Lipoteichoic acid

Details

• Internal ID: be012815-1430-4e44-ae7c-b0b688daa7ef
• Taxonomy: Lipids and lipid-like molecules > Glycerolipids > Glycosylglycerols > Glycosyldiacylglycerols
• IUPAC Name: [(2S)-1-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3-acetamido-5-amino-4-hydroxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-heptanoyloxypropan-2-yl] (E)-pentadec-7-enoate
• SMILES (Canonical): CCCCCCCC=CCCCCCC(=O)OC(COC1C(C(C(C(O1)CO)O)OC2C(C(C(C(O2)C)N)O)NC(=O)C)O)COC(=O)CCCCCC
• SMILES (Isomeric): CCCCCCC/C=C/CCCCCC(=O)O[C@@H](CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)C)N)O)NC(=O)C)O)COC(=O)CCCCCC
• InChI: InChI=1S/C39H70N2O13/c1-5-7-9-11-12-13-14-15-16-17-18-20-22-31(45)52-28(24-49-30(44)21-19-10-8-6-2)25-50-39-36(48)37(34(46)29(23-42)53-39)54-38-33(41-27(4)43)35(47)32(40)26(3)51-38/h14-15,26,28-29,32-39,42,46-48H,5-13,16-25,40H2,1-4H3,(H,41,43)/b15-14+/t26-,28-,29-,32+,33-,34-,35+,36-,37+,38+,39+/m1/s1
• InChI Key: PANDRCFROUDETH-YLSOAJEOSA-N
• Popularity: 1,637 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₇₀N₂O₁₃
• Molecular Weight: 775.00 g/mol
• Exact Mass: 774.48779029 g/mol
• Topological Polar Surface Area (TPSA): 226.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 27

Synonyms

• 56411-57-5
• [(2S)-1-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3-acetamido-5-amino-4-hydroxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-heptanoyloxypropan-2-yl] (E)-pentadec-7-enoate
• (2s)-1-({3-O-[2-(Acetylamino)-4-Amino-2,4,6-Trideoxy-Beta-D-Galactopyranosyl]-Alpha-D-Glucopyranosyl}oxy)-3-(Heptanoyloxy)propan-2-Yl (7z)-Pentadec-7-Enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9069	90.69%
Caco-2	-	0.8638	86.38%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6125	61.25%
OATP2B1 inhibitior	-	0.7193	71.93%
OATP1B1 inhibitior	+	0.7623	76.23%
OATP1B3 inhibitior	+	0.9125	91.25%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9484	94.84%
P-glycoprotein inhibitior	+	0.7105	71.05%
P-glycoprotein substrate	+	0.6529	65.29%
CYP3A4 substrate	+	0.6850	68.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.5724	57.24%
CYP2C9 inhibition	-	0.8912	89.12%
CYP2C19 inhibition	-	0.8523	85.23%
CYP2D6 inhibition	-	0.9102	91.02%
CYP1A2 inhibition	-	0.9290	92.90%
CYP2C8 inhibition	+	0.6295	62.95%
CYP inhibitory promiscuity	-	0.9046	90.46%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6343	63.43%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9105	91.05%
Skin irritation	-	0.7716	77.16%
Skin corrosion	-	0.9389	93.89%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6859	68.59%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.6200	62.00%
skin sensitisation	-	0.8792	87.92%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5190	51.90%
Acute Oral Toxicity (c)	III	0.6868	68.68%
Estrogen receptor binding	+	0.7956	79.56%
Androgen receptor binding	-	0.5658	56.58%
Thyroid receptor binding	-	0.5903	59.03%
Glucocorticoid receptor binding	+	0.5778	57.78%
Aromatase binding	+	0.5788	57.88%
PPAR gamma	+	0.6860	68.60%
Honey bee toxicity	-	0.7355	73.55%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.7548	75.48%
Fish aquatic toxicity	+	0.8738	87.38%

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	99.21%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.23%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.48%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.08%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	95.46%	92.50%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	94.53%	97.29%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.99%	95.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.73%	83.00%
CHEMBL299	P17252	Protein kinase C alpha	91.49%	98.03%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.93%	93.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	90.89%	92.08%
CHEMBL3401	O75469	Pregnane X receptor	90.87%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	90.46%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.32%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.84%	89.00%
CHEMBL4374	Q9Y5X4	Photoreceptor-specific nuclear receptor	89.18%	85.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.99%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.38%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.40%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.91%	92.86%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.66%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.07%	97.09%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.95%	92.78%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.94%	89.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.63%	95.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.08%	96.90%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	80.66%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.12%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 137349712
• LOTUS: LTS0182233
• wikiData: Q104396002