Dinoprostone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Dinoprostone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Dinoprostone?

The molecule Dinoprostone presents a molecular formula of C20H32O5 and its IUPAC name is (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid.

Dinoprostone is a molecule that is structurally similar to prostaglandin E2, and is used as a medication to induce labor, or to abort a pregnancy. It is also used to treat postpartum hemorrhage..

3D structure

Cartesian coordinates

Geometry of Dinoprostone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Dinoprostone XEYBRNLFEZDVAW-ARSRFYASSA-N chemical compound 2D structure molecule svg
Dinoprostone

 

Molecule descriptors

 
IUPAC name(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
InChI codeInChI=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 KeyXEYBRNLFEZDVAW-ARSRFYASSA-N
SMILESCCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+/-)-Prostaglandin E2
  • (-)-Prostaglandin E2
  • (15S)-Prostaglandin E2
  • (5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
  • (5Z,11-alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • (5Z,11.alpha.,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • (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,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
  • (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic
  • (5Z,11alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate
  • (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid
  • (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid
  • (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate
  • (5Z,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • (5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate
  • (5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoic acid
  • (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • (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
  • (Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,E)-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
  • (Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
  • (Z)-7-[(1r,2r,3r)-3-Hydroxy-2-[(E,3s)-3-Hydroxyoct-1-Enyl]-5-Oxo-Cyclopentyl]hept-5-Enoic Acid
  • 05D31BD5-818B-4A92-8CFC-BEC19926A5B3
  • 2-AMINO-1-BENZO[1,3]DIOXOL-5-YL-ETHANONEHYDROCHLORIDE
  • 22230-04-2
  • 363-24-6
  • 363P246
  • 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-
  • 5-Heptenoic acid, 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-
  • 5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxo-rosta-5,13-dien-1-oic acid
  • 7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
  • 7-[3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid
  • 9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic acid
  • A823207
  • AC-6098
  • AMY30102
  • AS-71847
  • B7005
  • BDBM35847
  • BML1-F07
  • BMS-279654 & PGE2
  • BSPBio_001490
  • C00584
  • CCG-208092
  • CCG-208256
  • CS-6932
  • Cervidil
  • Cerviprime
  • D00079
  • DB00917
  • DSSTox_CID_2947
  • DSSTox_GSID_22947
  • DSSTox_RID_76801
  • Dinoproston
  • Dinoprostona
  • Dinoprostone
  • Dinoprostone (JAN/USP/INN)
  • Dinoprostone Prostaglandin E2
  • Dinoprostone beta-Cyclodextrin Clathrate
  • Dinoprostonum
  • EX-A1773
  • Enzaprost E
  • GTPL1883
  • GTPL1916
  • Glandin
  • HMS1361K12
  • HMS1791K12
  • HMS1989K12
  • HMS2089D17
  • HMS3268J12
  • HMS3402K12
  • HMS3413C20
  • HMS3648F07
  • HMS3677C20
  • HY-101952
  • IDI1_033960
  • J-502620
  • K7Q1JQR04M
  • LMFA03010003
  • MFCD00077861
  • Minprositin E2
  • Minprostin E2
  • NCGC00092361-01
  • NCGC00092361-02
  • NCGC00092361-03
  • NCGC00092361-04
  • NCGC00092361-05
  • NCGC00092361-06
  • NSC 165560
  • NSC 196514
  • NSC-165560
  • NSC-196514
  • NSC165560
  • NSC196514
  • P1884
  • P2E
  • PGE2
  • PGE2-[3,3,4,4-d4]
  • PGE2alpha
  • Prepidil
  • Prestwick_793
  • Propess
  • 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)-
  • Prosta-5,13-dien-1-oic acid, (5Z,11-alpha,13E,15S)-11,15-dihydroxy-9-oxo-
  • Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11.alpha.,13E,15S)-
  • Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11alpha,13E,15S)-
  • Prostaglandin E
  • Prostaglandin E(2)
  • Prostaglandin E2
  • Prostaglandin E2 (PGE2)
  • Prostaglandin E2.alpha.
  • Prostaglandin E2alpha
  • Prostarmon E
  • Prostarmon E2
  • Prostenone
  • Prostin
  • Prostin E2
  • Q416554
  • SMP2_000056
  • SR-01000946417
  • SR-01000946417-1
  • SR-05000001459
  • SR-05000001459-1
  • SR-05000001459-3
  • SR-05000001459-4
  • U 12062
  • U,062
  • U-12,062
  • U-12062
  • [3H]-PGE2
  • [3H]PGE2
  • [3H]dinoprostone
  • [3H]prostaglandin E2
  • [3H]prostin E2
  • l-7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid
  • l-PGE2
  • l-Prostaglandin E2
  • prosta-glandin e2
  • s3003

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3830713
  • CAS-363-24-6
  • UNII-K7Q1JQR04M
  • AKOS015920228
  • BRD-K26521938-001-04-9
  • DTXSID4022947
  • DTXSID00859353
  • CHEMBL548
  • CHEBI:15551
  • Tox21_111196
  • Tox21_111196_1
  • EINECS 206-656-6
  • SCHEMBL25533

Physico-Chemical properties

IUPAC name(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
Molecular formulaC20H32O5
Molecular weight352.465
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity99.49
LogP3.3
Topological polar surface area94.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.