1,2-Di-O-alpha-linolenoyl-3-O-beta-galactopyranosyl-sn-glycerol

Details

• Internal ID: 3221a67b-48ab-4313-9bd1-5a940dd662f6
• Taxonomy: Lipids and lipid-like molecules > Glycerolipids > Glycosylglycerols > Glycosyldiacylglycerols > 1,2-diacyl-3-O-beta-D-galactosyl-sn-glycerols
• IUPAC Name: [(2S)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• SMILES (Canonical): CCC=CCC=CCC=CCCCCCCCC(=O)OCC(COC1C(C(C(C(O1)CO)O)O)O)OC(=O)CCCCCCCC=CCC=CCC=CCC
• SMILES (Isomeric): CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)OC(=O)CCCCCCC/C=C\C/C=C\C/C=C\CC
• InChI: InChI=1S/C45H74O10/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(47)52-36-38(37-53-45-44(51)43(50)42(49)39(35-46)55-45)54-41(48)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,38-39,42-46,49-51H,3-4,9-10,15-16,21-37H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-/t38-,39-,42+,43+,44-,45-/m1/s1
• InChI Key: QUZHZFAQJATMCA-QAZQWDDOSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₄O₁₀
• Molecular Weight: 775.10 g/mol
• Exact Mass: 774.52819855 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 10.00
• Atomic LogP (AlogP): 8.44
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 33

Synonyms

• 1,2-Di-O-alpha-linolenoyl-3-O-beta-galactopyranosyl-sn-glycerol
• (9Z,9'Z,12Z,12'Z,15Z,15'Z)-(S)-3-(((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propane-1,2-diyl bis(octadeca-9,12,15-trienoate)
• beta-D-Galactopyranoside, (2S)-2,3-bis[[(9Z,12Z,15Z)-1-oxo-9,12,15-octadecatrien-1-yl]oxy]propyl
• CCRIS 8067
• CHEMBL504351
• SCHEMBL2582163
• DTXSID901120179
• 18:3-18:3-MGDG
• 1-18:3-2-18:3-monogalactosyldiacylglycerol
• 3-O-beta-Galactopyranosyl-sn-glycerol, 1,2-Di-O-alpha-linolenoyl
• 1,2-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol
• (2S)-2,3-Bis[[(9Z,12Z,15Z)-1-oxo-9,12,15-octadecatrien-1-yl]oxy]propyl beta-D-galactopyranoside
• [(2S)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8101	81.01%
Caco-2	-	0.8406	84.06%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.9009	90.09%
OATP2B1 inhibitior	-	0.7168	71.68%
OATP1B1 inhibitior	+	0.7272	72.72%
OATP1B3 inhibitior	+	0.9343	93.43%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9765	97.65%
P-glycoprotein inhibitior	+	0.7401	74.01%
P-glycoprotein substrate	-	0.7649	76.49%
CYP3A4 substrate	+	0.6178	61.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8842	88.42%
CYP3A4 inhibition	-	0.8445	84.45%
CYP2C9 inhibition	-	0.9017	90.17%
CYP2C19 inhibition	-	0.7957	79.57%
CYP2D6 inhibition	-	0.9029	90.29%
CYP1A2 inhibition	-	0.8928	89.28%
CYP2C8 inhibition	-	0.6241	62.41%
CYP inhibitory promiscuity	-	0.9532	95.32%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7727	77.27%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.8335	83.35%
Skin corrosion	-	0.9672	96.72%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6644	66.44%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.7699	76.99%
skin sensitisation	-	0.9097	90.97%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8297	82.97%
Acute Oral Toxicity (c)	III	0.6501	65.01%
Estrogen receptor binding	+	0.7898	78.98%
Androgen receptor binding	-	0.6426	64.26%
Thyroid receptor binding	-	0.5672	56.72%
Glucocorticoid receptor binding	-	0.5231	52.31%
Aromatase binding	-	0.5232	52.32%
PPAR gamma	+	0.6323	63.23%
Honey bee toxicity	-	0.8322	83.22%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5424	54.24%
Fish aquatic toxicity	+	0.7667	76.67%

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	98.58%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.51%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	94.32%	92.50%
CHEMBL2581	P07339	Cathepsin D	93.34%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.83%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.48%	96.00%
CHEMBL220	P22303	Acetylcholinesterase	88.42%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	84.86%	94.73%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	84.27%	85.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.27%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.04%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.64%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.53%	96.47%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.49%	92.32%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.17%	93.56%

Plants that contains it

• Amaranthus tricolor
• Arabidopsis thaliana
• Capsicum annuum
• Ipomoea batatas
• Lepidonia jonesii
• Monodora angolensis
• Ranunculus fluitans
• Rosa canina
• Sonchus arvensis

Cross-Links

• PubChem: 21582567
• NPASS: NPC236649
• LOTUS: LTS0098315
• wikiData: Q104667635