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4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O

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catalystActivity	[CatalystActivity:1118281] monooxygenase activity of 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase (LOC_OS05G41440.1) [cytosol]
compartment	[Compartment:70101] cytosol
created	[InstanceEdit:1164949] Wu, Guanming, 2010-12-11
crossReference	[DatabaseIdentifier:1154334] EC-NUMBER:1.14.13.36 [DatabaseIdentifier:1145672] RiceCyc:RXN-2581
dbId	1120504
displayName	4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O
eventOf	[Pathway:R-OSA-1119316] Phenylpropanoid biosynthesis - Oryza sativa
followingEvent	[Reaction:R-OSA-1119735] caffeoylshikimate+coenzyme A->caffeoyl-CoA+shikimate - Oryza sativa
input	[SimpleEntity:R-ALL-1132067] 4-coumaroylshikimate [cytosol] [SimpleEntity:R-ALL-70106] H+ [cytosol] [SimpleEntity:R-ALL-29364] NADPH [cytosol] [SimpleEntity:R-ALL-29368] O2 [cytosol]
isInDisease	false
isInferred	false
modified	[InstanceEdit:11540225] Elser, Justin, 2025-03-27
name	4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O RXN-2581 biochemicalReaction86166
orthologousEvent	[Reaction:R-NCO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Nymphaea colorata [Reaction:R-STU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Solanum tuberosum [Reaction:R-SIN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Sesamum indicum [Reaction:R-MGU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Erythranthe guttata [Reaction:R-OGU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza glumaepatula [Reaction:R-OBR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza brachyantha [Reaction:R-OLO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza longistaminata [Reaction:R-SHI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Salvia hispanica [Reaction:R-VRA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Vigna radiata [Reaction:R-CSI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Citrus sinensis [Reaction:R-PAB-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Picea abies [Reaction:R-BRA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Brassica rapa [Reaction:R-AHY-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Arachis hypogaea [Reaction:R-FEX-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Fraxinus excelsior (European ash) [Reaction:R-OGL-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza glaberrima [Reaction:R-GMA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Glycine max [Reaction:R-EGR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Eucalyptus grandis [Reaction:R-CRU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Capsella rubella [Reaction:R-SIT-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Setaria italica [Reaction:R-OBA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza barthii [Reaction:R-SMO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Selaginella moellendorffii [Reaction:R-TTU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Triticum turgidum [Reaction:R-ALY-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Arabidopsis lyrata [Reaction:R-SBI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Sorghum bicolor [Reaction:R-PTI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Populus trichocarpa [Reaction:R-OAU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza australiensis [Reaction:R-LST-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Lathyrus sativus [Reaction:R-VFA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Vicia faba var. faba [Reaction:R-JCU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Jatropha curcas [Reaction:R-CAN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Capsicum annuum [Reaction:R-TAE-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Triticum aestivum [Reaction:R-LPR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Lolium perenne [Reaction:R-TSP-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Triticum spelta subsp. spelta [Reaction:R-BOL-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Brassica oleracea [Reaction:R-ZJA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Zoysia japonica [Reaction:R-MAC-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Musa acuminata [Reaction:R-VAN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Vigna angularis [Reaction:R-ECG-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Echinochloa crus-galli [Reaction:R-PVE-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Pistacia vera [Reaction:R-MTR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Medicago truncatula [Reaction:R-PED-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Phyllostachys edulis [Reaction:R-OSI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza sativa Indica Group [Reaction:R-ATA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Aegilops tauschii [Reaction:R-BVU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Beta vulgaris [Reaction:R-MES-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Manihot esculenta [Reaction:R-ATH-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Arabidopsis thaliana [Reaction:R-MDO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Malus domestica [Reaction:R-PTA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Pinus taeda [Reaction:R-DRO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Dioscorea rotundata [Reaction:R-ETE-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Eragrostis tef [Reaction:R-CSA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Cucumis sativus [Reaction:R-VUN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Vigna unguiculata [Reaction:R-HLH-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Humulus lupulus [Reaction:R-OES-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Olea europaea var. sylvestris [Reaction:R-MPO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Marchantia polymorpha [Reaction:R-ZMA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Zea mays [Reaction:R-BNA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Brassica napus [Reaction:R-ACH-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Actinidia chinensis [Reaction:R-CCD-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Cynara cardunculus var. scolymus [Reaction:R-SLY-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Solanum lycopersicum [Reaction:R-CSC-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Cannabis sativa [Reaction:R-HLP-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Humulus lupulus var. lupulus [Reaction:R-CML-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Cucumis melo [Reaction:R-CLA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Citrullus lanatus [Reaction:R-TCA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Theobroma cacao [Reaction:R-CCL-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Citrus clementina [Reaction:R-NAT-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Nicotiana attenuata [Reaction:R-VVN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Vitis vinifera [Reaction:R-PPE-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Prunus persica [Reaction:R-NNU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Nelumbo nucifera [Reaction:R-HAN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Helianthus annuus [Reaction:R-CCN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Coffea canephora [Reaction:R-PDA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Phoenix dactylifera [Reaction:R-CST-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Camelina sativa [Reaction:R-BJU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Brassica juncea [Reaction:R-OOF-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza officinalis [Reaction:R-TTI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Triticum timopheevii subsp. timopheevii [Reaction:R-GRA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Gossypium raimondii [Reaction:R-FCR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Ficus carica [Reaction:R-QSU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Quercus suber [Reaction:R-PHA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Panicum hallii ("FIL2") [Reaction:R-ATR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Amborella trichopoda [Reaction:R-OPU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza punctata [Reaction:R-OME-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza meridionalis [Reaction:R-SVI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Setaria viridis [Reaction:R-CSK-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Cannabis sativa subsp. indica [Reaction:R-PVU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Phaseolus vulgaris [Reaction:R-COL-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Corchorus olitorius [Reaction:R-ACO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Ananas comosus [Reaction:R-PSO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Papaver somniferum [Reaction:R-OMI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza minuta [Reaction:R-OEU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Olea europaea [Reaction:R-OGR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza meyeriana var. granulata [Reaction:R-ZMY-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Zea mays ver5 [Reaction:R-JRE-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Juglans regia [Reaction:R-ITR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Ipomoea triloba [Reaction:R-LAN-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Lupinus angustifolius [Reaction:R-AHA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Arabidopsis halleri [Reaction:R-ADU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Arachis duranensis [Reaction:R-PPA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Physcomitrella patens [Reaction:R-SSP-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Saccharum spontaneum [Reaction:R-AIP-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Arachis ipaensis [Reaction:R-CCA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Cajanus cajan [Reaction:R-TPR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Trifolium pratense [Reaction:R-DEX-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Digitaria exilis [Reaction:R-CCP-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Corchorus capsularis [Reaction:R-CAR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Cicer arietinum [Reaction:R-TDI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Triticum dicoccoides [Reaction:R-ASA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Avena sativa [Reaction:R-DCA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Daucus carota [Reaction:R-GSO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Glycine soja [Reaction:R-PSA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Pisum sativum [Reaction:R-ORU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza rufipogon [Reaction:R-CCI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Corymbia citriodora [Reaction:R-LPE-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Leersia perrieri [Reaction:R-AUM-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Aegilops umbellulata [Reaction:R-RCH-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Rosa chinensis [Reaction:R-TUR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Triticum urartu [Reaction:R-LSA-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Lactuca sativa [Reaction:R-PHH-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Panicum hallii var. hallii ("HAL2") [Reaction:R-ONI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Oryza nivara [Reaction:R-ECU-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Eragrostis curvula [Reaction:R-PAV-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Prunus avium [Reaction:R-FVE-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Fragaria vesca [Reaction:R-BDI-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Brachypodium distachyon [Reaction:R-QLO-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Quercus lobata [Reaction:R-SCR-1120504] 4-coumaroylshikimate+NADPH+O2->caffeoylshikimate+NADP++H2O - Secale cereale
output	[SimpleEntity:R-ALL-1130902] caffeoylshikimate [cytosol] [SimpleEntity:R-ALL-29356] H2O [cytosol] [SimpleEntity:R-ALL-29366] NADP+ [cytosol]
precedingEvent	[Reaction:R-OSA-1121060] 4-coumaroyl-CoA+shikimate+coumaroyl-CoA->4-coumaroylshikimate+coenzyme A - Oryza sativa
reviewed	[InstanceEdit:2958715] Dharmawardhana, DP, 2012-12-31
schemaClass	Reaction
species	[Species:186860] Oryza sativa
stId	R-OSA-1120504

Referrals

(hasEvent)	[Pathway:R-OSA-1119316] Phenylpropanoid biosynthesis - Oryza sativa
(precedingEvent)	[Reaction:R-OSA-1119735] caffeoylshikimate+coenzyme A->caffeoyl-CoA+shikimate - Oryza sativa