Compound
(9Z,12Z)-octadecadienoate
An octadecadienoate with cis- double bonds at the 9- and 12- positions; the conjugate base of linoleic acid.
Definition from ChEBI (CHEBI:30245), read 2026-09-23. CC BY 4.0.
Structure
Loading the model…
- Class
- Organic compound, anion
- Formula
- C18H31O2
- Mass
- 279.444 g/mol
- Charge
- -1
- InChIKey
- OYHQOLUKZRVURQ-HZJYTTRNSA-M
- SMILES
- CCCCC/C=CC/C=CCCCCCCCC(=O)[O-]
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
18 entities
18 entities reached.
0 reported hops18 assembled from the scaffold
- PTGS2ProteinUNIPROT:P35354substrate ofInferred only336 paths56 endpoints
- FABP5ProteinUNIPROT:Q01469transported byInferred only101 paths93 endpoints
- PTGS1ProteinUNIPROT:P23219substrate ofInferred only88 paths22 endpoints
- CYP2C9ProteinUNIPROT:P11712metabolized byInferred only86 paths43 endpoints
- CD36ProteinUNIPROT:P16671transported byInferred only82 paths77 endpoints
- CYP3A4ProteinUNIPROT:P08684metabolized byInferred only53 paths53 endpoints
- CYP1A2ProteinUNIPROT:P05177metabolized byInferred only39 paths39 endpoints
- ALOX15ProteinUNIPROT:P16050substrate ofInferred only32 paths32 endpoints
- ACSL3ProteinUNIPROT:O95573substrate ofInferred only29 paths29 endpoints
- ALOX12ProteinUNIPROT:P18054substrate ofInferred only28 paths28 endpoints
- PLA2G6ProteinUNIPROT:O60733substrate ofInferred only23 paths23 endpoints
- ALOX15BProteinUNIPROT:O15296substrate ofInferred only11 paths11 endpoints
Show the remaining 6
- ABHD16AProteinUNIPROT:O95870substrate ofInferred only8 paths8 endpoints
- ACSBG2ProteinUNIPROT:Q5FVE4substrate ofInferred only6 paths6 endpoints
- SLC27A3ProteinUNIPROT:Q5K4L6substrate ofInferred only6 paths6 endpoints
- PNPLA8ProteinUNIPROT:Q9NP80substrate ofInferred only6 paths6 endpoints
- SLC27A6ProteinUNIPROT:Q9Y2P4transported byInferred only4 paths4 endpoints
- SLC27A4ProteinUNIPROT:Q6P1M0transported byInferred only2 paths2 endpoints
What the reference databases state
Chemical structure
- 11-hydroxy-(9Z,12Z)-octadecadienoate has the functional parent (9Z,12Z)-octadecadienoateCompoundChEBI CHEBI:136522Inferred only
- 13-hydroxy-(9Z,11E)-octadecadienoate has the functional parent (9Z,12Z)-octadecadienoateCompoundChEBI CHEBI:133819Inferred only
- 9-hydroxy-(10E,12Z)-octadecadienoate has the functional parent (9Z,12Z)-octadecadienoateCompoundChEBI CHEBI:133820Inferred only
- N-(9Z,12Z-octadecadienoyl)-glycine has the functional parent (9Z,12Z)-octadecadienoateCompoundChEBI CHEBI:150011Inferred only
Statements
37 statements
37 statements · 1 reference database · Subject: (9Z,12Z)-octadecadienoate · Sources: Rhea
- (9Z,12Z)-octadecadienoate is converted to (13S)-hydroperoxy-(9Z,11E)-octadecadienoateCompoundRhea RHEA:22780Inferred only
- (9S)-hydroperoxy-(10E,12Z)-octadecadienoate is converted to (9Z,12Z)-octadecadienoateCompoundRhea RHEA:30291Inferred only
- (9Z,12Z)-octadecadienoate is converted to (9S)-hydroperoxy-(10E,12Z)-octadecadienoateCompoundRhea RHEA:30291Inferred only
- (9Z,12Z)-octadecadienamide is converted to (9Z,12Z)-octadecadienoateCompoundRhea RHEA:63020Inferred only
- (9Z,12Z)-octadecadienoate is converted to (9Z,12Z)-octadecadienoyl-CoACompoundRhea RHEA:51852Inferred only
- (9Z,12Z)-octadecadienoate is converted to (9Z,12Z)-octadecadienoyl-CoACompoundRhea RHEA:33651Inferred only
- (9Z,12Z)-octadecadienoyl-CoA is converted to (9Z,12Z)-octadecadienoateCompoundRhea RHEA:40143Inferred only
- (9Z,12Z)-octadecadienoyl-CoA is converted to (9Z,12Z)-octadecadienoateCompoundRhea RHEA:51852Inferred only
- (9Z,12Z)-octadecadienoate is converted to 13-hydroperoxy-(9Z,11E)-octadecadienoateCompoundRhea RHEA:48848Inferred only
- (9Z,12Z)-octadecadienoate is metabolised by CYP1A2ProteinRhea RHEA:52284Inferred only
- (9Z,12Z)-octadecadienoate is metabolised by CYP2C9ProteinRhea RHEA:52500Inferred only
- (9Z,12Z)-octadecadienoate is metabolised by CYP2C9ProteinRhea RHEA:52504Inferred only
Show the remaining 25
- (9Z,12Z)-octadecadienoate is metabolised by CYP3A4ProteinRhea RHEA:52284Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of ABHD16AProteinRhea RHEA:44516Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of ACSBG2ProteinRhea RHEA:33651Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of ACSL3ProteinRhea RHEA:33651Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of ALOX12ProteinRhea RHEA:22780Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of ALOX15ProteinRhea RHEA:22780Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of ALOX15BProteinRhea RHEA:48848Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PLA2G6ProteinRhea RHEA:52812Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PNPLA8ProteinRhea RHEA:52812Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS1ProteinRhea RHEA:75451Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS1ProteinRhea RHEA:75459Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS1ProteinRhea RHEA:75455Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS1ProteinRhea RHEA:75447Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS2ProteinRhea RHEA:50864Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS2ProteinRhea RHEA:75451Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS2ProteinRhea RHEA:75455Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS2ProteinRhea RHEA:75459Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS2ProteinRhea RHEA:75447Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of PTGS2ProteinRhea RHEA:50860Inferred only
- (9Z,12Z)-octadecadienoate is a substrate of SLC27A3ProteinRhea RHEA:33651Inferred only
- (9Z,12Z)-octadecadienoate is transported by CD36ProteinRhea RHEA:45264Inferred only
- (9Z,12Z)-octadecadienoate is transported by FABP5ProteinRhea RHEA:45264Inferred only
- (9Z,12Z)-octadecadienoate is transported by SLC27A1ProteinRhea RHEA:45264Inferred only
- (9Z,12Z)-octadecadienoate is transported by SLC27A4ProteinRhea RHEA:45264Inferred only
- (9Z,12Z)-octadecadienoate is transported by SLC27A6ProteinRhea RHEA:45264Inferred only
Reactions
52 reactions
(9Z,12Z)-octadecadienoateCHEBI:17539
Reaction pageDirection not assertedBalanced
Rhea RHEA:17381CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+dioxygenCHEBI:57467
Reaction pageDirection not assertedBalanced
Rhea RHEA:18993CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+dioxygen(13S)-hydroperoxy-(9Z,11E)-octadecadienoate
Reaction pageLeft to rightBalanced
Rhea RHEA:22780CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+AH2+dioxygenCHEBI:14030+A+2water
Reaction pageDirection not assertedBalanced
Rhea RHEA:23456CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+dioxygenCHEBI:58659
Reaction pageDirection not assertedBalanced
Rhea RHEA:25395CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+dioxygen(9S)-hydroperoxy-(10E,12Z)-octadecadienoate
Reaction pageDirection not assertedBalanced
Rhea RHEA:30291CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+dioxygenCHEBI:63323
Reaction pageDirection not assertedBalanced
Rhea RHEA:31691CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+dioxygenCHEBI:63324
Reaction pageDirection not assertedBalanced
Rhea RHEA:31695CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+ATP(4-)+coenzyme A(4-)(9Z,12Z)-octadecadienoyl-CoA+AMP+diphosphate(3-)
Catalysed by ACSL3 or ACSBG2 or SLC27A3
Reaction pageLeft to rightBalanced
Rhea RHEA:33651CC BY 4.0Reference data
CHEBI:64032+waterethanolamine+(9Z,12Z)-octadecadienoate
Reaction pageDirection not assertedBalanced
Rhea RHEA:35567CC BY 4.0Reference data
(9Z,12Z)-octadecadienoate+dioxygenCHEBI:75346
Reaction pageDirection not assertedBalanced
Rhea RHEA:37919CC BY 4.0Reference data
1,2,3-tri-(9Z,12Z)-octadecadienoylglycerol+water1,3-di-(9Z,12Z)-octadecadienoylglycerol+(9Z,12Z)-octadecadienoate+hydron
Catalysed by PNPLA2
Reaction pageLeft to rightBalanced
Rhea RHEA:38403CC BY 4.0Reference data
Where it reaches
10 systems, 24 regions, 121 tissues, 147 transporter routes — routes, not measurements: transporters known to carry (9Z,12Z)-octadecadienoate are expressed there, and no source reports it arriving.
Loading the model…
Other names
11 names
Resolves to: (9Z,12Z)-octadecadienoate
- Also called
- (9Z,12Z)-9,12-octadecadienoic acid, ion(1-)(9Z,12Z)-9,12-octadecadienoic acid, ion(1−)(Z,Z)-9,12-octadecadienoic acid, ion(1-)(Z,Z)-9,12-octadecadienoic acid, ion(1−)cis-Delta(9,12)-octadecadienoatecis-Δ9,12-octadecadienoatecis,cis-9,12-octadecadienoatecis,cis-linoleatelinoleic acid, ion(1-)linoleic acid, ion(1−)
- Systematic name
- (9Z,12Z)-octadeca-9,12-dienoate