propionyl-CoA

Three steps

• N-octadecanoylhexadecasphinganineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. hexadecasphinganine + octadecanoyl-CoA = N-octadecanoylhexadecasphinganine + CoA + H(+)

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphate = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• glycodeoxycholateReach from here →
  1. Propanoyl-CoA hydrolase
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. deoxycholoyl-CoA to glycodeoxycholate conversion

  Catalysed by ACOT7, SLC27A2, SLC27A5cytosolOne of 3 routes

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. Active Transport
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP2C9mitochondrial matrix, cytosol, endoplasmic reticulum

• sphinga-4E,14Z-dienineReach from here →
  1. Propanoyl-CoA hydrolase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = sphinga-4E,14Z-dienine + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by ACOT7, ASAH1, ACER2, ACER1 and 2 morecytosol, Golgi apparatus

• 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerolReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z,12Z)-octadecadienoyl-CoA = 1',3'-bis-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + octadecanoyl-CoA = a 1-acyl-2-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 5 morecytosol

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. Active Transport
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 23 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. Active Transport
  2. Utilized Transport
  3. unspecific monooxygenase (arachidonate)

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 22 moremitochondrial matrix, cytosol, endoplasmic reticulumOne of 3 routes

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• (9Z,12Z,15Z-octadecatrienoyl)-cholesterolReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + cholesterol = (9Z,12Z,15Z-octadecatrienoyl)-cholesterol + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• cholesteryl (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 7 morecytosol, endoplasmic reticulum

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. Active Transport
  2. Utilized Transport
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Amitochondrial matrix, cytosol, endoplasmic reticulum

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. Active Transport
  2. Utilized Transport
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Amitochondrial matrix, cytosol, endoplasmic reticulum

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. Active Transport
  2. Utilized Transport
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Amitochondrial matrix, cytosol, endoplasmic reticulum

• O-tetradecanoyl-(R)-carnitineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + (R)-carnitine = O-tetradecanoyl-(R)-carnitine + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• O-octadecanoyl-(R)-carnitineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 5 morecytosol

• O-eicosanoyl-(R)-carnitineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosol

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 5 morecytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 5 morecytosol

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 7 morecytosol, endoplasmic reticulumOne of 2 routes

• N-tetradecanoylglycineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• N-eicosanoylglycinateReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• N-docosanoylglycineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• N-hexacosanoylglycineReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 6 morecytosolOne of 2 routes

• an N(2)-acyl-L-glutamineReach from here →
  1. Propanoyl-CoA hydrolase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by ACOT7, ASAH1, ACER2, ACER1 and 3 morecytosol, Golgi apparatus

• (2E,5Z)-tetradecadienoyl-CoAReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (physeteric acid)
  3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 9 morecytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z)-hexadecadienoyl-CoAReach from here →
  1. Propanoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)
  3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)

  Catalysed by ACOT7, SLC27A2, ACSL4, ACSL3 and 9 morecytosol, mitochondrial matrixOne of 4 routes

• 3-methylmalateReach from here →
  1. propanoyl-CoA:carbon-dioxide ligase (ADP-forming)
  2. (S)-methylmalonyl-CoA + H(+) = propanoyl-CoA + CO2
  3. propanoyl-CoA + glyoxylate + H2O = 3-methylmalate + CoA + H(+)

  Catalysed by PCCA, PCCB, ECHDC1, CLYBLmitochondrial matrix

• cholesteryl (11Z)-octadecenoateReach from here →
  1. Propanoyl-CoA hydrolase
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by ACOT7, CPT1A, CPT1C, CPT1B and 1 morecytosol

• a 3-oxoacyl-CoAReach from here →
  1. Propanoyl-CoA hydrolase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

  Catalysed by ACOT7, ASAH1, ACER2, ACER1 and 5 morecytosol, Golgi apparatus

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Active Transport
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4F8mitochondrial matrix, cytosol, endoplasmic reticulum

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. Active Transport
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by ALOX15Bmitochondrial matrix, cytosol, endoplasmic reticulum

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Active Transport
  2. Utilized Transport
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by ALOX15Bmitochondrial matrix, cytosol, endoplasmic reticulum

• taurochenodeoxycholateReach from here →
  1. Propanoyl-CoA hydrolase
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. 3alpha,7alpha-dihydroxy-5beta-cholanoyl-CoA:taurine N-choloyltransferase

  Catalysed by ACOT7, ACAA1, SCP2, MYO5B and 1 morecytosol, peroxisomeOne of 5 routes

• 2-(1-hydroxyethyl)thiamine diphosphateReach from here →
  1. Propanoyl-CoA hydrolase
  2. transport of propanoate and pyruvate (cytosol to extracellular)
  3. pyruvate:thiamin diphosphate acetaldehydetransferase (decarboxylating)

  Catalysed by ACOT7, SLC16A4, SLC16A5, SLC16A3 and 6 morecytosol, extracellular space, mitochondrial matrix