1-18:3-2-18:3-Digalactosyldiacylglycerol

Details

• Internal ID: df936db7-f545-4b72-a705-0ca67eadbbb1
• Taxonomy: Lipids and lipid-like molecules > Glycerolipids > Glycosylglycerols > 3-O-beta-D-digalactosyl-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-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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)COC2C(C(C(C(O2)CO)O)O)O)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[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\C/C=C\CC
• InChI: InChI=1S/C51H84O15/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-42(53)61-36-39(64-43(54)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)37-62-50-49(60)47(58)45(56)41(66-50)38-63-51-48(59)46(57)44(55)40(35-52)65-51/h5-8,11-14,17-20,39-41,44-52,55-60H,3-4,9-10,15-16,21-38H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-/t39-,40-,41-,44+,45+,46+,47+,48-,49-,50-,51+/m1/s1
• InChI Key: KDYAPQVYJXUQNY-OPHDRXFHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₈₄O₁₅
• Molecular Weight: 937.20 g/mol
• Exact Mass: 936.58102197 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: 7.90
• Atomic LogP (AlogP): 6.26
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 36

Synonyms

• 63142-69-8
• (9Z,9'Z,12Z,12'Z,15Z,15'Z)-(S)-3-(((2R,3R,4S,5R,6R)-3,4,5-Trihydroxy-6-((((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)propane-1,2-diyl bis(octadeca-9,12,15-trienoate)
• 18:3-18:3-DGDG
• 1-18:3-2-18:3-digalactosyldiacylglycerol
• starbld0004985
• CHEMBL1951711
• CHEBI:136795
• HY-143693
• CS-0374636
• Q42403316
• DGDG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
• digalactosyldiacylglycerol 18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)
• 1,2-di-(alpha-linolenoyl)-3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-sn-glycerol
• (2S)-3-[(6-O-alpha-D-galactopyranosyl-beta-D-galactopyranosyl)oxy]propane-1,2-diyl (9Z,12Z,15Z,9'Z,12'Z,15'Z)di-octadeca-9,12,15-trienoate
• 1,2-di-(9Z,12Z,15Z-octadecatrienoyl)-3-[alpha-D-galactosyl-(1->6)-beta-D-galactosyl]-sn-glycerol
• 1,2-di-O-alpha-linolenoyl-3-O-(6-O-alpha-galactopyranosyl-beta-galactopyranosyl)-sn-glycerol
• Bis[(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid](2S)-3-[[6-O-(alpha-D-galactopyranosyl)-beta-D-galactopyranosyl]oxy]propane-1,2-diyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8475	84.75%
Caco-2	-	0.8586	85.86%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8966	89.66%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.7360	73.60%
OATP1B3 inhibitior	+	0.9128	91.28%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9739	97.39%
P-glycoprotein inhibitior	+	0.7333	73.33%
P-glycoprotein substrate	-	0.7016	70.16%
CYP3A4 substrate	+	0.6371	63.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8842	88.42%
CYP3A4 inhibition	-	0.8326	83.26%
CYP2C9 inhibition	-	0.8990	89.90%
CYP2C19 inhibition	-	0.8588	85.88%
CYP2D6 inhibition	-	0.9202	92.02%
CYP1A2 inhibition	-	0.9091	90.91%
CYP2C8 inhibition	-	0.5735	57.35%
CYP inhibitory promiscuity	-	0.9334	93.34%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7422	74.22%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.8328	83.28%
Skin corrosion	-	0.9641	96.41%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7243	72.43%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7699	76.99%
skin sensitisation	-	0.9233	92.33%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8213	82.13%
Acute Oral Toxicity (c)	III	0.6501	65.01%
Estrogen receptor binding	+	0.7981	79.81%
Androgen receptor binding	-	0.5955	59.55%
Thyroid receptor binding	-	0.5052	50.52%
Glucocorticoid receptor binding	-	0.4693	46.93%
Aromatase binding	-	0.4850	48.50%
PPAR gamma	+	0.6935	69.35%
Honey bee toxicity	-	0.8212	82.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5424	54.24%
Fish aquatic toxicity	+	0.8410	84.10%

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	98.53%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.60%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	95.11%	92.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.19%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.30%	96.00%
CHEMBL220	P22303	Acetylcholinesterase	88.22%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.07%	94.73%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	84.98%	85.94%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	84.72%	92.32%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.13%	96.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.22%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.46%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.29%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.49%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.09%	86.33%

Plants that contains it

• Adenia volkensii
• Arabidopsis thaliana
• Baccharis angustifolia
• Bauhinia racemosa
• Capsicum annuum
• Carallia brachiata
• Euphorbia clarkeana
• Ipomoea batatas
• Lepidonia jonesii
• Lycium barbarum
• Monodora angolensis
• Ranunculus fluitans

Cross-Links

• PubChem: 57400365
• NPASS: NPC38295
• LOTUS: LTS0118050
• wikiData: Q42403316