octadecanoate

Three steps

• 1-(9Z-octadecenoyl)-3-octadecanoyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 3-octadecanoyl-sn-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z-octadecenoyl)-3-octadecanoyl-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 1-octanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-octanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-dodecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-dodecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-octadecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-tetradecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-O-(9Z-octadecenyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-O-(9Z-octadecyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol

• 1-decanoyl-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• (5Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 2 routes

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by UGT1A9, UGT2B7, UGT1A6, UGT1A1 and 2 morecytosol, extracellular space

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 6 routes

• (7Z)-tetradecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 9 routes

• 3-oxo-(9Z)-eicosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. stearoyl-CoA 9-desaturase (stearoyl-CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase ((7Z)-octadecenoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 3 routes

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrix

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 2 routes

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. fatty acylamide amidohydrolase

  Catalysed by FAAHcytosol, extracellular space

• CHEBI:27540Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 14 morecytosolOne of 6 routes

• dodecanalReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 2 H+[r] + lauric acid[r] + NADH[r] = H2O[r] + NAD+[r] + dodecanal[r]

  Catalysed by ALDH3A2cytosol, extracellular space, endoplasmic reticulumOne of 3 routes

• CHEBI:28701Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, peroxisomeOne of 7 routes

• a fatty acidReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

• an N-acyl-(4R)-4-hydroxysphinganineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. dihydroceramide,ferrocytochrome b5:oxygen oxidoreductase (C4-hydroxylating)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 2 routes

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• (24S)-hydroxycholesterolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 more

• 12-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. alkane 1-monooxygenase (lauric acid)

  Catalysed by CYP4A11, CYP4A22cytosol, extracellular spaceOne of 2 routes

• cholesteryl hexadecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, peroxisome, endoplasmic reticulumOne of 2 routes

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• sphingosine 1-phosphateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  3. ATP:sphingosine 1-phosphotransferase

  Catalysed by ASAH1, ACER2, ASAH2, DBP and 2 morecytosolOne of 2 routes

• cholesteryl (9Z,12Z)-octadecadienoateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. (9Z,12Z)-octadecadienoyl-CoA + cholesterol = cholesteryl (9Z,12Z)-octadecadienoate + CoA

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 moreOne of 2 routes

• D-glucoseReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + H2O = N-octadecanoylsphing-4-enine + D-glucose

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 more

• 25-hydroxycholesterolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 moreOne of 3 routes

• N-octanoylsphing-4-enineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by ASAH1, ACER2, ASAH2, GBA1

• cholesteryl (9Z-octadecenoate)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. stearoyl-CoA desaturase (N-C18:0CoA -> N-C18:1CoA)
  3. Acyl-CoA:cholesterol O-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol, endoplasmic reticulumOne of 4 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  3. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2One of 2 routes

• a 1,3-diacylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acylglycerol + an acyl-CoA = a 1,3-diacylglycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• a 1,2-diacylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes

• (24R)-hydroxycholesterolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, GBA1 and 1 more

• taurineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes

• 1,2-di-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 3 routes

• 1,2-di-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 2-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 3 routes

• 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. fatty acid amide hydrolase (2-arachidonoylglycerol)

  Catalysed by FAAHcytosol, extracellular space

• an N-acylsphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. delta 4-desaturase, sphingolipid (dihydroceramide pool)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosolOne of 9 routes

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycerol + (9Z)-octadecenoyl-CoA = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosolOne of 4 routes

• 16-hydroxyhexadecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• glycineReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, mitochondrial matrixOne of 10 routes

• (R)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (stearate)
  2. Stearoyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA hydrolase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrix