oxalyl-CoA (CHEBI:15535)

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CHEBI:15535 - oxalyl-CoA

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ChEBI Name	oxalyl-CoA

ChEBI ID	CHEBI:15535

Definition	An ω-carboxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of oxalic acid.

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

Submitter	Joanne

Secondary ChEBI IDs	CHEBI:233756, CHEBI:49814, CHEBI:7817, CHEBI:14707, CHEBI:25738

Supplier Information	ZINC000008551141

Download	Molfile XML SDF

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M END): 20 ms

reading 89 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

89 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Formula

C23H36N7O19P3S

Net Charge

Average Mass

839.560

Monoisotopic Mass

839.09995

InChI

InChI=1S/C23H36N7O19P3S/c1-23(2,16(33)19(34)26-4-3-12(31)25-5-6-53-22(37)21(35)36)8-46-52(43,44)49-51(41,42)45-7-11-15(48-50(38,39)40)14(32)20(47-11)30-10-29-13-17(24)27-9-28-18(13)30/h9-11,14-16,20,32-33H,3-8H2,1-2H3,(H,25,31)(H,26,34)(H,35,36)(H,41,42)(H,43,44)(H2,24,27,28)(H2,38,39,40)/t11-,14-,15-,16+,20-/m1/s1

InChIKey

QVXMZFTWJVBUHP-IBOSZNHHSA-N

SMILES

O=C(O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC1OC(N2C=NC=3C(=NC=NC32)N)C(O)C1OP(=O)(O)O

Metabolite of Species	Details
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.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	oxalyl-CoA (CHEBI:15535) has functional parent oxalic acid (CHEBI:16995) oxalyl-CoA (CHEBI:15535) has role Escherichia coli metabolite (CHEBI:76971) oxalyl-CoA (CHEBI:15535) is a ω-carboxyacyl-CoA (CHEBI:37555) oxalyl-CoA (CHEBI:15535) is conjugate acid of oxalyl-CoA(5−) (CHEBI:57388)

Incoming	oxalyl-CoA(5−) (CHEBI:57388) is conjugate base of oxalyl-CoA (CHEBI:15535)

IUPAC Name

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

Synonyms	Sources
Oxalyl-CoA	KEGG COMPOUND
OXALYL-COENZYME A	PDBeChem

Manual Xrefs	Databases
C00313	KEGG COMPOUND
FDB031077	FooDB
HMDB0304445	HMDB
LMFA07050357	LIPID MAPS
OXK	PDBeChem
View more database links

Registry Number	Type	Source
15648689	Reaxys Registry Number	Reaxys

Citations

Huang D, Wang X, Liu WB, Ye BC (2023)
Remodeling metabolism of Corynebacterium glutamicum for high-level dencichine production.
Bioresource technology 388, 129800 [PubMed:37748563]
[show Abstract]

Li W, Zhou Z, Li X, Ma L, Guan Q, Zheng G, Liang H, Yan Y, Shen X, Wang J, Sun X, Yuan Q (2022)
Biosynthesis of plant hemostatic dencichine in Escherichia coli.
Nature communications 13, 5492 [PubMed:36123371]
[show Abstract]

Cheng N, Paris V, Rao X, Wang X, Nakata PA (2022)
A conserved oxalyl-coenzyme A decarboxylase in oxalate catabolism.
Plant signaling & behavior 17, 2062555 [PubMed:35510715]
[show Abstract]

Wanders RJ, Komen J, Ferdinandusse S (2011)
Phytanic acid metabolism in health and disease.
Biochimica et biophysica acta 1811, 498-507 (Source: SUBMITTER) [PubMed:21683154]
[show Abstract]

Berthold CL, Toyota CG, Richards NG, Lindqvist Y (2008)
Reinvestigation of the catalytic mechanism of formyl-CoA transferase, a class III CoA-transferase.
The Journal of biological chemistry 283, 6519-6529 [PubMed:18162462]
[show Abstract]

Alberty RA (2003)
Standard transformed Gibbs energies of coenzyme A derivatives as functions of pH and ionic strength.
Biophysical chemistry 104, 327-334 [PubMed:12834851]
[show Abstract]

Blackmore MA, Quayle JR (1970)
Microbial growth on oxalate by a route not involving glyoxylate carboligase.
The Biochemical journal 118, 53-59 [PubMed:5472155]
[show Abstract]

Last Modified

28 March 2025

CHEBI:15535 - oxalyl-CoA

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