Dinoprost (CHEM016672)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:40:01 UTC
Update Date2026-04-14 19:04:16 UTC
Accession NumberCHEM016672
Identification
Common NameDinoprost
ClassSmall Molecule
DescriptionA prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-Prostaglandin F2aChEBI
(5Z,13E)-(15S)-9alpha,11alpha,15-Trihydroxyprosta-5,13-dienoateChEBI
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acidChEBI
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acidChEBI
9a,11a-PGF2ChEBI
AmoglandinChEBI
CyclosinChEBI
DinoprostaChEBI
DinoprostumChEBI
EnzaprostChEBI
Enzaprost FChEBI
L-PGF2-alphaChEBI
L-Prostaglandin F2-alphaChEBI
PanacelanChEBI
PGF2aChEBI
PGF2alphaChEBI
Prostaglandin F2aChEBI
Prostin F 2 alphaChEBI
ProtamodinChEBI
U 14583ChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoateKegg
ProsmonKegg
(5Z,13E)-(15S)-9a,11a,15-Trihydroxyprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-9a,11a,15-Trihydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9alpha,11alpha,15-Trihydroxyprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9Α,11α,15-trihydroxyprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-9Α,11α,15-trihydroxyprosta-5,13-dienoic acidGenerator
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoateGenerator
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-OateGenerator
L-PGF2-aGenerator
L-PGF2-ΑGenerator
L-Prostaglandin F2-aGenerator
L-Prostaglandin F2-αGenerator
PGF2ΑGenerator
Prostin F 2 aGenerator
Prostin F 2 αGenerator
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoateGenerator
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoic acidGenerator
(5Z,9alpha,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoic acidGenerator
(5Z,9Α,11α,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoateGenerator
(5Z,9Α,11α,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoic acidGenerator
DinoprostChEBI
(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(e,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoateGenerator
9alpha,11beta-PGF2MeSH
Prostaglandin F2MeSH
9alpha,11beta PGF2MeSH
F2 alpha, ProstaglandinMeSH
F2alpha, ProstaglandinMeSH
Prostaglandin F2 alphaMeSH
Prostaglandin F2alphaMeSH
alpha, PGF2MeSH
EstrofanMeSH
PGF2MeSH
PGF2 alphaMeSH
Chemical FormulaC20H34O5
Average Molecular Mass354.487 g/mol
Monoisotopic Mass354.241 g/mol
CAS Registry Number551-11-1
IUPAC Name(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Nameglandin
SMILES[H]\C(CCCC(O)=O)=C(/[H])C[C@@]1([H])[C@@]([H])(O)C[C@@]([H])(O)[C@]1([H])C(\[H])=C(/[H])[C@@]([H])(O)CCCCC
InChI IdentifierInChI=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 KeyPXGPLTODNUVGFL-YNNPMVKQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.11ALOGPS
logP2.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.47 m³·mol⁻¹ChemAxon
Polarizability40.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0009000000-69d9553575061edad507Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pbc-0796000000-d5962a3a708504e86ccdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-2930000000-cd974d0610f6f3279559Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9700000000-32e8c42c1a30644feff4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0k96-0987000000-9101bdbb9c2393dd32beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-2c9767841fa4893c60b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-2297000000-8aa402b01c233708c42eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0103-9170000000-b6c0e28782ad3916af75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-43645725f77edc02f608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f7c-1049000000-d2fc6ca599de8bc5b9a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9611000000-80d02fb42a0a241d8e2bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12789
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID5Z13E-15S-9-ALPHA11-ALPHA15-TRIHY
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDinoprost
Chemspider IDNot Available
ChEBI ID15553
PubChem Compound ID5280363
Kegg Compound IDC00639
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11438482
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23807981