Dinoprost

Details

• Internal ID: 6e4ee045-126c-4583-a081-881aa405dc2f
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
• SMILES (Canonical): CCCCCC(C=CC1C(CC(C1CC=CCCCC(=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\CCCC(=O)O)O)O)O
• InChI: InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
• InChI Key: PXGPLTODNUVGFL-YNNPMVKQSA-N
• Popularity: 13,205 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.50 g/mol
• Exact Mass: 354.24062418 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

• prostaglandin F2alpha
• 551-11-1
• PGF2alpha
• Prostaglandin F2a
• amoglandin
• Enzaprost
• Protamodin
• panacelan
• l-PGF2-alpha
• Enzaprost F
• Prostaglandin F2 alpha
• Prostaglandin F2-alpha
• Dinoprosta
• Dinoprostum
• l-Prostaglandin F2-alpha
• Prostin F2alpha
• cyclosin
• Prostin F2-alpha
• PGF-2alpha
• PGF2 alpha
• PGF2-alpha
• Prosmon
• Prostarmon F
• 9alpha,11alpha-PGF2
• PGF2
• PGF2a
• U-14583
• CCRIS 4253
• Prostaglandin F2.alpha.
• HSDB 3315
• Dinoprostum [INN-Latin]
• U 14583
• Dinoprosta [INN-Spanish]
• UNII-B7IN85G1HY
• (+)-Prostaglandin F2alpha
• B7IN85G1HY
• Prostin F 2 alpha
• BRN 2225571
• DTXSID9022946
• CHEBI:15553
• CHEMBL815
• U-14,583
• 9a,11a-PGF2
• (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
• DTXCID602946
• (+)-Prostaglandin F2a
• (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)cyclopentyl)hept-5-enoic acid
• 7-(3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-5-heptenoic acid
• Dinaprost
• 5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, l-
• 5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, (1R-(1alpha(Z),2beta(S*,E),3alpha,5alpha))-
• NCGC00160385-01
• Dinoprostum (INN-Latin)
• Dinoprosta (INN-Spanish)
• DINOPROST (MART.)
• DINOPROST [MART.]
• (5Z,13E,15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dien-1-oic acid
• 9S,11R,15S-trihydroxy-5Z,13E-prostadienoic acid
• (5Z,13E)-(15S)-9alpha,11alpha,15-Trihydroxyprosta-5,13-dienoate
• PGF2.alpha.
• Prostaglandin F(sub 2a)
• 7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid
• (5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprosta-5,13-dien-1-oic acid
• (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• alpha, PGF2
• F2alpha, Prostaglandin
• 9alpha,11beta PGF2
• Dinoprost [USAN:INN:BAN:JAN]
• (+-)-PGF2alpha
• SR-01000721847
• (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid
• F2 alpha, Prostaglandin
• (+-)-PGF2-alpha
• dl-Prostaglandin F2-alpha
• PGF2-alpha racemic mixt.
• Prostaglandin F2alpha, dl-
• (5Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxyoct-1-en-1-yl)cyclopentyl)hept-5-enoic acid
• 9,11,15-Trihydroxyprosta-5,13-dien-1-oic acid
• Prosmon (TN)
• Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9alpha,11alpha,13E,15S)-
• Prostaglandin-F2alpha
• 15-epi PGF2alpha
• Prostaglandin F2-alpha, racemic mixt.
• PGF2alpha-[d4]
• 7-(3, 5-dihydroxy-2-(3-hydroxyl-1-octenyl) cyclopentyl)-5-heptenoic acid
• BRN 4153898
• DINOPROST [INN]
• DINOPROST [JAN]
• DINOPROST [HSDB]
• DINOPROST [USAN]
• (5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-3,13-dien-1-oic acid
• DINOPROST [WHO-DD]
• SCHEMBL24292
• BSPBio_001494
• 23518-25-4
• BML1-F08
• GTPL1884
• Dinoprost (JP17/USAN/INN)
• 15(R)-Prostaglandin F2 alpha
• 9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-oic acid
• EX-A4115A
• G02AD01
• PXGPLTODNUVGFL-YNNPMVKQSA-N
• HMS1361K16
• HMS1791K16
• HMS1989K16
• HMS2089F11
• HMS3402K16
• HMS3648N11
• (E,Z)-(1R,2R,3R,5S)-7-[3,5-Dihydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]cyclopentyl]-5-heptenoic acid
• AMY30098
• Tox21_111777
• BDBM50035622
• LMFA03010002
• MFCD00135231
• PDSP2_000079
• AKOS030526160
• PROSTAGLANDIN F2.ALPHA. [MI]
• CCG-208257
• CS-4232
• DB12789
• 5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-, (+-)-
• 5-HEPTENOIC ACID, 7-(3,5-DIHYDROXY-2-(3-HYDROXY-1-OCTENYL)CYCLOPENTYL)-, dl-
• IDI1_033964
• NCGC00160385-02
• NCGC00160385-04
• NCGC00160385-05
• NCGC00160385-06
• AS-56892
• CAS-551-11-1
• HY-12956
• P1885
• C00639
• D00081
• A830494
• EN300-21689745
• Q421375
• SR-01000946457
• SR-01000721847-2
• SR-01000721847-4
• SR-01000946457-1
• (5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoate
• (5z,9alpha,11alpha,13e,15s)-9,11,15-trihydroxyprosta-5,13-dienoic acid
• Prosta-10,13-dien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9.alpha.,11.alpha.,13E,15S)
• (Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-cyclopentyl)-hept-5-enoic acid
• (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-((s)-(e)-3-hydroxyoct-1-enyl)-cyclopentyl]hept-5-enoic acid
• (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-{(E)-(3S)-3-hydroxy-1-octenyl}-cyclopentyl]-5-heptenoic acid
• 13535-33-6
• Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9-alpha,11-alpha,13E,15S)-(+-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9523	95.23%
Caco-2	-	0.7551	75.51%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7055	70.55%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.7575	75.75%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9338	93.38%
BSEP inhibitior	-	0.5162	51.62%
P-glycoprotein inhibitior	-	0.8289	82.89%
P-glycoprotein substrate	-	0.6775	67.75%
CYP3A4 substrate	+	0.6000	60.00%
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	-	0.7842	78.42%
CYP inhibitory promiscuity	-	0.9098	90.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7417	74.17%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9676	96.76%
Skin irritation	+	0.5928	59.28%
Skin corrosion	-	0.8625	86.25%
Ames mutagenesis	-	0.8478	84.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.3943	39.43%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.8446	84.46%
skin sensitisation	-	0.7406	74.06%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.8014	80.14%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.6075	60.75%
Thyroid receptor binding	-	0.5578	55.78%
Glucocorticoid receptor binding	+	0.7569	75.69%
Aromatase binding	-	0.8149	81.49%
PPAR gamma	+	0.6959	69.59%
Honey bee toxicity	-	0.9384	93.84%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9769	97.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1811	P34995	Prostanoid EP1 receptor	380 nM	IC50	via Super-PRED
CHEMBL3710	P43115	Prostanoid EP3 receptor	322 nM	IC50	via Super-PRED
CHEMBL1987	P43088	Prostanoid FP receptor	2.5 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.13%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.83%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.77%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.85%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.05%	93.56%
CHEMBL230	P35354	Cyclooxygenase-2	90.13%	89.63%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	89.92%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.56%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	87.38%	92.08%
CHEMBL1781	P11387	DNA topoisomerase I	87.18%	97.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.05%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.97%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.92%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	86.64%	83.82%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.37%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.74%	100.00%
CHEMBL1881	P43116	Prostanoid EP2 receptor	84.62%	93.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.33%	85.14%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.71%	95.58%
CHEMBL2514	O95665	Neurotensin receptor 2	82.55%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.41%	92.50%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.95%	92.32%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.88%	89.50%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	81.82%	98.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.80%	90.71%
CHEMBL299	P17252	Protein kinase C alpha	81.78%	98.03%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.35%	82.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.23%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	80.40%	90.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.00%	97.29%

Plants that contains it

• Larix sibirica
• Mucuna membranacea

Cross-Links

• PubChem: 5280363
• LOTUS: LTS0205366
• wikiData: Q421375