N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine

362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API

440 compounds within 3 steps: 2 in 1, 94 in 2, 344 in 3

Two steps

S-methylmercury-L-cysteineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. S-methylmercury-L-cysteine(in) + L-phenylalanine(out) = S-methylmercury-L-cysteine(out) + L-phenylalanine(in)
Catalysed by PM20D1, SLC7A8inner side of the membrane, outer side of the membraneOne of 2 routes
O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP
Catalysed by PM20D1, UGT1A9, UGT2B7, UGT1A6 and 3 more
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. fatty acylamide amidohydrolase
Catalysed by PM20D1, FAAHcytosol
Phe-tRNA(Phe)Reach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. L-Phenylalanine:tRNA(Ala) ligase (AMP-forming)
Catalysed by PM20D1, FARSB, FARSAcytosol
chlorine(.)Reach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. Transport of L-Phenylalanine by Atb0 Transporter
Catalysed by PM20D1, SLC6A14extracellular space, cytosolOne of 2 routes
L-aspartateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. L-aspartate(in) + L-phenylalanine(out) = L-aspartate(out) + L-phenylalanine(in)
Catalysed by PM20D1, SLC7A13inner side of the membrane, outer side of the membraneOne of 2 routes
fatty acidReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (10Z)-heptadecenoic acid formation
Catalysed by PM20D1cytosolOne of 4 routes
L-ornithineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. transport of ornithine and phenylalanine (cytosol to extracellular)
Catalysed by PM20D1, SLC7A6extracellular space, cytosolOne of 2 routes
2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerolReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. fatty acid amide hydrolase (2-arachidonoylglycerol)
Catalysed by PM20D1, FAAHcytosol
glycineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. transport of glycine and phenylalanine (cytosol to extracellular)
Catalysed by PM20D1, SLC7A5extracellular space, cytosolOne of 7 routes
(5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 8 more
prostaglandin H2Reach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. prostaglandin-endoperoxide synthase (arachidonate)
Catalysed by PM20D1, PTGS1, PTGS2cytosolOne of 3 routes
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
Catalysed by PM20D1, ALOX5, ALOX15, ALOX12
(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
Catalysed by PM20D1, ALOX15B, ALOX15, ALOX12
(5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
Catalysed by PM20D1, ALOX5
leukotriene A4Reach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = leukotriene A4 + H2O
Catalysed by PM20D1, ALOX5
L-dopaReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. L-dopa(out) + L-phenylalanine(in) = L-dopa(in) + L-phenylalanine(out)
Catalysed by PM20D1, SLC7A8inner side of the membrane, outer side of the membraneOne of 2 routes
L-histidineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. L-histidine(in) + L-phenylalanine(out) = L-histidine(out) + L-phenylalanine(in)
Catalysed by PM20D1, SLC7A8inner side of the membrane, outer side of the membraneOne of 2 routes
L-methionineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. transport of methionine and phenylalanine (cytosol to extracellular)
Catalysed by PM20D1, SLC7A5extracellular space, cytosolOne of 6 routes
L-tryptophanReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. transport of phenylalanine and tryptophan (cytosol to extracellular)
Catalysed by PM20D1, SLC7A5extracellular space, cytosolOne of 6 routes
L-kynurenineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. Transport of L-Kynurenine
Catalysed by PM20D1, SLC7A8extracellular space, cytosolOne of 2 routes
L-alanineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. transport of alanine and phenylalanine (cytosol to extracellular)
Catalysed by PM20D1, SLC7A5extracellular space, cytosolOne of 6 routes
L-asparagineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. transport of asparagine and phenylalanine (cytosol to extracellular)
Catalysed by PM20D1, SLC7A5extracellular space, cytosolOne of 3 routes
L-tyrosineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-phenylalanine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine
Catalysed by PM20D1, PAH
N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
Catalysed by PM20D1, FAAH
18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. cytochrome P450 (arachidonate)
Catalysed by PM20D1, CYP4F8endoplasmic reticulumOne of 2 routes
(12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
Catalysed by PM20D1, ALOX12B
(8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. Arachidonate:oxygen 8-oxidoreductase
Catalysed by PM20D1, ALOX12cytosolOne of 2 routes
2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. fatty acid amide hydrolase (arachidonate)
Catalysed by PM20D1, FAAHcytosol
20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. arachidonic acid:oxygen 1-oxidoreductase
Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2E1 and 24 morecytosolOne of 3 routes
11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by PM20D1, CYP2C9
19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2C9 and 2 more
(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O
Catalysed by PM20D1, PTGS2One of 2 routes
(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O
Catalysed by PM20D1, PTGS2One of 2 routes
(15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
Catalysed by PM20D1, PTGS2
11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. Arachidonate: oxygen 11-oxidoreductase
Catalysed by PM20D1, ALOX12cytosolOne of 2 routes
prostaglandin G2Reach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. Arachidonate:oxygen oxidoreductase
Catalysed by PM20D1, PTGS1, PTGS2endoplasmic reticulumOne of 2 routes
(12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (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 PM20D1, CYP2C9
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. unspecific monooxygenase (arachidonate)
Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2E1 and 24 morecytosolOne of 4 routes
8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. unspecific monooxygenase (arachidonate)
Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2E1 and 23 morecytosolOne of 3 routes
1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. 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 PM20D1, ABHD16A
1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. 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 PM20D1, ABHD16A
1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. 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 PM20D1, ABHD16A
(18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (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 PM20D1, CYP4F8
15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
Catalysed by PM20D1, ALOX15B
5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
Catalysed by PM20D1, ALOX15B

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine

Two steps

Three steps