alpha-Glyceryl linoleate

Details

• Internal ID: 50635fdb-17a0-4c6f-b07f-3707fd6eedef
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
• IUPAC Name: [(2S)-2,3-dihydroxypropyl] (9Z,12Z)-octadeca-9,12-dienoate
• SMILES (Canonical): CCCCCC=CCC=CCCCCCCCC(=O)OCC(CO)O
• SMILES (Isomeric): CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO)O
• InChI: InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m0/s1
• InChI Key: WECGLUPZRHILCT-GSNKCQISSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₈O₄
• Molecular Weight: 354.50 g/mol
• Exact Mass: 354.27700969 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.70
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 17

Synonyms

• alpha-Glyceryl linoleate
• alpha-Monolinolein
• 1-linoleoyl-sn-glycerol
• 1-Monolinolein
• CHEBI:75561
• [(2S)-2,3-dihydroxypropyl] (9Z,12Z)-octadeca-9,12-dienoate
• 1-Linoleylglycerol
• 67968-46-1
• EINECS 218-901-4
• Oleinate 288
• 3-O-(9Z,12Z-Octadecadienoyl)glycerol
• 2,3-Dihydroxypropyl 9,12-octadecadienoate
• (+-)-2,3-Dihydroxypropyl 9(Z),12(Z)-octadecadienoate
• 1-Linoleoyl Glycerol
• MGG581HK1Y
• 2277-28-3
• Corn glycerides
• glycerin linoleate
• 1-glyceryl ester
• 1-linoleoyl-glycerol
• Glyceryl oleolinoleate
• (S)-1-monolinolein
• Maisine 35-1
• (+)-1-Monolinolein
• Linoleic acid glyceride
• sn-1-monolinoleoylglycerol
• UNII-MGG581HK1Y
• (S)-1-O-linoleoylglycerol
• 1-linoleoyl-sn-monoglyceride
• 1-LG
• CHEMBL188361
• SCHEMBL4350267
• MAG(18:2n6/0:0)
• MAG(18:2w6/0:0)
• MG(18:2n6/0:0)
• MG(18:2w6/0:0)
• 1-(9Z,12Z)-octadecadienoyl-sn-glycerol
• 1-(9Z,12Z-octadecadienoyl)-sn-glycerol
• BP-29878
• MAG(18:2/0:0)
• A17081
• MG(18:2/0:0)
• Linoleic acid, monoester with 1,2,3-propanetriol
• 9,12-Octadecadienoic acid, 2,3-dihydroxypropyl ester
• MG (18:2(n-6)/0:0/0:0)
• Q27145395
• MG(18:2(9Z,12Z)/0:0/0:0)
• (2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate
• 9,12-Octadecadienoic acid (Z,Z)-, 2,3-dihydroxy propyl ester
• 9,12-Octadecadienoic acid, monoester with 1,2,3-propanetriol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9325	93.25%
Caco-2	-	0.5726	57.26%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7531	75.31%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.7110	71.10%
OATP1B3 inhibitior	+	0.9268	92.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5125	51.25%
P-glycoprotein inhibitior	-	0.6909	69.09%
P-glycoprotein substrate	-	0.8766	87.66%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.7936	79.36%
CYP2C9 inhibition	-	0.8962	89.62%
CYP2C19 inhibition	-	0.8604	86.04%
CYP2D6 inhibition	-	0.9025	90.25%
CYP1A2 inhibition	-	0.6270	62.70%
CYP2C8 inhibition	-	0.8487	84.87%
CYP inhibitory promiscuity	-	0.9439	94.39%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.7190	71.90%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.6338	63.38%
Skin irritation	-	0.8264	82.64%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3994	39.94%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.9170	91.70%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	-	0.9778	97.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8560	85.60%
Acute Oral Toxicity (c)	IV	0.6238	62.38%
Estrogen receptor binding	+	0.6424	64.24%
Androgen receptor binding	-	0.9099	90.99%
Thyroid receptor binding	+	0.5201	52.01%
Glucocorticoid receptor binding	-	0.5641	56.41%
Aromatase binding	-	0.8064	80.64%
PPAR gamma	+	0.6623	66.23%
Honey bee toxicity	-	0.9652	96.52%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6089	60.89%
Fish aquatic toxicity	+	0.8677	86.77%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	98.72%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	97.59%	89.63%
CHEMBL2581	P07339	Cathepsin D	96.85%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.51%	96.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	95.71%	97.29%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	94.97%	85.94%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.72%	92.08%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	90.76%	92.86%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.50%	96.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.52%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.76%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.06%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	83.42%	91.81%
CHEMBL1781	P11387	DNA topoisomerase I	83.32%	97.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.17%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.83%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.61%	94.33%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.73%	100.00%

Plants that contains it

• Angelica dahurica
• Crotalaria crispata
• Nelumbo nucifera

Cross-Links

• PubChem: 6436630
• NPASS: NPC127091
• ChEMBL: CHEMBL188361
• LOTUS: LTS0103981
• wikiData: Q27145395