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Structure Database (LMSD)

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Common Name

cyclohexane-1-carbonyl-CoA

Systematic Name

3'-phosphoadenosine 5'-{3-[(3R)-4-{[3-({2-[(cyclohexane-1-carbonyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-3-hydroxy-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}

Synonyms

Coenzyme A, S-cyclohexanecarboxylate
Cyclohexanecarboxyl-coa
Cyclohexanecarboxyl-coenzyme A
cyclohexane-1-carbonyl-coenzyme A
cyclohexane-1-carboxyl-coenzyme A

LM ID

LMFA07050312

Formula

C₂₈H₄₆N₇O₁₇P₃S

Exact Mass

Calculate m/z

877.188384

Sum Composition

CoA 7:1

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Cyclohexanoyl-coenzyme A (CHCoA) is an acyl-CoA that contains a cyclohexane group. It is the activated form of cyclohexane carboxylic acid (CHC) in R. palustris.¹ CHC is converted to CHCoA by a succinyl-CoA CHC CoA transferase, and CHCoA is then degraded by a dehydrogenase. CHCoA is converted to hippuric acid in submitochondrial fractions isolated from guinea pig liver.²

This information has been provided by Cayman Chemical

References

1. Svardakm, A.M., and Scheline, R.R. The aromatization of cyclohexanecarboxyl-CoA to hippuric acid by guinea pig liver mitochondria: submitochondrial localization. Mol. Cell. Biochem. 67(2), 181-188 (1985).

2. Kung, J.W., Meier, A.-K., Mergelsberg, M., et al. Enzymes involved in a novel anaerobic cyclohexane carboxylic acid degradation pathway. J. Bacteriol. 196(20), 3667-3674 (2014).

Reactions

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String Representations

InChiKey (Click to copy)

QRSKGVRHSLILFG-TYHXJLICSA-N

InChi (Click to copy)

InChI=1S/C28H46N7O17P3S/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35/h14-17,20-22,26,37-38H,3-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,20-,21-,22+,26-/m1/s1

SMILES (Click to copy)

[C@@H]1([C@H](O)[C@H](OP(=O)(O)O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)([C@@H](O)C(=O)NCCC(=O)NCCSC(C2CCCCC2)=O)C)O1)N1C=NC2C(N)=NC=NC1=2