Digalactosyldiacylglycerol

Details

• Internal ID: 74985983-979e-42b0-ba96-f1308943d455
• Taxonomy: Lipids and lipid-like molecules > Glycerolipids > Glycosylglycerols > 3-O-beta-D-digalactosyl-sn-glycerols
• IUPAC Name: [(2S)-1-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate
• SMILES (Canonical): CCCCCCCCCCCCCCCC(=O)OCC(COC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)OC(=O)CCCCCCCC=CCC=CCCCCC
• SMILES (Isomeric): CCCCCCCCCCCCCCCC(=O)OC[C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO[C@@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O)O)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC
• InChI: InChI=1S/C49H88O15/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-41(52)62-37(34-59-40(51)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)35-60-48-47(58)45(56)43(54)39(64-48)36-61-49-46(57)44(55)42(53)38(33-50)63-49/h11,13,17-18,37-39,42-50,53-58H,3-10,12,14-16,19-36H2,1-2H3/b13-11-,18-17-/t37-,38-,39-,42+,43+,44+,45+,46-,47-,48-,49+/m1/s1
• InChI Key: QZXMUPATKGLZAP-DXLAUQRQSA-N
• Popularity: 184 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₈₈O₁₅
• Molecular Weight: 917.20 g/mol
• Exact Mass: 916.61232210 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: 9.80
• Atomic LogP (AlogP): 6.38
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 38

Synonyms

• 145033-48-3
• [(2S)-1-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate
• DTXSID201103106
• AKOS040762954
• (2S)-3-[(1-Oxohexadecyl)oxy]-2-[[(9Z,12Z)-1-oxo-9,12-octadecadien-1-yl]oxy]propyl 6-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7132	71.32%
Caco-2	-	0.8604	86.04%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8693	86.93%
OATP2B1 inhibitior	-	0.7190	71.90%
OATP1B1 inhibitior	+	0.6989	69.89%
OATP1B3 inhibitior	+	0.8729	87.29%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9522	95.22%
P-glycoprotein inhibitior	+	0.7146	71.46%
P-glycoprotein substrate	-	0.7039	70.39%
CYP3A4 substrate	+	0.6358	63.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8842	88.42%
CYP3A4 inhibition	-	0.6581	65.81%
CYP2C9 inhibition	-	0.9063	90.63%
CYP2C19 inhibition	-	0.8214	82.14%
CYP2D6 inhibition	-	0.9174	91.74%
CYP1A2 inhibition	-	0.8886	88.86%
CYP2C8 inhibition	+	0.4608	46.08%
CYP inhibitory promiscuity	-	0.9371	93.71%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7486	74.86%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9010	90.10%
Skin irritation	-	0.7817	78.17%
Skin corrosion	-	0.9618	96.18%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7293	72.93%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7699	76.99%
skin sensitisation	-	0.9343	93.43%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6930	69.30%
Acute Oral Toxicity (c)	III	0.6197	61.97%
Estrogen receptor binding	+	0.8185	81.85%
Androgen receptor binding	-	0.6261	62.61%
Thyroid receptor binding	-	0.5774	57.74%
Glucocorticoid receptor binding	-	0.4947	49.47%
Aromatase binding	+	0.5622	56.22%
PPAR gamma	+	0.6511	65.11%
Honey bee toxicity	-	0.8618	86.18%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.7258	72.58%
Fish aquatic toxicity	+	0.9599	95.99%

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	99.04%	99.17%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	97.09%	85.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.93%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	96.07%	92.50%
CHEMBL2581	P07339	Cathepsin D	95.98%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.39%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	90.80%	92.08%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.30%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	89.26%	94.73%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.13%	83.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.18%	92.86%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	85.97%	92.32%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	85.92%	97.29%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.07%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.92%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.71%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.65%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.81%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.57%	94.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.77%	96.47%
CHEMBL299	P17252	Protein kinase C alpha	82.18%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.76%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	81.17%	90.17%

Plants that contains it

• Aconitum variegatum
• Arisaema amurense
• Hemionitis pteridioides
• Ipomoea batatas
• Kaempferia parviflora
• Lycium barbarum
• Ostrya carpinifolia
• Stephania dielsiana
• Vangueria agrestis

Cross-Links

• PubChem: 10724471
• NPASS: NPC272958
• LOTUS: LTS0130074
• wikiData: Q105232440