Dinoprostone

Details

• Internal ID: 2c583a0f-f6af-4438-83bb-c3ccafc30319
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-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): CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=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)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
• InChI Key: XEYBRNLFEZDVAW-ARSRFYASSA-N
• Popularity: 41,403 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

Synonyms

• Dinoprostone
• PGE2
• 363-24-6
• Prostin E2
• Prepidil
• Cervidil
• Minprostin E2
• Propess
• Minprositin E2
• Dinoproston
• Prostarmon E
• (15S)-Prostaglandin E2
• Dinoprostonum
• l-Prostaglandin E2
• Cerviprost
• Dinoprostona
• Enzaprost E
• PGE2alpha
• Glandin
• l-PGE2
• Prostaglandin E2alpha
• (5Z,11alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
• Cerviprime
• Prostenone
• U-12062
• Dinoprostonum [INN-Latin]
• Dinoprostona [INN-Spanish]
• Dinoprostone Prostaglandin E2
• (E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid
• NSC 165560
• Prostaglandin E
• U 12062
• UNII-K7Q1JQR04M
• EINECS 206-656-6
• K7Q1JQR04M
• NSC 196514
• NSC-165560
• NSC-196514
• Prostaglandin E(2)
• [3H]PGE2
• (Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid
• DTXSID4022947
• CHEBI:15551
• [3H]prostaglandin E2
• 7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
• l-7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
• (-)-Prostaglandin E2
• Prostaglandin E2 (GMP)
• (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate
• CHEMBL548
• (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate
• U-12,062
• 5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-
• 5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-, l-
• Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11alpha,13E,15S)-
• (Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
• DTXCID002947
• (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
• PGE2 alpha
• (Z)-7-[(1r,2r,3r)-3-Hydroxy-2-[(E,3s)-3-Hydroxyoct-1-Enyl]-5-Oxo-Cyclopentyl]hept-5-Enoic Acid
• Prostglandin E2
• Dinoprostone [USAN:USP:INN:BAN:JAN]
• NCGC00092361-05
• Prostaglandin E2.alpha.
• Prostaglandin E2 alpha
• Dinoprostonum (INN-Latin)
• Dinoprostona (INN-Spanish)
• Prosta-5,13-dien-1-oic acid, (5Z,11-alpha,13E,15S)-11,15-dihydroxy-9-oxo-
• DINOPROSTONE (MART.)
• DINOPROSTONE [MART.]
• E2, Prostaglandin
• DINOPROSTONE (USP-RS)
• DINOPROSTONE [USP-RS]
• alpha, PGE2
• 9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic acid
• E2alpha, Prostaglandin
• DINOPROSTONE (EP MONOGRAPH)
• DINOPROSTONE (USP IMPURITY)
• DINOPROSTONE [EP MONOGRAPH]
• DINOPROSTONE [USP IMPURITY]
• alpha, Prostaglandin E2
• E2 alpha, Prostaglandin
• DINOPROSTONE (USP MONOGRAPH)
• DINOPROSTONE [USP MONOGRAPH]
• 7-[3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid
• Prostarmon E2
• C20H32O5
• Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11.alpha.,13E,15S)-
• Dinoprostone (USAN:USP:INN:BAN:JAN)
• Cervidil (TN)
• Prepidil (TN)
• (5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
• (Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid
• CAS-363-24-6
• ALPROSTADIL IMPURITY G (EP IMPURITY)
• ALPROSTADIL IMPURITY G [EP IMPURITY]
• U,062
• Prostin E2 (TN)
• PGE2-[3,3,4,4-d4]
• SR-05000001459
• Dinoprostone (JAN/USP/INN)
• (5Z,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
• BML1-F07
• PGE(2)
• Prosta-5, (5Z,11.alpha.,13E,15S)-11,15-dihydroxy-9-oxo-
• Prosta-5, 11,15-dihydroxy-9-oxo-, (5Z,11.alpha.,13E,15S)-
• Prosta-5, 11,5-dihydroxy-9-oxo-, (5Z,11.alpha.,13E,15S)-
• [3H]dinoprostone
• 5-Heptenoic acid, 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-
• Glandin-E2
• prosta-glandin e2
• NCGC00092361-06
• (E,2R,3R)-7-[3-hydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic acid
• (E,Z)-(1R,2R,3R)-7-[3-hydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic acid
• P2E
• Prestwick_793
• (5Z,11-alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
• (5Z,13E)-(15S)-11alpha15-Dihydroxy-9-oxoprost-13-enoate
• MFCD00077861
• (5Z,13E)-(15S)-11,15-dihydroxy-9-oxoprosta-5,13-dienoate
• [3H]prostin E2
• BMS-279654 & PGE2
• Dinoprostone beta-Cyclodextrin Clathrate
• (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic
• DINOPROSTONE [INN]
• DINOPROSTONE [JAN]
• DINOPROSTONE [USAN]
• (+/-)-Prostaglandin E2
• Prostaglandin E2 (PGE2)
• DINOPROSTONE [VANDF]
• SCHEMBL25533
• BSPBio_001490
• DINOPROSTONE [WHO-DD]
• PROSTAGLANDIN E2 [MI]
• GTPL1883
• GTPL1916
• [3H]-PGE2
• BDBM35847
• DTXSID00859353
• G02AD02
• DINOPROSTONE [ORANGE BOOK]
• HMS1361K12
• HMS1791K12
• HMS1989K12
• HMS2089D17
• HMS3268J12
• HMS3402K12
• HMS3413C20
• HMS3648F07
• HMS3677C20
• AMY30102
• EX-A1773
• Tox21_111196
• HB3460
• LMFA03010003
• NSC165560
• NSC196514
• s3003
• (5Z,11.alpha.,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
• AKOS015920228
• Tox21_111196_1
• AC-6098
• CCG-208092
• CCG-208256
• CS-6932
• DB00917
• HY-101952G
• IDI1_033960
• SMP2_000056
• NCGC00092361-01
• NCGC00092361-02
• NCGC00092361-03
• NCGC00092361-04
• AS-71847
• Dinoprostone 100 microg/mL in Acetonitrile
• HY-101952
• CS-0626105
• P1884
• C00584
• D00079
• Prostaglandin E2, >=93% (HPLC), synthetic
• A823207
• EN300-22411484
• Q416554
• SR-01000946417
• J-502620
• SR-01000946417-1
• SR-05000001459-1
• SR-05000001459-3
• SR-05000001459-4
• BRD-K26521938-001-04-9
• 05D31BD5-818B-4A92-8CFC-BEC19926A5B3
• 2-AMINO-1-BENZO[1,3]DIOXOL-5-YL-ETHANONEHYDROCHLORIDE
• Dinoprostone, European Pharmacopoeia (EP) Reference Standard
• (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid
• (5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate
• Dinoprostone, United States Pharmacopeia (USP) Reference Standard
• (5Z,11?,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1oic acid
• (5Z,11I+/-,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
• (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
• (5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoic acid
• 5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxo-rosta-5,13-dien-1-oic acid
• Prostaglandin E2, synthetic, powder, BioReagent, suitable for cell culture
• (5Z,11alpha,12alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
• (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-o xo-prosta-5,13-dien-1oic acid
• Prostaglandin E2, gamma-irradiated, powder, BioXtra, suitable for cell culture
• 22230-04-2
• Dinoprostone; (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E)-(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid; PGE2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

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	59 nM; 1.03 nM	EC50; Ki	via Super-PRED; via Super-PRED
CHEMBL3710	P43115	Prostanoid EP3 receptor	0.33 nM	Ki	via Super-PRED
CHEMBL1836	P35408	Prostanoid EP4 receptor	0.02 nM; 0.05 nM	EC50; EC50	via Super-PRED; via Super-PRED
CHEMBL1987	P43088	Prostanoid FP receptor	250 nM	EC50	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

• Larix sibirica
• Populus balsamifera

Cross-Links

• PubChem: 5280360
• LOTUS: LTS0074404
• wikiData: Q416554