acetoacetyl-CoA (CHEBI:15345)

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CHEBI:15345 - acetoacetyl-CoA

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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:CB8698780, eMolecules:478490, ZINC000000001011

Download	Molfile XML SDF

more structures >>

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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): 23 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
Benzoic acid () is a white (or colorless) solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring (C6H6) with a carboxyl (−C(=O)OH) substituent. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which is used for benzyl), thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. Benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates ().
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

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