Succinyl-CoA

Succinyl-CoA

Identifiers
CAS Number	604-98-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15380
ChemSpider	83179
ECHA InfoCard	100.009.163
MeSH	succinyl-coenzyme+A
PubChem	92133
InChI InChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20+,24-/m1/s1 Key: VNOYUJKHFWYWIR-ITIYDSSPSA-N InChI=1/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20+,24-/m1/s1 Key: VNOYUJKHFWYWIR-ITIYDSSPBJ
SMILES O=C(O)CCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O
Properties
Chemical formula	C25H40N7O19P3S
Molar mass	867.608
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Succinyl-Coenzyme A, abbreviated as Succinyl-CoA (/ˌsʌksᵻnəlˌkoʊˈeɪ/) or SucCoA, is a combination of succinic acid and coenzyme A.

Sources

It is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by α-ketoglutarate dehydrogenase through decarboxylation. During the process, coenzyme A is added.

With B12 as an enzymatic cofactor, it is also synthesized from propionyl CoA, the odd-numbered fatty acid, which cannot undergo beta-oxidation.^[1] Propionyl-CoA is carboxylated to D-methylmalonyl-CoA, isomerized to L-methylmalonyl-CoA, and rearranged to yield succinyl-CoA via a vitamin B₁₂-dependent enzyme. Succinyl-CoA is an intermediate of the citric acid cycle and can be readily incorporated there.

Fate

It is converted into succinate through the hydrolytic release of coenzyme A by succinyl-CoA synthetase (succinate thiokinase).

Another fate of succinyl-CoA is porphyrin synthesis, where succinyl-CoA and glycine are combined by ALA synthase to form δ-aminolevulinic acid (dALA).

Formation

Succinyl CoA can be formed from methylmalonyl CoA through the utilization of deoxyadenosyl-B₁₂ (deoxyadenosylcobalamin) by the enzyme methylmalonyl-CoA mutase. This reaction, which requires vitamin B₁₂ as a cofactor, is important in the catabolism of some branched-chain amino acids as well as odd-chain fatty acids.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

[[File:

[[<div style="display:block; width:30.1834671470831px; height:0px; overflow:hidden; position:relative; left:374.23731182425786px; top:602.398967699498px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:30.9999999999983px; height:0px; overflow:hidden; position:relative; left:466.4486251180706px; top:631.168519171318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:29.1504661757638px; height:0px; overflow:hidden; position:relative; left:816.8495338242362px; top:541.621487793808px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:41.841620626151px; height:0px; overflow:hidden; position:relative; left:649.9875435628912px; top:278.04945206398px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:33.7681761528873px; height:0px; overflow:hidden; position:relative; left:330.70153294231534px; top:297.610619807187px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:32.582089552239px; height:0px; overflow:hidden; position:relative; left:177.09689795536426px; top:425.87537485759px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:538.689173119075px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:88px; height:0px; overflow:hidden; position:relative; left:715.2163009404388px; top:401px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:503.0px; top:670.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:84.9238578680197px; height:0px; overflow:hidden; position:relative; left:692.0761421319803px; top:573.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:304.2323578810314px; top:716.549820282624px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:33.621221037988px; height:0px; overflow:hidden; position:relative; left:367.5646397813722px; top:175.627991937516px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:720.2375300176794px; top:702.001875326864px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:720.2375300176792px; top:682.337193696082px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:73.3148283021269px; height:0px; overflow:hidden; position:relative; left:258.0px; top:207.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:853.3602503491594px; top:486.042093313318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:853.3602503491594px; top:466.042093313318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:304.2323578810314px; top:696.549820282624px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:498.689173119076px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:48.2984700306043px; height:0px; overflow:hidden; position:relative; left:180.0px; top:310.519900497513px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:853.3602503491594px; top:506.042093313318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:720.2375300176792px; top:662.337193696082px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:70px; height:0px; overflow:hidden; position:relative; left:216.0px; top:374.674493554328px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:82px; height:0px; overflow:hidden; position:relative; left:264.0px; top:272.330227037402px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:61.4143272597748px; height:0px; overflow:hidden; position:relative; left:221.89453081488801px; top:475.826018808777px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:558.689173119075px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:52.4198466377163px; height:0px; overflow:hidden; position:relative; left:487.5801533622837px; top:199.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:47.2000923036619px; height:0px; overflow:hidden; position:relative; left:664.7999076963381px; top:198.406955168477px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:66px; height:0px; overflow:hidden; position:relative; left:277.0px; top:578px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:518.689173119076px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:174.797362167969px; height:0px; overflow:hidden; position:relative; left:111.0px; top:654.04700332349px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:154.310540655952px; height:0px; overflow:hidden; position:relative; left:575.6894593440477px; top:135.269018473869px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:170px; height:0px; overflow:hidden; position:relative; left:152.0px; top:124.074190177638px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:76px; height:0px; overflow:hidden; position:relative; left:682.0px; top:308.556556257706px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:46.2956622035883px; height:0px; overflow:hidden; position:relative; left:808.7043377964117px; top:363.951733482022px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:39px; height:0px; overflow:hidden; position:relative; left:813.9382716049388px; top:422.40772328832px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:36.5px; height:0px; overflow:hidden; position:relative; left:775.7640561670411px; top:541.621487793808px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:44.2885215390222px; height:0px; overflow:hidden; position:relative; left:670.9877017410322px; top:485.86403074685px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:41.8532982134678px; height:0px; overflow:hidden; position:relative; left:681.1902406172646px; top:427.288869264805px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:42.6019239578559px; height:0px; overflow:hidden; position:relative; left:692.5039932478962px; top:536.621487793808px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:28.5478699038022px; height:0px; overflow:hidden; position:relative; left:677.2474233020198px; top:598.540271103061px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:31.2611679545706px; height:0px; overflow:hidden; position:relative; left:642.4000247852737px; top:598.540271103061px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:32.9824561403508px; height:0px; overflow:hidden; position:relative; left:630.1160862354895px; top:693.89597205691px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:30.9999999999982px; height:0px; overflow:hidden; position:relative; left:466.4486251180698px; top:616.797517039126px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:30.1834671470831px; height:0px; overflow:hidden; position:relative; left:374.23731182425786px; top:588.027965567302px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:29.6136269214791px; height:0px; overflow:hidden; position:relative; left:289.5220258089487px; top:624.295539263445px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:70.9637798844278px; height:0px; overflow:hidden; position:relative; left:302.78215871956456px; top:542.264367816092px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:71.0094500492967px; height:0px; overflow:hidden; position:relative; left:302.75932363713014px; top:493.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:39.3831123868514px; height:0px; overflow:hidden; position:relative; left:278.6168876131486px; top:422.876981279349px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:29.7294003600621px; height:0px; overflow:hidden; position:relative; left:203.66666666666663px; top:343.688918684141px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:35.0113378684808px; height:0px; overflow:hidden; position:relative; left:290.45787084901383px; top:243.69018283712px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:28.2086167800452px; height:0px; overflow:hidden; position:relative; left:454.45588384607703px; top:173.001159642582px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:151px; height:0px; overflow:hidden; position:relative; left:103.0px; top:152.25px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:183px; height:0px; overflow:hidden; position:relative; left:310.0px; top:92px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:29.2970776041057px; height:0px; overflow:hidden; position:relative; left:659.0px; top:536.621487793808px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:27.0336779387258px; height:0px; overflow:hidden; position:relative; left:599.0px; top:693.89597205691px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:19.5546565671207px; height:0px; overflow:hidden; position:relative; left:466.350105337641px; top:690.298609635293px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:41.841620626151px; height:0px; overflow:hidden; position:relative; left:780.9875435628912px; top:330.04945206398px; background:transparent; border-top:3px blue solid"></div>]]

[[

]]

|{{{bSize}}}px|alt=TCA Cycle edit]]

TCA Cycle edit

1. The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

References

1. Halarnkar PP, Blomquist GJ (1989). "Comparative aspects of propionate metabolism". Comp. Biochem. Physiol., B. 92 (2): 227–31. doi:10.1016/0305-0491(89)90270-8. PMID 2647392.