Showing Compound 8-Isoprostaglandin E1 (FDB023405)

Record Information

Version

1.0

Creation date

2011-09-21 00:29:26 UTC

Update date

2015-07-21 06:57:41 UTC

Primary ID

FDB023405

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

8-Isoprostaglandin E1

Description

8-Isoprostaglandin E1 is an isoprostane. The isoprostanes embody a vast family of novel prostaglandin-like lipids that are produced by nonenzymatic peroxidation of arachidonic acid (AA) in response to free radicals and reactive oxygen species. Although free AA is required for the formation of prostaglandins by cyclooxygenases, the isoprostanes can be generated nonenzymatically from esterified AA in membrane phospholipids before being released by a phospholipase(s). Another dissimilarity is that isoprostanes feature side chains that are almost exclusively orientated cis relative to the cyclopentane ring and are therefore distinct from the prostaglandins, which always have side chains in the trans configuration. Nevertheless, isoprostanes are isomeric with prostaglandins and have been given the prefix D-, E-, and F{alpha}- to denote the prostane ring shared with PGD2, PGE2, and PGF2{alpha} respectively. An additional level of complexity is that peroxidation of AA can occur at one of any of four carbon atoms producing regioisomers, the so-called 5-, 12-, 8-, and 15-series isoprostanes, each consisting of eight racemic diastereomers. Thus, a total of 64 isomers can be generated for each of the D-, E-, and F{alpha}-ring isoprostanes. (PMID: 15528403) Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. [HMDB]

CAS Number

21003-46-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
11a,15-(S)-Dihydroxy-9-oxo-13-trans-8-isoprostenoate	HMDB
11a,15-(S)-Dihydroxy-9-oxo-13-trans-8-isoprostenoic acid	HMDB
8-iso-PGE1	HMDB
iso-PGE1	MeSH, HMDB
Isoprostaglandin e1	HMDB, MeSH
Isoprostaglandin E1	hmdb
Isoprostaglandin e1, (8beta,11alpha,12alpha,13E,15S)-isomer	MeSH, HMDB
Isoprostaglandin e1, (8beta,11beta,12alpha,13E,15R)-isomer	MeSH, HMDB
Isoprostaglandin e1, (8beta,11beta,12alpha,13E,15S)-isomer	MeSH, HMDB
Ovinonic acid	HMDB

Showing 1 to 10 of 10 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.59	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.32 m³·mol⁻¹	ChemAxon
Polarizability	41.51 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H34O5

IUPAC name

7-[(1S,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

InChI Identifier

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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17+,19+/m0/s1

InChI Key

GMVPRGQOIOIIMI-JCPCGATGSA-N

Isomeric SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Fatty alcohol
Hydroxy fatty acid
Cyclopentanol
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Isoprostanes (LMFA03110002 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Multicellular process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Modulator:

Immunomodulator

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	8-Isoprostaglandin E1, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03du-8496000000-7d3b810081e27f50d55e	Spectrum
Predicted GC-MS	8-Isoprostaglandin E1, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-5111690000-a4b76b0035fa00f6c191	Spectrum
Predicted GC-MS	8-Isoprostaglandin E1, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0019000000-f5b5a1445394c1875ab5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014u-3298000000-914d4dd2398f2330aadc	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-9210000000-cae0b0e2e44b318ffc15	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-0009000000-2ae4bda00bf8a87d2cc8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-2149000000-253cbdfcc6971a59bcbe	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9430000000-d886399479c4a7f3bafd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fri-0009000000-923c8a53409a3df92c03	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0069000000-1771266ae55287330e24	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001v-9481000000-4f3fb6bba04c2db22a67	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-48b67d3860a0408d6017	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-7369000000-67c0756e11758bfc63bd	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9600000000-b116946f56f764ec762e	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4446333

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5283212

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04686

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB