CHEBI:1146900
362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API
1,327 compounds within 3 steps: 109 in 1, 446 in 2, 772 in 3
Three steps
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + malonyl-CoA + H(+) = (7Z,10Z,13Z,16Z)-3-oxodocosatetraenoyl-CoA + CO2 + CoA
- long-chain-fatty-acid-CoA ligase (stearate)
- 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
- 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-octadecanoyl-sn-glycero-3-phosphocholine
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosolOne of 10 routes
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- sn-glycerol 3-phosphate + (9Z)-octadecenoyl-CoA = 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 15 morecytosol
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z)-octadecadienoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z,12Z,15Z)-octadecatrienoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z,15Z)-octadecatrienoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA
- long-chain-fatty-acid-CoA ligase (stearate)
- glycerol-3-phosphate 1-O-acyltransferase (sn-glycerol-3-phosphate)
- 1-octadecanoyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosolOne of 2 routes
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = (6Z,9Z,12Z)-octadecatrienoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA
- long-chain-fatty-acid-CoA ligase (myristic acid)
- glycerol-3-phosphate 1-O-acyltransferase (myristoyl-CoA)
- 1-tetradecanoyl-sn-glycerol 3-phosphate + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-icosatetraenoyl-sn-glycero-3-phosphocholine + CoA
- 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serineReach from here →
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serine + CoA
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- a 1-acyl-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = a 1-acyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 2 routes
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphate + CoA
Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 2 routes
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-dodecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-dodecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-eicosanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-eicosanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA
- 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach from here →
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z)-octadecenoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + CoA
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA
- Carnitine O-Palmitoyltransferase
- (2E)-hexadecenoyl-CoA + NADPH + H(+) = hexadecanoyl-CoA + NADP(+)
- 2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + CoA
Catalysed by CPT1A, CPT1C, CPT1B, TECR and 1 morecytosolOne of 2 routes
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-hexadecanoyl-sn-glycero-3-phospho-L-serine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serine + CoA
- acyl-CoA:sphingosine N-acyltransferase
- 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(+)
- 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + 1-O-hexadecyl-sn-glycero-3-phosphocholine = 1-octadecanoyl-sn-glycero-3-phosphoethanolamine + 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine
Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moreGolgi apparatus
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- a 1-acyl-sn-glycero-3-phospho-L-serine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-L-serine + CoA
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- a 1-acyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + CoA
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoyl-CoA = a 1-acyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + CoA
- 1'-[1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + (9Z)-octadecenoyl-CoA = 1'-[1-acyl-2-(9Z)-octadecenoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA
- 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-(9Z)-octadecenoyl-sn-glycero-3-phospho]-glycerolReach from here →
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + (9Z)-octadecenoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-(9Z)-octadecenoyl-sn-glycero-3-phospho]-glycerol + CoA
- long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
- 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z,12Z)-octadecadienoyl-CoA = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA
- 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z)-octadecenoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphate + 1-hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-tetradecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoyl-CoA = 1-tetradecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA
- long-chain-fatty-acid-CoA ligase (stearate)
- octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoyl-CoA = 1-acyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA
- 1'-[1-acyl-2-hexadecanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
- Carnitine O-Palmitoyltransferase
- Utilized Transport
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
Catalysed by CPT1A, CPT1C, CPT1B, ALOX12Bcytosol, endoplasmic reticulum
- long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
- (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
- a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = a 1-acyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + CoA