2,3-dinor-8-epi-prostaglandin F2alpha

Details

• Internal ID: b16fe5ae-9f4e-40a3-b86e-3c55d4e09241
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: (Z)-5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]pent-3-enoic acid
• SMILES (Canonical): CCCCCC(C=CC1C(CC(C1CC=CCC(=O)O)O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@H]1C/C=C\CC(=O)O)O)O)O
• InChI: InChI=1S/C18H30O5/c1-2-3-4-7-13(19)10-11-15-14(16(20)12-17(15)21)8-5-6-9-18(22)23/h5-6,10-11,13-17,19-21H,2-4,7-9,12H2,1H3,(H,22,23)/b6-5-,11-10+/t13-,14-,15+,16-,17+/m0/s1
• InChI Key: IDKLJIUIJUVJNR-JSEKUSAISA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₀O₅
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.20932405 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.26
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• 2,3-dinor-8-epi-prostaglandin F2alpha
• 2,3-DI-NOR-8-ISOPROSTAGLANDIN F2A
• 2,3-Dinor-8-iso PGF2alpha
• 2,3-Dinor-8-iso-PGF2alpha
• 2,3-Dinor-8-iso prostaglandin F2alpha
• (Z)-5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]pent-3-enoic acid
• 9S,11R,15S-trihydroxy-2,3-dinor-5Z,13E-prostadienoic acid-cyclo[8S,12R]
• 2,3-Dinor-8-isoPGF2alpha
• SCHEMBL2340561
• 2,3-Dinor iPF2.alpha.-III
• 2,3-Dinor-8-isoPGF2.alpha.
• CHEBI:34230
• IDKLJIUIJUVJNR-JSEKUSAISA-N
• DTXSID601315377
• LMFA03110010
• 2,3-dinor-8-iso Prostaglandin F2 alpha
• 2,3-Dinor-8-isoprostaglandin-F2.alpha.
• PD021085
• SR-01000946853
• SR-01000946853-1
• Q27115927
• (5Z,13E,15S)-9alpha,11alpha,15-trihydroxy-2,3-dinor-8beta-prosta-5,13-dien-1-oic acid
• 9.alpha.,11.alpha.,15S-Trihydroxy-2,3-dinor-(8.beta.)-prosta-5Z,13E-dien-1-oic acid
• (3Z)-5-{(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl}pent-3-enoic acid
• 3-Pentenoic acid, 5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-1-octen-1-yl]cyclopentyl]-, (3Z)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9523	95.23%
Caco-2	-	0.7682	76.82%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7055	70.55%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8518	85.18%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9338	93.38%
BSEP inhibitior	-	0.6345	63.45%
P-glycoprotein inhibitior	-	0.8527	85.27%
P-glycoprotein substrate	-	0.6893	68.93%
CYP3A4 substrate	+	0.5791	57.91%
CYP2C9 substrate	-	0.5844	58.44%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.7994	79.94%
CYP2C9 inhibition	-	0.9105	91.05%
CYP2C19 inhibition	-	0.8133	81.33%
CYP2D6 inhibition	-	0.9211	92.11%
CYP1A2 inhibition	-	0.8299	82.99%
CYP2C8 inhibition	-	0.8154	81.54%
CYP inhibitory promiscuity	-	0.9098	90.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7417	74.17%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9345	93.45%
Skin irritation	+	0.5928	59.28%
Skin corrosion	-	0.8625	86.25%
Ames mutagenesis	-	0.7478	74.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5510	55.10%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.7406	74.06%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7858	78.58%
Acute Oral Toxicity (c)	III	0.8014	80.14%
Estrogen receptor binding	+	0.8047	80.47%
Androgen receptor binding	+	0.5729	57.29%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5713	57.13%
Aromatase binding	-	0.6500	65.00%
PPAR gamma	+	0.6756	67.56%
Honey bee toxicity	-	0.9433	94.33%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5385	53.85%
Fish aquatic toxicity	+	0.9769	97.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.62%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.87%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.29%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.76%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	93.59%	89.63%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.35%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.16%	91.11%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	88.38%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.61%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.44%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.48%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.40%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.19%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.11%	97.29%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.00%	90.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.02%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.30%	90.17%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.21%	82.50%
CHEMBL299	P17252	Protein kinase C alpha	83.15%	98.03%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.69%	92.32%
CHEMBL2514	O95665	Neurotensin receptor 2	81.54%	100.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.36%	85.94%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	81.14%	92.08%
CHEMBL1881	P43116	Prostanoid EP2 receptor	81.00%	93.00%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	80.99%	95.58%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.87%	95.71%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.80%	97.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.10%	89.50%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 9548881
• LOTUS: LTS0230071
• wikiData: Q27115927