[(1R,2R,5S,9S,13S,14R,18S)-14-[(R)-acetyloxy(furan-3-yl)methyl]-8-ethoxy-3,16-dihydroxy-13,18-bis(2-methoxy-2-oxoethyl)-2,5,11,14-tetramethyl-7-methylperoxy-10,12,17-trioxahexacyclo[9.5.1.12,5.01,9.03,7.09,13]octadecan-6-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: db93a74c-a16d-4551-821d-ecbf00834908
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: [(1R,2R,5S,9S,13S,14R,18S)-14-[(R)-acetyloxy(furan-3-yl)methyl]-8-ethoxy-3,16-dihydroxy-13,18-bis(2-methoxy-2-oxoethyl)-2,5,11,14-tetramethyl-7-methylperoxy-10,12,17-trioxahexacyclo[9.5.1.12,5.01,9.03,7.09,13]octadecan-6-yl] (2S,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CCOC1C2(C(C3(CC2(C(C3CC(=O)OC)(C45C16C(C(CC4O)(C)C(C7=COC=C7)OC(=O)C)(OC(O5)(O6)C)CC(=O)OC)C)O)C)OC(=O)C8(C(O8)C)C)OOC
• SMILES (Isomeric): CCOC1[C@]23[C@@]4([C@@](CC([C@@]2([C@@]5([C@H]([C@@]6(CC5(C1(C6OC(=O)[C@@]7([C@H](O7)C)C)OOC)O)C)CC(=O)OC)C)OC(O4)(O3)C)O)(C)[C@@H](C8=COC=C8)OC(=O)C)CC(=O)OC
• InChI: InChI=1S/C40H54O18/c1-12-51-29-38(58-49-11)28(53-30(45)33(6)20(2)54-33)31(4)19-36(38,46)34(7,23(31)15-25(43)47-9)39-24(42)16-32(5,27(52-21(3)41)22-13-14-50-18-22)37(17-26(44)48-10)40(29,39)57-35(8,55-37)56-39/h13-14,18,20,23-24,27-29,42,46H,12,15-17,19H2,1-11H3/t20-,23+,24?,27-,28?,29?,31+,32-,33+,34-,35?,36?,37+,38?,39+,40+/m1/s1
• InChI Key: YFPOZFJELKYXGI-JINLTIMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₄O₁₈
• Molecular Weight: 822.80 g/mol
• Exact Mass: 822.33101487 g/mol
• Topological Polar Surface Area (TPSA): 227.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 18
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9626	96.26%
Caco-2	-	0.8443	84.43%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6214	62.14%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.7498	74.98%
OATP1B3 inhibitior	+	0.8569	85.69%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9840	98.40%
P-glycoprotein inhibitior	+	0.7815	78.15%
P-glycoprotein substrate	+	0.8132	81.32%
CYP3A4 substrate	+	0.7371	73.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	+	0.7450	74.50%
CYP2C9 inhibition	-	0.8133	81.33%
CYP2C19 inhibition	-	0.8092	80.92%
CYP2D6 inhibition	-	0.9123	91.23%
CYP1A2 inhibition	-	0.8099	80.99%
CYP2C8 inhibition	+	0.7590	75.90%
CYP inhibitory promiscuity	-	0.8489	84.89%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5443	54.43%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.8969	89.69%
Skin irritation	-	0.7274	72.74%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7271	72.71%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5342	53.42%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5133	51.33%
Acute Oral Toxicity (c)	I	0.3893	38.93%
Estrogen receptor binding	+	0.7445	74.45%
Androgen receptor binding	+	0.7737	77.37%
Thyroid receptor binding	+	0.6078	60.78%
Glucocorticoid receptor binding	+	0.7645	76.45%
Aromatase binding	+	0.7080	70.80%
PPAR gamma	+	0.7741	77.41%
Honey bee toxicity	-	0.6362	63.62%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9837	98.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.85%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.41%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.99%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.38%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.25%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.66%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.37%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.58%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.45%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.06%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.01%	95.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.83%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.77%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.69%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.59%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.36%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.72%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.54%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.81%	100.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.61%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.48%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.23%	97.21%
CHEMBL5028	O14672	ADAM10	81.79%	97.50%
CHEMBL3401	O75469	Pregnane X receptor	81.35%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.03%	91.07%

Plants that contains it

• Swietenia macrophylla

Cross-Links

• PubChem: 101486450
• LOTUS: LTS0189522
• wikiData: Q105347731