1,2-Distearoyl-sn-glycerol

Details

• Internal ID: c967b4d2-0398-4425-91fe-604e1aa0a312
• Taxonomy: Lipids and lipid-like molecules > Glycerolipids > Diradylglycerols > Diacylglycerols > 1,2-diacylglycerols
• IUPAC Name: [(2S)-3-hydroxy-2-octadecanoyloxypropyl] octadecanoate
• SMILES (Canonical): CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC
• SMILES (Isomeric): CCCCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCCCCCCCCCCCC
• InChI: InChI=1S/C39H76O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37,40H,3-36H2,1-2H3/t37-/m0/s1
• InChI Key: UHUSDOQQWJGJQS-QNGWXLTQSA-N
• Popularity: 38 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₇₆O₅
• Molecular Weight: 625.00 g/mol
• Exact Mass: 624.56927552 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 16.20
• Atomic LogP (AlogP): 11.96
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 36

Synonyms

• 10567-21-2
• 1,2-Distearin, S-
• L-1,2-Distearin
• DIACYL GLYCEROL
• 1,2-dioctadecanoyl-sn-glycerol
• 1,2-di-O-stearoyl-sn-glycerol
• [(2S)-3-hydroxy-2-octadecanoyloxypropyl] octadecanoate
• DG(18:0/18:0/0:0)
• (S)-3-Hydroxypropane-1,2-diyl distearate
• T9379Q535O
• (2S)-3-hydroxypropane-1,2-diyl dioctadecanoate
• UNII-T9379Q535O
• Glyceryl 1,2-distearate, (S)-
• D-,-Distearin
• C39H76O5
• SN-1,2-DISTEARIN
• 1,2-Distearin-sn-glycerol
• (S)-1,2-distearoylglycerol
• SCHEMBL351875
• (S)-glyceryl 1,2-distearate
• (S)-1,2-dioctadecanoylglycerol
• Diacylglycerol(18:0/18:0)
• CHEBI:41847
• DTXSID20147249
• 1,2-DISTEARIN, (S)-
• (2S)-1,2-bis-O-stearylglycerol
• EX-A5413
• (-)-(S)-Glycerin-1,2-distearat
• STEARIN, 1,2-DI-, L-
• LMGL02010037
• AKOS040745090
• (S)-(-)-1,2-distearoyl-sn-glycerol
• (S)-2,3-bis-stearoyloxy-propan-1-ol
• BP-29830
• BS-44605
• DAG(18:0/18:0)
• HY-112552
• (2S)-3-hydroxypropane-1,2-diyl distearoate
• CS-0046351
• E78394
• Q27120437
• OCTADECANOIC ACID, (1S)-1-(HYDROXYMETHYL)-1,2-ETHANEDIYL ESTER
• OCTADECANOIC ACID, 1-(HYDROXYMETHYL)-1,2-ETHANEDIYL ESTER, (S)-
• Octadecanoic acid,1,1'-[(1R)-1-(hydroxymethyl)-1,2-ethanediyl] ester
• Octadecanoic acid,1,1'-[(1R)-1-(hydroxymethyl)-1,2-ethanediyl]ester
• OCTADECANOIC ACID, 1,1'-((1S)-1-(HYDROXYMETHYL)-1,2-ETHANEDIYL) ESTER

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9418	94.18%
Caco-2	-	0.7256	72.56%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8436	84.36%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.8909	89.09%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7229	72.29%
P-glycoprotein inhibitior	+	0.6100	61.00%
P-glycoprotein substrate	-	0.8682	86.82%
CYP3A4 substrate	-	0.5498	54.98%
CYP2C9 substrate	-	0.8120	81.20%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.7665	76.65%
CYP2C9 inhibition	-	0.8795	87.95%
CYP2C19 inhibition	-	0.8707	87.07%
CYP2D6 inhibition	-	0.9212	92.12%
CYP1A2 inhibition	-	0.8429	84.29%
CYP2C8 inhibition	-	0.9083	90.83%
CYP inhibitory promiscuity	-	0.9434	94.34%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7423	74.23%
Carcinogenicity (trinary)	Non-required	0.6455	64.55%
Eye corrosion	-	0.8757	87.57%
Eye irritation	+	0.5730	57.30%
Skin irritation	-	0.9051	90.51%
Skin corrosion	-	0.9815	98.15%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6322	63.22%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	+	0.6660	66.60%
skin sensitisation	-	0.9560	95.60%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.9667	96.67%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	+	0.5248	52.48%
Acute Oral Toxicity (c)	III	0.4658	46.58%
Estrogen receptor binding	+	0.7228	72.28%
Androgen receptor binding	-	0.9224	92.24%
Thyroid receptor binding	-	0.6219	62.19%
Glucocorticoid receptor binding	-	0.5748	57.48%
Aromatase binding	-	0.7109	71.09%
PPAR gamma	+	0.6086	60.86%
Honey bee toxicity	-	0.9633	96.33%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.7084	70.84%
Fish aquatic toxicity	+	0.8656	86.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL299	P17252	Protein kinase C alpha	40.1 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	97.09%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.93%	96.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	95.00%	97.29%
CHEMBL2581	P07339	Cathepsin D	93.80%	98.95%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	92.77%	85.94%
CHEMBL230	P35354	Cyclooxygenase-2	89.38%	89.63%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.76%	92.86%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.32%	95.17%
CHEMBL5255	O00206	Toll-like receptor 4	87.75%	92.50%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	87.67%	92.08%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.43%	96.95%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	85.14%	91.81%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.14%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.09%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.05%	91.19%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.78%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.24%	100.00%

Plants that contains it

• Sciadopitys verticillata

Cross-Links

• PubChem: 9543705
• LOTUS: LTS0184756
• wikiData: Q27120437