6-Ketoprostaglandin F1 alpha

HCID 5280888

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Basic information

CAS: 58962-34-8
Standard SMILES: CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](CC(=O)CCCCC(=O)O)[C@@H](O)C[C@H]1O
InChIKey: KFGOFTHODYBSGM-ZUNNJUQCSA-N
Molecular formula: C20H34O6
Average molar mass: 370.5 g/mol
Monoisotopic mass: 370.2355388

Names & identifiers

Preferred name: 6-Ketoprostaglandin F1 alpha
IUPAC: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]-6-oxoheptanoic acid
English name: 13,14-DIHYDROPROSTAGLANDIN E1
Molecular formula: C20H34O6
Molecular weight: 370.48

Names & synonyms

58962-34-86-Ketoprostaglandin F1 alpha6 Oxo PGF1 alpha6-Oxo-PGF1 alpha6 Keto PGF1 alpha6-Keto-PGF1 alphaalpha, 6-Oxo-PGF1alpha, 6-Keto-PGF16 Oxoprostaglandin F1 alpha6-Oxoprostaglandin F1 alpha6 Ketoprostaglandin F1 alphaalpha, 6-Oxoprostaglandin F1

Show more names

6-Keto Prostaglandin6-KETOPROSTAGLANDIN F1A6-Oxo-prostaglandin F1α6-oxo-prostaglandin F1alphaKFGOFTHODYBSGM-ZUNNJUQCSA-N6-Keto-Prostaglandin F1-alfaPROSTAGLANDIN F1-ALPHA, 6-KETO-Epoprostenol Related CoMpound A

F1 alpha, 6-Oxoprostaglandinalpha, 6-Ketoprostaglandin F1F1 alpha, 6-KetoprostaglandinRefChem:3887586-Keto-prostaglandin F1alpha6-Keto-PGF1alpha6-Oxo-PGF1alpha6-KETOPROSTAGLANDIN F1alpha

Database identifiers

CAS: 58962-34-8
PubChem CID: 5280888
DTXSID: DTXSID001317937
ChEMBL: CHEMBL2074840
ChEBI: CHEBI:28158
UNII: 8URB805JJJ
EC Number: 682-018-4
Nikkaji: J240.195I

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 115 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 6
Rotatable bonds: 13
Heavy atoms: 26
Formal charge: 0
Complexity: 461

Experimental & physicochemical properties

Physical DescriptionSolid

Collision Cross Section · 2 items

195.0 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

196 Å² [M-H]-；202.9 Å² [M+Na]+

Physicochemical properties

Boiling point: 575.3 · 575.3±50.0 °C(Predicted)
Density: 1.191 · 1.191±0.06 g/cm3(Predicted)
RTECS: 8428300 · UK8428300
storage temp.: 20 °C · −20°C
solubility: 10 mg/mL, · ethanol: 10 mg/mL, clear, faintly yellow
pka: 4.69 · 4.69±0.10(Predicted)
form: White to off-white solid.
color: White to off-white
BRN: 2821925 · 2821925
Major Application: pharmaceutical (small molecule)
InChIKey: KFGOFTHODYBSGM-DFOLFLIJSA-N
SMILES: CCCCCC(O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O
FDA UNII: 8 URB805JJJ · 8URB805JJJ
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 317 · H317
Precautionary statements: 261 · P261-P280g-P302+P352a-P321-P333+P313-P501a
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
F: 8 · 8-10
HS Code: 2937909000 · 2937909000
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)；Acute Tox. 4 (100%)；Acute Tox. 4 (100%)

Safety data

F: 8-10
wgk: 3
hs_code: 2937909000
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H317
Precautionary statements: P261-P280g-P302+P352a-P321-P333+P313-P501a

Chemistry & industry

Pharmacology

Tissue LocationsAdipose Tissue；Kidney；Liver；Placenta；Platelet

Cellular LocationsExtracellular；Membrane

Metabolite PathwaysArachidonic Acid Metabolism

Applications · 2 items

Description6-keto prostaglandin F1α (6-keto PGF1α) is the inactive, non-enzymatic hydrolysis product of PGI2. 6-keto PGF1α serves as a useful marker of PGI2 biosynthesis in vivo. When [3H]-PGI2 is injected into healthy human males, 6.6% of the radioactivity is recovered from urine as [3H]-6-keto PGF1α.

Uses6-Ketoprostaglandin F1α is the stable hydrolysis product of prostacyclin (P839060), an eicosanoid which prevents the formation of platelet plugs and an effective vasodilator.