Linoleate (BioCAD00000013386)
blood cerebrospinal fluid (csf) feces saliva urine adipose tissue epidermis erythrocyte fibroblasts intestine kidney neuron placenta platelet prostate skeletal muscle spleen
Metabolite Card
Formula: C18H32O2 (280.2402)
SMILES: CCCCC\C=C/C\C=C/CCCCCCCC(O)=O
Synonyms [en]
linoleic acid; Linoleate; 9Z,12Z-octadecadienoic acid; cis,cis-Linoleic acid; (9Z,12Z)-Octadecadienoic acid; cis,cis-9,12-Octadecadienoic acid
Last reviewed on 2024-06-28.
Cite this Page
Linoleate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000013386). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by humans. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (From Stedman, 26th ed). Linoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
DBLinks
- CAS Registry Number: 60-33-3
- PubChem CID: 5280450
- ChEBI: 17351
- HMDB: HMDB0000673
- LipidMaps: LMFA01030120
- KEGG: C01595
- BioCyc: LINOLEIC_ACID
- NCBI MeSH: Linoleic Acid
- Wikipedia: Linoleic_acid
Other DBLinks
- CAS Registry Number: 2197-37-7
- CAS Registry Number: 506-21-8
- CAS Registry Number: 60-33-3
- CAS Registry Number: 6144-28-1
- CAS Registry Number: 8016-21-5
- CAS Registry Number: 8024-22-4
- CAS Registry Number: 80969-37-5
- CAS Registry Number: 85594-37-2
- PubChem: 3931
- PubChem: 4750
- PubChem: 5280450
- ChEBI: ChEBI:137735
- ChEBI: ChEBI:17351
- ChEBI: ChEBI:30245
- HMDB: HMDB0000673
- HMDB: HMDB00673
- LipidMaps: LMFA01030120
- KEGG: C01595
- BioCyc: LINOLEIC_ACID
- NCBI MeSH: Linoleic Acid
- Wikipedia: Linoleic acid
- Wikipedia: Linoleic_acid
- DrugBank: DB14104
- RefMet: RM0149976
- MoNA: BAF_UVA_POS000553
- MoNA: BAF_UVA_POS001464
- MoNA: CA000167
- MoNA: CCMSLIB00000479710
- MoNA: EMBL-MCF_spec347098
- MoNA: EQ331601
- MoNA: EQ331602
- MoNA: EQ331603
- MoNA: EQ331604
- MoNA: EQ331605
- MoNA: EQ331606
- MoNA: EQ331651
- MoNA: EQ331652
- MoNA: EQ331653
- MoNA: EQ331654
- MoNA: EQ331655
- MoNA: FiehnHILIC001299
- MoNA: FiehnHILIC002801
- MoNA: FiehnLib000703
- MoNA: HMDB0000673_c_ms_1870
- MoNA: HMDB0000673_ms_ms_286457
- MoNA: HMDB0000673_ms_ms_286458
- MoNA: HMDB0000673_ms_ms_286459
- MoNA: HMDB0000673_ms_ms_286460
- MoNA: HMDB0000673_ms_ms_286461
- MoNA: HMDB0000673_ms_ms_930
- MoNA: HMDB0000673_ms_ms_931
- MoNA: HMDB0000673_ms_ms_932
- MoNA: IA000127
- MoNA: IA000128
- MoNA: IA000129
- MoNA: IA000301
- MoNA: IA000302
- MoNA: IA000303
- MoNA: IA000496
- MoNA: IA000497
- MoNA: IA000498
- MoNA: KO001295
- MoNA: KO001296
- MoNA: KO001297
- MoNA: KO001298
- MoNA: KO001299
- MoNA: KZ000056
- MoNA: MetaboBASE1091
- MoNA: MetaboBASE1092
- MoNA: MetaboBASE1093
- MoNA: MetaboBASE1094
- MoNA: MetaboBASE1095
- MoNA: MoNA034672
- MoNA: MoNA034673
- MoNA: MoNA034675
- MoNA: MoNA038098
- MoNA: MT000114
- MoNA: PR010199
- MoNA: PS027801
- MoNA: PS027802
- MoNA: PS027803
- MoNA: PS027804
- MoNA: RP029501
- MoNA: RP029502
- MoNA: RP029503
- MoNA: RP029511
- MoNA: RP029512
- Metlin: METLIN_191
Class / Ontology
- WishartLab ClassyFire: [Lineolic acids and derivatives] Lineolic acids and derivatives
- RefMet: [Unsaturated FA] Unsaturated FA
- LipidMaps: [Unsaturated fatty acids [FA0103]] Unsaturated fatty acids [FA0103]
- ChEBI: [CHEBI:17351] linoleic acid
| ID | EC Number | Name |
|---|---|---|
| KEGG:R03626 | 1.13.11.12 | linoleate:oxygen 13-oxidoreductase |
| KEGG:R03627 | 5.2.1.5 | 9-cis,12-cis-octadecadienoate delta12-cis-delta11-trans-isomerase |
| KEGG:R05718 | 1.13.11.45 | linoleate:oxygen 11S-oxidoreductase |
| KEGG:R05740 | 1.14.19.39 | linoleate,ferrocytochrome-b5:oxygen oxidoreductase (12,13-dehydrogenating) |
| KEGG:R07055 | 1.14.14.1 | C01595 + C00007 + C00005 + C00080<=>C14825 + C00006 + C00001 |
| KEGG:R07056 | 1.14.14.1 | C01595 + C00007 + C00005 + C00080<=>C14826 + C00006 + C00001 |
| KEGG:R07057 | 1.13.11.58 | linoleate:oxygen 9-oxidoreductase |
| KEGG:R07061 | 1.13.11.60 | linoleate:oxygen (8R)-oxidoreductase |
| KEGG:R07063 | 1.14.19.3 | linoleoyl-CoA,hydrogen-donor:oxygen oxidoreductase |
| KEGG:R07064 | 3.1.1.4 | phosphatidylcholine 2-acylhydrolase |
| KEGG:R08177 | 3.1.2.2 | linoleoyl-CoA hydrolase |
| KEGG:R09811 | 1.13.11.62 | linoleate:oxygen (10R)-oxidoreductase |
| KEGG:R10577 | 1.13.11.77 | linoleate:oxygen (10S)-oxidoreductase |
| BioCyc:RXN-9673 | 6.2.1.3 | LINOLEIC_ACID + CO-A + ATP --> CPD-18 + PPI + AMP |
| BioCyc:LINOLEATE-ISOMERASE-RXN | 5.2.1.5 | LINOLEIC_ACID<=>9-CIS11-TRANS-OCTADECADIENOATE |
| BioCyc:RXN-22222 | 1.14.14.- | LINOLEIC_ACID + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> Vernolates + Ox-NADPH-Hemoprotein-Reductases + WATER |
| BioCyc:RXN-12760 | 1.13.11.61 | LINOLEIC_ACID + OXYGEN-MOLECULE --> CPD-13768 |
| BioCyc:RXN-16498 | 6.1.-.- | LINOLEIC_ACID + ATP + PROTON --> CPD-17731 + PPI |
| BioCyc:RXN-12761 | 1.13.11.62 | LINOLEIC_ACID + OXYGEN-MOLECULE --> CPD-13769 |
| BioCyc:RXN-12659 | 1.11.2.3 | CPD-8678 + LINOLEIC_ACID --> CPD-17614 + CPD-13636 |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| Plant Reactome:R-OAU-2744345 | Metabolism and regulation |
| Plant Reactome:R-TAE-2744344 | Secondary metabolism |
| Plant Reactome:R-MES-2744345 | Metabolism and regulation |
| Plant Reactome:R-MES-1119618 | 13-LOX and 13-HPL pathway |
| Plant Reactome:R-TDI-2744345 | Metabolism and regulation |
| Plant Reactome:R-TDI-1119618 | 13-LOX and 13-HPL pathway |
| Plant Reactome:R-DRO-2744345 | Metabolism and regulation |
| Plant Reactome:R-OGU-1119618 | 13-LOX and 13-HPL pathway |
| Plant Reactome:R-OMI-1119618 | 13-LOX and 13-HPL pathway |
| Plant Reactome:R-OMI-1119566 | Divinyl ether biosynthesis II (13-LOX) |
| Plant Reactome:R-PTI-2744345 | Metabolism and regulation |
| Plant Reactome:R-PTI-1119566 | Divinyl ether biosynthesis II (13-LOX) |
| Plant Reactome:R-GMA-2744345 | Metabolism and regulation |
| Plant Reactome:R-GMA-2744344 | Secondary metabolism |
| Plant Reactome:R-PDA-2744345 | Metabolism and regulation |
| Plant Reactome:R-PVU-2744345 | Metabolism and regulation |
| Plant Reactome:R-PVU-1119566 | Divinyl ether biosynthesis II (13-LOX) |
| Plant Reactome:R-BNA-1119566 | Divinyl ether biosynthesis II (13-LOX) |
| Plant Reactome:R-BRA-1119618 | 13-LOX and 13-HPL pathway |
| Plant Reactome:R-DCA-1119618 | 13-LOX and 13-HPL pathway |