Prostaglandin f1alpha

Details

• Internal ID: 7e4364cd-95ca-499f-ad8e-1f95d4870ae8
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acid
• SMILES (Canonical): CCCCCC(C=CC1C(CC(C1CCCCCCC(=O)O)O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1CCCCCCC(=O)O)O)O)O
• InChI: InChI=1S/C20H36O5/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/h12-13,15-19,21-23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-,19+/m0/s1
• InChI Key: DZUXGQBLFALXCR-CDIPTNKSSA-N
• Popularity: 332 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₆O₅
• Molecular Weight: 356.50 g/mol
• Exact Mass: 356.25627424 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 13

Synonyms

• Prostaglandin F1
• 745-62-0
• PGF1alpha
• PGF 1-alpha
• Prostaglandin f1-alpha
• Prostaglandin F1.alpha.
• MLS000069612
• 9S,11R,15S-trihydroxy-13E-prostaenoic acid
• CHEBI:28852
• prostaglandin F1a
• WJ72O6860W
• 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoic acid
• SMR000058791
• Cyclopentaneheptanoic acid, 3,5-dihydroxy-2-(3-hydroxy-1-octenyl)-
• Prost-13-en-1-oic acid,9,11,15-trihydroxy-, (9a,11a,13E,15S)-
• Protaglandin F1
• Prostaglandin F1 alpha
• PGF1
• UNII-WJ72O6860W
• Prostaglandin F1??
• Opera_ID_1669
• U 18714
• BSPBio_001492
• BML1-F09
• GTPL5412
• SCHEMBL1477281
• CHEMBL1325783
• Prostaglandin F1alpha, synthetic
• DTXSID901339475
• HMS1361K14
• HMS1791K14
• HMS1989K14
• HMS2231H22
• HMS3402K14
• HMS3648J19
• LMFA03010137
• (9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprost-13-en-1-oic acid
• AKOS040756112
• IDI1_033962
• PGF1 alpha (Prostaglandin F1 alpha )
• Prost-13-en-1-oic acid, 9,11,15-trihydroxy-, (9-alpha,11-alpha,13E,15S)
• NCGC00021875-03
• NCGC00021875-04
• NCGC00021875-05
• PGF1alpha, Prostaglandin F1alpha, powder
• C06475
• 9a,11a,15(S)-trihydroxy-13-trans-prostenoate
• SR-01000946441
• 9a,11a,15(S)-trihydroxy-13-trans-prostenoic acid
• SR-01000946441-1
• Q27088352
• (13E,15S)-9alpha,11alpha,15-trihydroxyprost-13-en-1-oic acid
• (+)-(9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprost-13-en-1-oic acid
• (13E,15S)-9alpha,11alpha-9,11,15-Trihydroxyprost-13-en-1-oic acid
• 3,5-dihydroxy-2-(3-hydroxy-1-octenyl)- (8CI)-cyclopentaneheptanoate
• 3,5-dihydroxy-2-(3-hydroxy-1-octenyl)- (8CI)-cyclopentaneheptanoic acid
• Prost-13-en-1-oic acid,9,11,15-trihydroxy-,(9a,11a,13e,15s)-
• 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxyoct-1-enyl)cyclopentyl)heptanoic acid
• PROST-13-EN-1-OIC ACID, 9,11,15-TRIHYDROXY-, (9-.ALPHA.,11-.ALPHA.,13E,15S)
• 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9523	95.23%
Caco-2	-	0.7456	74.56%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7055	70.55%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.8861	88.61%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9338	93.38%
BSEP inhibitior	-	0.6778	67.78%
P-glycoprotein inhibitior	-	0.8232	82.32%
P-glycoprotein substrate	-	0.6381	63.81%
CYP3A4 substrate	+	0.5673	56.73%
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	-	0.8011	80.11%
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	-	0.9615	96.15%
Skin irritation	+	0.5928	59.28%
Skin corrosion	-	0.8625	86.25%
Ames mutagenesis	-	0.9078	90.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.5283	52.83%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.6735	67.35%
skin sensitisation	-	0.7406	74.06%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8232	82.32%
Acute Oral Toxicity (c)	III	0.8014	80.14%
Estrogen receptor binding	+	0.8858	88.58%
Androgen receptor binding	-	0.4810	48.10%
Thyroid receptor binding	+	0.5979	59.79%
Glucocorticoid receptor binding	+	0.6400	64.00%
Aromatase binding	-	0.7742	77.42%
PPAR gamma	+	0.6871	68.71%
Honey bee toxicity	-	0.9451	94.51%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	+	0.5665	56.65%
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	97.73%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.97%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.37%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	93.68%	89.63%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.32%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.55%	91.11%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	90.02%	96.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.53%	100.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.45%	92.08%
CHEMBL340	P08684	Cytochrome P450 3A4	88.37%	91.19%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	87.78%	85.94%
CHEMBL299	P17252	Protein kinase C alpha	87.69%	98.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.28%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.17%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	86.89%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.65%	85.14%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.58%	97.29%
CHEMBL5255	O00206	Toll-like receptor 4	85.67%	92.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.57%	90.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.14%	95.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.05%	95.17%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	83.99%	92.32%
CHEMBL2514	O95665	Neurotensin receptor 2	83.64%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.01%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	82.98%	90.17%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.74%	82.50%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	82.25%	98.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.25%	91.81%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.70%	98.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.12%	96.47%
CHEMBL3629	P68400	Casein kinase II alpha	80.70%	98.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.37%	85.31%

Plants that contains it

• Larix sibirica

Cross-Links

• PubChem: 5280939
• LOTUS: LTS0061796
• wikiData: Q27088352