(3S)-5-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R)-4-[(1S)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxyoxan-4-yl]oxy-3-hydroxy-3-methyl-5-oxopentanoic acid

Details

• Internal ID: 43b55dad-0b51-4f0a-8f90-d63216c84d49
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: (3S)-5-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R)-4-[(1S)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxyoxan-4-yl]oxy-3-hydroxy-3-methyl-5-oxopentanoic acid
• SMILES (Canonical): CC1=CC(=O)CC(C1CCC(C)OC2C(C(C(C(O2)CO)O)OC(=O)CC(C)(CC(=O)O)O)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@@H]1CC[C@@H](C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)OC(=O)C[C@](C)(CC(=O)O)O)O)(C)C
• InChI: InChI=1S/C25H40O11/c1-13-8-15(27)9-24(3,4)16(13)7-6-14(2)34-23-21(32)22(20(31)17(12-26)35-23)36-19(30)11-25(5,33)10-18(28)29/h8,14,16-17,20-23,26,31-33H,6-7,9-12H2,1-5H3,(H,28,29)/t14-,16-,17-,20-,21-,22+,23-,25+/m1/s1
• InChI Key: QGINILJTTLZGAD-ILOGMZITSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₀O₁₁
• Molecular Weight: 516.60 g/mol
• Exact Mass: 516.25706209 g/mol
• Topological Polar Surface Area (TPSA): 180.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.70
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7881	78.81%
Caco-2	-	0.8212	82.12%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8817	88.17%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.8183	81.83%
OATP1B3 inhibitior	+	0.8387	83.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5067	50.67%
BSEP inhibitior	-	0.7982	79.82%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5341	53.41%
CYP3A4 substrate	+	0.6907	69.07%
CYP2C9 substrate	-	0.8050	80.50%
CYP2D6 substrate	-	0.9035	90.35%
CYP3A4 inhibition	-	0.7352	73.52%
CYP2C9 inhibition	-	0.7585	75.85%
CYP2C19 inhibition	-	0.8446	84.46%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	-	0.6382	63.82%
CYP inhibitory promiscuity	-	0.9193	91.93%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9828	98.28%
Carcinogenicity (trinary)	Non-required	0.7344	73.44%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9434	94.34%
Skin irritation	-	0.6219	62.19%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5205	52.05%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6623	66.23%
skin sensitisation	-	0.8714	87.14%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6724	67.24%
Acute Oral Toxicity (c)	III	0.6820	68.20%
Estrogen receptor binding	+	0.6011	60.11%
Androgen receptor binding	-	0.5452	54.52%
Thyroid receptor binding	+	0.5628	56.28%
Glucocorticoid receptor binding	+	0.6050	60.50%
Aromatase binding	+	0.6778	67.78%
PPAR gamma	+	0.5210	52.10%
Honey bee toxicity	-	0.7764	77.64%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9598	95.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.07%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.86%	97.25%
CHEMBL2581	P07339	Cathepsin D	97.82%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.01%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	94.59%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	94.18%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.97%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.87%	94.23%
CHEMBL3401	O75469	Pregnane X receptor	87.16%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.03%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.40%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	85.93%	92.50%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.61%	83.57%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.59%	96.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.16%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.63%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.02%	96.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.80%	91.07%
CHEMBL5028	O14672	ADAM10	81.70%	97.50%

Plants that contains it

• Allium obliquum

Cross-Links

• PubChem: 163037562
• LOTUS: LTS0054232
• wikiData: Q105220078