isovaleryl-CoA (CHEBI:15487)

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CHEBI:15487 - isovaleryl-CoA

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ChEBI Name	isovaleryl-CoA

ChEBI ID	CHEBI:15487

Definition	A methylbutanoyl-CoA is the S-isovaleryl derivative of coenzyme A.

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

Secondary ChEBI IDs	CHEBI:11856, CHEBI:1598, CHEBI:14481, CHEBI:20126

Supplier Information	ZINC000008551494

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

IVC - Ideal conformer

Mrv1927 06082116403D

starting HoverWatcher_5

Time for openFile(IVC - Ideal conformer

Mrv1927 06082116403D

98100 0 0 0 0 999 V2000

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-0.5540 3.7560 0.9810 P 0 0 2 0 0 5 0 0 0 0 0 0

0.3400 2.7230 1.8340 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9130 4.9150 1.8290 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2850 4.2640 -0.2960 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4760 5.0470 -0.1830 C 0 0 1 0 0 0 0 0 0 0 0 0

2.0170 5.3560 -1.5810 C 0 0 1 0 0 0 0 0 0 0 0 0

2.3340 4.0470 -2.3060 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9660 6.1370 -2.3730 C 0 0 0 0 0 0 0 0 0 0 0 0

3.2910 6.1940 -1.4600 C 0 0 1 0 0 0 0 0 0 0 0 0

2.9710 7.4700 -0.9020 O 0 0 0 0 0 0 0 0 0 0 0 0

4.2750 5.4870 -0.5640 C 0 0 0 0 0 0 0 0 0 0 0 0

4.5150 5.9270 0.5400 O 0 0 0 0 0 0 0 0 0 0 0 0

4.8880 4.3650 -0.9900 N 0 0 0 0 0 0 0 0 0 0 0 0

5.7630 3.6190 -0.0830 C 0 0 1 0 0 0 0 0 0 0 0 0

6.3280 2.3960 -0.8090 C 0 0 1 0 0 0 0 0 0 0 0 0

7.2280 1.6290 0.1250 C 0 0 0 0 0 0 0 0 0 0 0 0

7.4020 2.0220 1.2590 O 0 0 0 0 0 0 0 0 0 0 0 0

7.8410 0.5070 -0.3010 N 0 0 0 0 0 0 0 0 0 0 0 0

8.7170 -0.2390 0.6060 C 0 0 1 0 0 0 0 0 0 0 0 0

9.2820 -1.4610 -0.1200 C 0 0 1 0 0 0 0 0 0 0 0 0

10.3630 -2.3830 1.0010 S 0 0 0 0 0 0 0 0 0 0 0 0

10.8450 -3.6600 -0.0330 C 0 0 0 0 0 0 0 0 0 0 0 0

10.4300 -3.7070 -1.1720 O 0 0 0 0 0 0 0 0 0 0 0 0

11.7840 -4.7250 0.4720 C 0 0 1 0 0 0 0 0 0 0 0 0

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0.6120 1.9380 1.3400 H 0 0 0 0 0 0 0 0 0 0 0 0

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6.5830 4.2600 0.2400 H 0 0 0 0 0 0 0 0 0 0 0 0

5.1930 3.2930 0.7870 H 0 0 0 0 0 0 0 0 0 0 0 0

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6.8990 2.7220 -1.6790 H 0 0 0 0 0 0 0 0 0 0 0 0

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9.5370 0.4030 0.9290 H 0 0 0 0 0 0 0 0 0 0 0 0

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52 92 1 0 0 0 0

53 93 1 0 0 0 0

53 94 1 0 0 0 0

53 95 1 0 0 0 0

54 96 1 0 0 0 0

54 97 1 0 0 0 0

54 98 1 0 0 0 0

M END): 21 ms

reading 98 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

98 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Isovaleryl-coenzyme A, also known as isovaleryl-CoA, is an intermediate in the metabolism of branched-chain amino acids.
Read full article at Wikipedia

Formula

C26H44N7O17P3S

Net Charge

Average Mass

851.650

Monoisotopic Mass

851.17273

InChI

InChI=1S/C26H44N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1

InChIKey

UYVZIWWBJMYRCD-ZMHDXICWSA-N

SMILES

CC(C)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
Bacillus methanolicus (NCBI:txid1471)	From MetaboLights See: MetaboLights Study

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

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

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	isovaleryl-CoA (CHEBI:15487) has functional parent butyryl-CoA (CHEBI:15517) isovaleryl-CoA (CHEBI:15487) has functional parent isovaleric acid (CHEBI:28484) isovaleryl-CoA (CHEBI:15487) has role mouse metabolite (CHEBI:75771) isovaleryl-CoA (CHEBI:15487) is a methylbutanoyl-CoA (CHEBI:25286) isovaleryl-CoA (CHEBI:15487) is a short-chain fatty acyl-CoA (CHEBI:61905) isovaleryl-CoA (CHEBI:15487) is conjugate acid of isovaleryl-CoA(4−) (CHEBI:57345)

Incoming	isovaleryl-CoA(4−) (CHEBI:57345) is conjugate base of isovaleryl-CoA (CHEBI:15487)

IUPAC Name

3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-{[3-({2-[(3-methylbutanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl] dihydrogen diphosphate}

Synonyms	Sources
3-Methylbutanoyl-CoA	KEGG COMPOUND
3-methylbutanoyl-coenzyme A	ChEBI
3-methylbutyryl-CoA	ChEBI
3-methylbutyryl-coenzyme A	ChEBI
β-methylbutanoyl-CoA	ChEBI
β-methylbutanoyl-coenzyme A	ChEBI
β-methylbutyryl-CoA	ChEBI
β-methylbutyryl-coenzyme A	ChEBI
Isovaleryl-CoA	KEGG COMPOUND
isovaleryl-coenzyme A	ChemIDplus
S-(3-methylbutanoyl)-coenzyme A	ChemIDplus

Manual Xrefs	Databases
145017	ChemSpider
C02939	KEGG COMPOUND
FDB022430	FooDB
HMDB0001113	HMDB
Isovaleryl-CoA	Wikipedia
IVC	PDBeChem
LMFA07050336	LIPID MAPS
View more database links

Registry Numbers	Types	Sources
6244-91-3	CAS Registry Number	ChemIDplus
78268	Reaxys Registry Number	Reaxys

Citations

Bock T, Volz C, Hering V, Scrima A, Müller R, Blankenfeldt W (2017)
The AibR-isovaleryl coenzyme A regulator and its DNA binding site - a model for the regulation of alternative de novo isovaleryl coenzyme A biosynthesis in Myxococcus xanthus.
Nucleic acids research 45, 2166-2178 [PubMed:27940564]
[show Abstract]

Dong SH, Frane ND, Christensen QH, Greenberg EP, Nagarajan R, Nair SK (2017)
Molecular basis for the substrate specificity of quorum signal synthases.
Proceedings of the National Academy of Sciences of the United States of America 114, 9092-9097 [PubMed:28784791]
[show Abstract]

Bock T, Reichelt J, Müller R, Blankenfeldt W (2016)
The Structure of LiuC, a 3-Hydroxy-3-Methylglutaconyl CoA Dehydratase Involved in Isovaleryl-CoA Biosynthesis in Myxococcus xanthus, Reveals Insights into Specificity and Catalysis.
Chembiochem : a European journal of chemical biology 17, 1658-1664 [PubMed:27271456]
[show Abstract]

Mohsen AW, Vockley J (2015)
Kinetic and spectral properties of isovaleryl-CoA dehydrogenase and interaction with ligands.
Biochimie 108, 108-119 [PubMed:25450250]
[show Abstract]

Kitanishi K, Cracan V, Banerjee R (2015)
Engineered and Native Coenzyme B12-dependent Isovaleryl-CoA/Pivalyl-CoA Mutase.
The Journal of biological chemistry 290, 20466-20476 [PubMed:26134562]
[show Abstract]
Adenosylcobalamin-dependent isomerases catalyze carbon skeleton rearrangements using radical chemistry. We have recently demonstrated that an isobutyryl-CoA mutase variant, IcmF, a member of this enzyme family that catalyzes the interconversion of isobutyryl-CoA and n-butyryl-CoA also catalyzes the interconversion between isovaleryl-CoA and pivalyl-CoA, albeit with low efficiency and high susceptibility to inactivation. Given the biotechnological potential of the isovaleryl-CoA/pivalyl-CoA mutase (PCM) reaction, we initially attempted to engineer IcmF to be a more proficient PCM by targeting two active site residues predicted based on sequence alignments and crystal structures, to be key to substrate selectivity. Of the eight mutants tested, the F598A mutation was the most robust, resulting in an ∼17-fold increase in the catalytic efficiency of the PCM activity and a concomitant ∼240-fold decrease in the isobutyryl-CoA mutase activity compared with wild-type IcmF. Hence, mutation of a single residue in IcmF tuned substrate specificity yielding an ∼4000-fold increase in the specificity for an unnatural substrate. However, the F598A mutant was even more susceptible to inactivation than wild-type IcmF. To circumvent this limitation, we used bioinformatics analysis to identify an authentic PCM in genomic databases. Cloning and expression of the putative AdoCbl-dependent PCM with an α2β2 heterotetrameric organization similar to that of isobutyryl-CoA mutase and a recently characterized archaeal methylmalonyl-CoA mutase, allowed demonstration of its robust PCM activity. To simplify kinetic analysis and handling, a variant PCM-F was generated in which the αβ subunits were fused into a single polypeptide via a short 11-amino acid linker. The fusion protein, PCM-F, retained high PCM activity and like PCM, was resistant to inactivation. Neither PCM nor PCM-F displayed detectable isobutyryl-CoA mutase activity, demonstrating that PCM represents a novel 5'-deoxyadenosylcobalamin-dependent acyl-CoA mutase. The newly discovered PCM and the derivative PCM-F, have potential applications in bioremediation of pivalic acid found in sludge, in stereospecific synthesis of C5 carboxylic acids and alcohols, and in the production of potential commodity and specialty chemicals.

Jost M, Born DA, Cracan V, Banerjee R, Drennan CL (2015)
Structural Basis for Substrate Specificity in Adenosylcobalamin-dependent Isobutyryl-CoA Mutase and Related Acyl-CoA Mutases.
The Journal of biological chemistry 290, 26882-26898 [PubMed:26318610]
[show Abstract]

Bode HB, Ring MW, Schwär G, Altmeyer MO, Kegler C, Jose IR, Singer M, Müller R (2009)
Identification of additional players in the alternative biosynthesis pathway to isovaleryl-CoA in the myxobacterium Myxococcus xanthus.
Chembiochem : a European journal of chemical biology 10, 128-140 [PubMed:18846531]
[show Abstract]

Mahmud T, Wenzel SC, Wan E, Wen KW, Bode HB, Gaitatzis N, Müller R (2005)
A biosynthetic pathway to isovaleryl-CoA in myxobacteria: the involvement of the mevalonate pathway.
Chembiochem : a European journal of chemical biology 6, 322-330 [PubMed:15619721]
[show Abstract]

Tajima G, Sakura N, Yofune H, Dwi Bahagia Febriani A, Nishimura Y, Sakamoto A, Ono H, Shigematsu Y, Kobayashi M (2005)
Establishment of a practical enzymatic assay method for determination of isovaleryl-CoA dehydrogenase activity using high-performance liquid chromatography.
Clinica chimica acta; international journal of clinical chemistry 353, 193-199 [PubMed:15698607]
[show Abstract]

Däschner K, Couée I, Binder S (2001)
The mitochondrial isovaleryl-coenzyme a dehydrogenase of arabidopsis oxidizes intermediates of leucine and valine catabolism.
Plant physiology 126, 601-612 [PubMed:11402190]
[show Abstract]

Rhead WJ, Tanaka K (1980)
Demonstration of a specific mitochondrial isovaleryl-CoA dehydrogenase deficiency in fibroblasts from patients with isovaleric acidemia.
Proceedings of the National Academy of Sciences of the United States of America 77, 580-583 [PubMed:6928646]
[show Abstract]

Last Modified

05 August 2021

ChEBI

CHEBI:15487 - isovaleryl-CoA

Background

Methods

Results

Conclusions

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