3-[[(1R,14R,16R,18R,19R,20S)-18-(acetyloxymethyl)-14-hexyl-19-hydroxy-3-oxo-2,15,17-trioxabicyclo[14.4.0]icosan-20-yl]oxy]-3-oxopropanoic acid

Details

• Internal ID: 0fa0ca42-6021-4799-9fec-876ba41c420a
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: 3-[[(1R,14R,16R,18R,19R,20S)-18-(acetyloxymethyl)-14-hexyl-19-hydroxy-3-oxo-2,15,17-trioxabicyclo[14.4.0]icosan-20-yl]oxy]-3-oxopropanoic acid
• SMILES (Canonical): CCCCCCC1CCCCCCCCCCC(=O)OC2C(C(C(OC2O1)COC(=O)C)O)OC(=O)CC(=O)O
• SMILES (Isomeric): CCCCCC[C@@H]1CCCCCCCCCCC(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O1)COC(=O)C)O)OC(=O)CC(=O)O
• InChI: InChI=1S/C29H48O11/c1-3-4-5-12-15-21-16-13-10-8-6-7-9-11-14-17-24(33)39-28-27(40-25(34)18-23(31)32)26(35)22(19-36-20(2)30)38-29(28)37-21/h21-22,26-29,35H,3-19H2,1-2H3,(H,31,32)/t21-,22-,26-,27+,28-,29-/m1/s1
• InChI Key: SYNHBEBSRWLJAG-BTLXJWPCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₈O₁₁
• Molecular Weight: 572.70 g/mol
• Exact Mass: 572.31966234 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 4.20
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8814	88.14%
Caco-2	-	0.7642	76.42%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8509	85.09%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.8201	82.01%
OATP1B3 inhibitior	+	0.8923	89.23%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7571	75.71%
BSEP inhibitior	+	0.8600	86.00%
P-glycoprotein inhibitior	+	0.6265	62.65%
P-glycoprotein substrate	+	0.5183	51.83%
CYP3A4 substrate	+	0.6576	65.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8782	87.82%
CYP3A4 inhibition	-	0.7452	74.52%
CYP2C9 inhibition	-	0.9594	95.94%
CYP2C19 inhibition	-	0.9051	90.51%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	-	0.9044	90.44%
CYP2C8 inhibition	+	0.5152	51.52%
CYP inhibitory promiscuity	-	0.9885	98.85%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7341	73.41%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.8364	83.64%
Skin irritation	-	0.7869	78.69%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	-	0.7978	79.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5725	57.25%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5021	50.21%
skin sensitisation	-	0.9369	93.69%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7165	71.65%
Acute Oral Toxicity (c)	III	0.5981	59.81%
Estrogen receptor binding	+	0.7709	77.09%
Androgen receptor binding	-	0.6115	61.15%
Thyroid receptor binding	-	0.6543	65.43%
Glucocorticoid receptor binding	+	0.6251	62.51%
Aromatase binding	+	0.5238	52.38%
PPAR gamma	+	0.6347	63.47%
Honey bee toxicity	-	0.8844	88.44%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5557	55.57%
Fish aquatic toxicity	+	0.8907	89.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.83%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.53%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	94.79%	92.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.72%	91.11%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	92.90%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	92.79%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.13%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.33%	92.62%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.29%	96.38%
CHEMBL5957	P21589	5'-nucleotidase	90.19%	97.78%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.63%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.50%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.78%	95.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.69%	83.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	87.59%	93.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.17%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.00%	95.89%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	83.73%	80.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.69%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	82.62%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.41%	89.00%
CHEMBL2514	O95665	Neurotensin receptor 2	82.41%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.27%	95.56%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.80%	82.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.14%	100.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	81.06%	91.81%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.79%	96.00%
CHEMBL1968	P07099	Epoxide hydrolase 1	80.19%	98.57%

Plants that contains it

• Silene gallica

Cross-Links

• PubChem: 101519841
• LOTUS: LTS0145109
• wikiData: Q105263671