| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| December 3rd, 2005 | 20 | Yes |
Popular Name: Linoleic acid Linoleic acid
Find On: PubMed — Wikipedia — Google
CAS Numbers: 19704-83-7 , 3414-89-9 , 506-21-8 , 60-33-3 , 67674-19-5 , 822-17-3
(9Z,12Z)-Octadeca-9,12-dienoic acid
19704-83-7; Calcium linoleate (JAN); D01928
CHEBI:42395; CHEBI:6479; CHEBI:25047
Linoleic Acid (9c,12c) [60-33-3]
LINOLEIC ACID (9c,12c); [506-26-3]
LINOLEIC-9,10,12,13-D4 ACID; [79050-23-0]
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | 6.86 | 13.95 | -43.55 | 0 | 2 | -1 | 40 | 279.444 | 14 | ↓ |
| Lo Low (pH 4.5-6) | 6.86 | 11.98 | -5.39 | 1 | 2 | 0 | 37 | 280.452 | 14 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| Melting_Point | 12? | Alfa-Aesar |
| Melting_Point | 12° | Alfa-Aesar |
| Mp [°C] | 5 | Acros Organics |
| BP [°C] | 229 - 230 (p=16 torr) | Acros Organics |
| BP | 230 / 16 | TCI |
| Boiling_Point | 230?/16mm | Alfa-Aesar |
| Boiling_Point | 230°/16mm | Alfa-Aesar |
| Purity | 95% | Fluorochem |
| UniProt Database Links | ACBG2_HUMAN; ACBG2_MOUSE; ACBG2_RAT; ACSL1_CAVPO; ACSL1_HUMAN; ALOX8_MOUSE; COP4_COPC7; DOX1_ARATH; EXFAB_CHICK; EXFAB_COTJA; FAD12_CREAL; FAD12_MORAP; FAD12_MORIS; FADS1_HUMAN; FADS1_MOUSE; FADS1_PAPAN; FADS1_RAT; FADS2_BOVIN; FADS2_DANRE; FADS2_HUMAN; F | ChEBI |
| Patent Database Links | EP0803576; EP0870785; EP0947523; EP0962459; EP1375583; EP1493440; EP1498119; EP1508335; EP1529784; EP1547576; EP1557427; EP1559430; EP1570752; EP1582206; EP1600060; EP1609462; EP1614357; EP1618885; EP1621186; EP1629727; EP1632215; EP1632216; EP1634599; EP | ChEBI |
| H phrase | H315: Causes skin irritation | Acros Organics |
| H phrase | H315: Causes skin irritation; H319: Causes serious eye irritation; H335: May cause respiratory irritation | Acros Organics |
| P phrase | P261: Avoid breathing dust/fume/gas/mist/vapors/spray | Acros Organics |
| P phrase | P261: Avoid breathing dust/fume/gas/mist/vapors/spray; P302+ P352: IF ON SKIN: Wash with plenty of soap and water; P280: Wear protective gloves/protective clothing/eye protection/face protection; P305 + P351 + P338: IF IN EYES: Rinse cautiously with water | Acros Organics |
| R phrase | R36/37/38: Irritating to eyes, respiratory system and skin. | Acros Organics |
| Reactome Database Links | REACT_121204; REACT_160151; REACT_160208; REACT_160239; REACT_19175; REACT_23817 | ChEBI |
| S phrase | S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. | Acros Organics |
| S phrase | S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39: Wear suitable gloves and eye/face protection. | Acros Organics |
| Hazard | XI: Irritant | Acros Organics |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| FABP4-2-E | Fatty Acid Binding Protein Adipocyte (cluster #2 Of 3), Eukaryotic | Eukaryotes | 1000 | 0.42 | Binding ≤ 10μM |
| FABPH-3-E | Fatty Acid Binding Protein Muscle (cluster #3 Of 3), Eukaryotic | Eukaryotes | 1000 | 0.42 | Binding ≤ 10μM |
| LOX1-3-E | Seed Lipoxygenase-1 (cluster #3 Of 3), Eukaryotic | Eukaryotes | 1000 | 0.42 | Binding ≤ 10μM |
| FFAR1-1-E | Free Fatty Acid Receptor 1 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 540 | 0.44 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| FABP4_HUMAN | P15090 | Fatty Acid Binding Protein Adipocyte, Human | 1000 | 0.42 | Binding ≤ 1μM |
| FABPH_HUMAN | P05413 | Fatty Acid Binding Protein Muscle, Human | 1000 | 0.42 | Binding ≤ 1μM |
| LOX1_SOYBN | P08170 | Seed Lipoxygenase-1, Soybn | 1000 | 0.42 | Binding ≤ 1μM |
| FABP4_HUMAN | P15090 | Fatty Acid Binding Protein Adipocyte, Human | 1000 | 0.42 | Binding ≤ 10μM |
| FABPH_HUMAN | P05413 | Fatty Acid Binding Protein Muscle, Human | 1000 | 0.42 | Binding ≤ 10μM |
| LOX1_SOYBN | P08170 | Seed Lipoxygenase-1, Soybn | 1000 | 0.42 | Binding ≤ 10μM |
| FFAR1_HUMAN | O14842 | Free Fatty Acid Receptor 1, Human | 1800 | 0.40 | Functional ≤ 10μM |
| Description | Species |
|---|---|
| Activation of gene expression by SREBF (SREBP) | |
| BMAL1:CLOCK,NPAS2 activates circadian gene expression | |
| Circadian Clock | |
| Linoleic acid (LA) metabolism |
|
| PPARA activates gene expression | |
| Regulation of lipid metabolism by Peroxisome proliferator-activated receptor alp | |
| Retinoid metabolism and transport | |
| REV-ERBA represses gene expression | |
| RORA activates circadian gene expression | |
| The canonical retinoid cycle in rods (twilight vision) | |
| Transcriptional activation of mitochondrial biogenesis | |
| Transcriptional regulation of white adipocyte differentiation | |
| Transport of fatty acids | |
| YAP1- and WWTR1 (TAZ)-stimulated gene expression |
| Description | Species |
|---|---|
| Fatty Acids bound to GPR40 (FFAR1) regulate insulin secretion | |
| Free fatty acid receptors | |
| G alpha (q) signalling events | |
| Hormone-sensitive lipase (HSL)-mediated triacylglycerol hydrolysis | |
| Synthesis, secretion, and inactivation of Glucagon-like Peptide-1 (GLP-1) | |
| Synthesis, secretion, and inactivation of Glucose-dependent Insulinotropic Polyp | |
| Transcriptional regulation of white adipocyte differentiation |
