2-[(3Z,4R)-2-[(3S,4R,5S,6S)-4-[(4R,5Z)-4-(carboxymethyl)-5-ethylidene-6-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carbonyl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-ethylidene-5-methoxycarbonyl-4H-pyran-4-yl]acetic acid

Details

• Internal ID: e3f44489-b7ec-4fa6-882f-a9c3f93fab15
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: 2-[(3Z,4R)-2-[(3S,4R,5S,6S)-4-[(4R,5Z)-4-(carboxymethyl)-5-ethylidene-6-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carbonyl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-ethylidene-5-methoxycarbonyl-4H-pyran-4-yl]acetic acid
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC3C(C(OC(C3O)OC4C(=CC)C(C(=CO4)C(=O)OC)CC(=O)O)CO)O)CC(=O)O
• SMILES (Isomeric): C/C=C\1/[C@H](C(=COC1OC2[C@H]([C@@H]([C@H]([C@@H](O2)CO)O)O)O)C(=O)O[C@@H]3[C@H]([C@@H](OC([C@H]3O)OC4/C(=C\C)/[C@H](C(=CO4)C(=O)OC)CC(=O)O)CO)O)CC(=O)O
• InChI: InChI=1S/C33H44O21/c1-4-12-14(6-20(36)37)16(28(45)47-3)10-48-31(12)54-33-26(44)27(23(41)19(9-35)51-33)52-29(46)17-11-49-30(13(5-2)15(17)7-21(38)39)53-32-25(43)24(42)22(40)18(8-34)50-32/h4-5,10-11,14-15,18-19,22-27,30-35,40-44H,6-9H2,1-3H3,(H,36,37)(H,38,39)/b12-4-,13-5-/t14-,15-,18+,19+,22+,23+,24-,25+,26+,27-,30?,31?,32?,33?/m1/s1
• InChI Key: LVQWSJLRSMOALG-VVEMHLHGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₂₁
• Molecular Weight: 776.70 g/mol
• Exact Mass: 776.23750841 g/mol
• Topological Polar Surface Area (TPSA): 324.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -3.10
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8377	83.77%
Caco-2	-	0.8726	87.26%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6791	67.91%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.6972	69.72%
OATP1B3 inhibitior	+	0.9388	93.88%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5518	55.18%
P-glycoprotein inhibitior	+	0.6916	69.16%
P-glycoprotein substrate	-	0.6332	63.32%
CYP3A4 substrate	+	0.6165	61.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8889	88.89%
CYP3A4 inhibition	-	0.9179	91.79%
CYP2C9 inhibition	-	0.9042	90.42%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9185	91.85%
CYP1A2 inhibition	-	0.9393	93.93%
CYP2C8 inhibition	+	0.5609	56.09%
CYP inhibitory promiscuity	-	0.9464	94.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6744	67.44%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9107	91.07%
Skin irritation	-	0.8067	80.67%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4075	40.75%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.7716	77.16%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6639	66.39%
Acute Oral Toxicity (c)	III	0.6639	66.39%
Estrogen receptor binding	+	0.8074	80.74%
Androgen receptor binding	+	0.6839	68.39%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6991	69.91%
Aromatase binding	+	0.5721	57.21%
PPAR gamma	+	0.7327	73.27%
Honey bee toxicity	-	0.8051	80.51%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.6335	63.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.20%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.12%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.24%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.02%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.94%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.63%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.41%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.97%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.36%	85.14%
CHEMBL5028	O14672	ADAM10	82.26%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.41%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.58%	92.50%

Plants that contains it

• Olea europaea

Cross-Links

• PubChem: 163188167
• LOTUS: LTS0138686
• wikiData: Q105158000