8-iso PROSTAGLANDIN E2

Details

• Internal ID: 8d21c0fc-54e5-4a95-94d8-a610d112c623
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: 7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)-5-oxocyclopentyl]hept-5-enoic acid
• SMILES (Canonical): CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
• SMILES (Isomeric): CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
• InChI: InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)
• InChI Key: XEYBRNLFEZDVAW-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.22497412 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 12

Synonyms

• 154170-57-7
• 7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)-5-oxocyclopentyl]hept-5-enoic acid
• FT-0603385
• FT-0638702
• FT-0639169
• FT-0639504
• D92169
• 7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)-5-oxo-cyclopentyl] hepta-5-enoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9681	96.81%
Caco-2	-	0.8312	83.12%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8162	81.62%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.7797	77.97%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6578	65.78%
P-glycoprotein inhibitior	-	0.8266	82.66%
P-glycoprotein substrate	-	0.6205	62.05%
CYP3A4 substrate	+	0.5971	59.71%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9502	95.02%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8553	85.53%
CYP inhibitory promiscuity	-	0.9725	97.25%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7224	72.24%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9686	96.86%
Skin irritation	+	0.5568	55.68%
Skin corrosion	-	0.8674	86.74%
Ames mutagenesis	-	0.8532	85.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.4917	49.17%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.7476	74.76%
skin sensitisation	-	0.8636	86.36%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8032	80.32%
Acute Oral Toxicity (c)	III	0.6983	69.83%
Estrogen receptor binding	+	0.8450	84.50%
Androgen receptor binding	+	0.8532	85.32%
Thyroid receptor binding	-	0.5652	56.52%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	-	0.7625	76.25%
PPAR gamma	+	0.6238	62.38%
Honey bee toxicity	-	0.9348	93.48%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1811	P34995	Prostanoid EP1 receptor	3.7 nM	EC50	via Super-PRED
CHEMBL1881	P43116	Prostanoid EP2 receptor	1.03 nM; 59 nM	Ki; EC50	via Super-PRED; via Super-PRED
CHEMBL1836	P35408	Prostanoid EP4 receptor	0.05 nM; 0.02 nM	EC50; EC50	via Super-PRED; via Super-PRED
CHEMBL1995	P43119	Prostanoid IP receptor	260 nM	IC50	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	10 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.89%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.17%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.59%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.28%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.51%	97.25%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	90.49%	96.00%
CHEMBL299	P17252	Protein kinase C alpha	89.68%	98.03%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	88.84%	92.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.28%	85.14%
CHEMBL1781	P11387	DNA topoisomerase I	88.17%	97.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.96%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.59%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.83%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	85.08%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	83.93%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.59%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.03%	100.00%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	81.60%	92.26%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.09%	99.23%
CHEMBL230	P35354	Cyclooxygenase-2	80.89%	89.63%
CHEMBL1902	P62942	FK506-binding protein 1A	80.89%	97.05%

Plants that contains it

• Cryptocarya chinensis
• Larix sibirica
• Populus balsamifera

Cross-Links

• PubChem: 158
• LOTUS: LTS0013966
• wikiData: Q105256018