Lipid A

Details

• Internal ID: e10b25df-ff35-455c-91c1-440fc4f54b6b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Amino sugars > Acylaminosugars
• IUPAC Name: [(2R,3S,4R,5R,6R)-2-[[(2R,3R,4R,5S,6R)-3-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-6-(hydroxymethyl)-5-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-3-hydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-phosphonooxyoxan-4-yl] (3R)-3-hydroxytetradecanoate
• InChI: InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)/t75-,76-,77-,78-,79-,80-,87-,88-,89-,90-,91-,92-,93-,94-/m1/s1
• InChI Key: GZQKNULLWNGMCW-PWQABINMSA-N
• Popularity: 4,068 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉₄H₁₇₈N₂O₂₅P₂
• Molecular Weight: 1798.40 g/mol
• Exact Mass: 1798.22274800 g/mol
• Topological Polar Surface Area (TPSA): 406.00 Ų
• XlogP: 26.40
• Atomic LogP (AlogP): 20.60
• H-Bond Acceptor: 21
• H-Bond Donor: 10
• Rotatable Bonds: 84

Synonyms

• Diphosphoryl hexaacyl lipid A
• Lipid-A
• E. coli lipid A
• Epitope ID:135515
• synthetic E. coli lipid A
• SCHEMBL9625151
• CHEBI:47040
• CHEBI:134256
• GZQKNULLWNGMCW-PWQABINMSA-N
• Q27120766
• [(2R,3S,4R,5R,6R)-2-[[(2R,3R,4R,5S,6R)-3-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-6-(hydroxymethyl)-5-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-3-hydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-phosphonooxyoxan-4-yl] (3R)-3-hydroxytetradecanoate
• {[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid
• 2-deoxy-6-O-(2-deoxy-2-[(3R)-3-(dodecanoyloxy)tetradecanamido]-4-O-phosphono-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-beta-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-1-O-phosphono-alpha-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8107	81.07%
Caco-2	-	0.8564	85.64%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6240	62.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8361	83.61%
OATP1B3 inhibitior	+	0.9272	92.72%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9736	97.36%
P-glycoprotein inhibitior	+	0.7421	74.21%
P-glycoprotein substrate	+	0.6802	68.02%
CYP3A4 substrate	+	0.7179	71.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8700	87.00%
CYP3A4 inhibition	+	0.5870	58.70%
CYP2C9 inhibition	-	0.8207	82.07%
CYP2C19 inhibition	-	0.7753	77.53%
CYP2D6 inhibition	-	0.8888	88.88%
CYP1A2 inhibition	-	0.8682	86.82%
CYP2C8 inhibition	+	0.6104	61.04%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5788	57.88%
Eye corrosion	-	0.9786	97.86%
Eye irritation	-	0.8968	89.68%
Skin irritation	-	0.7645	76.45%
Skin corrosion	-	0.9210	92.10%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7781	77.81%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.5732	57.32%
skin sensitisation	-	0.8581	85.81%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.9281	92.81%
Acute Oral Toxicity (c)	III	0.5677	56.77%
Estrogen receptor binding	+	0.7916	79.16%
Androgen receptor binding	+	0.6927	69.27%
Thyroid receptor binding	+	0.5738	57.38%
Glucocorticoid receptor binding	+	0.6654	66.54%
Aromatase binding	+	0.6204	62.04%
PPAR gamma	+	0.7521	75.21%
Honey bee toxicity	-	0.6680	66.80%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5872	58.72%
Fish aquatic toxicity	+	0.8336	83.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	99.49%	97.29%
CHEMBL5255	O00206	Toll-like receptor 4	99.11%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.93%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	96.31%	92.86%
CHEMBL2581	P07339	Cathepsin D	94.72%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.38%	91.11%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	92.51%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.52%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.15%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.55%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.16%	96.61%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	88.99%	80.33%
CHEMBL340	P08684	Cytochrome P450 3A4	88.61%	91.19%
CHEMBL299	P17252	Protein kinase C alpha	88.17%	98.03%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.10%	82.50%
CHEMBL2996	Q05655	Protein kinase C delta	87.93%	97.79%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.92%	95.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.62%	96.47%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.27%	96.90%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.11%	93.56%
CHEMBL230	P35354	Cyclooxygenase-2	86.73%	89.63%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.72%	94.33%
CHEMBL256	P0DMS8	Adenosine A3 receptor	84.25%	95.93%
CHEMBL3776	Q14790	Caspase-8	83.77%	97.06%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.98%	94.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.71%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.49%	99.23%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.44%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.30%	96.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.00%	91.81%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.74%	95.89%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.51%	85.94%
CHEMBL2514	O95665	Neurotensin receptor 2	81.12%	100.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	81.05%	92.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.98%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.31%	89.05%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9877306
• LOTUS: LTS0113641
• wikiData: Q27120766