7620 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.1600 -1.4640 -0.7740 P 0 0 1 0 0 5 0 0 0 0 0 0

-2.5960 -1.1290 -0.6420 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.0090 -2.9490 -1.3750 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.4590 -1.3970 0.6730 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5070 -2.3370 2.8990 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.1280 -2.3500 1.5010 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.6520 -0.9420 3.5090 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9760 -2.6990 2.8010 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2240 -3.3580 3.7850 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.1880 -4.6420 3.1580 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5340 -3.4330 5.1230 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1580 -4.3900 5.3950 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.6880 -2.4370 6.0170 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.0020 -2.5000 7.3100 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.3440 -1.2540 8.1310 C 0 0 2 0 0 0 0 0 0 0 0 0

0.3610 -1.3200 9.4610 C 0 0 0 0 0 0 0 0 0 0 0 0

1.0670 -2.2690 9.7260 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2070 -0.3230 10.3550 N 0 0 0 0 0 0 0 0 0 0 0 0

0.8930 -0.3870 11.6480 C 0 0 2 0 0 0 0 0 0 0 0 0

0.5510 0.8580 12.4680 C 0 0 2 0 0 0 0 0 0 0 0 0

1.3980 0.7790 14.0660 S 0 0 0 0 0 0 0 0 0 0 0 0

0.8600 2.2480 14.7600 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1110 2.9740 14.1400 O 0 0 0 0 0 0 0 0 0 0 0 0

1.3150 2.6400 16.1420 C 0 0 2 0 0 0 0 0 0 0 0 0

0.7030 3.9650 16.5170 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0270 4.5330 15.7410 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0030 4.5810 17.8590 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1050 2.8870 -11.9570 H 0 0 0 0 0 0 0 0 0 0 0 0

6.6970 -0.8260 -11.4250 H 0 0 0 0 0 0 0 0 0 0 0 0

5.9930 -1.7100 -10.1820 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1500 -1.2140 -7.2950 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1170 2.3350 -8.2940 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2510 -0.3240 -8.9890 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2940 1.2170 -10.6420 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1470 0.3500 -7.7680 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.2850 3.1780 -8.9820 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3860 1.3050 -10.3840 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7480 2.3350 -6.1510 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1350 -0.6760 -5.8140 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2950 0.5750 -5.3100 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0990 -2.1980 -3.8400 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0610 -3.1270 -1.4450 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0250 -3.3450 1.0660 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1850 -2.0920 1.5710 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7050 -0.7360 3.7000 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0970 -0.8950 4.4450 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2570 -0.1990 2.8150 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0790 -3.6940 2.3670 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4860 -1.9720 2.1700 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4180 -2.6900 3.7970 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2600 -3.0520 3.9270 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2550 -4.8740 3.0510 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2530 -1.6770 5.8050 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0740 -2.5450 7.1490 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3260 -3.3900 7.8500 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.4210 -1.2100 8.2920 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0200 -0.3640 7.5910 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3570 0.4350 10.1420 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9700 -0.4320 11.4860 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5690 -1.2770 12.1870 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5250 0.9030 12.6300 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8750 1.7480 11.9290 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4020 2.7250 16.1560 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0010 1.8790 16.8580 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4750 5.5310 17.9490 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6750 3.9070 18.6500 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0750 4.7520 17.9490 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 6 1 0 0 0 0

2 3 1 0 0 0 0

2 55 1 0 0 0 0

3 4 2 0 0 0 0

4 5 1 0 0 0 0

4 10 1 0 0 0 0

5 6 2 0 0 0 0

5 8 1 0 0 0 0

6 7 1 0 0 0 0

7 56 1 0 0 0 0

7 57 1 0 0 0 0

8 9 2 0 0 0 0

9 10 1 0 0 0 0

9 58 1 0 0 0 0

10 11 1 0 0 0 0

11 12 1 0 0 0 0

11 21 1 0 0 0 0

11 59 1 1 0 0 0

12 13 1 0 0 0 0

12 14 1 0 0 0 0

12 60 1 6 0 0 0

13 61 1 0 0 0 0

14 15 1 0 0 0 0

14 20 1 0 0 0 0

14 62 1 1 0 0 0

15 16 1 0 0 0 0

16 17 2 0 0 0 0

16 18 1 0 0 0 0

16 19 1 0 0 0 0

18 63 1 0 0 0 0

19 64 1 0 0 0 0

20 21 1 0 0 0 0

20 22 1 0 0 0 0

20 65 1 1 0 0 0

22 23 1 0 0 0 0

22 66 1 0 0 0 0

22 67 1 0 0 0 0

24 23 1 6 0 0 0

24 25 2 0 0 0 0

24 26 1 0 0 0 0

24 27 1 0 0 0 0

26 68 1 0 0 0 0

28 27 1 6 0 0 0

28 29 2 0 0 0 0

28 30 1 0 0 0 0

28 31 1 0 0 0 0

30 69 1 0 0 0 0

31 33 1 0 0 0 0

32 33 1 0 0 0 0

32 34 1 0 0 0 0

32 35 1 0 0 0 0

32 36 1 0 0 0 0

33 70 1 0 0 0 0

33 71 1 0 0 0 0

34 72 1 0 0 0 0

34 73 1 0 0 0 0

34 74 1 0 0 0 0

35 75 1 0 0 0 0

35 76 1 0 0 0 0

35 77 1 0 0 0 0

36 37 1 0 0 0 0

36 38 1 0 0 0 0

36 78 1 1 0 0 0

37 79 1 0 0 0 0

38 39 2 0 0 0 0

38 40 1 0 0 0 0

40 41 1 0 0 0 0

40 80 1 0 0 0 0

41 42 1 0 0 0 0

41 81 1 0 0 0 0

41 82 1 0 0 0 0

42 43 1 0 0 0 0

42 83 1 0 0 0 0

42 84 1 0 0 0 0

43 44 2 0 0 0 0

43 45 1 0 0 0 0

45 46 1 0 0 0 0

45 85 1 0 0 0 0

46 47 1 0 0 0 0

46 86 1 0 0 0 0

46 87 1 0 0 0 0

47 48 1 0 0 0 0

47 88 1 0 0 0 0

47 89 1 0 0 0 0

48 49 1 0 0 0 0

49 50 2 0 0 0 0

49 51 1 0 0 0 0

51 52 1 0 0 0 0

51 90 1 0 0 0 0

51 91 1 0 0 0 0

52 53 2 0 0 0 0

52 54 1 0 0 0 0

54 92 1 0 0 0 0

54 93 1 0 0 0 0

54 94 1 0 0 0 0

M END): 22 ms

reading 94 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

94 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Acetoacetyl CoA is the precursor of HMG-CoA in the mevalonate pathway, which is essential for cholesterol biosynthesis. It also takes a similar role in the ketone bodies synthesis (ketogenesis) pathway of the liver. In the ketone bodies digestion pathway (in the tissue), it is no longer associated with having HMG-CoA as a product or as a reactant. It is created from acetyl-CoA, a thioester, which reacts with the enolate of a second molecule of acetyl-CoA in a Claisen condensation reaction, and it is acted upon by HMG-CoA synthase to form HMG-CoA. During the metabolism of leucine, this last reaction is reversed. Some individuals may experience Acetoacetyl-CoA deficiency. This deficiency is classified as a disorder ketone body and isoleucine metabolism that can be inherited. Additional mutations include those with the enzymes within pathways related to Acetoacetyl CoA, including Beta-Ketothiolase deficiency and Mitochondrial 3-hydroxy-3-methylglutaryl-CoA Synthase mutation. Additionally, it reacts with NADPH-dependent acetoacetyl-coenzyme A reductase, also known as PhaB, in a pathway that produces polyester polyhydroxyalkanoate (PHA). The reduction of acetoacetyl-coA by Pha creates (R)-3-hydroxybutyryl-CoA, which polymerizes to PHA. The pathway is present in bacteria such as Ralstonia eutropha and the PCC6803 strain of Synechocystis. Mover over, Acetoacetyl-CoA is involved with neuronal development involving lipogenesis and providing fats and cholesterol for neuronal cells.
Read full article at Wikipedia

Formula

C25H40N7O18P3S

Net Charge

Average Mass

851.610

Monoisotopic Mass

851.13634

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

InChIKey

OJFDKHTZOUZBOS-CITAKDKDSA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Mus musculus (NCBI:txid10090)	From MetaboLights See: MetaboLights Study
Mus musculus (NCBI:txid10090)	From MetaboLights See: MetaboLights Study
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	acyl donor Any donor that can transfer acyl groups between molecular entities. (via acyl-CoA )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	acetoacetyl-CoA (CHEBI:15345) has functional parent acetoacetic acid (CHEBI:15344) acetoacetyl-CoA (CHEBI:15345) has functional parent butyryl-CoA (CHEBI:15517) acetoacetyl-CoA (CHEBI:15345) has role Escherichia coli metabolite (CHEBI:76971) acetoacetyl-CoA (CHEBI:15345) has role mouse metabolite (CHEBI:75771) acetoacetyl-CoA (CHEBI:15345) is a 3-oxo-fatty acyl-CoA (CHEBI:15489) acetoacetyl-CoA (CHEBI:15345) is conjugate acid of acetoacetyl-CoA(4−) (CHEBI:57286)

Incoming	acetoacetyl-CoA(4−) (CHEBI:57286) is conjugate base of acetoacetyl-CoA (CHEBI:15345)

IUPAC Name

3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxobutanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}

Synonyms	Sources
3-Acetoacetyl-CoA	KEGG COMPOUND
acetoacetyl CoA	KNApSAcK
Acetoacetyl coenzyme A	KEGG COMPOUND
Acetoacetyl-CoA	KEGG COMPOUND
S-acetoacetyl-CoA	ChEBI
S-Acetoacetyl-coenzym A	ChEBI
S-acetoacetyl-coenzyme A	ChEBI

Manual Xrefs	Databases
Acetoacetyl-CoA	Wikipedia
C00007269	KNApSAcK
C00332	KEGG COMPOUND
c0229	UM-BBD
CAA	PDBeChem
DB03059	DrugBank
FDB022648	FooDB
HMDB0001484	HMDB
LMFA07050030	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
1420-36-6	CAS Registry Number	KEGG COMPOUND
1420-36-6	CAS Registry Number	ChemIDplus
78273	Reaxys Registry Number	Reaxys

Citations	Types	Sources
10806397	PubMed citation	Europe PMC
11137815	PubMed citation	Europe PMC
11451959	PubMed citation	Europe PMC
12501183	PubMed citation	Europe PMC
1682408	PubMed citation	Europe PMC
16887802	PubMed citation	Europe PMC
239468	PubMed citation	Europe PMC
24211201	PubMed citation	Europe PMC
26527136	PubMed citation	Europe PMC
27093562	PubMed citation	Europe PMC
27124816	PubMed citation	Europe PMC
28062645	PubMed citation	Europe PMC
29226071	PubMed citation	Europe PMC
32218776	PubMed citation	Europe PMC
6118268	PubMed citation	Europe PMC
6150478	PubMed citation	Europe PMC
7857927	PubMed citation	Europe PMC

Last Modified

08 June 2021

CHEBI:15345 - acetoacetyl-CoA

ChEBI is part of the ELIXIR infrastructure